Luxury Vacations
Pamper yourself with our chauffeured luxury series. Select among options of the best properties and experiences in each city. Upgrade to premium seats on flights. Avoid the hassle of transportation between destinations with hotel to hotel private transfers that include emblematic stops along the way that you would otherwise miss.
Best Luxury Vacation Packages
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Exclusive Rome - Florence - Venice (Chauffeured Collection)
9 nights from $3,849*This 9 nights sample itinerary includes:
- Flight into Rome and out of Venice
- Private arrival transfer in Rome
- 4-Star or better hotels for for 3 nights each in Rome, Florence, and Venice
- Private driver from Rome to Florence with stops in the UNESCO-listed Tuscan villages of San Gimignano and Montepulciano
- Private driver from Florence to Venice (Piazzale Roma Terminal) with a stop in the UNESCO-listed city of Ferrara
Please note: Boat transfer from Venice port to the closest hotel dock not included; guests must book it independently- Private departure transfer from Venice
- Live phone and chat support
Included Private Activities (Based on Availability): - Rome Colosseum Tour
- Food Tours in Rome and Venice
- Guided City Tour in Florence
- Accademia and Uffizi Galleries Visit in Florence
We do our best to fulfill all additional experiences; however, sometimes, our partners are unavailable on select dates. In those rare instances, your price will only reflect confirmed and available experiences. If an included activity becomes unavailable, alternate options may be available to purchase.
Learn more about: Rome | Florence | Venice
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Exclusive Prague - Vienna - Budapest (Chauffeured Collection)
9 nights from $2,339*This 9 nights sample itinerary includes:
- Flight into Prague and out of Budapest
- Private arrival transfer in Prague
- 4-Star or better hotels for 3 nights each in Prague, Vienna and Budapest
- Private driver from Prague to Vienna with stops at the UNESCO-listed Kutna Hora and Lednice Chateau
- Private driver from Vienna to Budapest with stops at Liechtenstein Castle and the UNESCO-listed Pannonhalma Archabbey
- Private departure transfer from Budapest
- Live phone and chat support
Included Private Activities (Based on Availability): - Guided City Tours in Prague, Vienna, and Budapest, visiting iconic sites and popular neighborhoods
- Food Tour around Prague
- Classic Music Concert in Vienna (Public Venue)
We do our best to fulfill all additional experiences; however, sometimes, our partners are unavailable on select dates. In those rare instances, your price will only reflect confirmed and available experiences. If an included activity becomes unavailable, alternate options may be available to purchase.
Learn more about: Prague | Vienna | Budapest
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Exclusive Arenal - Monteverde - Manuel Antonio (Chauffeured Collection)
8 nights from $4,119*This 8 nights sample itinerary includes:
- Flight into and out of San Jose City
- Private arrival transfer from San Jose City to Arenal Volcano Area
- Upgraded, curated hotels for 3 nights in Arenal Volcano Area and Monteverde and 2 nights in Manuel Antonio (Quepos)
- Private driver from Arenal Volcano to Monteverde Cloud Forest, including a sightseeing tour of Arenal's hanging bridges and rainforest
- Private driver from Monteverde Cloud Forest to Manuel Antonio (Quepos) with a sightseeing stop at the famous Tarcoles Bridge
- Private departure transfer from Manuel Antonio (Quepos) to San Jose City
- Live phone and chat support
Included Private Activities (Based on Availability): - Guided hike around the Arenal Volcano, visit the La Fortuna waterfall, and enjoy a typical Costa Rican-style lunch
- Enjoy a morning sloth-spotting tour and later bask in the relaxing Paradise Hot Springs, ending with dinner
- Hike the Reserva Santa Elena in Monteverde
- Savor the Don Juan Coffee and Chocolate Tour in Monteverde
We do our best to fulfill all additional experiences; however, sometimes, our partners are unavailable on select dates. In those rare instances, your price will only reflect confirmed and available experiences. If an included activity becomes unavailable, alternate options may be available to purchase.
Learn more about: Arenal | Monteverde | Manuel Antonio
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Exclusive Lisbon and Porto Experience (Chauffeured Collection)
6 nights from $1,739*This 6 nights sample itinerary includes:
- Flight into Lisbon and out of Porto
- Private arrival transfer in Lisbon
- 4-Star or better hotels for 3 nights each in Lisbon and Porto
- Private driver from Lisbon to Porto with a stop at the UNESCO-listed Monastery of Batalha
- Private departure transfer from Porto
- Live phone and chat support
Included Private Activities (Based on Availability): - Guided City Tours of Lisbon and Porto, visiting iconic sites and popular neighborhoods
- Dinner and Fado Show in Lisbon
- Day Trip to Douro Wine Valley from Porto
We do our best to fulfill all additional experiences; however, sometimes, our partners are unavailable on select dates. In those rare instances, your price will only reflect confirmed and available experiences. If an included activity becomes unavailable, alternate options may be available to purchase.
Learn more about: Lisbon | Porto
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Exclusive Rome - Sorrento - Amalfi (Chauffeured Collection)
7 nights from $3,339*This 7 nights sample itinerary includes:
- Flight into Rome and out of Naples
- Private arrival transfer in Rome
- 4-Star or better hotels 3 nights in Rome and 2 nights each in Sorrento and Amalfi Town
- Private driver from Rome to Sorrento with a stop at UNESCO-listed Pompeii (entrance not included)
- Private driver from Sorrento to Amalfi Town with stops at Stabia Archeological Site (entrance not included) and Positano
- Private departure transfer from Amalfi Town to Naples Airport
- Live phone and chat support
Included Private Activities (Based on Availability): - Colosseum Tour in Rome
- Food Tour in Rome
- Capri Island Cruise from Sorrento (Small Group)
We do our best to fulfill all additional experiences; however, sometimes, our partners are unavailable on select dates. In those rare instances, your price will only reflect confirmed and available experiences. If an included activity becomes unavailable, alternate options may be available to purchase.
Learn more about: Rome | Sorrento | Amalfi
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Exclusive Marrakech - Casablanca - Fez (Chauffeured Collection)
7 nights from $2,079*This 7 nights sample itinerary includes:
- Flight into Marrakech and out of Fez
- Private arrival transfer in Marrakech
- 4-Star or better hotels for 3 nights in Marrakech and 2 nights each in Casablanca and Fez
- Private driver from Marrakech to Casablanca with a stop at UNESCO-listed El Jadida
- Private driver from Casablanca to Fez with stops at UNESCO-listed Volubilis and Sale
- Private departure transfer from Fez
- Live phone and chat support
Included Private Activities (Based on Availability): - Guided Tour of the Medina in Marrakech
- Traditional Dinner in Marrakech
- Guided City Tours of Casablanca and Fez, visiting iconic sites and popular neighborhoods
We do our best to fulfill all additional experiences; however, sometimes, our partners are unavailable on select dates. In those rare instances, your price will only reflect confirmed and available experiences. If an included activity becomes unavailable, alternate options may be available to purchase. - Ramadan is a month of spirituality and purification during which participants abstain from eating, drinking, and smoking. Ramadan is typically celebrated in late winter or early spring.
Please verify dates before booking travel because food and entertainment services in hotels and other public places may be affected.
Looking for something else? For a curated package with wider hotel and activity options, try our Experience Series that includes recommended hotels and transportation and optional hand-picked activities that you can customize based on your preferences and availability!
Learn more about: Marrakech | Casablanca | Fez
Don’t see the perfect fit? Build Your Own Luxury Trip
BUILD YOUR OWN LUXURY TRIP
Curating the Extraordinary
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What makes Tripmasters "Expertly-Curated" travel itineraries different?
Our expertly-curated journeys focus on the "5 C's" of luxury: culture, cuisine, community, content, and customization. Unlike standard tours, our bespoke travel itineraries are designed exclusively for you, pairing you with dedicated staff and flexible daily schedules. This ensures your travel is purposeful, private, and entirely exclusive.
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What's included in a Tripmasters luxury vacation package?
Our luxury vacation packages typically include 5-star accommodations, private chauffeur transfers between destinations, expertly guided custom tours, and curated VIP experiences tailored to your interests. Many itineraries also offer suite upgrades, premium flight options, and exclusive access to cultural, culinary, or scenic highlights.
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What transportation services are included in my luxury vacation package?
You will have a private chauffeur who provides discreet door-to-door transportation between hotels, airports, and key attractions. Many routes include scenic stops for sightseeing, dining, or photography, turning transfers into immersive travel experiences rather than simple point-to-point rides.
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Which destinations does Tripmasters offer for luxury vacation experiences?
Tripmasters offers unique tailor-made adventures across the world’s most extraordinary destinations, including the Amalfi Coast, Morocco, Costa Rica, Tokyo, Osaka, and other iconic regions in Europe, Africa, and Asia. Each destination is carefully selected and personalized to your interests.
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Why choose Tripmasters for your luxury vacation experience?
Tripmasters offers a seamless, concierge-level planning experience for less. Our expertly crafted, privately guided vacation packages are ready to book, but can be easily customized with alternate hotels and activities to suit your interests. Our personalized, multi-destination itineraries deliver the same level of luxury offered by top travel agencies, but at a significantly lower price. You’re in good hands with Tripmasters dedicated travel specialists.