Covid-19 Updates

Caribbean Locations for Trips with Friends

Once the world gets back to normal and it’s safe to stop considering trips from our bedroom to our kitchen “vacations”, there are two things I’m sure we’ll all want to do: hang out with our friends (in person) and travel (around the world). One of the best destinations to bond with your besties has to be the Caribbean. The Caribbean is a melting pot of cultures, with 13 sovereign states and 17 dependent territories in the mix. Whether you’re looking to relax on the beach, traverse the great outdoors, or anything in between, these five locations truly deliver in terms of making the most out of quality time.

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Harbour Island, Bahamas

Harbour Island is a quick getaway for East Coasters ideal for many reasons—the biggest one being that it’s entirely surrounded by water. The island’s lifestyle revolves around the ocean: playing in it, eating by it, drinking by it, and fishing in it. Plus, a large amount of vacationers from NYC that always make their way here give the island a pretty sizable social scene. Fine dining and nightlife can be found at the luxury resorts on the shoreline. When it comes to your vacation headquarters, I’m partial to Rosalita, a new beachfront villa. Rosalita sits on beautifully landscaped oceanfront grounds. The villa features six bedrooms and sleeps twelve guests. Five of the bedrooms are located in the villa’s main house. The sixth bedroom is located in the guest house and features a king bed. All bedrooms have en-suite bathrooms, and four have alfresco showers. Both the master and the guest house bedroom suites have private terraces with fantastic views, while the other bedrooms have private entrances from the veranda or garden.

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Sugar Beach, Saint Lucia

Once you arrive in Sugar Beach, you won’t want to leave. Surrounded by St. Lucia’s twin volcanic Pitons, the Beachfront Collection villa blends seamlessly into Sugar Beach’s untouched beauty, with sweeping views of the Pitons and the Caribbean Sea. This four-bedroom villa has an infinity pool and suites has floor-to-ceiling sliding glass doors for an unobstructed view. You and your friends can relax, take in the epic views and enjoy the private walled garden. Make sure to connect with Blue Sky Luxury Travels to make plans ahead of time, we can arrange for private chef and spa services and luxury catamarans for a day on the water.

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St. John, U.S. Virgin Islands

St. John is an exclusive enclave that offers the convenience and flexibility of staying within the U.S., with the tropical splendor of the Caribbean. Located on the north shore of St. John, Estate Solenborg is a luxury Caribbean vacation rental villa overlooking the Sir Frances Drake Passage and Denis Bay. This secluded estate is a private paradise with seven bedrooms, all with en-suite bathrooms and ocean views. Gather with friends and enjoy the luxe modern design, two heated pools, an expansive terrace, and outdoor living and dining areas.

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Sailing Catamaran, British Virgin Islands

Island hopping in the BVIs is the ultimate way to enjoy the Caribbean with friends. Ten guests can explore the coves, go diving, fishing, and paddleboarding among the islands in the spectacular Bella Vita sailing catamaran. This super luxury catamaran offers an all-inclusive crewed yacht charter experience with a crew of six. It was formerly named Necker Belle, was owned by Richard Branson, and won a World Superyacht Award in 2010. In true Branson spirit, the Bella Vita was built to maximize fun, featuring a spacious trampoline, a diving board, and a unique crow’s nest that can lift you to the top of her mast.

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West End, Anguilla

With easy access to St. Maarten, Puerto Rico and Antigua, Anguilla attracts a high-end, sophisticated crowd. It also boasts more than 30 beaches (some of the best in the entire Caribbean), a wealth of fine dining and enough outdoor activities to satisfy any nature lover. For groups who want the ultimate private villa and spa experience, the Four Seasons Villas are the only choice. The oceanfront villas with private pools combine the privacy of a villa with the luxury of a world-class resort. Your group of up to 13 guests can relax at the indoor and outdoor bars while the Four Seasons’ legendary staff caters to your every desire. Whether you want to spend your days relaxing at the beach club, working on your cardio on private tennis courts or vacationing like celebrities in a private spa, the Four Seasons Villas certainly won’t disappoint. Savor tailored luxury, privacy and service on one of the world’s most beautiful beaches.