It's well known the Caribbean is a popular destination for solo travelers and couples, but it's also a fun, family friendly vacation destination! In addition to the historical, archaeological, and natural sites that are sure to fascinate kids, hotels and resorts increasingly offer activities and amenities geared directly to them, allowing them to have fun experiences like snorkeling, kayaking, and ziplining - making memories to ensure it isn't just a vacation for the parents.
Explore Fun Family-Friendly Destinations and Vacation Packages Across the Caribbean, where tropical beaches, kid-friendly resorts, exciting activities, and cultural attractions create the perfect getaway for travelers of all ages.
4 nights from $1,784
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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
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4 nights from $1,062
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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
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4 nights from $1,209
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 ...
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.
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4 nights from $883
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 ...
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.
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Plan Your Ideal Family Vacation in the Caribbean with top travel deals that include beachfront resorts, kid-approved activities, cultural tours, and multi-destination packages. All TripMasters Suggested Itineraries Are Fully Customizable, offering travelers unique flexibility to create their dream vacation across the Caribbean, Mexico, and beyond.
4 nights from $797
Escape to the Caribbean Paradise with this holiday package in Bahamas. Immerse yourself in an incredible Bahamian experience spending amazing days in ...
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.
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4 nights from $938
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 ...
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.
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4 nights from $2,386
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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
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4 nights from $2,386*
Customize it4 nights from $747
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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Includes:
4 nights from $939
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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
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Discover the Best Caribbean Islands for Family-Friendly Vacations, offering cultural experiences, safe beaches, kid-approved adventures, and entertainment for the whole family.
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 ...
Vicky was absolutely wonderful about accommodating our requests for the trip. Everything went smoothly and we had a wonderful time in Nassau.
First class seats and beautiful views from our hotel room. The price was great and we will definitely use y ...
Atlantis Hotel was beautiful. The staff was somewhat rude and unaccommodating, with the exception of the front desk when we checked in. They upgraded us to a room overlooking the ocean. Absolutely beautiful!! And we were so grateful.
Your suggestio ...
Discover More Caribbean Adventures, Excursions, and Activities, including scuba diving, hiking tropical rainforests, heritage tours, nightlife, and family-friendly attractions.
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.
The Western Caribbean coastline from Mexico down through Central America to Colombia in northern South America offers some of the most desired honeymoon vacation destinations in the world.
The Caribbean Islands that are best suited for a honeymoon vacation are far-flung, from Jamaica east to Grenada. They have some of the most beautiful landscapes in the world as well as very luxurious accommodations.
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 Stunning Beaches to Rich Culture, Explore the Best Caribbean Activities and Experiences, from island-hopping and adventure tours to local cuisine and heritage sites.

Surfing in Central America offers surfers some of the most treasured breaks in the world, this land is blessed with waters on the Pacific and Caribbean sides. World-class surfing opportunities can be found in Costa Rica, Panama, and Guatemala with the Pacific side providing some of the top waves in the region.

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 once-in-a-lifetime experience.

When you think of the idyllic islands of Mexico, you might think of the islands off the Yucatán Peninsula, like Isla Mujeres, Cozumel, and Isla Holbox, but these beautiful island getaways can be found nationwide. There are beautiful and majestic barrier islands hugging all three major coastlines: the Caribbean, the Gulf of Mexico, and the Pacific. Which idyllic islands will you visit? We firmly believe if you visit the islands once, you`ll be back again and again!