Greater Antilles Islands Vacation Packages
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.
Best Vacation Packages
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.
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San Juan Escape
4 nights from $719
Escape to the Caribbean Paradise with this holiday package in Puerto Rico. Enjoy San Juan an island, known for its beautiful beaches and Spanish ...
San Juan Escape
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.
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 San Juan
- Hotel for 4 nights in San Juan - Puerto Rico
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Miami and Cayman Islands by Air
6 nights from $1,580
Florida State and Cayman Islands are great options for an unforgettable holiday!. With this package, visit; Miami (Miami and South Beach, food, music ...
Miami and Cayman Islands by Air
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.
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 Grand Cayman
- Hotel for 3 nights in Miami
- Flight from Miami and Cayman Islands
- Hotel for 3 nights in Gran Cayman
6 nights from $1,580*
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Suggested Itineraries
Explore 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.
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Miami and Puerto Rico by Air
6 nights from $1,469
Florida State and Puerto Rico are great options for an unforgettable holiday!. With this package, visit; Miami (Miami and South Beach, food, music and ...
Miami and Puerto Rico by Air
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.
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 San Juan
- Hotel for 3 nights in Miami
- Flight from Miami and San Juan
- Hotel for 3 nights in San Juan
6 nights from $1,469*
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Runway to Road: Orlando - Miami - Punta Cana
9 nights from $1,487
A thrilling combination between USA and Dominican Republic is offered in this holiday package. Start in The Sunshine State with pleasant stays in ...
Runway to Road: Orlando - Miami - Punta Cana
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 Republicans', and in Punta Cana (amazing beaches with white sands await you).
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 Orlando and out of Punta Cana
- Rental Car for 7 days
- Hotel for 3 nights in Orlando
- Hotel for 3 nights in Miami
- Flight form Miami to Punta Cana
- Hotel for 3 nights in Punta Cana
Driving Time
Orlando - Miami: 3 hr. 30 mins. approx.
9 nights from $1,487*
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Negril Escape
4 nights from $839
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 ...
Negril Escape
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.
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 Montego Bay
- Transfer from Montego Bay Airport to Hotel in Negril
- Hotel for 4 nights in Negril
- Transfer from Hotel in Negril to Montego Bay Airport
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Miami and Ocho Rios by Air
6 nights from $1,555
Two exotic and beautiful cities await you in this package that combines Florida State and Jamaica for an unforgettable vacation. Visit Miami (well ...
Miami and Ocho Rios by Air
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.
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 Montego Bay
- Hotel for 3 nights in Miami
- Flight from Miami to Montego Bay
- Transfer from Montego Bay Airport to Hotel in Ocho Rios
- Hotel for 3 nights in Ocho Rios
- Transfer from Hotel in Ocho Rios to Montego Bay Airport
6 nights from $1,555*
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Miami and Negril by Air
6 nights from $1,390
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 ...
Miami and Negril by Air
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 Skylark> is located on one of the most famous) with a flight and private transfers.
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 Montego Bay
- Hotel for 3 nights in Miami
- Flight form Miami to Montego Bay
- Transfer from Montego Bay Airport to Hotel in Negril
- Hotel for 3 nights in Negril
- Transfer from Hotel in Negril to Montego Bay Airport
6 nights from $1,390*
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Runaway Bay Escape
4 nights from $1,558
A truly Caribbean holiday awaits you in this package in the amazing Jamaica, visiting one of its main destinations. Explore Runaway Bay, a paradise ...
Runaway Bay Escape
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.
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 Montego Bay
- Transfer from Montego Bay Airport to Hotel in Runaway Bay
- Hotel for 4 nights in Runaway Bay
- Transfer from Hotel in Runaway Bay to Montego Bay Airport
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Grand Cayman Escape
4 nights from $1,206
With pristine white sand and amazing beaches Cayman Island is a fantastic choice for a Caribbean Holiday. Stay in the stunning Grand Cayman (very well ...
Grand Cayman Escape
With pristine white sand and amazing beaches Cayman Island is a fantastic choice for a Caribbean Holiday. Stay in the stunning Grand Cayman (very well known for its unique coral reefs and underwater sea walls), along with a number of shipwrecks and its "Seven Miles Beach"; and a variety of restaurants with traditional food, bars, resorts, as well as hotels.
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 Grand Cayman
- Hotel for 4 nights in Grand Cayman
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Panama and The Dominican Republic are fantastic destinations for an incredible vacation. With this package, combine with an intercity flight and ...
Essential Panama City and Punta Cana by Air
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).
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 Punta Cana
- Hotel for 3 nights in Panama City
- Flight from Panama City to Punta Cana
- Hotel for 3 nights in Punta Cana
6 nights itinerary
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Samana Escape
4 nights from $873
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 ...
Samana Escape
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.
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 Punta Cana
- Transfer from Punta Cana Airport to Hotel in Samana
- Hotel for 4 nights in Samana
- Transfer from Samana Hotel to Punta Cana Airport
4 nights from $873*
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Miami and Runaway by Air
6 nights from $1,890
Combine Florida and Jamaica with this fun vacation, traveling between these cities by flight. In Florida, visit Miami (well known for its active ...
Miami and Runaway by Air
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).
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 Montego Bay
- Hotel for 3 nights in Miami
- Flight from Miami to Montego Bay
- Transfer from Montego Bay Airport to Hotel in Runaway Bay
- Hotel for 3 nights in Runaway Bay
- Transfer from Hotel in Runaway Bay to Montego Bay Airport
6 nights from $1,890*
Customize it
Islands
Discover 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.
Customer Reviews
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Traveled on: 07/13/20265 out of 5
A more user friendly websit ...
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Traveled on: 07/01/20265 out of 5
It would have been nice if the deal would have started at a better hotel and/or there was an easier way to get to the resort hotels. The first one was on the street and had some negative reviews ...
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Traveled on: 06/27/20265 out of 5
Trip masters has been great- from putting together great deals to the agents that helped me make some modifications after we booked. I have already been recommending to friends and family! Given I had very little control over my booking without payin ...
Explore the Caribbean
Get inspired with Caribbean-themed travel ideas, offering curated itineraries across top islands with activities like snorkeling, sailing, nightlife, and heritage tours.
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Honeymoon in the Caribbean
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.
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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 on some of the most luxurious islands in the Caribbean.
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Family Fun 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!
More to Explore
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.
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Riviera Maya
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.
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Belize
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.
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Honduras
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.