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From the iconic ruins of Rome to the romantic canals of Venice and from the serenity of the northern Italian Lakes to the dramatic cliffs of the Amalfi coast, experience Italy like never before! Tripmasters expertly curated, privately guided luxury vacation packages are ready to book, but can be easily customized with alternate hotels and activities to suit your interests.
This exclusive and easy-to-customize vacation package is perfect for families, couples, friends, or solo travelers, whether it is your first or fifth visit to fascinating Italy! Experience its most iconic and historic cities, exploring engaging Rome, captivating Florence, and enchanting Venice.
Essential Highlights and Recommended Experiences:
- Discover all the main monuments, landmarks and vibrant history of Rome, including the Colosseum, Roman Forum, Pantheon and Vatican
- Experience lively festivals, street performances, authentic Roman street food, wine and local markets
- Visit Renaissance masterpieces by artists like Michelangelo and da Vinci at the Accademia and Uffizi Galleries in Florence
- Enjoy an unforgettable gondola ride through the romantic Grand Canal and hidden channels in Venice
- Visit St. Mark's Basilica, the Doge's Palace, and charming islands like Murano, Burano, and Torcello
- Relax with stress-free private transfers that include sightseeing stops at fascinating, UNESCO-listed medieval Tuscan villages San Gimignano and Ferrara
This premier vacation package features thoughtfully curated services and is fully flexible. You can customize it to suit your needs and preferences by adjusting the number of nights in each city and browsing our hand-picked selection of hotels, transportation options, activities, and experiences.
Includes:
Discover the best of ancient Rome, artistic Florence, and captivating Venice, plus an unforgettable stay at La Spezia (the port city and the gateway to dreamy UNESCO World Heritage Cinque Terre Villages) in style and ease! Our package is more than a vacation; it is an experience full of curated hotels, activities, and convenient transportation.
Essential Highlights and Recommended Experiences:
- Visit the impressive ruins and main monuments of the Roman Empire; such as The Colosseum, the Roman Forum, and the iconic Gladiator Arena
- Marvel at artstic treasures in the vast collections at the Vatican Museum, as well of other such as the Uffizi and Accademia Galleries in Florence, and the Guggenheim Museum in Venice
- Relax and enjoy vibrant squares and markets like Piazza Navona, del Duomo, and San Marco to get a glimpse at everyday Italian life
- Treat yourself to culinary delights or enroll in cooking classes featuring premier Tuscan wines and classic aperitivi
- Hike the Blue Trail (Sentiero Azzurro), walk the reopened Via dell'Amore (Path of Love), or take a Gozzo boat tour at sunset from one of the charming Cinque Terre Villages
This premier vacation package features thoughtfully curated services and is fully flexible. You can customize it to suit your needs and preferences by adjusting the number of nights in each city and browsing our hand-picked selection of hotels, transportation options, activities, and experiences.
Includes:
10 nights from $3,563*
Customize it
Discover the magic of Italy with our customizable guided journey: from the iconic landmark of Rome to dreamy, lemon-scented alleys of Sorrento and Amalfi. Explore UNESCO World Heritage site Pompeii and the cliffside splendor of Positano. Tripmasters offers flexible itineraries with hand-picked hotels and private transportation. Book your dream Italian getaway today!
Essential Highlights and Recommended Experiences:
- Discover the monuments and landmarks of the Roman Empire, such as the Colosseum
- Experience vibrant Roman traditions and culture with local markets, street food, and lively piazzas
- Visit Villa Comunale for panoramic views of the Bay of Naples and Mount Vesuvius
- Explore the artisinal heritage in old-town Sorrento and Amalfi while wandering the old-town alleys of Via San Cesareo to discover authentic tarsia (inlaid wood crafts)
- Enjoy a lemon sorbet in the piazza outside the mighty Duomo in Amalfi
- Travel by private car through the cliffside roads with stops at the charming vertical village of Positano and at UNESCO-listed Pompeii (tickets not included)
This premier vacation package features thoughtfully curated services and is fully flexible. You can customize it to suit your needs and preferences by adjusting the number of nights in each city and browsing our hand-picked selection of hotels, transportation options, activities, and experiences.
Includes:
Are you seeking “la dolce vita?”... Our curated luxury package to captivating Italy can help you find it! Stay in three iconic cities and discover the best that each offers: historic Rome, artistic Florence, and stunning Venice.
Essential Highlights and Recommended Experiences:
- Ruins of the Roman Empire including the Colosseum, Forum, and Palatine Hill
- Cultural and artistic treasures at The Vatican Museums, Uffizi and Accademia Galleries, and The Guggenheim
- Bustling piazzas and local markets such as Piazza Navona, Piazza del Duomo, and Piazza San Marco
- Authentic Italian cuisine and award-winning Tuscan wine and other aperitivi
This premier vacation package features thoughtfully curated services and is fully flexible. You can customize it to suit your needs and preferences by adjusting the number of nights in each city and browsing our hand-picked selection of hotels, transportation options, activities, and experiences.
Includes:
Your private chauffeur navigates the sun-drenched Tuscan Countryside, seamlessly connecting the Renaissance splendor of Florence with the medieval majesty of Siena and the scenic Cinque Terre Villages in ultimate luxury and comfort! Enjoy door-to-door service between these destinations and discover medieval cities (and a few UNESCO World Heritage Sites) including: Monteriggioni, San Gimignano, Lucca, Colle Val dElsa, Pisa, and Montecatini Alto.
Essential Highlights and Recommended Experiences:
- Climb Brunelleschi's Dome for breathtaking Florence city views
- Visit the Uffizi Gallery, Michelangelo's David at the Accademia Gallery, and walk along the Ponte Vecchio Bridge
- Explore the shell-shaped Piazza del Campo, Torre del Mangia, and admire the striped Gothic architecture of the Duomo in Siena
- Walk the Via dell'Amore in La Spezia, Hike the Sentiero Azzurro (Blue Trail) connecting the five colorful villages or take a Ferry/Boat Trip along the coast for stunning views of the cliffside towns of the Ligurian Sea
- Sample authentic Tuscan cuisine, award-winning Chianti wines, the freshest seafood, and other delectable aperitivi
This premier vacation package features thoughtfully curated services and is fully flexible. You can customize it to suit your needs and preferences by adjusting the number of nights in each city and browsing our hand-picked selection of hotels, transportation options, activities, and experiences.
Includes:
8 nights from $2,539*
Customize itThe stunning beaches and cobblestone streets of the Amalfi Coast await your discovery with our easy-to-customize and stress-free vacation package! Enjoy stays in Naples, Amalfi Town, and Sorrento with convenient private transfers from city to city.
Essential Highlights and Recommended Experiences:
- Enjoy the lemon-scented, winding streets of Amalfi and Sorrento, where local artisans sell handmade wood crafts (tarsia) and intimate cafes offer refuge from the bright sun
- Explore piazzas teeming with local life, such as the Piazza del Duomo in Amalfi or the Piazza Tasso in Sorrento
- Book a day trip to Pompeii, the famous archaeological site just outside Naples in the shadow of the mighty Vesuvius Volcano- Savory local delicacies like Neopolitan pizza, limoncello or gelato in Amalfi, or fresh-caught fish in Sorrento
- Immerse yourself in local culture, walking the seafront promenades
- Explore local street art as well as fine paintings and sculptures housed in the churches and museums like the Convento San Francesco or the Correale di Terranova Museum
- Relax during private, chauffeured car service from city to city and discover exciting stops along the way, including Villa de Poppea, Ravello, Positano, and the Stabia Archeological Site
This premier vacation package features thoughtfully curated services and is fully flexible. You can customize it to suit your needs and preferences by adjusting the number of nights in each city and browsing our hand-picked selection of hotels, transportation options, activities, and experiences.
Includes:
7 nights from $3,648*
Customize itIn Italy, food is a way of life, and food is love. Regional, seasonal, and as fresh as possible - from gourmet Michelin-star restaurants to street vendors - you'll be satisfied with every new flavor. Trust us. We've done our best to arrange a wonderful culinary experience for you in Rome and Florence; we hope you'll be delighted!.
Essential Highlights and Recommended Experiences:
- Visit iconic sites such as the Colosseum, Ponte Vecchio, The Vatican Museums, Uffizi and Accademia Galleries
- Wander bustling piazzas and local markets such as Piazza Navona, Piazza del Duomo and shop wonderful local handicrafts and unique gifts
- Visit stunning royal villas and palaces such as Villa d’Este and Pitti Palace
- Savor authentic Italian cuisine and award-winning Tuscan wine and other aperativos
This premier vacation package features thoughtfully curated services and is fully flexible. You can customize it to suit your needs and preferences by adjusting the number of nights in each city and browsing our hand-picked selection of hotels, transportation options, activities, and experiences.
Includes:
10 nights from $3,099*
Customize it
Discover Italy with Tripmasters Chauffeured Collection packages, including private car transfers between your destinations with stops at charming towns, local attractions, UNESCO World Heritage Sites, and more! Let your journey become an unforgettable experience with our door to door service.
Food and wine are central to daily life in Italy, reflecting regional identity, history, and tradition. Each region, from Tuscany to Sicily, offers distinct dishes influenced by local ingredients, seasonal cooking, and time-honored recipes. Meals are social rituals, bringing family and friends together to celebrate culture and community.
Italy is home to more UNESCO World Heritage Sites than any other country in the world with 61 designated cultural and natural landmarks. From the Dolomites to the Amalfi Coast, discover ancient ruins, historic city centers, and beautiful natural landscapes.
