The Caribbean Islands Vacation Packages
The Caribbean Islands are what tropical dreams are made of! The region is made up of the Caribbean Sea, thirty island territories, and thousands more islets, reefs, and cays. Every island has its own history and culture, making each one a unique experience. Whether you're an adventure seeker looking to hike the mountains and dive with the stingrays, or you're simply looking to relax and sunbathe near the beach at a luxury resort, the Caribbean Islands have it all!
Best Vacation Packages
Whether you’re an adventure seeker, a scuba diving enthusiast, or simply looking to relax on a tropical beach, Tripmasters’ customizable Caribbean vacation packages have something for everyone. Explore top attractions like Harrison’s Cave in Barbados, the UNESCO-listed Pitons of St. Lucia, and the ancient Mayan ruins of Tulum in Mexico. With curated tours, stunning destinations, and flexible itineraries, your dream Caribbean getaway is just a click away.
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St. Croix Island Escape (US Virgin Islands)
4 nights from $834
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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Miami and Nassau (Bahamas) by Air
6 nights from $1,453
One of our most requested combinations of cities in Bahamas and Florida. Visit Miami (the city and the metropolitan area are well known for its ...
Miami and Nassau (Bahamas) by Air
One of our most requested combinations of cities in Bahamas and Florida. Visit Miami (the city and the metropolitan area are well known for its beaches, such as Miami Beach and South Beach), then Nassau (capital of the Bahamas, popular cruise-ship stop, known for beaches, offshore coral reefs, popular for diving and snorkeling). These destinations are connected by flights.
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 Nassau (Bahamas)
- Hotel for 3 nights in Miami
- Flight from Miami to Nassau (Bahamas)
- Hotel for 3 nights in Nassau (Bahamas)
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Aruba Island Escape
4 nights from $1,389
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!
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Georgetown (Exuma Islands) Escape
4 nights from $1,041
Escape to the Caribbean Paradise with this holiday package in Bahamas. Immerse yourself in an incredible Bahamian experience spending amazing days in ...
Georgetown (Exuma Islands) Escape
Escape to the Caribbean Paradise with this holiday package in Bahamas. Immerse yourself in an incredible Bahamian experience spending amazing days in Georgetown (located on Great Exuma Island, famous for its pristine beauty, outstanding anchorages, and breathtaking views). A popular spot for yachting, sailing, and diving, as well as other leisure activities like for example, an excursion to The Exuma Cays Land and Sea Park (first of its kind in the world).
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 Georgetown
- Hotel for 4 nights in Georgetown
Suggested Itineraries
Discover more of Tripmasters’ fully customizable vacation deals and uncover the beauty of the Caribbean. From islands celebrated for their white-sand beaches and luxury resorts to those famed for world-class scuba diving, deep-sea fishing, and sailing, every destination offers its own unique charm and a chance to experience authentic local life.
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Barbados Island Escape
4 nights from $955
Under the Caribbean Sun enjoy an unforgettable holiday in the stunning Barbados. As a matter of fact, the most easterly island in the Caribbean island ...
Barbados Island Escape
Under the Caribbean Sun enjoy an unforgettable holiday in the stunning Barbados. As a matter of fact, the most easterly island in the Caribbean island chain, was once part of Britain but is now an independent island country; the unique Barbados Island is very well known for its tropical beaches and the birthplace of rum.
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 Barbados Island
- Hotel for 4 nights in Barbados Island
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St. Barts Escape
4 nights from $2,362
Discover why St. Barthelemy or St. Barths is one of the most amazing island at the Caribbean!. With this holiday package spend unforgettable moments ...
St. Barts Escape
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.
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. Barts Island
- Hotel for 4 nights in St. Barts
4 nights from $2,362*
Customize it -
St. Kitts and Nevis Islands Escape
4 nights from $1,319
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 ...
St. Kitts and Nevis Islands Escape
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).
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. Kitts and Nevis Island
- Hotel for 4 nights in St. Kitts and Nevis Island
4 nights from $1,319*
Customize it -
Curacao Island Escape
4 nights from $946
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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Montego Bay Escape
4 nights from $872
Take Jamaica in your hands, with this unforgettable holiday package. Visit Montego Bay, on Jamaica’s north coast and major cruise ship port. Spend ...
Montego Bay Escape
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.
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
- Hotel for 4 nights in Montego Bay
- Transfer from Hotel to Montego Bay Airport
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Grand Cayman Escape
4 nights from $1,169
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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Turks and Caicos Escape
4 nights from $1,015
An exciting adventure through The Caribbean! Discover Turks and Caicos an archipelago of 40 low-lying coral islands in the Atlantic Ocean, a British ...
Turks and Caicos Escape
An exciting adventure through The Caribbean! Discover Turks and Caicos an archipelago of 40 low-lying coral islands in the Atlantic Ocean, a British Overseas Territory southeast of the Bahamas.
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 Turks and Caicos Island
- Hotel 4 night in Turks and Caicos Islands
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Negril Escape
4 nights from $879
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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Anguilla Island Escape
4 nights from $8,928
An exciting adventure through the Caribbean. Discover Anguilla Island one of the most northerly of the Leeward Islands in the Lesser Antilles, lying ...
Anguilla Island Escape
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.
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 Anguilla
- Hotel 4 nights in Anguilla Island
4 nights from $8,928*
Customize it -
Runaway Bay Escape
4 nights from $1,843
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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Dominica Island Escape
4 nights from $1,333
Discover Dominica, The "Nature Isle of the Caribbean" with this Package!. Dominica Island, it is the youngest island in the Lesser Antilles, with ...
Dominica Island Escape
Discover Dominica, The "Nature Isle of the Caribbean" with this Package!. Dominica Island, it is the youngest island in the Lesser Antilles, with natural hot springs (the world's second-largest hot spring, called Boiling Lake), tropical rainforests and miles of white sandy 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 Dominica Island
- Hotel for 4 nights in Dominica Island
4 nights from $1,333*
Customize it -
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*
Customize it -
Nassau Escape
4 nights from $1,831
A true Caribbean experience with a visit to the idyllic Bahamas. Enjoy the capital of Bahamas; Nassau, a popular cruise-ship stop and top beach ...
Nassau Escape
A true Caribbean experience with a visit to the idyllic Bahamas. Enjoy the capital of Bahamas; Nassau, a popular cruise-ship stop and top beach destination in the Caribbean. The island boasts stunning white sand beaches, offshore coral reefs and offer diverse options for diving and snorkeling.
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 Nassau
- Hotel for 4 nights in Nassau
Island Groups
Explore over 7,000 Caribbean islands surrounded by turquoise waters and pristine white-sand beaches just waiting to be discovered. The Greater Antilles, Lesser Antilles, and Lucayan Archipelago make up the heart of the Caribbean Islands, each offering unique island landscapes, from vibrant coral reefs and lush rainforests to dramatic volcanic mountains.
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 ...
Tropical Countries
Countries along the Caribbean Sea and Pacific Ocean offer the perfect blend of adventure and culture. From Costa Rica’s world-class surfing shores and lush rainforests to Mexico’s historic Mayan ruins and Belize’s stunning Caribbean beaches, these Central American gems invite travelers to explore diverse landscapes, vibrant traditions, and unforgettable experiences.
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Mexico
Mexico, a country rich with diversity and culture. For travelers looking to relax and sip on margaritas by the beach, visit Cancun. For those in search of a bustling city where you can learn about the history of the country, take a trip to Mexico City. Or maybe you want to cool off in the gem-colored waters of Tulum.
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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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Costa Rica
With jaw-dropping landscapes, friendly locals and epic adventures to be had, Costa Rica is offers it all. Adventure to the beautiful waterfalls, volcanoes and amazing surf in this Central American gem.
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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.
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Panama
Since the creation of the world-famous Panama Canal in 1914, Panama has been at the heart of international shipping, serving as a connection point between the Pacific and the Caribbean. In recent years, Panama has also become a major tourist destination for their charming old cities, stunning landscapes, beautiful beaches, and varied outdoor adventure.
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Colombia
Colombia has a whopping 10% of the world’s biodiversity. Over the years, it has transformed into one of the best places to visit in South America. From the many museums of Bogota to the beautiful beaches on the coast, Colombia has something for every kind of traveler.
More to Explore
The Caribbean truly has something for everyone, from world-class diving and snorkeling in coral reefs to family-friendly attractions, romantic getaways, and lively nightlife. Explore these exciting ways to experience the beauty of the Caribbean 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, how luxurious and peaceful the honeymoon will be, and what kinds of memories can you create together in your first days wed. 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! Whether you`re in the islands or on the mainland in Mexico, Central America, or South America, the Caribbean offers some of the best nightlife in the Americas, with bars and nightclubs buzzing all twelve months of the year.
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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. From the Cayman Islands east to St. Vincent, you too can be treated like a king or queen in personalized and pampered opulence.
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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? In addition to the historical and archaeological sites across the Caribbean that will fascinate kids, hotels and resorts increasingly offer amenities geared directly to them, allowing them to have fun experiences and make memories that will ensure it won`t be just a vacation for the parents.
Experiences & Adventures
Explore unforgettable adventures in the Caribbean and Central America! From flavorful food and wine, awe-inspiring glaciers, and fascinating culture, this vast region is full of unique experiences and adventures!
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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. These designations have been given to fantastic locations such as the Pitons in St. Lucia, the mesmerizing Belize Barrier Reef, and the magical Mornet Trois Pitons National Park in Dominica filled with flowing rivers, cascading waterfalls, glistening lakes, fierce volcanoes, verdant forests, soaring mountains and much more.
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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. The term “carnival” often refers to the Catholic celebration of decadence and revelry, a hedonistic celebration that culminates on Fat Tuesday, or Madi Gras the day before Lent begins. Carnival in the Caribbean is always a good time with the opportunity to dress up, and dance through the streets at this raucous celebration is a once-in-a-lifetime experience.
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Best of Central America
The spectacular Central America region spans over 7 countries brimming with stunning natural and cultural attractions that never end. A fantastic array of countries to explore including Costa Rica with its soaring Arenal Volcano and breathtaking beaches, Belize and its vibrant barrier reef, the second largest in the world teeming with marine life, Nicaragua home to the verdant tropical rainforest and captivating scenery, Guatemala`s ancient Mayan ruins take you back in time and historic Honduras filled with stunning natural landscapes and some of the best diving in the world.
Two Cities Packages
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Miami and Georgetown (Exuma Islands) by Air
Travel through Bahamas and Florida like never before, visiting Miami (well known for its beaches, such as Miami Beach and South Beach, as ...
6 nights from $1,882* -
Orlando and Nassau (Bahamas) by Air
Beauty, entertainment and white sand beaches in USA and Bahamas. Start in Florida; with a nice stay in Orlando (place known for its ...
6 nights from $1,004* -
Miami and Turks and Caicos by Air
Florida and Caribbean Highlights!. Visit the unique Miami, very well known for its beaches, such as Miami Beach and South Beach, as well as ...
6 nights from $1,501* -
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!. ...
4 out of 56 nights from $1,589* -
Miami and Aruba by Air
Florida and Caribbean Highlights! Visit Miami well known for its beaches, such as Miami Beach and South Beach, as well as endless shopping ...
6 nights from $1,519* -
Miami and Curacao Island by Air
Discover Florida and Curacao with this holiday package. Combine Miami (well known for its beaches, such as Miami Beach and South Beach, as ...
6 nights from $1,695* -
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 ...
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Miami and Montego Bay by Air
Explore this lovely cities in Florida and Jamaica with nearly endless opportunities to experience culture, excitement and beauty. Combine ...
6 nights from $1,699* -
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 ...
6 nights from $1,683* -
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 ...
6 nights from $1,887* -
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 ...
6 nights from $2,472* -
Miami and Punta Cana by Air
Visit two of the most requested cities in Florida State and The Dominican Republic with this unique, flexible vacation package. Start your ...
5 out of 56 nights from $1,069* -
Miami and St. Thomas Island (US Virgin Islands) by Air
Holidays under the sun is offered in this package, visiting; Florida State and US Virgin Islands. Have a splendid stay in Miami (with its ...
6 nights from $2,449* -
Miami and St. Maarten Island by Air
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 ...
6 nights from $1,641* -
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 ...
6 nights from $1,725* -
Miami and St. Lucia Island by Air
Explore this lovely cities in Florida and Caribbean with nearly endless opportunities to experience culture, excitement and beauty. Combine ...
6 nights from $1,860* -
Miami and St. Vincent Island by Air
What better combination for an unforgettable vacation, that to visit Florida State in USA and St. Vincent and The Grenadines with this ...
6 nights from $1,941* -
Miami and Grenada Island by Air
Set forth on an adventure like never before, with a travel to Florida State in USA and Grenada at your disposal in this customizable ...
6 nights from $1,414* -
Essential Panama City and Barbados by Air
What better combination for your vacation than the sophistication of Panama and the beauty of Barbados in this customizable vacation. Enjoy ...
4 out of 56 nights from $2,149*