Lesser Antilles Islands Vacation Packages
The Windward Islands and the Leeward Islands make up the Lesser Antilles of the Caribbean. This is a sizeable region that stretches from the Caribbean's northern edge to the coast of South America. The common threads throughout are the gorgeous idyllic beaches and annual warm temperatures. The area has drawn visitors for centuries seeking epic adventures, relaxation, jaw-dropping landscapes, and amazing surf while being surrounded by stunning turquoise waters.
Best Vacation Packages
Explore the best vacation packages for the Lesser Antilles Islands. This tropical paradise forms one of the most sought-after destinations in the Caribbean. Stretching from the northern edge of the Caribbean Sea down to the coast of South America, the Lesser Antilles offer travelers breathtaking beaches, lush landscapes, and a mix of cultures that make every island unique.
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Antigua Island Escape
4 nights from $1,418
Under the Caribbean Sun, enjoy unforgettable moments with this vacation package in Antigua and Barbuda. Have an splendid stay in Antigua Island; this ...
Antigua Island Escape
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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into and out of Antigua Island
- Hotel for 4 nights in Antigua Island
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Miami and Antigua Island by Air
6 nights from $1,745
What better combination for your vacation than the pure excitement of Florida and the breathtaking views in Antigua and Barbuda!. Start in Miami ...
Miami and Antigua Island by Air
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!).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into Miami and out of Antigua Island
- Hotel for 3 nights in Miami
- Flight from Miami and Antigua Island
- Hotel for 3 nights in Antigua Island
6 nights from $1,745*
Customize it -
Aruba Island Escape
4 nights from $1,379
Discover the fascinating Caribbean visiting Aruba with this holiday package. Explore Aruba Island, North of Venezuela, famous for its stunning blonde ...
Aruba Island Escape
Discover the fascinating Caribbean visiting Aruba with this holiday package. Explore Aruba Island, North of Venezuela, famous for its stunning blonde beaches, wind-sculpted desert landscapes, and some of the best wreck diving in the Caribbean. Enjoy this package for 4 days.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into and out of Aruba
- Transfer from Airport to Hotel
- Hotel for 4 nights in Aruba Island
- Transfer from Hotel to Airport
Easily upgrade your vacation to a Luxury Private Guided Experience, featuring upgraded hotels, private transportation between cities, and more!
Suggested Itineraries
Discover Featured Vacation Itineraries Across the Lesser Antilles, Caribbean Islands, and Beyond, where turquoise waters, pristine beaches, and vibrant island cultures create unforgettable travel experiences. From the idyllic Leeward and Windward Islands to other top Caribbean getaways, explore customizable vacation packages designed for every type of traveler.
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Essential Panama City and Aruba by Air
6 nights from $1,559
The Hub of the Americas; Panama and The Happy Island; Aruba awaits you with this customizable package offering an unforgettable experience!. Visit ...
Essential Panama City and Aruba by Air
The Hub of the Americas; Panama and The Happy Island; Aruba awaits you with this customizable package offering an unforgettable experience!. Visit Panama City (most attractive Capital City and a curious blend of old Spain, modern America and the bazaar atmosphere of the East) and then, spend glorious days under the sun in paradise; Aruba Island (famous for its stunning blonde beaches, wind-sculpted desert landscapes, and some of the best wreck diving in the area).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into Panama City and out of Aruba Island
- Hotel for 3 nights in Panama City
- Flight from Panama City to Aruba Island
- Hotel for 3 nights in Aruba Island
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Curacao Island Escape
4 nights from $872
A Caribbean holiday in Curacao! One of the beautiful Dutch Antilles Islands is offered in this customizable package! Under the Caribbean Sun, enjoy ...
Curacao Island Escape
A Caribbean holiday in Curacao! One of the beautiful Dutch Antilles Islands is offered in this customizable package! Under the Caribbean Sun, enjoy unforgettable moments in Curacao Island; with its European-style architecture, white sand beaches and its moving pontoon bridge. It's also very famous for its orange-flavored liqueur.
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 supportIncludes:
- Flight into and out of Curacao Island
- Hotel for 4 nights in Curacao Island
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A holiday under the sun with this customizable package visiting Panama and Curacao. Combine the exciting Panama City (known for the Panama Canal, ...
Essential Panama City and Curacao by Air
A holiday under the sun with this customizable package visiting Panama and Curacao. Combine the exciting Panama City (known for the Panama Canal, this lively Latin American city also borders one of Central America's richest rain forest); and then, take a flight to Curacao (famous for its moving pontoon bridge, European-style architecture, orange-flavored liqueur and white sand beaches).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into Panama City and out of Curacao Island
- Hotel for 3 nights in Panama City
- Flight from Panama City to Curacao Island
- Hotel for 3 nights in Curacao Island
6 nights itinerary
Customize it -
St. Croix Island Escape (US Virgin Islands)
4 nights from $749
A holiday under the sun with this customizable package visiting the Caribbean The Virgin Islands. Explore the exciting St. Croix, one of the most ...
St. Croix Island Escape (US Virgin Islands)
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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into and out of St. Croix Island
- Hotel for 4 nights in St. Croix Island
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St. Thomas Island Escape (US Virgin Islands)
4 nights from $1,388
US Virgin Islands is the perfect destination for an unforgettable holiday in the Caribbean. The St. Thomas Island (is the second largest and most ...
St. Thomas Island Escape (US Virgin Islands)
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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into and out of St. Thomas Island
- Hotel for 4 nights in St. Thomas Island (US Virgin Islands)
Island Groups
Stretching in a sweeping arc from the northeastern Caribbean (Virgin Islands) down to the South American coast are the Lesser Antilles Islands. Surrounded by the Caribbean Sea and Atlantic Ocean, they're famous for white-sand beaches, cultural richness, coral reefs, and turquoise waters.
Customer Reviews
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5 out of 5
Yet another amazing vacation made easier and less expensive by Tripmasters! Don''t change a thing ...
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5 out of 5
We stayed at the Sugar cane club and Spa. It was a beautiful hotel. The staff were very friendly and helpful with all our needs. We added the all inclusive package at the hotel which was well worth it.The end of February and the beginning of March wa ...
Interests
Discover More Caribbean Attractions and Activities with These Interest-Themed Vacations, from sun-soaked beaches and world-class diving spots to vibrant cultural festivals, historical landmarks, and eco-adventures that showcase the diversity of the islands.
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Honeymoon in the Caribbean
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.
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Best Nightlife in the Caribbean
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!
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Luxury Islands of the Caribbean
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 located.
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Family Fun in the Caribbean
People know that the Caribbean is a popular destination for solo travelers and for couples, but did you know that the Caribbean is known for its fun family vacation destinations as well?
More to Explore
Uncover additional fascinating travel destinations, including the Lucayan Archipelago, Costa Rica, and the Greater Antilles, each offering a unique blend of natural wonders, vibrant cultures, lush rainforests, and unforgettable vacation experiences.
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Greater Antilles
The Greater Antilles is a grouping of the larger islands in the Caribbean Sea, including Cuba, Hispaniola, Puerto Rico, Jamaica, and the Cayman Islands.
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Costa Rica
With jaw-dropping landscapes, friendly locals and epic adventures to be had, it’s no wonder why tourists flock to Costa Rica. Discover the waterfalls, volcanoes and amazing surf in this Central American gem.
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Lucayan Archipelago
The Lucayan Archipelago, also known as the Bahama Archipelago, is an island group comprising the Commonwealth of The Bahamas and the British Overseas Territory of the Turks and Caicos Islands.
Experiences & Adventure
Unforgettable Experiences Await in Mexico, Central America, and the Idyllic Islands of the Caribbean, from ancient UNESCO World Heritage Sites and tropical beaches to lively Carnival celebrations and unique cultural encounters.
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Carnival in Mexico and the Caribbean
Carnival in Mexico and the Caribbean showcases some of the best aspects of Caribbean culture, with music, dance, history, and vibrancy of West Indians.
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UNESCO World Heritage Sites of the Caribbean
The Caribbean is filled with some of the most brilliant and beautiful places in the world, an exceptional place offering 23 UNESCO World Heritage Sites spread across 14 islands.
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Idyllic Islands of Central America
Central America is packed with outstanding natural beauty and is home to some of the most magnificent idyllic islands in the entire world.
