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Located towards the north of the Lesser Antilles island chain, the Leeward Islands are a beautiful, interesting, and diverse group of islands that for centuries, have drawn explorers, boaters, traders and adventurers! Discover the fabulous beaches of St. Maarten and St Barts, delve into the history of St Kitts, climb Nevis Peak and sample many of the superb eateries that Anguilla has to offer. This is also where you'll find the palm-fringed US Virgin Islands and British Virgin Islands, along with Guadeloupe, a French Caribbean island.
Discover the best vacation packages for the Leeward Islands, featuring the stunning beaches of St. Maarten and St. Barts, the rich history of St. Kitts, the scenic hike up Nevis Peak, and the world-class dining experiences of Anguilla. Explore these Caribbean gems with easy, customizable, curated itineraries that combine relaxation, adventure, and culture for an unforgettable island getaway.
A holiday under the sun with this customizable package visiting Florida State and The Virgin British Islands Start in the exciting Sunshine State; in ...
A holiday under the sun with this customizable package visiting Florida State and The Virgin British Islands Start in the exciting Sunshine State; in Miami (where Miami and South Beaches await you); and then, catch a fight to the largest of the British Virgin Islands; St. Croix Island (one of the most renowned attractions in the U.S.V.I. The Buck Island National Park is located a short distance from the St).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
6 nights from $1,449*
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A Caribbean holiday in the largest of the British Virgin Islands!. Tortola Islands; a lush mountainous Island which was formed by volcanic activity, ...
A Caribbean holiday in the largest of the British Virgin Islands!. Tortola Islands; a lush mountainous Island which was formed by volcanic activity, it features several white-sand beaches, including Cane Garden Bay and Smuggler’s Cove to enjoy pleasant days under the sun.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
4 nights from $1,319*
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Panama and Sint Maarten await you, ready to be explored. Start in the "The Hub of the Americas"; Panama City (known for the Panama Canal, this lively ...
Panama and Sint Maarten await you, ready to be explored. Start in the "The Hub of the Americas"; Panama City (known for the Panama Canal, this lively Latin American city also borders one of Central America's richest rain forest). Continue, with an fantastic stay in St. Maarten Island (the Dutch side is known for its festive nightlife, beaches and casinos. The island's French side is known for its nude beaches, shopping and food). Connect these destinations with an intercity flight.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
6 nights from $1,553*
Customize it
A holiday under the sun with this customizable package visiting Florida State and The Virgin British Islands. Start in the exciting Sunshine State; ...
A holiday under the sun with this customizable package visiting Florida State and The Virgin British Islands. Start in the exciting Sunshine State; in Miami (where Miami and South Beaches await you); and then, catch a fight to the largest of the British Virgin Islands; Tortola Island (a lush mountainous Island which was formed by volcanic activity, it features several white-sand beaches, including Cane Garden Bay and Smuggler’s Cove to enjoy pleasant days under the sun).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
6 nights from $1,739*
Customize itExplore the Leeward Islands and beyond with completely customizable multi-destination vacation packages. Tailor your getaway by choosing your hotels, tours, activities, and more for the ultimate Caribbean travel experience.
Discover Florida and St Bart's with this holiday package. Combine Miami (well known for its beaches, such as Miami Beach and South Beach, as well as ...
Discover Florida and St Bart's with this holiday package. Combine Miami (well known for its beaches, such as Miami Beach and South Beach, as well as endless shopping opportunities) and St Barts (French-speaking Caribbean island commonly known as St. Barts, is known for its white-sand beaches and designer shops). These destinations are connected by flights.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
6 nights from $5,589*
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Under the Caribbean Sun, enjoy unforgettable moments with this vacation package in Antigua and Barbuda. Have an splendid stay in Antigua Island; this ...
Under the Caribbean Sun, enjoy unforgettable moments with this vacation package in Antigua and Barbuda. Have an splendid stay in Antigua Island; this former British colony, has become a culinary destination because of its beautiful beaches, historic buildings, the wealth of seafood in its oceans, the quality rums in its glasses, and the joy in its people.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
A Caribbean holiday in these two lesser Antilles Islands; St. Kitts and Nevis, for a stay that won't be forgotten. Explore St Kitts (first Caribbean ...
A Caribbean holiday in these two lesser Antilles Islands; St. Kitts and Nevis, for a stay that won't be forgotten. Explore St Kitts (first Caribbean island to be colonized by the British, known for its historic downtown, Scenic Railway, national parks, and beaches) and Nevis (known as The "Queen of the Caribbean; boasts amazing mountain views, stunning white sand beaches, rich cuisine and wildlife).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
4 nights from $942*
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Holidays under the sun is offered in this package, visiting; Florida State and US Virgin Islands. Have a splendid stay in Miami (with its nightlife ...
Holidays under the sun is offered in this package, visiting; Florida State and US Virgin Islands. Have a splendid stay in Miami (with its nightlife attractions, and well known beaches, like Miami and South Beach). After that, take a flight to the second largest and most developed of the US Virgin Islands; St. Thomas Island (the gateway to the Caribbean, with its amazing beaches and snorkeling spots).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
6 nights from $1,899*
Customize it
A Caribbean unforgettable holiday waits to you in this package in St. Maarten. Officially known as "The Friendly Island"; St. Maarten Island, ...
A Caribbean unforgettable holiday waits to you in this package in St. Maarten. Officially known as "The Friendly Island"; St. Maarten Island, comprises of 2 separate countries, divided between its northern French side, called Saint-Martin, and its southern Dutch side, Sint Maarten. While, St. Martin's Dutch side is known for its festive nightlife, beaches and casinos; the island's French side is known for its nude beaches, shopping and French and Indian Caribbean cuisine.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
A holiday under the sun with this customizable package visiting the Caribbean The Virgin Islands. Explore the exciting St. Croix, one of the most ...
A holiday under the sun with this customizable package visiting the Caribbean The Virgin Islands. Explore the exciting St. Croix, one of the most renowned attractions in the U.S.V.I., the Buck Island National Park is located a short distance from the St. Croix..
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
What better combination for your vacation than the pure excitement of Florida and the breathtaking views in Antigua and Barbuda!. Start in Miami ...
What better combination for your vacation than the pure excitement of Florida and the breathtaking views in Antigua and Barbuda!. Start in Miami (active nightlife, great food and beaches). Then, catch a flight to Antigua and Barbuda, in the Eastern Caribbean; in Antigua Island (a culinary destination because of the wealth of seafood in its oceans, the quality rums in its glasses, and the joy in its people, and of course its amazing beaches!).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
6 nights from $1,149*
Customize it
US Virgin Islands is the perfect destination for an unforgettable holiday in the Caribbean. The St. Thomas Island (is the second largest and most ...
US Virgin Islands is the perfect destination for an unforgettable holiday in the Caribbean. The St. Thomas Island (is the second largest and most developed of the US Virgin Islands, known as the gateway to the Caribbean) and offer you unlimited miles of beaches with white sands, perfect for relaxation.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
Get away from it all with this customizable package that lets you visit Florida State and St. Maarten. Start your trip in Miami (the city and the ...
Get away from it all with this customizable package that lets you visit Florida State and St. Maarten. Start your trip in
Miami (the city and the metropolitan area are well known for its beaches, such as Miami Beach and South Beach). Then, catch a flight to
St. Maarten Island (St. Martin's Dutch side is known for its festive nightlife, beaches and casinos. The island's French side is known for its nude beaches, shopping and French and Indian Caribbean cuisine).
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
6 nights from $1,089*
Customize it
Travel through Florida and Caribbeanlike never before, visiting Miami (well known for its beaches, such as Miami Beach and South Beach, as well as ...
Travel through Florida and Caribbeanlike never before, visiting Miami (well known for its beaches, such as Miami Beach and South Beach, as well as endless shopping opportunities) and St. Kitts and Nevis Islands (the larger of the 2 Caribbean islands that comprise the nation of Saint Kitts and Nevis. It’s known for rain forested mountains and beaches of white, gray, and black sands) by air.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
6 nights from $1,079*
Customize it
Discover why St. Barthelemy or St. Barths is one of the most amazing island at the Caribbean!. With this holiday package spend unforgettable moments ...
Discover why St. Barthelemy or St. Barths is one of the most amazing island at the Caribbean!. With this holiday package spend unforgettable moments in this glamorous French-speaking Caribbean island; with its white sandy tropical beaches, boutiques, duty free shops, fancy restaurants and art galleries line the streets, luring passengers disembarking from the many cruise-ships that call here.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
4 nights from $2,167*
Customize it
An exciting adventure through the Caribbean. Discover Anguilla Island one of the most northerly of the Leeward Islands in the Lesser Antilles, lying ...
An exciting adventure through the Caribbean. Discover Anguilla Island one of the most northerly of the Leeward Islands in the Lesser Antilles, lying east of Puerto Rico and the Virgin Islands and directly north of Saint Martin.
What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support
Includes:
4 nights from $3,183*
Customize itExplore the best of the stunning Leeward Islands in the Caribbean, from pristine white-sand beaches and turquoise waters to vibrant culture and unforgettable vacation experiences.
Yet another amazing vacation made easier and less expensive by Tripmasters! Don''t change a thing ...
The 68 room all adult hotel was superb!!! Although not equipped with all the amenities that we have become so accustomed to, it was most adequate for us. Additionally, the staff was simply magnificent ...
Discover exciting ways to experience the Caribbean Islands with top vacation ideas designed for every type of traveler. From luxury resorts and cultural escapes to family-friendly fun and unforgettable adventures, the Caribbean offers endless opportunities to explore.
When travelers look into booking a honeymoon vacation, they are usually looking for three things: how romantic the locale is, and how luxurious and peaceful the honeymoon will be.
Millions of travelers come to the Caribbean each year for the heady nightlife. When you are done sightseeing or sunbathing for the day, take some time for yourself to rest and renew, and then get ready for a night on the town!
The Caribbean is well-known for being the playground of the rich, and even if you aren`t a millionaire yourself, you can get a taste of the good life at a large number of hotels and resorts.
When travelers look into booking a honeymoon vacation, they are usually looking for three things: how romantic the locale is, and how luxurious and peaceful the honeymoon will be.
Uncover more travel opportunities across the Caribbean, including Mexico and the Greater Antilles, highlighting stunning beaches, vibrant culture, and exciting experiences.
The Greater Antilles is a grouping of the larger islands in the Caribbean Sea, including Cuba, Hispaniola, Puerto Rico, Jamaica, and the Cayman Islands.
Mexico, a country rich with diversity and culture. For travelers looking to relax and sip on margaritas by the beach, visit Cancun.
For being such a small country (330,000 people), Belize has it all: caving, snorkeling, kayaking, gambling, and of course, amazing new foods and drinks.
