The World Tour • Travel Adventure Club
Saturday, October 9 – Saturday, October 23, 2027
U.S. travel dates • Italy sightseeing October 10–23
Experience the very best of Italy, from the spectacular Amalfi Coast to ancient Rome and glorious Tuscany. Outstanding sightseeing, memorable meals, local experts and time to explore!
Amalfi Coast • Capri • Pompeii • Rome • Vatican • Tuscany • Pisa • Florence • Cinque Terre & more!
Capri & Amalfi Coast
Rome • The Eternal City
Tuscan CountrysideAn exceptional sightseeing experience! Our October 2027 route features 4 nights in Sorrento, 3 nights in Rome and 6 nights in Montecatini, Tuscany, with 4-star hotel accommodations and professional local guides. We combine Italy's most celebrated sights with special food and wine experiences and the freedom to discover charming towns at your own pace.
Flexible sightseeing: Join all our organized excursions, choose your favorites, or enjoy free time exploring local cafés, shops, and charming Tuscan towns at your own pace. Venice self-guided sightseeing opportunity for guests wishing to explore farther afield, as some members enjoyed on our previous Italy tours.
Here's our Italy journey, refined from our popular previous tours. You travel from the Bay of Naples through Rome to the heart of Tuscany, avoiding repeated hotel changes while still visiting many of Italy's greatest sights.
Naples Airport → Sorrento (4 nights) → Rome (3 nights) → Montecatini (6 nights) → Florence Airport
Depart the United States for Naples, Italy. Travel with our Boston flight group or make your own air arrangements. Most transatlantic flights travel overnight. If you plan to arrive early, please coordinate airport meeting and transfer details with the club.
Airfare is additional to the $4,695 land-only price
We meet as a goup at Naples Airport and continue by private transfer to Sorrento. Settle into our hotel, then enjoy a welcome dinner together with local Italian flavors and a celebratory toast.
Overnight: Sorrento • Dinner
Set off by ferry for the beautiful island of Capri. Discover its celebrated Piazzetta, the Gardens of Augustus and dramatic island scenery with our local guide and included island transportation. Return to Sorrento for dinner.
Overnight: Sorrento • Breakfast & dinner
Travel the breathtaking Amalfi Coast with a local guide. We'll take in the celebrated viewpoints of Positano, explore Amalfi and its historic streets, visit Vietri sul Mare, known for its ceramics, and enjoy a short boat journey from Amalfi toward Maiori. An Italian lunch is included along the way.
Overnight: Sorrento • Breakfast, lunch & dinner
Walk the astonishing excavations of Pompeii with an expert guide and discover the streets and daily life preserved by the eruption of Mount Vesuvius in A.D. 79. Then enjoy a local winery visit, wine tasting and lunch on the volcanic slopes.
Overnight: Sorrento • Breakfast, winery lunch & dinner
Leaving Sorrento, stop at the spectacular Royal Palace of Caserta, a UNESCO World Heritage Site, for guided sightseeing. Continue north to Rome, check into our hotel and enjoy dinner.
Overnight: Rome • Breakfast & dinner
Explore ancient Rome with our guide, including a visit to the Colosseum and sightseeing at the Roman Forum and Palatine Hill. Later discover Rome's famous squares and landmarks, including the Trevi Fountain, Piazza Navona, Spanish Steps and Pantheon area. Enjoy dinner in Rome's lively Trastevere district.
Overnight: Rome • Breakfast & dinner
Our guided visit features the renowned Vatican Museums and Michelangelo's Sistine Chapel, and St. Peter's Basilica, subject to visitor access. Enjoy independent time for sightseeing, shopping or relaxing before a special Roman dinner and entertainment.
Overnight: Rome • Breakfast & dinner
Leaving Rome, we travel through the beautiful rolling hills of Tuscany to the celebrated Chianti wine region, where we’ll visit a local winery and enjoy an included wine tasting and traditional Tuscan lunch.
We continue to Siena, one of Italy’s most beautiful medieval cities, for a guided tour of its magnificent historic center. Discover the famous Piazza del Campo, home of the legendary Palio horse race, and admire the city’s narrow streets, remarkable architecture and centuries of Tuscan history.
Our journey continues through the scenic countryside to Montecatini Terme, where we’ll settle into our 4-star superior hotel for six nights exploring Tuscany.
Overnight: Montecatini • Breakfast, winery lunch & dinner
Enjoy a day discovering Montecatini Terme, our charming Tuscan spa-town home. Stroll through its elegant parks and historic thermal spa district, explore local boutiques, cafés and piazzas, or enjoy the hotel's amenities. For an independent outing, take the historic funicular (subject to operating schedule) to hilltop Montecatini Alto, with its medieval streets, inviting restaurants and panoramic Tuscan views. For those wishing to venture farther, nearby Pistoia offers beautiful historic squares, churches and authentic Italian atmosphere, easily explored independently by train. Relax, explore or create your own Tuscan adventure at your own pace.
Overnight: Montecatini • Breakfast & dinner
See the cultural treasures of Florence with our local guide, including the Duomo area, Piazza della Signoria, Ponte Vecchio and the Accademia Gallery to admire Michelangelo's David. Free time allows you to enjoy Florence's art, shopping, cafés and history.
Overnight: Montecatini • Breakfast & dinner
Visit Pisa's celebrated Field of Miracles, admire the Leaning Tower from outside and tour the beautiful Baptistery. Continue to the elegant city of Lucca for guided sightseeing in its charming historic center.
Overnight: Montecatini • Breakfast & dinner
Explore the colorful seaside villages of Cinque Terre. Our excursion includes guided visits and a combination of boat and rail transportation to experience coastal scenery and enchanting villages such as Riomaggiore, Vernazza and Monterosso.
Overnight: Montecatini • Breakfast & dinner
Enjoy an unscheduled day to revisit a favorite place, explore Montecatini Alto or Pistoia independently, shop for Italian specialties or simply relax before the journey home. For those interested in Venice, the day also offers a self-guided sightseeing opportunity, enjoyed by many on previous tours.
Overnight: Montecatini • Breakfast & dinner
After breakfast, take our coordinated private group transfer to Florence Airport (FLR) for your return journey, whether traveling with our Boston group or on independently arranged flights matched to the transfer schedule. Arrivederci, Italia!
Breakfast • End of land tour
Outstanding destination hotels are one of the pleasures of traveling with our club! We carefully select comfortable, welcoming 4-star hotels that complement the places we visit: a lively Sorrento location near its cafés and piazzas, a relaxing base for exploring the treasures of Rome, and a lovely Tuscan spa-town hotel where we can truly settle in. These are places to enjoy, not simply somewhere to sleep. From leisurely breakfasts and inviting lounges to a drink together after sightseeing, our hotels add another dimension to the Italian experience.
Best of all, we stay 4 nights in Sorrento, 3 in Rome and 6 in Tuscany—giving us time to unpack, get comfortable, discover each neighborhood and enjoy the hotel atmosphere between our included excursions. All three featured hotels also offer swimming pools, a welcome extra amenity.
October 10–14, 2027 • 4-Star Hotel
What a wonderful place to begin our Italian adventure! The Grand Hotel Cesare Augusto combines the warm, easygoing atmosphere of Sorrento with the comfort and conveniences of a classic 4-star hotel. Just a short stroll from Piazza Tasso, the town's bustling central square, it puts inviting cafés, restaurants, shops and Sorrento's picturesque streets within easy reach. Its comfortable rooms, garden, restaurant and welcoming spaces make it a delightful home base for four nights on the Bay of Naples.
After unforgettable outings to Capri, Pompeii and the Amalfi Coast, you can return to the hotel, relax over a drink or head back into town for an evening passeggiata. The rooftop terrace, panoramic views and seasonal swimming pool are lovely additional touches. This is the joy of staying several nights in Sorrento: enjoying the destination long after our sightseeing day has ended.
October 14–17, 2027 • 4-Star Hotel
Our Roman adventure deserves a comfortable retreat! Precise House Mantegna Roma offers a stylish, contemporary setting for our three nights in the Eternal City. Its generously sized guest rooms, attractive lounges and on-site dining provide plenty of room to unwind, socialize and recharge before another spectacular day among Rome's ancient monuments and celebrated neighborhoods.
With our organized sightseeing and group transportation, we can enjoy the Colosseum, Roman Forum, Vatican City and Rome's famous fountains and squares without worrying about navigating our principal tour days. Back at the hotel, its relaxed atmosphere and amenities—including fitness facilities and an indoor swimming pool—make an appealing contrast to the city's lively streets. It is a welcoming place to gather, recount the day's discoveries and look forward to what's next.
October 17–23, 2027 • 4-Star Superior Hotel
Six nights in Tuscany—time to truly enjoy the Italian way of life! Our stay at Grand Hotel Croce di Malta, a 4-star superior hotel in Montecatini Terme, is a highlight of the trip in its own right. This elegant spa town, known for its beautiful architecture, historic thermal baths, leafy avenues, cafés and shops, makes an especially inviting home for our final week in Italy.
The hotel offers comfortable accommodations, a welcoming restaurant and lounges, the Thai Silk Spa, and indoor and outdoor swimming facilities. It's a wonderful base for our adventures to Florence, Pisa, Lucca, Siena and Cinque Terre, but just as appealing on days when you prefer a slower pace. Enjoy a leisurely breakfast, explore the town, discover local restaurants or take an independent outing. With six nights here, there is time to make Montecatini feel like our own little corner of Tuscany—and to enjoy the friendships and camaraderie that make our club tours special.
Hotel pools and wellness amenities are subject to seasonal schedules, opening hours and any applicable access charges. Featured hotels or comparable 4-star accommodations may be used.
Our U.S. departure date is Saturday, October 9, 2027, arriving at Naples Airport (NAP) on Sunday, October 10, with return flights from Florence Airport (FLR) on Saturday, October 23.
Boston group flight options and pricing are expected in December 2026. Travelers are also welcome to arrange their own flights, use frequent-flyer miles or points, or extend their stay in Italy.
Our private airport transfers operate according to the coordinated group arrival and departure schedule. Guests arranging their own flights must coordinate airport arrival and departure times with the club before booking. Flights from other U.S. cities are welcome if they fit the approved transfer schedule. Additional hotel nights or independent transfer arrangements are at the traveler's expense.
Early Special: $4,695 per person, land-only, double occupancy. Includes 13 nights in 4-star hotels, daily breakfasts and dinners, our extensive guided sightseeing program, specialty winery lunches, excursions and group transportation.
Single-occupancy accommodations are limited and available at an additional cost. Please contact us for availability and room options.
Reserve your place with a $495 per person deposit. Pay the remaining balance or select a payment plan by January 15, 2027.
Manage your reservation through your member account. Payment options include check, bank transfer and online payment, subject to the arrangements provided with your reservation.
Questions? Call 888.828.0096 or email the club. We're happy to help with reservations, flight options and travel planning.
For over 25 years The World Tour – Travel Adventure Club has been bringing members together for international adventures. Italy remains one of our favorite and most-requested destinations. Our 2027 sightseeing tour builds on the locations and experiences our members enjoyed during past Italy trips, while giving everyone time to discover the magic of Italian life at their own pace.
Ready for a memorable Italy adventure? Contact our club for more information and reservations.
