La Dolce Roam - Tuscany, Italy
May 24, 2026 to May 31, 2026
Tuscany + Cinque Terre, Italy
La Dolce Roam - Tuscany + Cinque Terre, Italy
Trip Highlights:
- Lucca, Pisa, San Gimignano, Siena, Vici, Montecatini Terme, Florence
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Cinque Terre
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Michelangelo’s David
What's Included
- 4-Star Accommodations at Grand Hotel Croce di Malta
- 13 Included Meals and Wine Tasting
- Guided activities with a local expert
- Airport Transfers
- Transportation to All Scheduled Activities
What's Not Included
- Airfare (Complimentary booking assistance available).
- Travel Insurance
Itinerary:
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 amid the town’s elegant architecture and close to shopping and restaurants. Enjoy a welcome drink and dinner with your group at the hotel this evening.
Day 2: Pisa, Lucca & Fattoria il Poggio Farm
Day 3: 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 stroll the streets with their 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 4: 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 & Winery Dinner
Your morning and afternoon will be free to spend in Montecatini Terme as you wish. Perhaps you’ll relax in your hotel’s pool, visit the town’s weekly market, or take the short walk to the funicular to Montecatini Alto, a small walled town on the hill above Montecatini Terme. In the evening, visit a winery for a tour, tasting, and dinner of traditional cuisine.
Meals Provided: Breakfast, Dinner
Day 6: San Gimignano & Siena
Meals Provided: Breakfast, Dinner
Day 7: San Miniato, Truffle Hunting, Farewell Lunch
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. Delight in a farewell lunch at a local restaurant, savoring truffle specialties. Return to Montecatini Terme to relax and spend the evening as you please.
Meals Provided: Breakfast, Lunch
Day 8: Tour Ends in Montecatini Terme
- Your tour ends after breakfast.
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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. Travelers may choose to pay in full at the time of booking or enroll in an installment plan, which allows the trip cost to be divided into scheduled payments prior to the final payment deadline.
For those who prefer additional flexibility, some travelers independently choose to finance their travel through third-party services such as Affirm or Flex Pay by Upgrade. Why Not Roam is not affiliated with or endorsed by these providers and does not offer or manage financing. Any arrangements with third-party financing companies are made directly between the traveler and the provider.
Can Why Not Roam help with flight arrangements?
Absolutely. While flights are not included in the tour package, we're happy to help you arrange 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. 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 such as trip cancellations, medical emergencies, lost luggage, or flight delays. We can direct you to reputable suppliers upon request. 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.
Payment & Cancellation Policy
A $250 non-refundable deposit per traveler is required to secure your reservation through December 31, 2025. This deposit is applied toward the total trip cost. Bookings made between January 1, 2026 and March 1, 2026 may choose to pay in full at the time of booking or enroll in an installment plan. Bookings made after March 1st must be paid in full at the time of booking.
Installment Plan:
For travelers not paying in full within the installment eligibility window, the total trip cost may be paid in up to three installments. Travelers may pay off their remaining balance at any time before the final payment deadline.
If you have questions about payment timing or options, feel free to reach out. We're happy to help you find a plan that works.
Cancellations:
Our cancellation terms are in alignment with supplier policies. Please review the schedule below to understand how fees apply should you need to cancel your reservation.
- On or before March 19, 2026: 30% cancellation fee
- March 20 – May 16, 2026: 50% cancellation fee
- May 17 – May 23, 2026: 90% cancellation fee
- Day of departure (May 24, 2026): 100% cancellation fee
- In the unlikely event the trip is canceled by Why Not Roam or the supplier, refunds will be issued for all amounts paid (including deposits).
Cancellation requests must be received in writing at info@whynotroam.com.
- A valid passport with an expiration date at least 6 months beyond the travel date is required.
- While every effort is made to deliver the itinerary as described, certain activities, accommodations, or other elements may be subject to change until departure. In such cases, comparable alternatives of equal quality will be provided to ensure the integrity of your experience.
- Additional questions before booking? Message info@whynotroam.com or call +1.678.509.2729.
- Follow Why Not Roam and subscribe to Roam & Revel for Roamie updates and info on future group experiences.
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Sheree is the heart behind Why Not Roam and your on-site host for this experience. She curates intimate group journeys rooted in culture, community, and connection—creating a travel experience that feels both immersive and genuinely welcoming. | |
| Sheree Holt, Founder & Chief Roaming Strategist |
