The Windward Islands, the most southerly islands of the Lesser Antilles is where you'll find beautiful Barbados, the relatively unknown islands of Bequia and Mustique in St Vincent and the Grenadines, picturesque St Lucia, Grenada, and Dominica. No matter which of these islands you explore, you'll find warm turquoise waters, brightly colored birds, endless variations of tropical flowers, and balmy air perfumed with the scent of sensual spices and sweet tropical fruits. Experience the stunning white and black sand beaches, colorful reefs, and some of the world's best snorkeling and diving, as well as the unique cultures and rich histories of the islands.
Explore the Windward Islands with Tripmasters’ customizable vacation packages, where stunning turquoise waters, vibrant coral reefs, and rich history await. Discover top attractions like the UNESCO-listed Pitons in St. Lucia, enjoy world-class sailing adventures in the steady Caribbean Tradewinds, and dive into some of the best snorkeling in the Caribbean at Tobago Cays, Chatham Bay on Union Island, and Sandy Island in Carriacou.
Discover Dominica, The "Nature Isle of the Caribbean" with this Package!. Dominica Island, it is the youngest island in the Lesser Antilles, with ...
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.
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 $1,194*
Customize itWhat better combination for your vacation than the sophistication of Panama and the beauty of Barbados in this customizable vacation. Enjoy a nice ...
What better combination for your vacation than the sophistication of Panama and the beauty of Barbados 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 Barbados Island (a beautiful island, was once part of Britain but is now an independent island country. Known for its tropical beaches and the birthplace of rum).
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:
What better combination for an unforgettable vacation, that to visit Florida State in USA and St. Vincent and The Grenadines with this package. Visit ...
What better combination for an unforgettable vacation, that to visit Florida State in USA and St. Vincent and The Grenadines with this package. Visit Miami (with its nightlife, food, and famous beaches) and St. Vincent Island (part of the Windward Caribbean islands rugged with lush jungle and vegetation; active volcano 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:
6 nights from $1,159*
Customize itSet forth on an adventure like never before, with a travel to Florida State in USA and Grenada at your disposal in this customizable package. In ...
Set forth on an adventure like never before, with a travel to Florida State in USA and Grenada at your disposal in this customizable package. In Florida, enjoy a nice stay in
Miami (famous for its diverse culinary, entertainment choices as well as its nightlife and beaches). After that, take a flight to Grenada, in the Caribbean, and spend wonderful time in Grenada Island (small island with soft sands, beautiful beaches and famous for its species like mace, cinnamon, ginger and cloves).
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 $1,219*
Customize itDiscover more of Tripmasters' fully customizable vacation deals, and explore all the wonders the Caribbean islands have to offer. Adventure awaits with unique experiences like hiking to the top of Gros Piton, indulging in a beach lobster barbecue in the Tobago Cays, or rubbing shoulders with the rich and famous on the private island of Mustique.
Explore St. Lucia as you enjoy some of its most iconic cities. Enjoy St. Lucia Island, a tropical island country in the eastern Caribbean Sea. It is a ...
Explore St. Lucia as you enjoy some of its most iconic cities. Enjoy St. Lucia Island, a tropical island country in the eastern Caribbean Sea. It is a part of the Lesser Antilles, and it is north of the islands of Saint Vincent.
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:
Have a splendid holiday at the Spice Island: Grenada, with this customizable package. Spend splendid moments in Grenada Island, discovering its main ...
Have a splendid holiday at the Spice Island: Grenada, with this customizable package. Spend splendid moments in Grenada Island, discovering its main white sand beaches, natural areas and diving sites. Don't miss the opportunity to visit its Market Square, in the center and see its handmade crafts, fresh produce, and, of course, spices (specially mace, cinnamon, ginger and cloves). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
Includes:
4 nights from $964*
Customize itFlorida State and Dominica are combined to offer you an amazing holiday!. Visit in The Sunshine State; Miami (with its boulevards, stoppings, ...
Florida State and Dominica are combined to offer you an amazing holiday!. Visit in The Sunshine State; Miami (with its boulevards, stoppings, restaurants and Miami and South Beaches). After that, take a flight to Dominica Island (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).
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 $1,989*
Customize itEnjoy the beautiful white-sand beaches in this holiday package in St. Vincent and the Grenadines. An ideal location to soak up the Caribbean sun, St. ...
Enjoy the beautiful white-sand beaches in this holiday package in St. Vincent and the Grenadines. An ideal location to soak up the Caribbean sun, St. Vincent Island, with its nice beaches, excellent snorkeling areas and its active volcano you definitely will find in there!.
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 $877*
Customize itUnder the Caribbean Sun enjoy an unforgettable holiday in The Barbados. The most easterly island in the Caribbean island chain, was once part of ...
Under the Caribbean Sun enjoy an unforgettable holiday in The Barbados. The most easterly island in the Caribbean island chain, was once part of Britain but is now an independent island country; Barbados Island is known for its tropical beaches and the birthplace of rum.
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:
The Caribbean Windward Islands make up the southern arc of the Lesser Antilles, one of the most scenic island groups in the Caribbean. Stretching in a north-to-south chain, the main islands include Martinique, St. Lucia, St. Vincent, and Grenada. Just to the east lie the equally captivating islands of Barbados, Trinidad, and Tobago, each offering pristine beaches, vibrant culture, and unforgettable Caribbean vacation experiences.
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 ...
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.
The Caribbean is one of the most popular travel destinations in the world. For beach bums, honeymooners, and anyone looking to soak up the sun and enjoy the outdoors, check out these destinations that offer endless opportunities.

The Greater Antilles is a grouping of the larger islands in the Caribbean Sea, including Cuba, Hispaniola, Puerto Rico, Jamaica, and the Cayman Islands. Six island states share the region of the Greater Antilles in total, with Haiti and the Dominican Republic sharing the island of Hispaniola.

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. The archipelago is in the western North Atlantic Ocean, north of Cuba along with the other Antilles, and east and southeast of Florida.

Colombia is famous for being the second most populated country in South America. From the many museums of Bogota to the beautiful beaches on the coast, Colombia has something for every kind of traveler.
Experience unforgettable adventures in the tropical paradise of the Caribbean and Central America, designed for every type of traveler.
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.
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 - a once-in-a-lifetime experience!
Mexican cuisine is one of the world`s most popular cuisines. Foods originating from Mexico, such as corn, beans, avocados, tomatoes, papayas, cacao, and chile peppers, have transformed the culinary landscape worldwide. The food and drink options that await you in Mexico are immense...just think of all the tacos, enchiladas, tamales, chilaquiles, and sopes you can eat, in addition to sweet breads (pan dulce), Mexican beers and wines, tequila, and mezcal! (And that's just the beginning!)