Caribbean Island Hopping Trip

Volcanic mountain peaks, cool turquoise waters, centuries-old sugar plantations, the Caribbean offers diverse experiences from the destination's natural beauty, cultural heritage and rich history that retains its authentically Caribbean feel.

Most people wait until it gets cold where they live to visit the Caribbean but the low season of the summer and fall is the best time to go. There are fewer crowds and your trip costs are significantly lower. Extend your summer and let's plan a customized trip to one or more of these Caribbean islands.

The larger or more popular islands like St. Thomas or Puerto Rico are great starting points for visiting multiple islands in one trip. For people that live in the northern part of the country, Bermuda is the perfect location to get some sun, sand, and vitamin sea.

Antigua and Barbuda

Antigua, the largest of the Leeward Islands, boasts 365 beaches. It's a 108 square mile limestone, clay, and volcanic rock, low-lying coral island known for its natural landscape and pink and white sand beaches. You'll find reefs, coves, and clear waters to go with the beauty of the sandy beaches. Antigua's most popular and best beaches include Fort James Beach, Hawksbill Beach, Ffryes Bay, Darkwood Beach, Dickenson Bay, and Turners Beach on the southwest coasts. On the east side of the island, the top beaches include Half Moon Bay, voted the number one beach by the Travel Channel, and Long Bay, known for amazing snorkeling.

There are also many trails and tracks available for exploration. Most of the popular hikes lead to one or another of the island’s many hilltop fortifications such as Fort George or Fort Barrington, to scenic views such as Signal Hill, or secluded beaches like Rendezvous Bay. Pick the one that suits your needs and take to the hills for this incredible and uplifting experience.


Pristine pink-sand beaches and wide-open natural spaces are within easy reach from the east coast of the United States. Savor everything from fresh ocean breezes to fresh island fare and get lost in the Bermuda way of life. Walk lush forest trails, swim in idyllic turquoise grottoes and explore subterranean caves in Blue Hole Park, a 12-acre East End nature reserve locally known as Tom Moore’s Jungle.

Head to Miles Market for a basket filled with the likes of curried chicken salad sandwiches and cookies and then picnic in one of the many parks. The lush Botanical Gardens stars 36 acres of trees and blossoms with plenty of places to lounge – and dine – on the grass. Or, travel to the serene Bermuda Arboretum offering 22 acres of gorgeous open space, with shady trails, ornamental bridges and peaceful meadows.


Grenada is a hidden gem with unspoiled beauty. The tri-island destination of Grenada, Carriacou, and Petite Martinique are located in the eastern Caribbean just south of Barbados. Famed for its aromatic spices and organic chocolate, its 40 white sandy beaches including the world-famous Grand Anse Beach, 15 breathtaking waterfalls, 5 chocolate factories, 3 rum distilleries, and more than 30 unforgettable dive sites, including the largest shipwreck in the Caribbean ‘Bianca C’ and the World’s First Underwater Sculpture Park. Grenada is also home to some of the world's most luxurious all-inclusive resorts. This year's Chocolate Festival has been re-scheduled for July 2021. For chocolate connoisseurs, the Chocolate Festival is the perfect time to experience some of the world's finest chocolate direct from the source.

Puerto Rico

Puerto Rico is a place where the Old World is mashed up with the new on an island that is small in size but offers an immense bounty of one-of-a-kind experiences. Rich history and culture, exceptional food, pristine beaches, majestic mountains, relaxation, adventure — all packed into one sun-kissed Caribbean paradise. Plan a soul-refreshing escape to an enchanted rainforest park and be immersed in nature with a visit to El Yunque National Forest. You can visit for a hike on one of its many trails, bathe in natural pools beneath waterfalls, or just relax and enjoy the scenery.

US Virgin Islands

The US Virgin Islands is made up of 3 of the most popular islands in the Caribbean. St. Croix is the largest and least populated. Like most islands in the Caribbean, St. Croix provides gorgeous beaches, world-class resorts and recreational activities like golf, find dining, and casinos. Visiting the two main towns of St. Croix will give you a glimpse of the island's incredible history - from regal 18th and 19th century buildings in Christiansted to a tropical rainforest in Frederiksted.

St. Thomas is the second largest and the most well-known and popular of the 3 islands. You will find plenty of duty-free shopping, spectacular diving, world-class dining, golf-courses, world-famous beaches, and vibrant nightlife. The Skyride takes you 700 feet above the city for amazing views of the island from above.

St. John is the smallest of the 3 islands. Two-thirds of St. John is a national park. St. John has some of the world's most beautiful beaches, like Trunk Bay. This beach is renowned for its crystal sands and underwater nature trail, and it's just one of the many memorable beaches on St. John.

If you want to visit multiple islands in one trip, we can start your trip in St. Thomas or Puerto Rico. Local ferries can take you to nearby islands like St. John, Water Island, Anguilla, and Tortola. Regional air carriers will fly you to larger islands like Dominica, St. Vincent and the Grenadines, and Guadeloupe.