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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 as our friendly local drivers share their insights or give tips on what to do at your destinations. With our door to door service, you can sit back and enjoy the ride while we handle the driving, allowing you to discover unique destinations and make memories to last a lifetime!
Travel in style with Tripmasters Chauffeured Collection packages! From iconic cities like Rome, Florence, and Venice to the idyllic countryside of Tuscany and the rugged coastlines of Cinque Terre, Amalfi, and Sicily, see ancient ruins, world class art and architecture, and enjoy delicious food and wine.
Explore our favorite Italian cities and hidden gems, including Montepulciano and UNESCO-listed cities Ferrara and San Gimignano, with private transfers. Begin this twist on our classic Italy getaway in historic Rome (the Eternal City) where the Colosseum looms large and the Vatican's treasures await discovery, and after that, travel to Florence (the capital of Tuscany and cradle of the Renaissance), until you finally reach Venice (the intimate city set on canals famous for gondola rides). Enjoy private transfers between each city that allow you to avoid the hassle of train stations and explore the following scenic towns: Montepulciano (renowned for its exquisite Vino Nobile Wine), San Gimignano (characterized by its medieval architectural towers) and Ferrara (a well-preserved UNESCO-listed city with rich history).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
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Experience Southern Tuscany and Cinque Terre in depth. From Florence (the capital of Tuscany and birthplace of the Renaissance), travel through Southern Tuscany and visit Siena (famous for its cuisine, art, museums, medieval cityscape, and horse races in Piazza del Campo). After that, have a pleasant stay at La Spezia (a Ligurian seaside resort), very close to the marvelous Cinque Terre Area (a string of centuries-old seaside villages on the rugged Italian Riviera Coastline). 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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Includes:
7 nights from $2,609*
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Italy`s boot and capital city!. Combine pleasant stays in Rome (the Eternal City) with the essential highlights of Sicily Island, including: Palermo (history, culture, architecture and outdoor street markets), the Greek influenced of Agrigento (with its Valley of the Temples), Taormina (with its famous Ancient Greek Theatre) and Catania (cultural, artistic, economical and political centre in Sicily, with imposing mountains and marine reserves). An intercity flight and a private door-to-door service with a stop to visit the UNESCO Heritage Site of Castello di Caccamo (Sicily's largest and best-preserved Norman castles).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
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The 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.
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7 nights from $3,751*
Customize itDreamy Italian Tuscany and Riviera!. Combine unforgettable stays at these Tuscany cities: Florence (capital of Tuscany; home to Renaissance Art and Architecture) and Lucca (fantastic medieval city walls that still encircle most of the historic old town); with Santa Margherita Ligure (a charming fishing village) and port city of Genoa (rich cultural heritage encompassing art, music, and culinary traditions) in Italy's Riviera Coast. By private door to door service stops along your way, visit Pisa (world-renowned Leaning Tower), Prato (textil industry, traditional cuisine and wines) and at the Genoese Coast, Castello di Lerici (medieval prison and fortress with spectacular views).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Includes:
8 nights from $1,943*
Customize itDiscover Italy's charms: Rome, Sorrento, Pompeii, and the Amalfi Coast. Begin your journey in Rome (the Eternal City, where you can discover iconic landmarks such as the Colosseum and the Roman Forum, along with world-renowned Italian cuisine and vibrant street life). Continue to Sorrento (charming coastal town overlooking the Bay of Naples). Along the way, stop at the UNESCO World Heritage Site of Pompeii (entrance tickets not included), one of Italy’s most important archaeological destinations. End your trip in breathtaking Amalfi (celebrated for its dramatic cliffs and crystal-clear waters). En route, visit the fascinating Stabia Archaeological Site and the iconic village of Positano, known for its steep streets, pastel houses, and coastal charm.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
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Tuscany and Italian Riviera!. Combine pleasant stays in Florence (capital of Tuscany; home to Renaissance Art and Architecture) with Santa Margherita Ligure (a charming fishing village) and port city of Genoa (rich cultural heritage encompassing art, music, and culinary traditions) in Italy's Riviera Coast, thanks to private door to door service including stops at Montecatini Alto (medieval hilltop town with ancient fortress ruins) and Lucca (with well-preserved Renaissance-era city walls).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Includes:
7 nights from $1,782*
Customize itWonderful Italian Sicily!. Discover Palermo (noted for its history, culture, architecture and outdoor street markets), Agrigento (home to the Valley of the Temples with the best preserved Greek ruins outside Greece), Syracuse -Siracusa- (a former stronghold of the Greek empire; full of medieval and Baroque buildings), and finally Taormina (overlooking the Ionian Sea, with countless stores, cafes, piazzas, and breathtaking vistas). Connect these destintions along your way, by door-to-door service with stops at these UNESCO Heritage Sites: Castello di Caccamo (Sicily's largest and best-preserved Norman castles), Piazza Armerina (famous Villa Romana del Casale and Roman mosaics) and Necropolis of Pantalica (most important Iron and Bronze Age necropolis).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
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Explore Italy!. Visit artistic Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture), continue to Assisi (best known as the birthplace of St. Francis, Italy's patron saint, in Umbria's rolling hills) with a stop in Loro Ciuffenna and Perugia. After that, visit Cortona (famous for its traditions, history, culture and its magnificent landscapes as well as its artisan industries) with a stop in Castiglio Fiorentino. Lastly, Lucca (it is known throughout Italy for its fantastic medieval city walls that still encircle most of the historic old town) with a stop in Pisa and Montecatini Alto. Before heading back home, return to Florence with a stop in Prato.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Includes:
8 nights from $2,619*
Customize itDiscover rich heritage sites of the Italian capital and other main cities!. Explore historic highlights and consequential neighborhoods of the Eternal City of Rome (with its stunning architecture like the Colosseum and the Roman Forum and delicious food) then take a transfer to Amalfi Town (beautiful small seaside resort, with distinctive architecture, crystal blue waters, and local delicacies), on the scenic Amalfi Coast (known for its stunning coastline, cliffs, and beaches and colorful villages with steep and narrow streets) with a stop in Pompeii.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Includes:
6 nights from $1,524*
Customize itSouthern Tuscany Getaway!. From Florence (capital of Tuscany; home to Renaissance Art and Architecture), travel Southern Tuscany and visit Siena (famous for its cuisine, art, museums, medieval cityscape, horse races in Piazza del Campo). After that, have a pleasant stay at Cortona (famous for its traditions, history, culture and its magnificent landscapes as well as its artisan industries). Finally, get back for one last night stay in Florence. Along your way, by door-to-door service between these destinations discover: medievals Monteriggioni and San Gimignano (famous towers and wine); Montepulciano and Lucignano.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Includes:
7 nights from $1,990*
Customize itVisit Florence and Umbria!. Visit artistic Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture), continue to Assisi (best known as the birthplace of St. Francis, Italy's patron saint, in Umbria's rolling hills) with a stop in Loro Ciuffenna and Perugia. After that, visit Orvieto (a small city perched on a rock cliff in Umbria, Italy) via Todi. Lastly, Siena (famous for its cuisine, art, museums, medieval cityscape, horse races in Piazza del Campo) with a stop in Montepulciano and Lucignano. Before heading back home, return to Florence, visting on the way Monteriggioni and San Gimignano.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Includes:
8 nights from $2,368*
Customize itFind the soul of Italy in the warm glow of the Tyrrhenian sun! Walking down the streets of Naples (a vibrant, edgy city that defines La Dolce Vita, for which Italy is famous) you find markets and main atractions; but even better, you will enjoy unforgettable views over the sea cruising along the scenic Amalfi Coast (stunning cliffs, beaches and colorful villages with steep and narrow streets) and to Capri Island from Sorrento (a lively coastal town famous for its Limoncello liquor and a good base for visiting the ancient sites of Pompeii and Herculaneum). Your Chauffeured Collection Transfers ensure effortless exploration, with stops to discover: the Roman frescoes of Villa de Poppaea and Ravello, the Stabia Archeolofical Site and the beauty of Positano (dramatic vertical landscape, colorful houses cascading down to the sea).
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!
Includes:
6 nights from $2,500*
Customize itExplore Europe your way with Tripmasters customizable vacation packages. Discover the continent’s timeless beauty, where centuries of history, vibrant cultures, and breathtaking landscapes come together at every turn. From grand capitals like London, Paris, and Rome to charming villages and bucolic countryside, every journey offers something new to experience.
Europe is a dream come true for foodies with charming cafes, five star restaurants, sensational street food, and delicious desserts. And don't forget to top it off with a glass of wine!
Experience Europe from the comfort of 'home' with our Apartment Edition packages. Our curated apartment-style accommodations are ideal for families!
As over tourism continues to impact some of Europe's most popular destinations, travelers are seeking less crowded alternatives that offer a similar experience, often at a lower cost.
Tripmasters has taken the guesswork out of your travel plans with our premier vacation package options! From apartment stays to inclusive packages with private door-to-door transfers or curated activities, you deserve a vacation tailored just for you!
For travelers seeking a more immersive, stress-free vacation, staying in one destination and exploring its surroundings provides a richer, more meaningful travel experience.
Experience the 'Best of' Europe with thoughtfully curated packages including activities to suit a variety of interests from culture & history to art & cuisine!
Immerse yourself in the diverse tapestry of experiences on offer with Tripmasters' expertly curated luxury packages tailored to your individual preferences.
Tripmasters Chauffeured Collection Transfers are private, door-to-door transfers between cities. This service replaces commonly used alternative methods, such as trains, buses, or rental cars. It also gives you the opportunity to explore sights and attractions along the way. We drive, you discover.
The drivers are locals who are familiar with the cities you are visiting, as well as any stops included. While they are not guides, they are more than happy to discuss their personal knowledge and make recommendations. Our partner drivers speak English in addition to their native language, so if you’re looking to practice your Italian, go ahead! Additionally, all drivers must submit their traffic records. All cars must be less than ten years old, in excellent operating condition, and insured as required by local law. Drivers must provide the registration, insurance, and technical inspection record. And because the drivers are locals, they’re familiar with the rules and customs of the road. This provides a safer, more relaxing experience for you.
You will receive the vehicle that best suits the number of travelers in your group, ranging from sedans to vans for groups of up to six. Depending on where you travel, you may end up with anything from a sedan comparable to a Toyota Corolla to a Mercedes V-Class. While the exact model may vary, we always ensure that the vehicle provided meets your needs in terms of safety, reliability, and comfort. You may be upgraded to a larger vehicle class free of charge depending on availability. Since the largest vehicle seats six, for groups larger than six, a combination of vehicles will be used. We will send you the exact vehicle details a few days before your trip.
Your driver can pick you up at your hotel, apartment, or any other pick-up point accessible by car. This also applies to your drop-off location. No need to worry about buses, cabs, or other connections – we provide door-to-door service! If you happen to be in a pedestrian-only area, your driver will meet you at a designated pick-up location.
Your driver will meet you at the agreed time and place and won’t be contacting you before, unless necessary. You’ll receive a reminder with your driver’s name and mobile number a few days before departure in case you need to contact them.
We understand that sometimes it’s hard to tear yourself away from your sightseeing stop. If you find you’d like extra time, please make arrangements directly with your driver. There will be an hourly fee based on the country in which you are traveling. While they’ll do their best to accommodate, sometimes their schedule won’t allow for them to stay longer.
Everywhere except the USA, drivers will supply appropriate child seats (just let us know during booking). In the USA, certain states require you to supply your own child seats.
