How to Plan the Perfect Honeymoon in Tuscany

A honeymoon in Tuscany: can you picture anything more romantic?

Though we (before our love of traveling Italy on repeat set in) honeymooned in the Bahamas, we have long said that Tuscany is our perfect honeymoon destination.

In Tuscany, romance reigns supreme. From the lighting to the landscape to the activities available, everything in the atmosphere conspires to make a Tuscany honeymoon an utterly unforgettable affair.

Trying to plan the perfect honeymoon in Tuscany? This guide will help!

We’ve intentionally kept this romantic Tuscany guide fairly high-level, as many things about planning a honeymoon in Tuscany overlap with planning a trip to Tuscany in general… but not everything does. For even more detail, we’ll link to many of our 30-ish other Tuscany blog posts and 150-ish Italy blog posts as we go!

Here are some great ideas on where to go, what to do, and how to make sure your honeymoon in Tuscany is as perfect as the wedding day that precedes it.

What to Do on Your Honeymoon in Tuscany

There are countless things to do in Tuscany, from the classic to the offbeat.

Here are some of the most romantic things to do in Tuscany that should definitely make it onto your honeymoon itinerary!

Explore Florence.

As the Cradle of the Renaissance, Florence is home to gorgeous architecture, beautiful art, and some of the best food in the world.

It is, hands down, one of our all-time favorite cities, and it is a romantic gem just waiting to be explored.

Admire views of the city at from Brunelleschi’s Dome or Giotto’s Bell Tower, steal a kiss from your new spouse in the Boboli Gardens, sample delicious gelato, admire iconic artwork like Michelangelo’s David, and get lost hand-in-hand down picturesque streets.

Here’s the exact 2-day Florence itinerary that we recommend, and here are our picks for the best things to do in Florence!

Take a luxurious countryside and wine tour.

There are a million and one options for multi-stop countryside and wine tours in the region, but for a honeymoon in Tuscany, you’ll want only the best.

Pick an all-day tour with a small group (or even just the two of you if you want to splurge!), and settle in for one of the best days of your life as you work your way through vineyard after vineyard.

This incredible day trip offered by one of our favorite tour companies in Italy is a fantastic way to get a (figurative and literal) taste of the Tuscan countryside on a day trip from Florence!

Book your San Gimignano, Siena, and winery day trip from Florence today!

Indulge in incredible Tuscan food.

Tuscany is nothing if not a food destination: indulge in long, slow, romantic meals here, complete with multiple courses and wine!

There are endless dishes to try, but the bistecca alla fiorentina is arguably one of the most honeymoon-friendly dishes in Tuscany: not only is this steak one of Tuscany’s best-known dishes, each steak typically serves two!

If you want to learn more about Tuscan cuisine before diving in, consider taking a food tour together to learn the basics.

For example, we loved this evening food tour of the Oltrarno neighborhood in Florence. The food was delicious, the guide excellent, and we learned quite a bit about Tuscan food!

Want to explore independently? Here are 17 traditional Tuscan foods to sample on your honeymoon!

Book the same Florence food tour we loved today!

Take a cooking class.

Do you and your new spouse love to bond in the kitchen? If so, break out your creativity and learn to cook some Tuscan dishes together on your honeymoon!

Cooking classes in Tuscany tend to come with large amounts of food, plenty of opportunities to work together, and endless glasses of wine: it’s the perfect honeymoon activity!

We loved this cooking class held at a Tuscan farmhouse, but for a true honeymoon experience, you might consider booking a private class for just the two of you, too!

Book the Tuscany cooking class we loved, or your own private culinary adventure, today!

Wander the small streets of Tuscan towns.

The Tuscan countryside is dotted with oodles of adorable towns and villages, most of them dating back to the Middle Ages or beyond.

These spots are perfect for wandering aimlessly together, learning a bit of history, and enjoying a quiet meal down a small side street.

A few of our favorites include but definitely aren’t limited to Montepulciano, Volterra, San Gimignano, Pienza, and Montalcino.

Somehow we haven’t managed to make it to Monteriggioni or Pitigliano yet, though both look incredible and are on our list!

For something extremely tiny, head to Montefioralle.

Tuscan cities like Siena, Arezzo, Lucca, and Pisa are all worthy of a visit too, though they’re much larger than the places mentioned above!

Shop for some gourmet souvenirs.

Don’t let your Tuscany honeymoon end on the plane ride home: many of the best Italian souvenirs available in Tuscany are all edible!

Take (or ship) home bottles of wine, olive oil, or prosecco, along with plenty of cheese (most shops will vacuum pack some impeccable parmigiano-reggiano or pecorino for you), cantucci cookies, limoncello, spices, truffle oil, balsamic vinegar, and more!

Here are our picks for what to buy in Florence (which applies to much of Tuscany overall).

Admire the Tuscan countryside from far above.

There are countless incredible towers to climb in Italy for beautiful views, but for something even more exceptional, consider traveling even higher!

A honeymoon in Tuscany is the perfect time to splurge on a hot air balloon experience you’ll never forget.

Tuscany’s landscape is iconic, and admiring it from above with your beloved is the perfect addition to any Tuscany honeymoon.

Book your hot air balloon ride over the hills of Tuscany today!

Ride a Vespa through the rolling hills together.

Cling to each other on the back of a vintage Vespa and take to the open road: of all the things to do on a Tuscany honeymoon, I’d have to say this is the one I’d be most insistent on squeezing into the itinerary.

We absolutely loved our experience traveling through the countryside on Vespa, and consider it one of the most romantic things we’ve ever done in Tuscany!

And many Vespa tours, the one we loved included, feature a lunch at a beautiful overlook, as well.

Book the Vespa tour we loved in Tuscany today!

Go horseback riding through the Tuscan vineyards.

Hoping to get up close and personal with the vineyards?

Ahorseback ride through the countryside provides the perfect romantic backdrop for any honeymooning couple looking to admire Tuscany’s iconic vineyard from another angle!

Most rides will also include other perks, like a wine tasting, a lunch, or a visit to a beautiful Tuscan town (if you’re starting from Florence, San Gimignano is a popular choice).

Book your horseback ride in Tuscany today!

Where to Stay (& Epic Honeymoon Hotels)

To pull off the perfect honeymoon in Tuscany, you’ll need to find the perfect place to stay.

We strongly recommend spending at least half your time based in Florence (to explore the city as well as to use it as a base to take day trips to surrounding areas), and if you’d like to try another area, moving onto either Siena or to a small town in the countryside for a taste of something different.

Montepulciano and the famous Val d’Orcia are better accessed from the general Siena area, while places like the Chianti region, Lucca, and Pisa are closer to Florence.

If you stay in Florence or Siena, you can generally explore the countryside and smaller towns through a series of bus and/or train trips and organized day trips like this, if you prefer.

However, to have the maximum amount of flexibility in seeing Tuscany’s less-crowded corners, strongly consider renting a car and driving!

We have quite a few tips for pulling that off in our Tuscany road trip guide.

For now, here are a few popular places in Tuscany that make excellent bases for day trips around the region:

Florence

As the capital of Tuscany, the Cradle of the Renaissance, and one of our favorite cities in the world, Florence is our unabashed first choice for a base when looking for where to stay during your honeymoon in Tuscany, and you should definitely spend at least part of your trip here.

In addition to charms like the Ponte Vecchio, the Piazzale Michelangelo, the delicious restaurants, The Uffizi Gallery, and more, Florence is also home to dozens of excellent tour companies, making it a great base for exploring the Tuscan countryside from.

Here’s the exact 2-day Florence itinerary that we recommend, and here are our picks for the best things to do in Florence!

Florence Honeymoon Hotels to Consider

Overwhelmed by where to stay?

Here are a handful of well-reviewed hotels that we think are worthy of a honeymoon:

Antica Dimora Firenze — If you’re willing to compromise a bit on a central location, Antica Dimora Firenze can offer you a picture-perfect bed & breakfast setting at a very competitive price for Florence!

Palazzo Graziani — If you’re looking for a beautiful view of Florence’s skyline, Duomo and all, for your honeymoon in Tuscany, be sure to check out the Palazzo Graziani!

Hotel Lungarno — Nestled right against the Arno River and home to one of the best views of the Ponte Vecchio in Florence (not to mention some of the best views of the rest of Florence from their top deck), Hotel Lungarno is our personal “if we ever really want to splurge” hotel in Florence.

If you’re looking to pamper yourself, you can’t go wrong using Hotel Lungarno as your base for your honeymoon in Florence!

Helvetia & Bristol Firenze — Stunning views, opulent rooms furnished with antiques, and an excellent location just a 5-minute walk from the Duomo: Helvetia & Bristol makes a fantastic choice of where to spend your honeymoon in Tuscany.

Siena

Tuscany’s second-largest city manages to feel a world away from Florence while still also feeling incredibly Tuscan.

This is an excellent place to base yourself if you want to try a second spot in Tuscany but don’t want to leave city life behind after Florence, if you’re a fan of amazing views (Siena has a high concentration of beautiful viewpoints), and if you’re interested in medieval history.

You won’t need more than a couple of days here unless you’re using it as a base to explore parts of the Tuscan countryside, but Siena is definitely an asset to any Tuscany honeymoon itinerary.

Siena Honeymoon Hotels to Consider

Budget

Hotel Santa Caterina — Housed in an 18th-century villa with sweeping views of the Tuscan countryside, Hotel Santa Caterina is a fabulous combination of affordable and romantic!

Hotel Italia — Light, airy, and beautiful, Hotel Italia is the perfect romantic getaway in Siena.

Set about a 20-minute walk from the center, you’ll likely find you won’t mind compromising on location: the walk through Siena to reach its main attractions is half the fun of being there.

Hotel Athena — Located inside Siena’s walls, you’ll have trouble pulling yourselves away from Hotel Athena’s stunning terrace and restaurant to explore Siena!

Countryside Splendor

Not much of a city person? Grab a rental car (more on that below) and take to the Tuscany countryside!

There are countless beautiful, tiny cities and towns–not to mention beautiful hikes and Tuscan spas–surrounded by rolling hills and beautiful vineyards in this incredible region.

If your idea of the perfect Tuscany honeymoon is to find some seclusion, find an epic hotel and cozy up with your beloved in a setting fit for a movie.

We personally think the Val d’Orcia area is perfect for first-timers looking for a countryside honeymoon retreat, but the Chianti region also has many charms!

Countryside Honeymoon Hotels to Consider

When staying in the Tuscan countryside, you’ll likely want to consider an agriturismo (farmstay properties, typically featuring a restaurant, that are wildly popular across Italy), and/or renting a portion of a Tuscan villa.

Often, these categories overlap!

Here are a few beautiful examples:

Agriturismo Merigge Montepulciano — Located just outside of Montepulciano, an on-site spa, delicious restaurant, and gorgeous pool are just a few things you’ll find to love at this classic agriturismo!

This is our idea of the ideal Tuscan honeymoon retreat!

Il Casale del Cotone — What honeymoon in Tuscany would be complete without a stay in a Tuscan farmhouse?

This renovated home-turned-hotel boasts antique furnishings, beautiful panoramic views, gorgeous rooms, and a setting among olive trees nestled in the Tuscan countryside. It’s the ultimate honeymoon escape!

Castello Banfi – Il Borgo — Want the ultimate Tuscany honeymoon experience and have some cash to blow? Try staying in a castle!

Castello Banfi will spoil you with its enchanting rooms, impeccable grounds, and beautifully decorated interiors… not to mention its romantic atmosphere!

More Tuscan Towns to Explore

Beyond Florence and Siena, Tuscany is bursting with beautiful towns waiting to be discovered.

I’ve highlighted just a handful of memorable options below to get you started, but suffice it to say that a lifetime wouldn’t be enough to uncover all of Tuscany’s gems!

Whether you have a whole day or merely an afternoon to spare, consider working these spots into your Tuscany honeymoon itinerary:

Lucca

Lucca is one of our favorite cities in Tuscany, and is famous for its intact town walls, for being the “City of 100 Churches” (more than one complete with a mummy!), its oval-shaped Piazza dell’Anfiteatro, and its unique Torre Guinigi, where you can enjoy a garden in the sky while admiring views of Tuscany.

It’s also an easy day trip by train from Florence, though we also consider it a magical place to spend the night.

Here are the best things to do in Lucca!

Pisa

While we wouldn’t necessarily consider Pisa a must-see on a Tuscan honeymoon (it’s insanely crowded, and while it’s a lovely town, there are plenty to choose from), there’s no doubt it’s among the most popular!

… and yes, the Leaning Tower of Pisa really is exceptionally gorgeous.

Here are our tips for pulling off the perfect day trip to Pisa.

Wondering whether that famous tower is worth the climb? I answer that question here.

Volterra

Dating back to the Etruscans, Volterra sits proudly on top of one of Tuscany’s hills and appears both imposing and regal as you approach it from below.

Volterra’s winding stone streets and setting overlooking the Tuscan countryside will have you two smiling and walking hand-in-hand the moment you arrive.

Volterra is ever-so-slightly off the beaten path in Tuscany, not because it lacks fame but simply because it’s a bit harder to get to. We love it there!

If you’re a millennial woman like me, you may also remember Volterra as a setting in New Moon (though they actually filmed the movie version in Montepulciano, and for the record, neither main piazza boats a fountain!).

Cortona

Set in the eastern part of Tuscany, Cortona is full of sunny piazzas and beautiful viewpoints that show Lake Trasimeno shimmering in the distance.

It makes the perfect stop if you’re looking for a quaint Tuscan village setting with fewer crowds than somewhere like Florence or Siena, while also staying somewhat on the beaten path in Tuscany.

While Cortona is famous thanks to Under the Tuscan Sun, it’s a bit of a pain to get to, which keeps the crowds down.

Consider stopping by on a weekend, when markets are lively!

(And while it’s outside of Tuscany, I can’t help but mention that the Umbrian capital city of Perugia is fairly close to Cortona, and well worth a visit, too).

San Gimignano

With 15 proud towers still standing where once there were hundreds, San Gimignano is as interesting as it is beautiful.

Once a major stop along the road for pilgrims, traders and more en route to Rome, San Gimignano spent centuries as an extremely wealthy city, spawning the habit of noble families building taller and taller towers to compete with each other over time.

For video game fans, you’ll be able to pick out a scene from Assassin’s Creed II in the main square here!

Thanks to its beauty and proximity, many day trips from Florence include stops in San Gimignao, including this incredible one.

Book your visit to San Gimignano today!

Montepulciano

Even if you’ve never done much research into the region before planning a honeymoon in Tuscany, there’s still a good chance you’ve seen the name “Montepulciano” several times before… on a wine bottle.

The outskirts of the city are overflowing with vineyards producing the famous wine, while the center is a maze of cobblestone streets and lovely piazzas just waiting to be explored.

Montepulciano is also close to the legendary, UNESCO-listed Val d’Orcia, and makes an excellent launchpad for visiting places like Pienza and Montalcino.

Here’s our guide to visiting Montepulciano!

Elba

Sadly, a traditional Tuscany honeymoon like the one outlined here likely won’t have time for far-flung Elba, but just to tickle your fancy in case you have time for a particularly long summer honeymoon in Tuscany: Tuscany is home to its very own Mediterranean archipelago, and Elba is its best-known island.

That’s right: without ever leaving the borders of Tuscany you can find yourself on a relaxing on a sailboat, going scuba diving, or eating fresh-caught seafood.

For history lovers, Elba is also the first place that Napoleon was exiled to (he escaped back to France a little under a year later).

You can reach Elba via ferry from the mainland, and there’s no doubt that it makes a thoroughly romantic addition to a Tuscan honeymoon.

Getting Around During Your Tuscany Honeymoon (Should You Rent a Car?)

There are essentially two methods for getting around easily during your honeymoon in Tuscany: relying on a combination trains/buses/organized day trips, or renting a car.

Which choice is right for you is entirely dependent on your travel style.

We’ve enjoyed Tuscany both with and without a car over the years and while there’s no right or wrong answer to this question, there may be a clear right answer for you!

Ultimately, renting a car is not necessary: between trains, buses, and organized day trips, you can enjoy a wonderful and fulfilling trip without getting behind the wheel.

However, if you’re a confident driver who hopes to easily and independently access smaller villages without train stations (or with train stations that are a few kilometers away from town–a common issue with hilltop towns), get off the beaten path, or stay in the countryside, then you’ll want a car for your romantic Tuscany vacation.

If you’re on the fence about whether driving in Tuscany for a few days sounds idyllic or stressful, check out our driving tips in our Tuscany road trip guide, as they’ll give you a good idea of what to expect.

If you do decide to rent a car in Tuscany, we recommend searching through Discover Cars, which will allow you to compare prices and inclusions of multiple companies at the same time and choose the best car for you from there.

Shop rental cars for your trip to Tuscany today!

Think you’d prefer not to get behind the wheel?

Regional trains are simple to use between Tuscan cities (you can browse tickets here, though generally you’ll only need to book ahead to travel on the high-speed trains that leave Tuscany) and usable for some smaller towns… but not all.

If trains aren’t available, buses are generally an option, but aren’t always effficent. In those cases, organized day trips like this are an excellent way to fill in your itinerary (and you won’t have to worry about a designated driver that way, either!).

When to Honeymoon in Tuscany

In our totally biased opinion, we would say that the absolute best time to honeymoon in Tuscany is in the fall (particular in October), followed by the spring (particularly in May).

The truth is, though, that any time of year provides delightful options for your Tuscan honeymoon!

Ultimately, if Tuscany is the honeymoon destination of your dreams, I wouldn’t let any time of year stop you from going.

Here are a few pros and cons of each season:

Spring

Spring brings beautiful flowers to Tuscany, and some potentially amazing weather, though there is a higher risk of rain.

A spring honeymoon in Tuscany will allow you to visit before tourism and the heat pick up dramatically in the summer.

That being said, March is much different than May (whcih is basically high season these days).

Here’s our detailed guide to spring in Tuscany!

Summer

Summer is the high season in Tuscany, so while you will have to deal with larger crowds and probably some hot weather when visiting popular places like Florence, Siena, and Pisa, you’ll get the added benefits of having tons of tours available to you, plenty of access to delicious gelato and prosecco that are perfect to counteract the heat, and lots of sunny days.

If you do decide on a summer honeymooon, I strongly suggest spending some time at the beach!

That can include visiting the Tuscan archipelago, a simple stop in a mainland Tuscan city like Viareggio, a detour to nearby Cinque Terre, or even somewhere further afield.

Though it’s not Tuscany-specific, here are our best tips for planning a summer trip to Italy, which is all about taking the very good with the bad.

Fall

If you ask us, a fall honeymoon in Tuscany is an absolutely perfect option.

Crowds start to clear out as the season marches on (late October has long been the sweet spot in our opinion, though admittedly the crowds seem to thicken every year), but most tours are still operating and the weather can be majestic.

Fall is also the season of the olive harvest, and if you’ve never had fresh olive oil, you’re in for a treat!

The olive harvest tends to happen in November, which gives you an excellent excuse for planning a late-season trip.

Winter

Winter will see the harshest weather in Tuscany, but it also brings the smallest crowds and the lowest prices.

Winters are generally mild, but they can be gray and wet.

However, Tuscan towns are beautiful in the rain, art museums and restaurants can be cozy and romantic in the cold, and bundling up together to wander through streets is definitely an idyllic honeymoon memory!

The Tuscan city of Arezzo is known for having one of the best Christmas markets in Italy, and is a must-see during a December trip!

What to Pack for a Tuscany Honeymoon

Generally speaking, our detailed Italy packing list has everything you ned for a memorable honeymoon!

To get you started, though, here are a few things to consider throwing in your suitcase:

Travel Adapters for Italy — If you’re coming from outside of Europe, you’ll definitely need adapters for your electronics.

From a sheer ease of travel standpoint, this is probably one of the best things to bring to make your arrival easier.

Tracking down adapters in-country as you’re jetlagged and your phone’s battery is draining is never fun.

Cell Phone eSIM or SIM Card — Back in our backpacking days, we spent more than a year traveling without working cell phones, just relying on wifi… and while that was completely fine, we would never go back.

Consider buying an eSIM, purchasing an international plan for your cell phone (most carriers offer them), or, if you have an unlocked phone, you can just buy a local SIM card once you land in Italy.

Personally, these days we simply buy an eSIM from Airalo before each trip, and marvel every time at how much easier using our phones abroad has gotten since we started traveling!

Beautiful Clothes — There’s a very good chance you’ll take more photos of yourselves on this trip than any other, and you’ll want to look lovely for them!

Be sure to bring your favorite outfits along, and possibly some new ones… though don’t forget you’ll likely want to shop in Tuscany, as well.

Pacsafe — We can’t recommend our Pacsafe enough! Honeymoons are all about indulging in fun and forgetting your worries, so make that a bit easier on yourselves and pick up a Pacsafe before you go.

This travel safe is affordable, sturdy, easy to pack, and will help keep your valuables safe in your hotel room (not that you should need to worry much about theft in Italy, but it’s better to be safe than sorry!).

Extra Luggage Space — I’m normally not an enormous advocate of shopping a ton while traveling, but your honeymoon is the perfect exception. After all, you’ll never be able to say “we picked this up on our honeymoon in Tuscany” again!

I recommend buying at least one thing to wear, one thing to go in your shared home together, and one thing to eat (if it’s preservable, like wine, you might even consider saving it for your first anniversary)… and making sure that you can get them home safely.

Florence is also known for its stationery, so if you’d like something memorable to compose your thank you notes on, you might pick up some of that as well!

If you don’t want to deal with large bags, though, almost every souvenir establishment in Tuscany will be happy to help you ship your purchases home (for a fee).

Travel Journal — Take it from someone whose honeymoon is blur 13 years on: you’re going to want to remember this.

Take a few minutes each day to journal about what happened, as those memories are so, so precious.

If you don’t think you’ll commit to writing long prose, I recommend the One Line a Day Journal, which is what I use now. The journal is set up so you can easily look back over a five-year period, and your only commitment is one sentence a day: how easy is that?

I’m almost through with my second volume now and desperately wish I had started it when we first got married!

Reusable Water Bottle — You’re definitely going to want to carry water with you as you explore Tuscany (especially if you’re visiting Italy during the summer).

Cut down on plastic waste and bring a reusable water bottle instead! I love this metal one and have been carrying it for years.

Swiss Army Knife — Bit of a strange item for this list? Perhaps, but when you want to pop open a bottle of wine in your hotel room or cut a piece of parmigiano-reggiano that you picked up at the market, you’ll sure be glad you have it!

Just be sure to place the knife in your checked luggage while traveling: airport security doesn’t tend to take kindly to knives in carry-on luggage.

International Driving Permit — If you’re coming from outside the EU and plan to rent a car in Tuscany, you’ll need to make sure to acquire an International Driving Permit in your home country before coming to Italy.

It is required for all car rentals in Italy, and while the rental company may not ask, it’s not worth the risk of being refused a car once you arrive or getting a fine if you’re pulled over without one.

Play it safe, and if you plan to drive during your trip, add an International Driving Permit to your honeymoon packing list!

Read More About Planning a Trip to Tuscany & Beyond

If you found this Tuscany honeymoon guide helpful, we’d love to continue to be part of your Italy trip planning here on Our Escape Clause!

We are Kate and Jeremy Storm, and if you add up all our trips to Tuscany, we’ve spent several months savoring the region (and over a year each exploring Italy as a whole).

You can browse our ~150 Italy blog posts here, read more about us here, or check out these other Italy travel guides:

• Climbing the Dome vs. Bell Tower in Florence: Which View is Best?
• Driving from Rome to Florence: Where to Stop + Travel Tips
• What to Buy in Florence: 13 Fantastic Souvenirs (+ Florence Shopping Tips)
• Amalfi Coast or Cinque Terre: Which Sublime Italian Coastline is Best?
• How to Spend One Flawless Day in Florence (Itinerary + Offbeat Options)