Morning: Land at Florence Airport, pick up your rental car and enjoy a leisurely drive to the historic city centre. Check into the boutique hotel and freshen up.
Afternoon: Stroll to the Florence Duomo and climb the dome for panoramic views, then wander through the Uffizi Gallery to admire Renaissance masterpieces.
Evening: Dine at a romantic riverside trattoria with a view of the Arno, followed by a gentle walk across the Ponte Vecchio under the lantern light.
Find HotelsMorning: Visit the Accademia Gallery to see Michelangelo’s David, then explore the bustling San Lorenzo market for local snacks.
Afternoon: Enjoy a guided tour of the Pitti Palace and its beautiful Boboli Gardens, perfect for a leisurely stroll hand‑in‑hand.
Evening: Savor a candlelit dinner in the Oltrarno district, sampling Tuscan steak (bistecca alla fiorentina) and local wines.
Find HotelsMorning: Depart Florence and drive through the rolling hills of the Chianti region, stopping at a scenic viewpoint over vineyards.
Afternoon: Arrive at your countryside villa near Greve in Chianti, settle in, and enjoy a private wine tasting of Chianti Classico with a local sommelier.
Evening: Relax on the villa terrace with a homemade antipasto platter and watch the sunset over the vineyards.
Find HotelsMorning: Visit the historic Castello di Brolio for a guided tour of its cellars and a tasting of aged reds.
Afternoon: Head to the charming town of Radda in Chianti for a leisurely lunch and explore its medieval streets.
Evening: Return to the villa for a cooking class where you learn to prepare classic Tuscan pasta dishes together.
Find HotelsMorning: Drive to Siena and begin with a walk through the Piazza del Campo, the famous shell‑shaped square.
Afternoon: Tour the magnificent Siena Cathedral and climb the Torre del Mangia for sweeping valley views.
Evening: Dine at a historic osteria, enjoying pici pasta and a glass of local Vino Nobile.
Find HotelsMorning: Drive to the UNESCO‑listed Val d’Orcia, stopping in Pienza to taste its famous pecorino cheese.
Afternoon: Continue to Montepulciano for a wine tasting tour of its renowned Vino Nobile, followed by a stroll through its Renaissance streets.
Evening: Return to the villa for a relaxed dinner featuring fresh ingredients from a nearby farm.
Find HotelsMorning: Visit the fortified town of Montalcino and explore its historic castle.
Afternoon: Tour a prestigious winery for a Brunello di Montalcino tasting, learning about the aging process.
Evening: Picnic among the vineyards at sunset, followed by a nightcap of Vin Santo with cantucci.
Find HotelsMorning: Sleep in and enjoy a leisurely breakfast on the terrace with fresh fruit and espresso.
Afternoon: Take a private spa treatment at the villa’s wellness center, followed by a dip in the pool.
Evening: Enjoy a private chef‑prepared dinner under the stars, paired with a selection of Tuscan wines.
Find HotelsMorning: Drive to the medieval town of San Gimignano, famous for its towers, and explore its historic centre.
Afternoon: Continue to Volterra to visit the alabaster workshops and the Etruscan Museum.
Evening: Return to the villa, stopping for a sunset view over the Tuscan hills in the small village of Certaldo.
Find HotelsMorning: Arrive in Lucca and rent bicycles to ride atop its well‑preserved city walls.
Afternoon: Head to Pisa to photograph the iconic Leaning Tower, Baptistery, and Cathedral on the Piazza dei Miracoli.
Evening: Enjoy a seaside dinner in the fishing village of Viareggio, tasting fresh seafood and local whites.
Find HotelsMorning: Travel to the hill‑top town of Cortona, explore its Etruscan sites and art galleries.
Afternoon: Drive to Lake Trasimeno for a relaxing boat ride and a lakeside lunch.
Evening: Return to the villa, enjoying a quiet night with a movie or board games.
Find HotelsMorning: Visit Arezzo to see the frescoes by Piero della Francesca in the Basilica of San Francesco.
Afternoon: Spend time at a family‑run wine farm near Arezzo, participating in a harvest‑style tasting of organic wines.
Evening: Dine at a traditional agriturismo, savoring ribollita soup and Tuscan honey‑glazed pork.
Find HotelsMorning: Drive back to Florence and wander the leather markets of the San Lorenzo area for souvenirs.
Afternoon: Visit the Boboli Gardens for a final stroll, then enjoy a gelato on Piazza della Signoria.
Evening: Celebrate your honeymoon with a gourmet dinner at a Michelin‑starred restaurant, toasting with a bottle of Brunello.
Find HotelsMorning: Pack and enjoy a relaxed breakfast on the villa terrace, taking in the last views of the Tuscan countryside.
Afternoon: Drive to Florence Airport, return the rental car, and board your flight home with cherished memories.
Evening: Arrive back home, ready to share stories of a magical Tuscan honeymoon.
Find HotelsTo extend the trip, add a few extra days in the Val d’Orcia to explore the thermal baths of Bagno Vignoni or take a day trip to the coastal town of Castiglione della Pescaia for beach time. If you need to shorten the itinerary, combine Days 9 and 10 by visiting San Gimignano and Pisa in a single day and skip the optional Lake Trasimeno excursion, allowing you to depart directly from Florence after Day 12.