Trip Highlights:

Day 1: Montecatini Terme

• Depart from your hotel at 4:00 PM for an orientation tour of Montecatini Terme.
• Discover the town’s rich history of restorative waters and baths dating back to Roman times and see why it is recognized as a UNESCO World Heritage site.
• Your hotel is centrally located, offering convenient access to shopping and dining establishments for your exploration. This evening, enjoy a welcome drink followed by dinner with the group at the hotel. 

Day 2: Pisa & Lucca

• Visit the medieval town of Pisa to see the famed Leaning Tower and its neighboring buildings in the marvelous Piazza dei Miracoli: the grand white marble cathedral and the amazing round baptistry.
• Next, go to Lucca, a beautiful walled city with cobblestone streets where you’ll have time for independent exploration and lunch.
• You might choose to visit some of the churches for which this small city is known, admire the medieval architecture of the towers, or buy a souvenir from the shops specializing in artisanal paper, ceramic, jewelry, and leather products.
• Back in Montecatini, your evening will be free to explore and dine as you wish. 

Day 3: Florence & Accademia Gallery

• Discover the wonders of Florence, the birthplace of the Renaissance, on a walking tour. Marvel at iconic sights like the Duomo, Palazzo Vecchio, and Piazza della Signoria in the city center.
• Next, experience the awe-inspiring beauty of Michelangelo’s David up close on a visit to the Accademia Gallery.
• Take free time to soak in the atmosphere of this beautiful city before an early dinner at a local restaurant with your group. 

Day 4: Montecatini & Fattoria il Poggio Farm

• Your morning and early afternoon will be free to spend in Montecatini Terme as you wish. Perhaps you’ll relax in your hotel’s outdoor swimming pool or take the short walk to the funicular to Montecatini Alto, a small walled town on the hill above Montecatini Terme.
• This evening, visit Fattoria il Poggio, an ‘agriturismo’ farm that embodies the spirit of sustainability. Explore the vineyard and olive grove, savor wine and olive oil tastings, and sit down with your group for traditional, home-cooked cuisine. 

Meals Provided: Breakfast, Dinner

Day 5 Cinque Terre

• Embark on a full day visiting the Cinque Terre, a string of five picturesque fishing villages perched on the Italian Riviera, accessible only by train and hiking trails.
• Take in the sights of fishing boats in the harbors and lemon trees on the hillsides, and explore the stone houses, medieval churches, and small boutiques.
• Board the train between villages and enjoy free time to explore and relax as you wish: savor lunch in one of the local restaurants, explore the shops, or indulge in gelato on the harbor.
• Return to your hotel in Montecatini for dinner. 

Day 6: San Gimignano, Siena & Castello di Verrazzano

• Start your day with a visit to the hilltop town of San Gimignano and behold its captivating skyline, adorned with its iconic medieval towers.
• Continue on to Siena and immerse yourself in this medieval walled city on an orientation walk with your tour director, followed by time for independent exploration.
• Conclude the day with a tour, tasting and a gourmet dinner at Castello di Verrazzano, a renowned vineyard producing Chianti Classico wine. 

Meals Provided: Breakfast, Dinner

Day 7: San Miniato, Truffle Hunting, Farewell Lunch & Vinci

• Embark on a journey to San Miniato, a charming medieval gem famed for the wild truffles that flourish there. Join a local expert and his skilled truffle-hunting dog to search for these prized delicacies in their natural habitat.
• Enjoy a farewell lunch at a local restaurant, savoring truffle specialties. Then, a quick stop in Vinci, the birthplace of Leonardo da Vinci, the genius of the Italian Renaissance, before returning to Montecatini Terme. 

Meals Provided: Breakfast, Lunch

Day 8: Tour Ends in Montecatini Terme

• Your tour ends after breakfast. 

Who is this trip for?

La Dolce Roam is designed for curious, cultured travelers who want to explore Italy in good company.  With ample time for independent exploration and relaxation built in, this is otherwise an active tour that involves standing and walking throughout the day, including on uneven surfaces, stairs, and slopes. Whether you're traveling solo, with a partner, or bringing your bestie, you're in for an amazing experience with like-minded adventurers.

What’s included in the trip package?

Your trip includes:
✔️ 7 nights at the Grand Hotel Croce di Malta, Montecatini Terme
✔️ 13 meals (7 breakfasts, 1 lunch, 5 dinners)
✔️ Guided sightseeing and activities with a local expert
✔️ Transportation during the tour
✔️ A Why Not Roam ambassador to vibe with you throughout the journey

Is a payment plan available for this trip?

Yes!  A deposit is required to secure your reservation, and the remaining balance can be paid in three installments.  

Can Why Not Roam help with flight arrangements?

Absolutely. While flights are not included in the tour package, we're happy to help you get the best flights to and from Italy, and recommend flying in the day before the tour starts.

Can I arrive early or stay later in Italy?

Yes, you can! We know some travelers like to roam a little longer. If you’d like to fly in early or extend your stay after the tour ends, we can assist with additional hotel nights (based on availability) and help you customize your travel plans.

Is travel insurance required?

While not required, it is strongly recommended. Travel insurance can cover unexpected events like trip cancellations, medical emergencies, lost luggage, or flight delays. You’ll be given the option to purchase coverage when booking, or we can guide you to another trusted provider if you are interested in exploring other options.  A signed waiver is required if you decide to decline coverage.

When is the final payment due?

Your trip must be paid in full by March 30, 2026.  You’ll receive reminders along the way to keep you on track.