Planning Your Honeymoon in Tuscany: Itinerary Ideas & Romantic Experiences

Planning Your Tuscan Honeymoon

Less can truly be more when it comes to planning your honeymoon in Tuscany, where a degree of spontaneity can be a blessing. This is one of Italy’s biggest regions, so it’s best to focus your attention on one specific part of it rather than trying to do it all.

Consider this 14-day Explore Tuscany tour. You'll start in Florence to see Da Vinci's 'The Annunciation' and other famous Renaissance works in the Uffizi Gallery. Look for treasures in the San Lorenzo market, browse shops on the medieval Ponte Vecchio, and explore history in the medieval cities of Siena and Lucca. 

When to Go

Tuscany wears every season well. Spring is perfect for long rambles and bike rides, when hillsides are combed with wildflowers, and in summer the cities leap to life with music and folk festivals. Fall brings slightly cooler climes, new wine in the vineyards, colorful foliage in the woodlands, and the chance to sample rustic Tuscan home cooking prepared with chestnuts, game, and truffles.  

You'll want to avoid the peak summer season (July to August) for fewer crowds and more affordable room rates. See more about when to visit in our Tuscany Monthly Guides. 

Where to Stay

Florence is the entry point for most travelers⁠—and it’s an enticingly romantic one at that—but this need not be the sum of your vacation. There’s medieval magic to be had in Siena, Lucca, and Pisa, too. Or you could opt to stay at a gloriously rustic agriturismo (farmstay) embedded deep in the vine-streaked hills of Chianti, at a sea-facing boutique hotel on the chic yet unspoiled Maremma Coast, or in an off-the-radar hill town for total post-wedding peace and quiet. 

For unique lodging ideas, see Beyond Hotels: Unique Places to Stay in Italy.

Tuscany's Romantic Experiences 

Swoon-Worthy Cities

Tuscany's cities fire romantic imaginations with their rich history, bewitching medieval back alleys and peerless collections of Renaissance art. You'll most likely kick off your Tuscany honeymoon in Florence, city of domes, medieval towers and fountain-splashed piazzas on the Arno River. Here you'll be drawn to the Botticelli collection at the Uffizi, the marble wonder of the Renaissance Duomo and Michelangelo's David at the Galleria dell’Accademia. For expert tips on exploring the city, check out 24 Hours in Florence. 

Beyond Florence, you'll find plenty to love about other Tuscan cities such as Siena, full of Gothic grandeur and historic contrade (districts) filled with palazzi and piazzas, bakeries, cafes and restaurants. Encircled by some of Europe's longest and best-preserved city walls, Lucca is another charmer, with botanical gardens, medieval towers to climb and Puccini's birthplace museum. 

Heavenly Hill Towns

Tuscany’s sleepy hill towns are rightfully billed as Italy’s most romantic. They make great escapes year-round, but particularly when the region’s cities heave with visitors in summer.

Here you can slow the pace with hand-in-hand strolls through cobbled alleyways bathed in painterly light, linger over morning coffee and evening aperitivi (aperitifs) on a ringside piazza as the lanterns flick on to illuminate the Romanesque duomo (cathedral), and peer out across terracotta rooftops, vineyards, fields and mountains from viewpoints atop medieval walls.

Choosing the best hill towns in Tuscany is a tough call as there are simply so many, each with their own personality. Driving through Tuscany’s heartland, between Florence and Siena, you can tick them off one after the next like rosary beads. Swing along cypress tree-lined country lanes by car, bicycle or Vespa and before long a beautiful, soft-stone village cresting a hillside will slide into view.

The Middle Ages were a busy time for wealthy Tuscany merchants and many indulged in flamboyant displays of one-upmanship by building towers bigger than better than their neighbors, the result of which you can see in the likes of Unesco-listed San Gimignano (often nicknamed Tuscany’s ‘medieval Manhattan) and immaculately preserved, circular-walled Monteriggione.

Not far from here is Montepulciano, a gracious medieval town that sits astride a volcanic outcrop that rises above vineyards producing ruby red Vino Nobile wines. Volterra is another favorite, with impressive ramparts, a warren of twisting cobbled streets, ancient palazzi and one of Italy’s most intact Roman theaters to discover.

Or for a shot of movie-style romance, head further east to Cortona. This endearing hill town is where early Renaissance master Fra’ Angelico lived and worked (his work is displayed in the Diocesan Museum). Many scenes in the romantic comedy drama Under the Tuscan Sun were filmed here.

See more in this article about Italy's Best Hidden Hill Towns.

Culinary Delights

Indulging in Tuscan cuisine is likely to be one of your most lasting memories of your honeymoon, whether you opt for a low-key, family-run osteria, Michelin-starred dining by candlelight in a Renaissance palazzo, a picnic among the vines, or a blow-out farm-to-table meal at an agriturismo.

It’s all about the riches of the land here, with food that sings of the seasons, including porcini, chestnuts, truffles, and naturally superb wines (courtesy largely of Chianti and Montepulciano). Specialties to look out for include bistecca alla fiorentina (T-bone steak) with Chianina beef, cinta senese (Tuscan pork) and castagnaccio (chestnut-flour cake). Extra-virgin olive oil from Montalcino and Tuscan pecorino sheep’s cheese are excellent, too.

If you're in the mood for a more immersive experience, try a pizza- and gelato-making class in Florence, go white truffle hunting in the woods of San Miniato near Lucca, or take drive the region's wine roads, where you can pause for tastings and romantic strolls among the vines at an enoteca or cantina.

With this two-week food and wine itinerary, you'll visit a number of Italy's culinary regions and major cities. Pair a bottle of Tuscan Chianti with a farm-to-table charcuterie board, then spend four days on the Amalfi Coast. Explore medieval fishing villages and make the perfect Neopolitan pizza before ending your trip in a local gelateria in Rome. 

Back-to-Nature Escapes

With mountains, vine-ribboned hills, woods lush with chestnut, olive and oak trees, valleys where jade-green rivers flow, and beaches backed by dunes and pines—Tuscany is a real natural beauty. And you’ll soon fall for the romance of its near lyrical landscapes, which are best explored in slow motion: on foot or by bicycle. 

Lesser-known than many places in Tuscany, and as a result less touristed, the Apuan Alps that pop up in the northwest of the region form the backbone of a wild regional park that tops out at 6387ft Monte Pisanino. For views out over craggy mountains that dip to the sea, factor in a panoramic, high-level drive from Massa to Arni through the thickly forested, wildflower-daubed Pietro Pellegrini Botanical Gardens.

Tuscany might be mostly feted for its countryside, but it also has an often-overlooked coastline that can rival Italy’s best, with long sandy beaches shelving into the Ligurian sea. Some of the finest beaches and coves for honeymooners are tucked away in the southern Maremma region, especially on the ravishing little island of Elba and on the Monte Argentario peninsula.