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How To Plan A Dreamy Honeymoon In Tuscany

One of our first trips together included 5 nights in Tuscany. I remember standing on the edge of a medieval town overlooking the picture-perfect landscape. From its rolling green hills, olive groves, and cypress-lined alleys this place is amazing and is one of the best places in the world for a honeymoon.

We loved seeing its treasure-trove of art masterpieces like The David and famed domes, exploring the cathedrals, and enjoying the small towns. As the birthplace of the Renaissance, offers visitors a journey through history and beauty, uncovering riches at every turn.

And the food! Wine tasting in the countryside, traditional family meals in cucina contadina (farmer’s kitchen), and all the gelato your heart could desire. Renowned as a gourmet destination, Tuscany is sure to please the palette with its emphasis on local, seasonable, and sustainable produce. Dishes vary from town to town, meaning there is always something new and scrumptious to try out on the menu. Romance is at an all-time high in a region that charms and seduces and is sure to leave you wanting more.

Tuscany Honeymoon Destinations

Florence

As the capital of Tuscany, Florence is packed with must-sees and situated perfectly to act as a base for the rest of the region during your honeymoon. This well-preserved city, on the banks of the Arno river, has hardly changed since the time of the Renaissance, retaining much of the magnificent grandeur of the 15th-16th century- including fresco-adorned churches, world-class paintings and sculptures by the likes of Michelangelo and Botticelli, stunning palaces and intricately decorated basilicas.

Its medieval backstreets gave birth to Italy’s iconic fashion industry, with designers such as Guccio Gucci and Salvatore Ferragamo setting up boutiques in the 1920s, and its deeply entrenched eating and drinking culture make Florence a place of glorious indulgence. Be sure to try out the regional specialty Bistecca Alla Florentina- a large T-bone steak weighing between two-eight pounds.

We loved the food in Florence. Make sure you order some pasta with truffles. Also, just enjoy some walking around the town and grab some gelato. We recommend at least 3 days in Florence, but you can stay more if you plan on taking day trips.

TOP THINGS TO DO In Florence For Your Honeymoon

  • Piazzale Michelangelo– Here you will find the best view of the city during sunset. Come early to get a good spot to enjoy it together to watch the sunset and see the sky and city change.
  • Uffizi Gallery Marvel at the world’s greatest collection of Italian Renaissance art bequeathed to the city by the Medici family in 1743. To avoid standing in a queue all day, purchase a fast-track ticket and be sure to visit Sala del Botticelli- a room full of Botticelli masterpieces.
  • Dumo (Santa Maria del Fiore)- Climb Florence’s most iconic landmark, Filippo Brunelleschi’s breath-taking cathedral. The intricately carved pink, white and green marble façade is enough to leave you in wonder, but for unparalleled views over the city, journey on to the exclusive rooftop terraces.
  • Ponte Vecchio- Stroll the city’s oldest and most well-known bridge over the Arno river. The Ponte Vecchio has housed various businesses since the 13th century, but it is the goldsmiths and jewelers that make their name here.
  • Pitti Palace- The Medici family’s primary residence is a must-see for its enormity, numerous museums, and enchanting Boboli gardens.

Florence Honeymoon Accommodations

B&B San Remigio

Located right in the historic center, this charming B&B is just a stone’s throw away from all key Firenze attractions, restaurants, and bars. The accommodation’s six rooms are spacious yet comfy and are equipped with air conditioning, free Wi-Fi, an in-room safe, kettle, and tv. The hosts are known for their attentive, personal service- they are readily available to recommend classic Tuscan trattorias, wineries, and unmissable events. For spectacular views of the San Remigio church, opt to have your typical Italian breakfast while lounging on the B&B’s terrace. Affordable yet chic, B&B San Remigio is a great choice for those wanting to be right at the center of one of the most beautiful cities in the world.

Hotel Calimala

Another gem of the historic center is the dazzling 4-star boutique Hotel Calimala. Where 16th century architecture meets modern design, Hotel Calimala is housed in the remarkable Palazzo degli Angeli- dubbed the home of intellectuals. Perhaps its most outstanding feature is the Angel Roofbar and Dining, where panoramic dining takes place under the starry Florence sky, set against the sounds of live music. The 5th, 6th, and 7th floors of the hotel are comprised of a rooftop restaurant, two indoor and outdoor bars, a floral garden patio, and a plunge pool. For an extra special stay, request a balcony room and make use of the various wellness treatments on offer.

Hotel Lungarno

Boasting 65 luxury rooms and suites with astounding views over the Arno River, Hotel Lungarno is set out to be memorable. This 5-star hotel is decorated with more than 450 works of exquisite art, including pieces from Picasso, Bueno, and Cocteau. You won’t have to go far to taste some of Florence’s famed cuisine. Chef Claudio Mengoni has refined and elevated the classic flavors of the Tuscan region at the Michelin starred restaurant Borgo San Jacopo, located right in the hotel.

Sienna

Siena’s strong local traditions make it an essential stop on any Tuscany honeymoon itinerary. With a history dating back to the Etruscan era, Siena remains rich in medieval monuments, spectacular palaces, and churches, and is home to an extensive and extraordinary art collection.

It is here that Italy’s riveting Palio takes place twice a year (2nd July and 16th August). Piazza del Campo is transformed into one big sand track for the famed horse race between the city’s 12 districts. And if the buzz and excitement of the Palio are not enough, be certain to visit the largest market in Tuscany, held every Wednesday at La Lizza, to explore the wealth of souvenirs, clothes, and food goods on offer.

Sienna Honeymoon Activities

  • Piazza del Campo- Siena’s social center, now a hub of delightful coffee shops and some of the best Aperitivo (pre-dinner drinks) spots in the area, is divided into 9 sections as a symbol of the Consiglio dei Nove (Council of Nine) who ruled the city in the mid-12th century.
  • Duomo (Cathedral of Santa Maria Assunta)– The work of countless accomplished medieval and Renaissance artists and architects, Santa Maria Cathedral is awe-inspiring. It took 40 artists over 200 years to complete the intricate flooring alone, which consists of 56 panels showcasing various historical and biblical scenes.
  • Torre del Mangia- At 87m high, the Torre del Mangia is one of Italy’s tallest secular towers that we really enjoyed climbing together. Built to be the exact height of Siena’s cathedral, an indication of the Church’s and State’s equal power.
  • La Vecchia Latteria- Treat yourself to a scoop or two of local’s favorite gelato (or frozen yogurt). Choose between velvety, rich flavors, and refreshing fruity ones.

SIENNA HONEYMOON Accommodations

Casacenti Centi Stefano

An authentic stay at the heart of it all, Casacenti Centi Stefano is situated a mere 150m from the magnificent Duomo and 300m from central Piazza del Campo. All major historical attractions are just minutes away! Its four rooms are decorated in a classic-style with artworks by the talented member of the Centi family, Fabio Centi. Breakfast, air conditioning, Wi-Fi, and an exceptionally large private bathroom are all included.

Residenza d’Epoca Palazzo Borghesi

A dazzling boutique hotel situated within Siena’s historic center, notably steps from renowned artisanal shops, jewelers, and antique dealers. Residenza d’Epoca Palazzo Borghesi boasts six rooms, each distinctively designed, and an underground wine cellar where bottles of vintage Brunello Biondi-Santi are preserved and can be tasted.

SAN GIMIGNANO

It may be a small town, but this was one of our favorite spots. Step back in time and experience the fascinating medieval walled town of San Gimignano. Its 14 towers rise to the skies, a reminder of the town’s past prominent families who saw it fit to flaunt their wealth and dominance by building a tower taller than that of their neighbors (there were originally 72). Sample locally produced white wine and saffron, and roam the idyllic rural surroundings of this UNESCO World Heritage Site.

San Gimignano is a day trip for most people. Because of that the town is crowded during the day until the tour buses leave. Stay for 2 nights instead to really enjoy the city when the crowds fade and you can have a relaxing meal at one of the delicious restaurants.

San Gimignano Honeymoon Activities

  • Horseback Riding – Go for a romantic ride through the rolling Tuscan hills through Vineyards and olive trees to get a true feel for the area.
  • Collegiata- San Gimignano’s Romanesque cathedral features captivating frescoes such as those within Saint Fina Chapel, which featured in the 1999 film ‘Tea with Mussolini’.
  • Palazzo Comunale– Hike the 218 steps of the 54m Torre Grossa (San Gimignano’s tallest medieval tower) for stunning views of the town and surrounding countryside.
  • Galleria Continua– Surprising as it is, this medieval townhouse one of Europe’s best commercial art galleries. Hop across four venues, a tower, a vaulted cellar, an old cinema, and an apartment, and marvel at impressive contemporary art by big-name artists.
  • La Mandragola-  Dine under twinkling lights in The Mandrake’s enchanting courtyard. Sample handmade pasta dishes made with extra virgin oil from local farms and truffles from nearby woods.

San Gimignano Honeymoon Accommodations

Guardastelle

Choose between Bed and Breakfast or self-catering at this charming farm estate overlooking endless stretches of olive groves and vineyards. Guardastelle’s blooming garden and pool area marks the perfect spot for recuperation and appreciation of the blissful, beautiful environs Tuscany is famous for. Taste Guardastelle wine or learn the secrets of traditional family recipes at a Tuscan cookery class.

Casanova di Pescille:

Scenic beauty surrounds this 19th century stone farmhouse nestled in a natural reserve. Expect roaming pheasants, hares, partridges, and flying glow-worms in the summer months. Casanova di Pescille comprises eight rooms (Bed and Breakfast) and one apartment, a shop selling fresh farm products and goodies of the San Gimignano region, and a traditional family-run restaurant. You can also book onto a saffron tour and experience making some of those delicious traditional recipes at a cookery class.

LUCCA

Characterized by the historic, high walls that surround it, Lucca is a trace of the ancient, military city that was before. Dubbed ‘the city of 100 churches’, Lucca is teeming with numerous treasures from the Renaissance and Roman period, including piazzas, galleries, and gardens. Its imposing walls have since modernized, becoming a picturesque pathway for pedestrians and cyclists alike. It’s a destination easily explored by foot and one that retains a tranquil atmosphere compared to the surrounding towns and cities of Tuscany.   

LUCCA Honeymoon Activities

  • Church of San Michele in Foro- Admire three art masterpieces- Madonna and Child by Andrea della Robbia, Pala Magrini by Filippino Lippi, and The Virgin by Rafaello di Montelupo, within Lucca’s towering basilica.
  • Torre Guingi-  Climb 230 steps to discover the legend surrounding the Guinigi family tower.
  • City Walls- Four kilometers of scenic pathways overlooking Lucca’s entirety provide a unique view, especially given that most Tuscan cities had their walls destroyed following modernization. 
  • Buccellato Taddeucci Pastry Shop- Opened in 1881 by Jacopo Taddeucci, this delightful pastry shop is now run by his family’s 5th generation. Authentic filoni (loaves) and ciambelle (rings) of Buccellato Lucchese are a must-try. 

Lucca Honeymoon Accommodations

BB La Butterfly Relais

This 14th-century palazzo is situated in Lucca’s center, just 400 yards from San Michele Church. Laura, the B&B’s host, is known for her incredible attention to detail- she caters every stay to the individual, ensuring your time in Lucca is more than special. Not to mention she is a wonderful pastry chef. Romantic brunches can be arranged on request- fuel up for the day on homemade pastries, jams, jellies and, eggs any way you like them.

L’antica Bifore

As part of the 14th-century Torre del Travaglio (one of three medieval towers in Lucca), guest house L’antica Bifore offers a rare and memorable lodging experience. Its four spacious suites vary in architectural design and are adorned with marvelous frescoes and antique furniture. The rooms arched stained-glass windows (Bifore in Italian) look out onto Lucca’s main street- Via Fillungo.

Pisa

Home of the world-famous Leaning Tower, Pisa is never short of tourists and makes for a good day trip during your honeymoon. If you’ve come for this architectural project gone south, you should stay for the incredibly preserved Gothic Churches, Renaissance piazzas, Romanesque structures, and vibrant local life brought on by the city’s elite university.

Pisa Honeymoon Activities

  • Leaning Tower (Torre Pendente)- Stereotypical tourist picture out the way, make your way up Torre Pendente’s 251 marble steps for astounding views of the city, encircling mountains, and the Arno river.
  • Duomo- A picture of Roman-Pisan gothic architecture, Santa Maria dell’Assunta is both striking and beautiful.
  • Battistero- With one dome stacked on another and topped off by John the Baptist in bronze, Pisa’s unusual baptistry is a rather unmissable site.
  • Gelateria de’Coltelli- A treat for the senses, this gelateria is renowned for its delightful zesty flavors made with organic, artisanal, and 100% natural ingredients.

VOLTERRA

Nestled among the Tuscan hills, this famous ancient town once wore a different name- Velathri, and made up one of the 12 main towns of the Etruscan confederation. Best-known for its artisanal heritage, Volterra marks the perfect place for souvenir hunting. Alabaster carving is a common talent amongst locals, so you won’t have to look far for one-of-a-kind handicraft pieces, reminiscent of a time well spent touring the astonishing region of Tuscany.

Volterra Honeymoon Activities

  • Museo Etrusco Guarnacci- As one of Europe’s oldest public museums, Museo Etrusco Guarnacci has an incredibly vast collection to unpack. The Etruscan artifacts were all found locally, including the 600 funerary urns.
  • Gloria Giannelli- The award-winning Gloria Giannelli is one of only four female alabaster carvers in Volterra. Her work is highly intricate and rich in fretwork detail.
  • L’Incontro- Always crowded with locals sipping hot coffee or enjoying an Aperitivo or two, this bar is a top spot for some delicious pastries or a quick lunch.
  • Museo Diocesano D’Arte Sacra Volterra- Admire sacred art housed in the still functioning Church of Sant-Agostino.

Best Time of Year For A Honeymoon in Tuscany

Between April-October, when the weather is at its warmest, Florence transforms into an open-air museum. Restaurant dining spills out onto the streets, and music and art festivals take place from morning to night. July and August do see temperatures rise to the high 80s and 90s, but nevertheless, as a city best explored on foot, these peak months are optimal for tourists.

Getting Around Tuscany

The major cities and towns of Tuscany are conveniently connected by train, and the main station in each town is generally located in its center. Train prices are affordable and connections high-speed. Florence’s Santa Maria Novella Station is regarded as a gateway into Tuscany with two lines to the West (Livorno via Pisa and Empoli and Viareggio via Prato, Pistoia, and Lucca) and an indirect line to Siena through Empoli. To access smaller towns near the main ones, you will need to take a short bus ride or, alternatively, walk.

In order to explore Tuscany’s hill towns, vineyards, and winding back roads, you will need to rent a car. Ensure you purchase car insurance and drive carefully- Italians are known for their aggressive driving. As a whole, roads are straight forward with most state and provincial roads with only a single lane in each direction.  We rented a car in Florence and used it to drive to the other small towns. Keep in mind you need to make sure your accommodations have parking and know that parking can be tricky near city centers.

Another way to get around is to mix in a few organized day trips with tour groups.

OTHER ITALY CITIES TO ADD TO YOUR HONEYMOON:

CINQUE TERRE

A UNESCO World Heritage Site since 1997, Cinque Terre offers some of the most dramatic coastal scenery found across the world. The Cinque Terre’s idyllic landscapes are made up of five fishing villages, vineyards, pastel-colored homes, and the Mediterranean Sea. Just an hour away from Lucca, Cinque Terre is so close and a must-see. If you are in Tuscany, make the trip over to Cinque Terre for a beautiful coastal retreat.

BOLONGA

A short distance from Tuscany lies another wonder, capital of the northern Emilia Romagna region: Bologna. It’s a city of many names, each one pertaining to a unique quality Bologna holds. La Dotta (the learned) a reference to the world’s oldest university and the educated that make a home of the city, La Rossa (the red) for its gorgeous, terracotta-colored buildings, and La Grassa (the fat) for its title as Italy’s gastronomic capital.

ROME

Once caput mundi (capital of the world), Rome comprises layers and layers of history going back nearly 3,000 years. Discover the reason why the entire city is deemed a UNESCO World Heritage Site by touring the famed sites such as the Colosseum, Pantheon, Palatine Hill, as well as the numerous piazzas, Renaissance and Baroque churches and art museums. Don’t forget to visit the smallest sovereign state on the planet- Vatican City, the centre of the Roman Catholic Church.

MILAN

With the highest Michelin stars in the country, the remarkable Last Supper mural by Leonardo da Vinci, the most famous shopping district in the world, and a grand Gothic Cathedral that took 600 years to complete, Milan is not to be missed.

LAKE COMO

Welcoming flocks and flocks of tourists in the high summer months, Lake Como’s serene surroundings are nothing short of sensational. Italy’s deepest lake is surrounded by mountains, charming villages, stunning villas, tranquil gardens, and lakeshore restaurants. Water taxis and ferries whizz across the lake, taking passengers to the towns of Bellagio, Varenna and, of course, the city of Como.

VENICE

A fairy-tale city built on a lagoon and famed for its Grand Canal; Venice is small in size but packed full of treasures. And what could be more romantic than touring the waters around the 100+ small islands in a gondola, sipping on Veneto’s signature prosecco, and indulging in seafood and cicheti (tapas) made with products unique to the area?

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