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The Greater Antilles are the largest islands in the northwestern portion of the Caribbean Sea and include the Cayman Islands, Haiti and the Dominican Republic, Cuba, Jamaica, and Puerto Rico. Come to the Greater Antilles for relaxation or adventure, and to experience these French, Spanish, English, and Creole speaking islands as well as their vibrant cultures, cuisine, and history.
Discover the beauty of the Greater Antilles with our customizable vacation packages, designed to highlight the region’s most iconic islands. Enjoy pristine beaches, lively nightlife, rich history, and cultural traditions that make each island unique.
Escape to the Caribbean Paradise with this holiday package in Puerto Rico. Enjoy San Juan an island, known for its beautiful beaches and Spanish ...
Escape to the Caribbean Paradise with this holiday package in Puerto Rico. Enjoy San Juan an island, known for its beautiful beaches and Spanish Caribbean culture with an American twist.
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:
Florida State and Cayman Islands are great options for an unforgettable holiday!. With this package, visit; Miami (Miami and South Beach, food, music ...
Florida State and Cayman Islands are great options for an unforgettable holiday!. With this package, visit;
Miami (Miami and South Beach, food, music and nightlife await you there) and in Grand Cayman (the largest of the three Cayman Islands, with its seven mile beach strip with clubs, restaurants/ bars, resorts, and hotels) you will spend fabulous days in the Caribbean. A flight connects these destinations.
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 $1,029*
Customize it
Take Jamaica in your hands, with this unforgettable holiday package. Visit Montego Bay, on Jamaica’s north coast and major cruise ship port. Spend ...
Take Jamaica in your hands, with this
unforgettable holiday package. Visit Montego Bay, on Jamaica’s north coast and major cruise ship port. Spend your days soaking in the glorious sunshine on one of its main beaches; like: Doctor’s Cave Beach and Walter Fletcher Beach, as well as other outdoor activities, such diving and snorkeling, at the coral reefs protected waters.
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:
Explore this lovely cities in Florida and Jamaica with nearly endless opportunities to experience culture, excitement and beauty. Combine Miami (the ...
Explore this lovely cities in Florida and Jamaica with nearly endless opportunities to experience culture, excitement and beauty. Combine Miami (the city and the metropolitan area are well known for its beaches, such as Miami Beach and South Beach) and Montego Bay (the capital of Saint James Parish on Jamaica’s north coast, is a major cruise ship port). 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 $1,569*
Customize itExplore the Caribbean with custom suggested itineraries for the Greater Antilles, featuring top islands like Cuba, Jamaica, Puerto Rico, and the Dominican Republic. Each itinerary is fully customizable, offering travelers the chance to enjoy white-sand beaches, historic landmarks, vibrant culture, and unforgettable adventures.
What better combination for your vacation than the sophistication of Panama and the beauty of Jamaica in this customizable vacation. Enjoy a nice stay ...
What better combination for your vacation than the sophistication of Panama and the beauty of Jamaica in this customizable vacation. Enjoy a nice stay in 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). After that, catch a flight to beautiful Jamaican coastal city of Montego Bay (a major cruise ship port, with its numerous beach resorts and golf courses outside its commercial core).
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 $1,830*
Customize it
Florida State and Puerto Rico are great options for an unforgettable holiday!. With this package, visit; Miami (Miami and South Beach, food, music and ...
Florida State and Puerto Rico are great options for an unforgettable holiday!. With this package, visit; Miami (Miami and South Beach, food, music and nightlife await you there) and in San Juan (a Caribbean island and U.S. territory with a landscape of mountains, waterfalls, tropical rainforest and beautiful beaches) you will spend fabulous days in the Caribbean. A flight connects these destinations.
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 $899*
Customize it
A thrilling combination between USA and Dominican Republic is offered in this holiday package. Start in The Sunshine State with pleasant stays in ...
A thrilling combination between USA and Dominican Republic is offered in this holiday package. Start in The Sunshine State with pleasant stays in Orlando (known for Walt Disney World Resort in Orlando, Florida and all the other awesome theme parks like Universal) and Miami (with its beaches, such as Miami Beach and South Beach, as well as endless shopping opportunities). After that, catch a flight to The Dominican Republican, and in Punta Cana (amazing beaches with white sands await you).
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:
Driving Time
Orlando - Miami: 3 hr. 30 mins. approx.
9 nights from $1,590*
Customize it
Take Jamaica in your hands, with this unforgettable holiday package. Visit Negril, a small beach resort town, known for its miles of sandy beaches and ...
Take Jamaica in your hands, with this unforgettable holiday package. Visit Negril, a small beach resort town, known for its miles of sandy beaches and shallow bays, and Skylark is located on one of the most famous.
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:
Panama and Puerto Rico are great options for an unforgettable holiday!. With this package, visit; Panama City (known for the Panama Canal, this lively ...
Panama and Puerto Rico are great options for an unforgettable holiday!. With this package, visit; Panama City (known for the Panama Canal, this lively Latin American city also borders one of Central America's richest rain forest) and San Juan ("the island of enchantment", with a landscape of mountains, waterfalls, tropical rainforest and beautiful beaches). A flight connects these destinations.
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:
Two exotic and beautiful cities await you in this package that combines Florida State and Jamaica for an unforgettable vacation. Visit Miami (well ...
Two exotic and beautiful cities await you in this package that combines Florida State and Jamaica for an unforgettable vacation. Visit Miami (well known for its beaches, such as Miami Beach and South Beach as well as its active nightlife) and then, catch a flight to Jamaica where in Ocho Rios beautiful beaches with white sands are great, for relaxing days under the Caribbean 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 $1,236*
Customize it
Discover Florida and Jamaica with this holiday package. Combine Miami (well known for its beaches, such as Miami and South Beach, as well as endless ...
Discover Florida and Jamaica with this holiday package. Combine Miami (well known for its beaches, such as Miami and South Beach, as well as endless shopping opportunities) and Negril (small beach resort town, known for its miles of sandy beaches and shallow bays, and
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 $1,029*
Customize it
A truly Caribbean holiday awaits you in this package in the amazing Jamaica, visiting one of its main destinations. Explore Runaway Bay, a paradise ...
A truly Caribbean holiday awaits you in this package in the amazing Jamaica, visiting one of its main destinations. Explore Runaway Bay, a paradise with beautiful white sandy beaches, turquoise water, and its caves, like Green Grotto, and surrounded by big resorts and outdoor leisure activities.
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:
With pristine white sand and amazing beaches Cayman Island is a fantastic choice for a Caribbean Holiday. Stay in Grand Cayman (known for its coral ...
With pristine white sand and amazing beaches Cayman Island is a fantastic choice for a Caribbean Holiday. Stay in Grand Cayman (known for its coral reefs and underwater sea walls along with a number of shipwrecks and its "Seven Miles Beach"; strip with clubs, restaurants, bars, resorts, and hotels.
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:
Panama and The Dominican Republic are fantastic destinations for an incredible vacation. With this package, combine with an intercity flight and ...
Panama and The Dominican Republic are fantastic destinations for an incredible vacation. With this package, combine with an intercity flight and visit:
Panama City (the most attractive Capital City and a curious blend of old Spain, modern America and the bazaar atmosphere of the East. Panama is a regional hub of trade and immigration), and Punta Cana (the easternmost tip of the Dominican Republic, known for its golden 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 $1,421*
Customize it
Dominican Republic is regarded as one of the most dynamic countries in Caribbean. Fly in and out of Punta Cana and visit the city of Samana, on the ...
Dominican Republic is regarded as one of the most dynamic countries in Caribbean. Fly in and out of Punta Cana and visit the city of Samana, on the northeastern coast of the Atlantic Ocean, known for its mountains, whale watching and beautiful 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:
4 nights from $1,108*
Customize it
Combine Florida and Jamaica with this fun vacation, traveling between these cities by flight. In Florida, visit Miami (well known for its active ...
Combine Florida and Jamaica with this fun vacation, traveling between these cities by flight. In Florida, visit Miami (well known for its active nightlife and beaches, like Miami and South Beach). In Jamaica spend amazing days under the Caribbean sun in
Runaway Bay (with its beautiful white sandy beaches, turquoise water, and its caves, like Green Grotto).
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 $1,529*
Customize itDiscover top Greater Antilles destinations for your next Caribbean escape, featuring world-class resorts, vibrant nightlife, cultural landmarks, and breathtaking natural beauty that make every getaway truly memorable.
Hotel was an historic and lovely hotel in the heart of old San Juan. The service was good. Cleaning service was spotty and the food from the restaurant was not good. The flight was just fine ...
We booked a trip to Puerto Rico over Christmas. The hotel (Coral Princess) was okay but not great. Requested a ground floor room, we were right up front by office and the street - a lot of street noise at night and early, office/breakfast noise in mo ...
This trip was AWESOME. I previously have had bad experiences in Jamaica, but Secrets St. James resort was absolutely wonderful. The accommodation were very good, the food was excellent, and the service was exceptional ...
Get inspired with Caribbean-themed travel ideas, offering curated itineraries across top islands with activities like snorkeling, sailing, nightlife, and heritage tours.
The Caribbean, whether you`re on the mainland in Central and South America, or visiting one (or many) islands in the Caribbean Sea, offers some of the most desired honeymoon vacation destinations in the world.
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 located on some of the most luxurious islands in the Caribbean.
There is nothing like planning a Caribbean vacation with kids to win the winter blues. Calm and warm waters, white and soft beaches, swaying palm trees are the perfect recipe, and Caribbean destinations have just that and more!
Discover More Caribbean Experiences and Adventure Travel Ideas in the Riviera Maya, Belize, and Honduras, where travelers can enjoy pristine beaches, ancient ruins, scuba diving, and vibrant cultural traditions.
The sunny Caribbean coastline of Riviera Maya, referred to as the 100-mile stretch on the Yucatan Peninsula, is one of the top vacation spots of Mexico. With idealistic, white sand beaches, a stunning coral reef, underground rivers, vibrant nightlife and laid back beach towns, this is the perfect place to escape to.
Formerly known as the British Honduras, Belize has a lot to offer to travelers who are seeking a mix of adventure and culture. Being the youngest country in Central America, the tourism infrastructure is still being developed.
Home to biodiverse jungles, ancient Mayan Ruins, and vast national parks brimming with wildlife, Honduras offers so much adventure. It’s one of the cheapest countries in Central America that is relatively untrodden on the tourist past and the best value in the region.
