Cypress trees line on the sides of a road in the Val d'Orcia in Tuscany, Italy.

9 Most Romantic Places in Tuscany

Are you heading to Tuscany on your honeymoon?

Perhaps you’ve just started planning a romantic vacation to Tuscany with your partner?

Or maybe you’re looking for ideas for a romantic Valentine’s Day getaway to Italy?

I’m based in Tuscany and have been helping others visit the area since 2004.  Here’s some romantic inspiration for you – whatever the purpose of your trip is.  I know you’ll find the perfect Tuscan destinations and activities for your viaggio (trip) with your amore (love)!

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Chianti Villages

Vespa next to a wall on a small lane in San Donato in Poggio in Chianti, Italy.
Small lane in San Donato in Poggio

The territory of Chianti has all the ingredients for romance – gorgeous small roads that wind through forests and vineyards, charming hilltop villages, excellent wines, castles, and quality restaurants.  Throw in a spa or two and amazing views and you won’t want to leave!

Some of the most romantic villages in Chianti include:

  • Castellina in Chianti – I’m partial to Castellina because my husband and I stopped here on one of our first dates (at the Gelateria di Castellina); excellent views; go for a passeggiata (stroll); get a gelato
  • Gaiole in Chianti – quiet village close to the hamlet of Vertine, Castello di Meleto (wine tasting!), and Castello di Spaltenna (Michelin-star dining)
  • Panzano in Chianti – village with views and the famous butcher, Dario Cecchini
  • Greve in Chianti – one of the area’s best main piazzas; visit the Saturday morning market; have aperitivo on the square
  • Radda in Chianti – tiny hilltop village with an excellent enoteca; romantic setting for a stroll through town or dinner with a view
  • San Donato in Poggio – outdoor summer dining at its best
  • Volpaia – hamlet with a unique wine tour and tasting
  • Montefioralle – a gem nestled in the hills above Greve; easy to explore quickly or linger at a café or restaurant; nice as part of a loop hike
  • Monticchiello – a quiet village set in the countryside between Pienza and Montepulciano; plenty of dining options with a view
  • San Casciano in Val di Pesa – lively, functioning Tuscan village with a beautiful center that’s easy to reach from Florence by bus; perfect for a stroll and aperitivo or dinner

Don’t Miss:

  • Being active – go for a walk, hike, or bike ride in the Chianti hills
  • Dining outdoors in the summer or early autumn
  • Sampling Chianti Classico wines, especially while watching the grapes being harvested
  • Exploring the area’s castles (we love Castello di Brolio)
  • Picnicking in a vineyard or olive grove

Romantic Restaurant:

  • La Bottega del 30 – Michelin star dining in the hamlet of Villa a Sesta; reserve an outdoor table with countryside views; incredibly romantic

Romantic Hotels:

  • Borgo Scopeto – a ‘neighborhood’ nestled in the vineyards above Siena; setting for the romantic film, ‘Letters to Juliet’
  • Borgo San Felice – another ‘neighborhood’ surrounded by vineyards, Borgo San Felice makes a great base for exploring Chianti and its castles and wineries

Val d’Orcia

Main piazza in Bagno Vignoni in the Val d'Orcia of Tuscany, Italy.  The piazza is a thermal spring.
Bagno Vignoni

A UNESCO UNESCO World-Heritage site, the Val d’Orcia (Orcia Valley) is located in southern Tuscany and has a more open landscape than its northern counterpart.  Still famous for its wines (thanks mostly to Montalcino and Montepulciano), the valley boasts gorgeous hilltop towns, simple Tuscan cuisine, and photogenic rolling hills.

Don’t Miss:

  • Soaking in hot springs in Bagno Vignoni
  • Sampling pecorino (sheep’s milk) cheese in Pienza
  • Finding the ‘streets of love:’ via dell’Amore (of love), via del bacio (of the kiss), via della fortuna (of fortune) in Pienza
  • Photographing the Vitaleta chapel, cypress-lined roads, and small villages
  • Trying Brunello di Montalcino and Vino Nobile di Montepulciano wines
  • Walking through the medieval streets of Montepulciano up to Piazza Grande
  • Having aperitivo and seeing ‘real life’ in charming San Quirico d’Orcia
  • Cycling or hiking in the area

Romantic Restaurant:

  • Lupaia (Località Lupaia, 74, Torrita di Siena) – Classic Tuscan cuisine with gorgeous views

Romantic Hotels:

  • Agriturismo Il Rigo – quiet agriturismo (traditionally, working farm accommodation) in the Orcia Valley, with organic food and views of Pienza
  • ADLER Spa Resort Thermae – Luxury spa hotel just outside of Bagno Vignoni

Read more about Visiting the Val d’Orcia

Lucca

Piazza dell'Anfiteatro in Lucca, Italy.
Piazza dell’Anfiteatro

Lucca has something for everyone, and romance-seekers will appreciate its quiet piazzas, ‘real’ atmosphere, outdoor restaurants, and pleasant views from the city’s walls.  It’s a nice base for visiting Tuscany, as you can reach nearby beaches and other Tuscan cities by train or car.

Don’t Miss:

  • Riding bikes or walking on the city’s walls
  • Having aperitivo in Piazza dell’Anfiteatro
  • Making the climb to the top of the unique, tree-topped Torre Guinigi
  • Attending a concert at Lucca Summer Festival

Romantic Restaurant:

  • Ristorante Il Giglio (Piazza del Giglio, 2) – creative, modern, Michelin-star cuisine in an elegant palazzo; time your evening to attend a performance at the neighboring Teatro del Giglio

Romantic Hotel:

  • Grand Universe Lucca – prime location in Lucca on Piazza del Giglio / Piazza Napoleone; simple but interesting decor

Gorgeous beaches, turquoise water, and fantastic views.  And it’s low-key and relaxed too!  If you’re looking for a no-fuss romantic beach vacation, hop on the ferry to Isola d’Elba. 

Elba Island

Beach on Isola d'Elba (Elba Island) on the Tuscan Archipelago in Italy.

Napolean and exile probably don’t bring romance to mind, but the largest island in the Tuscan archipelago is full of sandy and rocky beaches, turquoise waters, and a relaxed, easy-going vibe.

Don’t Miss:

  • Relaxing at the beach – of course
  • Trying watersports (diving, snorkeling, SUPing, kayaking)
  • Hiking up Monte Capanne (or enjoying the views from the cable car)

Romantic Restaurant:

  • Pepenero (via dell’Amore, 48) – located on the street ‘of love,’ creative cooking

Romantic Hotel:

  • Hotel Ilio – casual boutique hotel close to the beach

Bolgheri

View of Bolgheri, Tuscany from above.

Bolgheri is a small hamlet close to the Tuscan coast, and it’s often overlooked for its more fancy neighbors in Florence, Chianti, and the Val d’Orcia.  If you’re wine lovers, you won’t want to pass by Bolgheri, which packs a mighty punch for its size.

Don’t Miss:

  • Driving in the area and exploring the Tuscan countryside
  • Having a romantic dinner for two in the tiny hamlet
  • Photographing one of Tuscany’s most iconic cypress-lined roads
  • Explore some of the best beaches in the area
  • Sampling Super Tuscan wines from estates like Tenuta San Guido, Ornellaia, and Guado al Tasso

Romantic Restaurant:

  • Osteria Magona (Strada Provinciale Bolgherese, 16b, Loc. Vallone dei Messi, 199) – memorable fine Tuscan dining without the fuss; sit outdoors

Romantic Hotel:

  • Relais Sant’Elena (Bibbona) – elegant, small hotel with beautiful outdoor areas (including the swimming pool); perfect for a romantic getaway

Cortona

Cortona at sunset.  Southern Tuscany, Italy.
Cortona at sunset

Popular, for a reason.  This small hilltop town in Southern Tuscany is loved by artists and those looking for a spectacular view, Cortona began to see an influx of visitors after Frances Mayes’ ‘Under the Tuscan Sun’ (followed by the movie starring Diane Lane).  But don’t fret, the hilltop town is still charming, full of art and clothing boutiques, and delicious restaurants. 

Don’t Miss:

  • Perfecting your passeggiata on the main drag,
  • August’s Tuscan Sun Festival, an international cultural event
  • Sharing a bistecca fiorentina, made from the beef of the namesake valley’s chianina cows
  • Sitting on the steps of the town hall and watching life pass by in Piazza della Repubblica
  • Taking in the stunning view of the Valdichiana (Chiana Valley) from Piazza Garibaldi

Romantic Restaurant:

  • Osteria del Teatro (via Maffei, 2) – typical Tuscan fare in a cozy setting

Romantic Hotels:

  • Il Falconiere – Relais & Chateaux hotel with a Michelin-star restaurant, impeccable service, and unforgettable Tuscan views; a quick taxi ride from Cortona
  • Villa Marsili – lovely terrace breakfast and conveniently located a short walk from the town center

San Miniato

Inside Ristorante Maggese in San Miniato, Italy.  You can see people working in the bar area and at the register.
Ristorante Maggese

A foodie’s delight, San Miniato isn’t as ‘noticed’ as her neighbors, but she doesn’t really care.  She’s got restaurants, bars, and cafes galore.  Head to San Miniato to dine well with Italians, stroll the tiny lanes of town, and sample some tartufi (truffles).

Don’t Miss:

  • Bar-hopping to sample all of the hip bars and aperitivo spots
  • Getting truffled-out at the yearly autumn white truffle festival

Romantic Restaurant:

  • Ristorante Maggese (via IV Novembre, 29) – my husband ‘heed and hawed’ about this vegetarian restaurant for months – I’d eat here weekly if they weren’t so booked; incredible food in a tiny restaurant; reserve a table and enjoy the tasting menu

Romantic Hotel:

  • Villa Petriolo (via di Petriolo, 7) – luxurious countryside setting near Cerreto Guidi; you won’t want to leave the pool; quick taxi ride to San Miniato

Florence

View of the Ponte Vecchio in Florence Italy on a cloudy day

Don’t Miss:

  • Having a walk through one of Florence’s beautiful gardens (especially the Rose Garden, Iris Garden, or Boboli Gardens). Read more about Boboli Gardens and the Best Gardens in Florence.
  • Enjoying a rooftop aperitivo – salute!
  • Walking up to Piazzale Michelangelo (or even further, up to Monte San Miniato) for a spectacular sunset view of Florence
  • Buying each other products from the Santa Maria Novella Farmacia and Profumeria
  • Getting gelato in its birthplace

Romantic Restaurants:

  • Borgo San Jacopo (Borgo San Jacopo, 62/r) – fine dining on the Arno River, with unforgettable views of the Ponte Vecchio
  • Enoteca Pinchiorri (via Ghibellina, 87) – one of Italy’s prime dining experiences, with a wine list to match

Romantic Hotels:

  • Ad Astra (via del Campuccio, 53) – quiet, stylish hotel overlooking the private Torrigiani Garden; book a garden room
  • Four Seasons Florence (Borgo Pinti, 99) – luxury stay in a historic building and garden complex; amazing Sunday brunch; divine spa

Siena

View looking down on Siena's Piazza del Campo from the top of the Torre del Mangia.

Siena is one of the most romantic small cities in Italy. It’s got a lively main piazza (Piazza del Campo), but there are plenty of small lanes, tiny restaurants, and beautiful viewpoints. This is a place to walk hand-in-hand, feed each other sweet treats, and spend an entire afternoon at an outdoor cafe.

Don’t Miss:

  • The Palio, a biannual bareback horse race held in the incredible Piazza del Campo
  • Finding each other’s favorite contrada (neighborhood)
  • Ricciarelli cookies
  • Climbing to the top of the Torre del Mangia for incredible views of the city
  • Having an aperitivo on the Piazza del Campo

Romantic Restaurant:

  • Osteria La Sosta di Violante (via Pantaneto, 115) – simple, classic Tuscan dishes away from the crowds; reserve an outdoor table

Romantic Hotels:

Tips for Planning a Romantic Visit to Tuscany

Green, grassy hillside in the Val d'Orcia in Southern Tuscany, Italy.  It's a sunny day with puffy white clouds.
No, it’s not a Microsoft screensaver – it’s the Val d’Orcia on a spring day!
  • Rent a car – With your own two wheels, you’ll see so much more, and you’ll be able to stop and take pictures with sunflowers or have a picnic in a vineyard. I recommend using a search consolidator like Discover Cars (it’s the one I use when I rent a car in Italy). Read more about Renting a Car in Tuscany.
  • Book restaurants in advance – If you have a special restaurant in mind, be sure to make a reservation.  This is especially important for dinner (usually only one seating) and for Michelin-starred restaurants.
  • Leave extra space in your itinerary – You’ll want time to relax and enjoy the slow Italian life.  Remember, rushing does not equal romance.
  • Participate in the passeggiata – Stroll hand-in-hand through town in the evening before or after dinner.
  • Plan a special sunset – It could be at a bar for aperitivo, at a special lookout point (like Piazzale Michelangelo in Florence), or from a chosen spot in the Tuscan countryside.
  • If possible, visit outside of busy seasons – For example, Tuscan beaches are beyond crowded in August, and Florence is especially busy from May through September.  If you must visit your chosen destination during its high season, try to venture out in the early morning or late in the evening – you’ll see the place in a new light (figuratively and literally).

Romantic Things to Do in Tuscany

Grapes on the vine in Tuscany, Italy are ready to be harvested.
  • Wine Tasting
  • Hot-Air Balloon Ride
  • Cooking Class
  • Rooftop Aperitivo
  • Bike or Vespa Ride
  • Soak in Hot Springs
  • See a Concert
  • Truffle Hunting
  • Beach Time
  • Fine-Dining
  • Hiking in the Vineyards
  • Road Trip through Tuscany

Romantic Tuscany FAQ

Is the Cinque Terre a romantic place to visit in Tuscany?

The Cinque Terre are five gorgeous and romantic villages in the region of Liguria (adjacent to Tuscany).  You could easily visit them on the same trip.

Is San Gimignano a romantic destination in Tuscany?

While San Gimignano can be incredible romantic (especially in the evening), it’s a tough city to plan a romantic trip to because it’s so popular and crowded.  If you’re able to visit in the off-season (winter), you’ll find a much more romantic atmosphere. 

Is climbing the Leaning Tower of Pisa a romantic date idea?

You’ll get beautiful views of the city of Pisa and the Piazza dei Miracoli, but keep in mind you’ll be waiting in line and walking up and down the tower’s steps with other visitors.  Be sure to visit other parts of the Piazza and the city of Pisa

Is the grape harvest romantic?

Honestly, the grape harvest is hard work! But, being in the area for the grape harvest could be romantic for you and your partner – go on a road trip, visit wineries during this exciting time of year, have a picnic in the vineyards, or take photos in the colorful vines.