With a plan to spend two weeks in Italy, you may just be wondering where to begin…

First off, welcome to the club! I was exactly in your shoes once, desperately trying to cram all of the gems of this wonderful country into a digestible, 14-day timeframe. Let’s just say it didn’t exactly go as I’d anticipated…

So if you’re anything like I was – determined to do and see it all in one go – perhaps it’s time to take a step back.

First off, Italy isn’t a destination to be rushed. In fact, slow living is kind of a thing in Italy. Referred to as ““lo struscio,” this practice emphasizes a slower approach to everyday life – and it’s considered to be an art form! So if you don’t want your rushed pace to scream “tourist,” then I suggest narrowing down your visit to a few select regions on your first go.

Secondly, there’s just so much to see here. Although the country is “only” roughly around the size of Arizona, you’ll find incredible diversity in each of the different regions. For instance, Northern Italy is a significant departure from central Italy, which is really nothing like southern Italy. (Oh, and then there’s Sicily, which may as well be its own country, from what I’ve heard. I’ll report back on this after we finally get there!)

Now, you may notice that the exceptionally famous cities of Rome and Venice are notably absent from this 2-week Italy itinerary. This is by design, with the intention of introducing you to more of the country’s natural beauty and giving you a little breathing room from the city crowds.

In lieu of these heavily-touristed hotspots, you can look forward to additional time in the serene Tuscan countryside and along the breathtaking Amalfi Coast! I’d say that’s a pretty fair trade-off, no?

But not to worry – you’ll still enjoy a taste of Italian city life with a stopover in fantastic Florence, a.k.a the “Cradle of the Renaissance.”

That all being said, Rome and Venice are still very much on my bucket list, so perhaps there will be a 3-week itinerary to look forward to in the future…

For now, here are my recommendations for two weeks in Italy with a sampling of the best terrains – cities, coasts, and countryside!

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Yes! Although you obviously can’t cover the entire country in a 14-day timeframe, two weeks in Italy is an ideal amount of time to spend on a first trip. This will allow you to explore a variety of different regions and give you sufficient time to enjoy each one. A two-week itinerary will also introduce you to a number of the highlights Italy is famous for.

One of the key things to know about Italy is that you can actually enjoy it year-round! The “best” time to visit will really depend on the regions you’re most interested in and what you’re looking to do.

My personal preference for the best time to visit (and what most guidebooks will tell you) is spring and fall. You can enjoy the best of all worlds during these times – lower prices, fewer crowds, and gorgeous weather. To take advantage of these wonderful perks, the best months to visit Italy are May, June, September, and October.

That said, the northern Italian regions can be ideal during the colder months if winter activities such as skiing are of interest.

As with anything else, costs are relative. For instance, compared to northern European destinations such as the UK or Scandinavia, Italy prices are quite reasonable. Mid-range travelers can typically expect to spend between $60 to $150 a day.

That said, compared to other Southern European countries, Italy is often considered one of the pricier ones. Then again, the question will really depend on the areas you’re visiting. For example, the Italian Riviera tends to be cheaper than the Amalfi Coast.

We’re kicking off an awesome two weeks in Italy with a few days in the Italian Riviera. Also known as Italy’s Liguria region, the Italian Riviera forms the shape of a crescent in northwestern Italy, between Southern France and Tuscany.

While I may be introducing you to some of these towns for the first time, I can honestly say it’s worth a trip to this vastly underrated section of Italy. (That said, you’ve most likely heard of the Cinque Terre, which we’ll visit next.)

My husband and I began our 14 days in Italy in the under-the-radar gem of Sanremo. Once a winter sun destination for the Russian elite (including Tsar Nicolas of Russia), Sanremo is now a vastly underrated resort town along the Italian Riviera.

There are a few different options for flying to Sanremo. While there’s no airport in Sanremo itself, the closest airport is the Nice Côte d’Azur Airport (NCE), located in the French Riviera Capital of Nice.

Given how close Sanremo is to the French Riviera, we actually spent a significant amount of time there on this trip, which I’ll get into a bit later.

If you’d prefer to fly directly into Italy instead of France (even though the Nice Côte d’Azur Airport is closest), that’s also an option.

Here are Italian airports to consider:

• Genoa Cristoforo Colombo Airport (GOA) – Approx 2h, 20min from Sanremo
• Turin Aiport (TRN) – Approx 4 hours from Sanremo
• Pisa International Airport (PSA) – Approx 4 hours from Sanremo
• Milan Malpensa (MXP) – Approx 4h, 20min from Sanremo

Once we flew into the airport in Nice, we took the shuttle to Nice’s Old Port and walked a few blocks to the Nice Riquier train station. From this station, we traveled to Ventimiglia, which is the border between France and Italy.

We then transferred at Ventimiglia and rode the line until we reached the Sanremo station.

I definitely recommend renting a car once you’re in Sanremo.

However, I also suggest flying into Nice Côte d’Azur Airport initially. Since renting a car in Nice and driving it to Sanremo is impractical and pricey, I think it’s best to get yourself to Sanremo by train first and then pick up your rental there.

However, if you’re looking to travel in from one of the other Italian cities I mentioned (and potentially spend time there before Sanremo), you’d probably want to drive down.

Known as the “City of Flowers,” Sanremo is home to many beautiful gardens and parks. I suggest visiting at least one while you’re here.

My personal recommendation is Giardini Regina Elena. Although the park itself seems like nothing much at first glance, just wait until you look down upon this view below!

There are many, many churches in Italy, so after a while, they can all start to look the same.

Well, I’m happy to report that this is not at all the case with the Santuario della Madonna della Costa. I’ve honestly never seen a church quite like this on my travels.

Designed in a beautiful Baroque style, the front of the church looks as though it features a perfect powder-blue heart – far from your average church!

In addition to numerous gardens and churches, Sanremo is also home to several impressive villas, which is testament to its former glory as a winter escape for the wealthy elite!

Villa Nobile, for instance, is where you’ll find the lovely Giardini Nobel.

You can check out the best villas and how to reach them in my guide to the best things to do in Sanremo.

While I’m personally not much of a gambler, it didn’t seem right to leave one of Sanremo’s most significant landmarks out of this itinerary.

The Casinò Municipale di Sanremo is a thing in this city, to say the least. So even if you’re not feeling particularly lucky, you’ll definitely need to at least check out the impressive venue. The entranceway and flowers alone make it worth the visit!

By far, my favorite thing that we did while staying in Sanremo wasn’t actually in the city itself but on the outskirts in Bussana Vecchia.

If you’ve never heard of this town before, not to worry – I hadn’t, either! Frankly, that’s part of its unique charm. Few know of this special place, but those who do tend to fall in love with it immediately!

Located atop a hill in Liguria, this unique artists’ village can only be described as a European fairytale, from its iconic pink restaurant to its gorgeous ivy-covered facades.

As I mentioned earlier, my husband and I also spent a lot of time in the French Riviera, even though we technically based ourselves in Sanremo.

Although this itinerary is for two weeks in Italy, I think you’ll be missing out if you don’t visit at least one French Riviera town while you’re here, given how close France is. In reality, three days in the Riviera is enough to enjoy the best of both worlds!

If you’re interested in the French Riviera but looking to spend minimal time driving, I’d suggest visiting the charming town of Menton, located just 45-50 minutes from Sanremo by car. In addition, you can check out all of my French Riviera guides below.

Alternatively, if you’d prefer to limit your trip to Italy and avoid any border crossings, here are some other lovely Italian Riviera towns to consider during your stay:

• Seborga
• Ventimiglia
• Alassio
• Genoa
• Camogli
• Portofino

Keep in mind that the Cinque Terre is also located in Italy’s Liguria region, but I intentionally left it out here and covered it in the next section, instead. This wonderful area of Italy definitely deserves more attention than a quick day trip!

We spent our time in Sanremo in a comfy, self-catering apartment in a prime city location. You can check out the details of our stay in my Sanremo guide below.

On the other hand, if you’re more interested in a formal hotel stay, you can check out the available properties here:

Check Out My Italian (& French) Riviera Guides Before You Travel:

• 10 Fun Things to Do in Sanremo, Italy Beyond the Annual Music Festival
• A Taste of Southern France: 3-Day French Riviera Itinerary
• Dreamy Menton Photo Spots to Inspire Your French Riviera Escape
• Top 20 Things to Do in Nice, France & Beyond
• Plan the Perfect Day Trip from Nice to Villefranche-sur-Mer

Just recalling the Cinque Terre puts a huge smile on my face. This was my favorite stop on our 2-week Italy itinerary and I’m already dreaming of when we can go back!

If you’re not already familiar, the Cinque Terre is Italian for “five lands,” which refers to the five seaside villages that make up this unique destination: Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. Each of the towns hug the Italian Riviera coastline and feature dramatic terraces and colorful, fishing-boat-filled harbors.

While the towns have gained undeniable popularity in recent years – so much so that overtourism has become an issue – it’s frankly unsurprising, especially considering all the attention they receive on Instagram.

And if you can manage to avoid the tourist-choked summer months of June through August, you can experience a taste of seaside living from centuries past with some spectacular panoramic views to boot.

Traveling by train is my top recommendation for reaching the Cinque Terre. We took the train from Sanremo to Levanto and from Levanto to Vernazza.

In addition to being the most efficient way to get to the Cinque Terre initially, it’s also the easiest way of bouncing around to the different towns once you’re here. Regardless of which city you’re traveling in from, you’ll want to get yourself to either La Spezia Centrale or Sestri Levante. From there, you can change over for the Cinque Terre Express and travel to whichever one of the five towns you’re staying in.

While it’s technically possible to travel by car, I don’t recommend this option because you won’t be able to drive into the villages. Since the five towns are pedestrian-only, you’ll need to keep your car in either La Spezia or Levanto and then hop on the Cinque Terre Express to the towns.

Personally, I find that keeping a car in a lot on the outskirts of the Cinque Terre is an unnecessary expense and burden.

Unsurprisingly, the Cinque Terre does not have an airport, so you won’t be able to fly in directly. The closest major airport is Pisa International Airport (PSA), which would make sense to travel in from if you’re planning to spend time in Pisa first.

If, however, you’re adhering to this itinerary and traveling in from the Italian Riviera, I’d recommend traveling by train.

If you’re traveling to the Cinque Terre from March until October, you can catch a ferry from either La Spezia, Lerici, Levanto, or Portovenere.

General Note: Ferries may be suspended in the case of inclement weather, so this is the least reliable means of travel to the Cinque Terre.

For the ultimate views over the Cinque Terre, hiking is practically mandatory!

Okay, okay, no one is going to make you hike here, but honestly, you’ll be doing yourself a huge disservice if you don’t. Hiking is one of the main reasons people visit the Cinque Terre in the first place, and once you see the views from the top for yourself, you’ll understand why!

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There are actually 48 hiking trails to choose from, so you’re bound to find something that’s suitable for your sensibilities and fitness level.

I recommend doing the Blue Path, the Cinque Terre’s most popular hiking trail, consisting of four main sections.

Blue Path Sections:

1. Riomaggiore to Manarola (via dell’Amore) – The easiest hike of the four sections, this path runs for about 1.5 km and takes between 20 and 30 minutes. *This path is currently closed.
2. Manarola to Corniglia – Another easy, mostly-flat hike (at least until you reach steep Corniglia), this hike runs for about 3 km and takes about an hour to walk.
3. Corniglia to Vernazza – While the downhill start seems easy at first, there are steep segments as well as switchbacks to reckon with later. This moderate-difficulty hike is about 4 km and takes approximately 90 minutes to complete.
4. Vernazza to Monterosso – The most difficult hike of the four, prepare for steep climbs, numerous staircases, and many narrow pathways. At about 4 km, this hike can take anywhere from 90 minutes to about two hours, depending on your fitness level (and how often you stop to catch your breath and take in the view)!

My husband and I did the most challenging trek from Vernazza to Monterosso; however, we did it in reverse.

The picturesque town harbors are some of the best Cinque Terre Instagram spots you’ll find here.

The most photogenic harbors are located in the towns of:

• Vernazza (pictured above)
• Manarola (pictured left)
• Riomaggiore (pictured right)

You’ll need to arrive early at each of these harbors in order to capture some photos without a crowd (or else get really creative with your compositions).

You may also notice that both Corniglia and Monterosso al Mare are absent from this list. Corniglia is the one town without direct sea access, and as a result, it doesn’t have a harbor area.

Monterosso al Mare, on the other hand, has a large sand beach instead of the characteristic harbor.

While not every town has the iconic harbor, each of the five villages boasts a charming old town. Although Monterosso gets a bad rep for being the “least charming” of the five, I personally love the vibe of the old town.

As for Corniglia, I could go on for days about how it doesn’t receive the respect and admiration it deserves. That said, I’ve already carried on about that in my guide to the best Cinque Terre town, so you can read more on that if you’re interested in my mini rant.

In any case, regardless of which town we’re discussing, each has an old town that’s definitely worth visiting, in my humble opinion! If nothing else, you can give each one a quick stroll, shop for some fun treasures to take back home, and be on your merry way.

Now for the tastiest part of your Cinque Terre adventures – the pesto!

And since I can’t resist sharing a fun fact about Italian food, did you know that pesto originated in the Italian Riviera? It just so happens that the local climate is ideal for basil production, so you’ll reap the delicious reward in this Northern-Italian region!

Take my advice and don’t leave the Cinque Terre without at least one taste!

Due to the unique terrain in the region, the Cinque Terre produces a local wine with a distinct flavor. This sweet white dessert wine is known as Sciacchetrà and its made with the finest grapes grown nearest to the sea.

There are a number of wine tours you can join while you’re in the area, particularly in Monterosso al Mare and Manarola.

While you’re in Manarola, you can’t miss a late afternoon aperitif at Nessun Dorma, one of the trendiest restaurants in town.

I’ve already covered how to secure a seat at this hotspot with their non-traditional reservation system in my Cinque Terre tips, so be sure to check that out before you go.

In the meantime, prepare to be wowed!

If you’re a fan of seafood, you’ll have to give a seafood cone – a.k.a fritto misto – a whirl while you’re here!

Considered a local delicacy, you can find little fish-and-chip-takeaways that sell these throughout the different villages.

As for what’s in the cone itself, you’ll have your pick of calamari, cod, octopus, squid, prawns, and anchovies.

For whatever reason, these treats seem to be most popular and prevalent in Riomaggiore, so I suggest going there first if you’re on the hunt for one.

Recommended Seafood Cone Spots:

• Tutti Frutti (Via Colombo, 161, Riomaggiore)
• Il Pescato Cucinato (Via Colombo, 199, Riomaggiore)

While you may not necessarily associate the Cinque Terre with beaches, Monterosso al Mare will surely change your perspective!

The largest of the five towns, it’s also home to the largest and most famous sand beach in the area, Spiaggia Fegina.

Even if a relaxing beach day isn’t on the agenda, you’ll at least need to come and check out this beauty – and the impressive rock formation jutting out of the water!

For a dose of history, be sure to swing by Doria Castle in Vernazza. As the longest-standing fortification in the entire Cinque Terre, this spot is a fascinating place to witness ruins and a castle, of course!

You can check out the details for visiting in my 3-day Cinque Terre itinerary.

One of my biggest regrets from our Cinque Terre adventures is missing out on the chance to see the five villages from a sea perspective.

That said, don’t be like me and make sure to add this special experience to your list. (And if you can do it at sunset, even better!)

From what I’ve heard, it’s one of the best ways to capture the villages and get the full scope of the Cinque Terre as a whole.

Monterosso al Mare

• Enoteca da Eliseo for wine (Piazza Giacomo Matteotti, 3)
• Miky for Ligurian food with a twist (Via Fegina, 104)
• Ristorante L’Ancora della Tortuga for seafood & pasta (Salita dei Cappuccini, 4)

 Vernazza

• La Torre* (Preteccia, 1)
• Bar Gianni Franzi*  (Piazza Guglielmo Marconi, 1)
• Ristorante Belforte* (Viale Alessandro Guidoni) 

*Seafood restaurant

 Corniglia  

• Ristorante La Posada for Ligurian (Via Stazione, 11)
• Bar Pan e Vin for Italian (Via Fieschi, 123)
• KMO for Italian (Via Fieschi, 151)

Manarola

• Nessun Dorma for appetizer platters, salads & sandwiches (Località Punta Bonfiglio)
• Trattoria dal Billy for seafood (Via A. Rollandi, 122)
• Ristorante Il Porticciolo for seafood & Italian (Via Renato Birolli, 98)
  

Riomaggiore

• Trattoria La Lampara for seafood (Via Malborghetto, 10)
• Rio Bistrot  for Ligurian (Via S. Giacomo, 46)
• Fuori Rotta for Ligurian (Via Telemaco Signorini, 48)

Typically, the accommodations you can expect in the Cinque Terre are self-catering apartments. If you’re not sure which area to stay in, have a look at the best Cinque Terre town for you based on your travel style.

I recommend booking several months in advance since the area is quite popular and the limited number of properties tend to book up quickly.

You can search for available properties here:

Check Out My Cinque Terre Guides Before You Travel:

• Best Cinque Terre Town to Stay in Based on Your Travel Style
• 50 Key Cinque Terre Tips for First-Time Visitors: The Ultimate Guide
• 15 Stunning Cinque Terre Instagram Spots You Can’t Miss
• 3-Day Cinque Terre Itinerary: A Taste of Italy’s 5 Lands

The impressive “Cradle of the Renaissance” as it’s commonly known, Florence is the capital of Italy’s incomparable Tuscany region. The city is a true treasure for history buffs, connoisseurs of culture, the artistically-inclined, and lovers of gourmet Tuscan cuisine.

Florence is home to countless masterpieces, from Michelangelo’s David, to Botticelli’s Birth of Venus, to Brunelleschi’s Dome. While this would be an impressive feat for any city, it’s even more extraordinary considering Florence’s relatively small size, at just under 40 square miles.

Although my husband and I only spent one full day in Florence (during our 2-night stay), I recommend that you dedicate two full days to exploring this romantic and fascinating city.

Although you can see a great deal in a day’s time, having the second day opens you up to the option of doing some fun Florence day trips.

Alternatively, you may just want to take things a bit slower and spread out your city-focused agenda over two days.

While there are no direct trains from the Cinque Terre to Florence, you can catch one of the 20 Trenitalia trains that travel to the city. These trains depart at Monterosso al Mare (Cinque Terre’s northernmost village) and go to Firenze Santa Maria Novella station.

When we left the Cinque Terre for Florence, we went from Vernazza to La Spezia, from La Spezia to Pisa Centrale, and from there to Firenze Santa Maria Novella station.

Another option is to rent a car in La Spezia (if you’re traveling from the Cinque Terre) and drive to Florence. The drive takes just over two hours.

While this is definitely doable, I don’t think it’s necessary to have a car while in Florence, so you’ll really want to consider that factor when you make your decision. Florence is extremely walkable, so you’ll be able to get around to all of the major sites on foot.

However, if you’re interested in doing some day trips from Florence to surrounding Tuscan towns, you may want to arrange to have a car.

If you’re coming to Florence from the Cinque Terre, you obviously won’t need to concern yourself with flying into an airport.

If, however, you decide to begin your two weeks in Italy in Florence, then you can fly into Florence Airport, Peretola (FLR), one of the most popular international airports in Itay. In Italian, the airport will either be referred to as Aeroporto di Firenze-Peretol or the Amerigo Vespucci Airport.

In this case, I suggest arranging an airport transfer in advance to avoid any delays. You can book your transfer here:

Florence is home to some of Italy’s most beautiful squares and each one is remarkably unique.

3 Florence Squares You Can’t Miss:

1. Piazza del Duomo (pictured left) – The city’s most famous square, it features the Florence Cathedral and Brunelleschi’s Dome, Giotto’s Bell Tower, the Opera del Duomo Museum, and more.
2. Piazza della Signoria (pictured right) – More of an outdoor museum than a traditional Italian square, you’ll find fascinating 14th-century sculptures and even a fountain here.
3. Piazza della Repubblica (pictured below) – Considered the city center, this piazza features a classic golden carousel and wonderful restaurants.

While you’re at Piazza del Duomo, take advantage of the opportunity to climb Brunelleschi’s Dome.

Featuring some of the most impressive views of the city, it’s well worth the 463-step climb to the top! Keep in mind that you’ll need to purchase tickets – preferably in advance – in order to make the climb.

Italy’s cities are famous for having some pretty spectacular churches, and Florence is no exception.

You’ll have to fit some church exploration time into your schedule, even if it’s just enough to see one or two. My top recommendations are the Basilica of Santa Maria Novella and Santa Croce.

How would you like to check out some of the best skyline views of Florence?

If I’ve piqued your curiosity, you must pay a visit to Piazzale Michelangelo. While you’ll need to make a noble climb up quite a few steps, the view is worth it, I promise!

If you thought Florence was a concrete jungle without any nature, think again! The city is actually home to a number of beautiful gardens bursting with natural beauty.

Giardino delle Rose is a wonderful free option, located just below Piazzale Michelangelo.

I could probably dedicate an entirely separate article just to the museums of Florence; that’s how many there are!

But for now, I’ll narrow it down to some of the top favorites/must-sees within a 2-day timeframe.

Top Museums in Florence: 

• Galleria dell’Accademia
• Uffizi Gallery
• Museo Archaeologico Nazionale
• Museo Galileo
• Galleria Palatina
• Museo di Palazzo Vecchio
• Leonardo Interactive Museum
• Bargello Palace National Musuem
• Church and Museum of Orsanmichele

Plus, for every museum, there’s at least a dozen tours to accompany it!

Here are some of the best museum tour & ticket options to consider:

If you’re curious to know where I found the best pizza in Florence (and in Italy thus far), you’ll just have to see (and taste) for yourself  at Pizza Napoli 1955.

Besides, who could resist a heart-shaped pizza for two?

If you think Tuscany’s capital is beautiful during the daytime, just wait until you catch a glimpse of Florence at night!

While there are many beautiful places to soak up the spectacular sunset views, one of my favorite places to do it is by the Ponte Vecchio Bridge. The Arno River looks super romantic at dusk when it reflects all of the stunning sunset colors!

You really have to see it for yourself!

• Trattoria Da Ruggero for traditional Tuscan fare (Via Senese, 89 Rosso)
• Trattoria Sergio Gozzi for traditional Tuscan fare (Piazza di San Lorenzo, 8R)
• Trattoria Mario for traditional Tuscan fare (Via Rosina, 2r)
• Il Latini for traditional Tuscan fare (Via dei Palchetti, 6R)
• Parione for seasonal specialties (Via del Parione, 74/76 r)
• Il Santo Bevitore for seasonal specialties (Via Santo Spirito, 64r)
• Il Guscio for traditional Tuscan with a modern twist (Via dell’Orto, 49)
• Borgo San Jacopo for traditional Tuscan with a modern twist (Borgo San Jacopo, 62/R)
• Konnubio for traditional Tuscan with a modern twist (Via dei Conti, 8r)
• Regina Bistecca for steak (Via Ricasoli, 14r)
• Perseus for steak (Viale Don Giovanni Minzoni, 10/R)
• Cestello Ristoclub for seafood (P.za di Cestello)
• L’Angolo del Mare for seafood (Viale Edmondo de Amicis, 1)
• Fishing Lab alle Murate for seafood (Via del Proconsolo, 16r)

While in Florence, I highly recommend booking a hotel in a central location so that you can easily access the city’s best sites.

Personally, my top priority was to be close to the Duomo. You can check out my guide to the most amazing Florence hotels near the Duomo for the ultimate stay in Tuscany’s capital.

Alternatively, you can search for additional Florence properties here:

Check Out My Florence Guides Before You Travel:

• 20 Fantastic Florence Hotels Near the Duomo (with Killer Views)
• 20 Incredible Places to See the Florence Skyline
• 20 Awesome Things to Do in Florence at Night
• One Day in Florence: A Concise Itinerary to Maximize Sightseeing
• 20 Best Day Trips from Florence (Within Two Hours)

The Tuscan countryside is truly unlike any other place I’ve ever been. Just imagine rolling hills as far as the eye can see and a distinct feeling of oneness with nature.

While Florence is obviously an important part of Tuscany and a must-see, I also highly recommend venturing beyond the city limits to spend a few days in the countryside. It’s a completely different experience and a real opportunity to disconnect.

My husband and I decided to base ourselves in the medieval hilltop town of Montepulciano in southern Tuscany and I couldn’t be happier with our decision. This charming Tuscan town is in the Siena province (and just over an hour’s drive from Siena, which is more well-known).

If you’re not sure where to base yourself, check out these awesome Italian towns, many of which are in Tuscany.

We decided to rent a car for the journey from Florence to Montepulciano. We picked up our rental at Hertz Firenze Sud located at Via Giorgio Ambrosoli, 30 in Florence and drove about 90 minutes to Montepulciano.

If you’re traveling to Montepulciano by train from Florence, you’ll need to catch the Firenze S.M.N heading to Chiusi-Chianciano T, a journey of just over one hour.

From there, you’ll need to transfer to a bus at Chiusi Stazione-P.Zza Dante. The bus ride will take nearly 50 minutes and will end at P.Ta Delle Farine Opp.

If you’re beginning your journey in the Tuscan countryside, there are two main airports you can fly into:

1. Florence Airport, Peretola (FLR) (a.k.a Amerigo Vespucci Airport)
2. Galileo Galilei International Airport in Pisa (PSA)

Did you know that Montepulciano is famous for producing some of the best wines in the world?! The area is most popularly known for its red wine, particularly its Vino Nobile di Montepulciano, a medium-bodied red with fruity aromas.

Whether you’re an oenophile, a full-fledged wine connoisseur, or a curious newbie in the wine world, I highly recommend basing yourself here so that you can sample the wonderful wineries of Montepulciano. In addition to a tasting, you’ll also have an opportunity to tour the vineyards and cellars and learn about the history of winemaking in the region.

Here are some wonderful wine tour options in Montepulciano:

If charming European villages are up your alley, you’ll absolutely love wandering around Montepulciano’s old town.

For all of the details on where to go and what to see, you can check out my guide on the best things to do in Montepulciano.

In the meantime, here are some old town highlights:

• Piazza Grande – The beautiful main square dating back to the 14th-century
• Torre del Pulcinella – The town’s iconic clock tower featuring a giant Pulcinella
• Cathedral Saint Mary of the Assumption – Also known as the Montepulciano cathedral, this is the most famous church in town
• Il Corso – The lively main street featuring charming boutiques with souvenirs aplenty
• Museo Cívico – A popular art gallery & museum housed in a historic 14th-century building

You didn’t think I was going to leave out traditional Tuscan pasta on this Italy itinerary, did you?

When in Montepulciano, you must try pici, the delicious regional pasta that I still can’t stop dreaming about.

Although it’s surprisingly simple with a base of just water and flour, don’t let that fool you! This pasta is next level and will probably ruin – err, spoil – you for life!

Montepulciano is undeniably special, but it’s one of many gems you’ll find in Tuscany!

So if you cover your Montepulciano wish-list and want to uncover more of this beautiful region, I highly recommend doing so. 

Here are some other Tuscan towns to put on your radar:

• Arezzo
• Cortona
• Greve in Chianti
• Livorno
• Lucca
• Montalcino
• Monteriggioni
• Pienza
• Pisa
• Pitigliano
• Radda in Chianti
• San Gimignano
• San Quirico d’Orcia
• Siena
• Viareggio
• Vinci
• Volterra

Don’t worry if this is the first you’re hearing of San Quirico d’Orcia – I didn’t know about it until I started planning our Tuscan adventures, myself!

While this town is definitely more under-the-radar compared to some of the others I mentioned in this guide, it’s actually really well-known for a very specific feature.

Since this is Tuscany, cypress trees are obviously involved – but so is a unique statue made of reflective glass that sits in the center of the trees!

Pretty neat, huh?

You can uncover more details about this and the following landmarks below in my guide to the most impressive landscapes of Tuscany.

If you love cypress trees as much as I do, then you’ll fall head-over-heels for one of the most impressive driveways in all of Tuscany – Poggio Covili!

This storybook spot actually leads up to Pasquini Adriano Farm, but unless you’re a guest of the property, make sure not to cross behind the barrier that’s set up here.

No trip to Tuscany would be complete without a visit to Agriturismo Baccoleno. This stunning landscape is truly breathtaking, especially at sunset.

Plus, you can even book a stay here if you feel so inclined! You can check out more details in my Tuscan landscapes post.

Considering Tuscany’s incredible beauty, it should probably come as no surprise that its unique landscapes have been featured in many motion pictures!

If you’re interested in a behind-the-scenes perspective of these natural “sets,” you can actually tour some of the most famous locations!

Looking for a place to unwind after a long day? Well, Tuscany is definitely the destination to do it!

Given its many natural springs, Tuscany is home to numerous spa towns featuring thermal pools. These pools contain mineral-rich waters with various healing properties, serving as relaxation centers for the mind, body, and soul.

So if you could use a little self-care time, book yourself a reservation and get ready to relax in a whole new way!

Why keep your feet planted when you can soar? For an unrivaled perspective of the rolling hills that only drones can typically enjoy, consider a hot air balloon ride!

P.S. If you have the opportunity to do this, please drop me a comment so that I can be super jealous – err, I mean happy for you!

There are a number of wonderful places to stay in the region, but none are quite as special as the romantic wine hotels in Tuscany!

My husband and I stayed at the lovely Borgo Tre Rose – included in the aforementioned wine hotel guide – and it was one of our favorite hotel experiences to date!

If you’re a fan of fabulous wine and picturesque countryside properties, you really can’t go wrong with a stay at any one of the 25 Tuscan gems I’ve included in the guide.

Alternatively, if you’re after a more traditional hotel experience, you can take a look at the other available properties in Tuscany:

Check out my Tuscany guides before you travel:

• 25 Most Romantic Wine Hotels in Tuscany
• 20 Awesome Things to Do in Montepulciano
• 15 Wonderful Wineries in Montepulciano
• Breathtaking Landscapes of Tuscany: An Essential Photo Guide

It’s time to trade the romantic rolling hills for the craggy coastline as we continue this Italian journey to the Amalfi Coast!

This 50-kilometer expanse of coastline has been a UNESCO World Heritage Site since 1977 and runs along the Sorrentine Peninsula in Italy’s Campania region. One of the most sought-after regions for relaxation in the country, the Amalfi Coast may as well be the birthplace of la dolce vita.

While my husband and I decided to spend the final leg of our journey exclusively in Positano, there are actually a total of 13 dreamy towns that line the coast.

The 13 Amalfi Coast towns are: 

1. Amalfi (the capital)
2. Atrani
3. Cetara
4. Conca de’ Marini
5. Furore
6. Maiori
7. Minori
8. Positano
9. Praiano
10. Ravello
11. Scala
12. Tramonti
13. Vietri sul Mare

For three days, I recommend selecting one town as your home base and then hopping around by boat or bus to check out some of the other areas. For instance, the island of Capri can be a great day-trip option if you’re staying in Positano.

Alternatively, if you decide to eliminate one of the other destinations from this itinerary, you could easily spend 5-7 days soaking up all of the beauty of the Amalfi Coast instead.

I’ve actually covered all of the details on how to get to Positano in a previous post, so make sure to check that out if you’re heading there first and/or exclusively. As you’ll soon find, Positano isn’t the easiest destination to reach, but I can promise you that the journey will be worth it!

Essentially, you’ll ultimately need to transit to the Amalfi Coast from either Naples, Sorrento, or Salerno, as it’s not reachable directly by train from the more famous cities. Definitely check out my helpful transportation guide above, as getting here can get pretty confusing!

Hiking is one of the best ways to witness the special beauty that is the Amalfi Coast. The most famous and popular hike here is the Path of the Gods. This clifftop trail begins in a small hamlet known as Bomerano and ends in Nocelle, a teeny-tiny village perched above Positano.

While you can technically start the hike at either end, it’s considered best to begin in Bomerano, at the Piazza Paolo Capass, where the hike starts downhill.

While we didn’t complete the Path of the Gods this time, we did really enjoy hiking Amalfi Coast Drive, which we were able to connect with right from Positano.

You can read more details about how to get here in my guide to the best Positano views.

With 13 different towns that make up the Amalfi Coast, you’ll probably want to uncover a few during your stay! I actually wish that we’d ventured beyond Positano, but it’s definitely an excuse to come back to this amazing region for more.

Here are some boat tours to consider:

Alternatively, if boats aren’t really your speed, you can also travel by SITA bus which travels all throughout the Amalfi Coast.

If traveling on land is more your speed and you’d love the ability to move about freely without the hassle of a car, consider renting a scooter. As I’ve discussed when sharing the best things to do in Positano, I’m personally a bit of a scaredy cat when it comes to scooters.

But hey, perhaps you have a more adventurous streak than I do!

Just be aware that the roads along the coast are tight and windy – and speed limits are often seen as mere suggestions. This is definitely not something to “wing” if you’re not comfortable driving in these sorts of environments.

However, more experienced drivers may enjoy the adrenaline rush and freedom of not adhering to a public transportation schedule.

Or, if you’d like to experiment with a scooter but you’d prefer the experience and security of having a guide, that’s an option, too!

As a coastal destination, the Amalfi Coast offers a range of beaches just waiting to be explored. I’ve actually covered the best beaches in Positano to get you started!

In there, you’ll find not only the best beaches in Positano itself, but in neighboring towns as well.

In case you didn’t know, lemons are kind of a thing along the Amalfi Coast. Like, a really big thing. In fact, Amalfi Coast lemons are in a league of their own. This unique lemon variety is long, tapered, and massive in size!

Given their ubiquity along the coast, lemons are used in practically everything, from candles and soaps to delicious desserts. My personal favorite is the lemon sorbet!

You can snag one of these babies at select gelato shops in town.

Dinner with a view, anyone?

It’s almost harder to find a restaurant without a fabulous view on the Amalfi Coast, so you’ll definitely have your pick! My personal favorite is Il Tridente in Positano.

You can read more about this gem – and several others – in my Positano restaurant guide.

On the Amalfi Coast, you can expect plenty of fabulous hotels with a view. However, if you’re in search of large chain hotels, you won’t find them here. Instead, what you’ll come across are charming, locally-owned, boutique-style properties (which happen to be the best stays, in my opinion). As such, you can often expect personalized service, traditional Italian décor, and killer views, of course!

Plus, since we spent our final three days in Positano, I’ve already broken down the best boutique hotels in Positano for you. Whether you’re looking for an understated 3-star experience (with 5-star views), 5-star luxury, or something in between, you can’t go wrong with any of the fab hotels in there.

Alternatively, if you’re looking to base yourself in one of the other Amalfi Coast towns, you can check out what’s available here:

Check Out My Positano Guides Before You Travel: 

• 20 Dreamy Boutique Hotels in Positano with Amazing Views
• How to Get to Positano: An Essential Guide for a Seamless Journey
• 25 Fun Things to Do in Positano on Your First Visit
• Best Views in Positano (& Exactly Where to Find Them)
• 10 Best Restaurants in Positano with Killer Views
• Best Beaches in Positano & Beyond

While I’ve already covered how to reach each of the different destinations on this itinerary, I want to also provide some insight into the best ways to get around once you’re in each area.

Each transportation method has its pros and cons, as I’ve shared below. The main things to consider are what activities are most important to you and if you’re more willing to sacrifice time or money as you travel around.

Pros: You can enjoy the ultimate freedom of movement without being beholden to a particular schedule.
Cons: Parking can often be challenging to find and costly, particularly in major metropolitan cities like Florence as well as in Positano.

Destinations where I suggest having a car:

• The Italian Riviera (if you’re planning to visit the French Riviera and/or more than one town in Italy)
• Tuscany (unnecessary in Florence, but I highly recommend it in the countryside)

Pros: This can be a cost-effective way to get around and will save you the hassle of finding/paying for parking.
Cons: Traveling on public transportation can eat up more of your travel time, particularly with buses. Italy is also notorious for public transportation delays, so this isn’t a great option if you have to be somewhere at a specific time.

Destinations where I suggest traveling by train:

• Cinque Terre (via the Cinque Terre Express) 

*I personally don’t prefer traveling by bus, as I find that the additional time commitment isn’t worth the savings. However, an exception would be if a train doesn’t travel directly into where I’m going and a train/bus combo is needed.

Pros: Free in every way, you don’t have to pay and you have the ultimate freedom to stop and take in the scenery, take photos, etc.  You never have to worry about parking or holding yourself to a schedule.
Cons: It can get tiring (especially if you’re visiting places with a lot of steps, such as the cliffside destinations). You can only get so far on foot unless you’re in a little town or a small city like Florence.

Destinations where I suggest traveling on foot:

• Sanremo (but only if you’re not visiting other Italian or French Riviera towns)
• Cinque Terre (if you’re planning to hike in conjunction with taking the train)
• Florence (small and conducive to pedestrians)
• Positano

Let’s stay you ultimately don’t have the luxury of spending two weeks in Italy. Not to worry! I’ve laid out what I think would be good alternatives for a 5-day trip, one-week trip, and 10-day trip.

With 5 Days in Italy

With only five days in Italy, you’ll want to focus on just two or three regions, tops. Here are some area combinations I suggest:

Option 1:

• Italian Riviera
• Cinque Terre

Option 2:

• Cinque Terre
• Florence

Option 3:

• Florence
• Tuscany (countryside)

Option 4: (This will be tight)

• Cinque Terre
• Florence
• Tuscany (countryside)

Option 5:

• Tuscany (countryside)
• Amalfi Coast

Option 6:

• Amalfi Coast (exclusively)

With 7 Days in Italy

One week in Italy is a decent amount of time to get a taste of some different areas. I’d say you can tack on one additional region to whichever 5-day option appeals most to you.

With 10 Days in Italy

Ten days is a solid amount of time to work with when planning a trip to Italy. I’d remove one region from the original itinerary as I have it (and perhaps subtract a day in one area) and you should be good to go.

Personally, I’d remove the Amalfi Coast and do that as a separate trip later on.

Whew! That brings us to the end of a fabulous two weeks in Italy. I hope you’ve enjoyed coming along for the virtual ride – and that you’re now inspired to get out there and take on this incredible country yourself!

If you have any questions at all about putting together your 2-week trip to Italy, please don’t hesitate to get in touch via the comments. I’m happy to help turn your dreams of la dolce vita into reality!

Now tell me, have you been to this amazing country before? If so, which spots have you crossed off your list? If not, which locations are calling your name? Let me know in the comments below!