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.


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.


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.

MSI/Interiors Ingrao Villa

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.


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.


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.

Nine Private Islands for the Ultimate Vacation in 2020

Over the past 10 years of expanding Blue Sky, we have added nine private islands to our catalog. They range from $10,000 per week for two people up to $1,900,000 per week for 90 people. These private islands are the ideal option for a couple looking for something extra special as well as large family reunions, destination weddings, and corporate incentive trips/retreats.

laucalaLaucala, Fiji

Owned by the owner of Red Bull, this stunning private island in the South Pacific unites dramatic rainforest-laced landscaped and white sandy beaches with unparalleled levels of luxury and privacy. Set over 1,400 hectares, Lacuala epitomizes the seclusion and graceful hospitality for which Fiji is known. No expense has been spared at this exclusive tropical hideaway which includes 25 Fijian-styled villas atop the island’s volcanic mountains, set amid coconut plantations and surrounded by deserted beaches—all overlooking fertile coral reefs and endless jungle. Style and sustainability are the name of the game here. From the natural fibers and woods used in its design to the wild orchids harvested in gardens and organic produce grown on island farms, you’ll be completely immersed in the natural beauty of the island. Rent an individual villa for two for up for $50,000 per week or rent out the entire island for up to 90 people for a totally private island experience starting at $1,900,000 per week.
kokomoKokomo Island, Fiji

Named one of the “Best of the Best” by Robb Report and the “Best New Hotel in the World” by Travel + Leisure, Kokomo Private Island fuses unscripted luxury with the bounty of space and generosity of time, giving you everything your heart desires. Absorb your idea of luxury in one (or all) of their 21 beachfront villas and 5 luxury residences. Cradled by the world’s fourth-largest reef, the Great Astrolabe—which provides a virtual portal into an unparalleled underwater world—their stunning, unspoiled and naturally immaculate island is more than a backdrop, it’s your home. Kokomo offers a paradise for adventure seekers, a restorative sanctuary for families and an enticing retreat for honeymooners and can be yours for as long as you choose to linger. Rent a space for up to two people for $30,000 per week or buy out the entire island for up to 75 people starting at $1,000,000 per week.
over yonder

Over Yonder Cay, Exuma, Bahamas

Breathtaking views, sunrise, sunset, and sea breeze await you on Over Yonder Cay in any one of their four individually designed villas. Each one features an infinity pool, jacuzzi, private beach, private alfresco dining, and lounging areas and comfortable, fully air-conditioned living spaces, along with satellite TVs, a Kaleidescape entertainment library and Crestron control system, WiFi Internet and iPads. Outside your villa, take advantage of the endless activities and adventures that await you on, off and around the island. Take some lessons or show off your skills with tennis and golf pros on their nine-hole golf course and floodlit tennis court. Workout at the gym or book a massage with one of their spa therapists at their spa cabana. Play some beach volleyball or catch a flick in their movie theater. Have fun in the game room or chill out in the beach club. See the beautiful sights throughout the island on their cycling and nature trails. Set sail on your very own Tenacious or superyacht and ride a jet ski or paddleboard with the help of their water sports instructors. Over Yonder also offers trips to sandbanks, diving excursions with a divemaster, game fishing and snorkeling safaris with their ocean masters, and breathtaking sunset sailing cruises. Rent out the entire island for up to 30 people beginning at $350,000 per week.…/bahamas/over-yonder-cay/

middle cayMiddle Cay, North Eleuthera, Bahamas

The ultimate Caribbean getaway is awaiting you at Middle Cay, a luxurious private island just off the coast of Harbour Island. This two-acre island combines five-star amenities with a secluded location and features a coconut tree grove and two villas with WiFi, AC and daily housekeeping. The four-bedroom Main House has an open kitchen, dining space that seats eight, living room with a flat-screen cable TV and a private patio. There’s also a heated pool and outdoor shower. The three-bedroom Cottage has a common area, a living room with a flat-screen cable TV, a dining area, a patio with windows that reveal breathtaking ocean views and a kitchen. The island’s two docks—one with an automatic boat life—make docking sailboats, yachts, and rentals a breeze. There’s also a working lighthouse on the island which adds a touch of nautical charm, as well as a walkway that winds around the entire island and a fire pit, perfect for roasting s’mores. Grab some fishing gear, a canoe, a standup paddleboard or a kayak and spend a relaxing day at sea or take advantage of the island’s snorkeling equipment and discover an underwater paradise in the surrounding islands’ pink sand beaches, coral reefs, and shipwrecks. The island offers boat rides twice a day to Harbour Island where you’ll find jet skis, boats, bicycles and golf cart rentals, as well as several beaches and restaurants. Guests staying for a week can even choose two complimentary four-hour activities: water tubing, water skiing, feeding the pigs in Meeks Patch, underwater diving with a Yamaha Sea Scooter or touring nearby islands. Buyout the island for up to 17 people beginning at $50,400 per week and experience the ultimate in privacy and luxury.
73006831_10157861203119558_1489438316871811072_nNecker Island, British Virgin Islands

One of the most exclusive and private island destinations in the Caribbean, Necker Island’s 74-acre estate has all the makings of a vacation of a lifetime. Situated in the picturesque British Virgin Islands, guests can look forward to days relaxing on private white sand beaches, a full array of exciting water sports, delicious and refreshing drinks complementing gorgeous sunset views and multiple pristine freshwater infinity pools. You can also book a private tennis lesson with a resident professional coach and end your day at one of the island’s legendary parties. Test your luck at Casino Night, complete with poker and roulette tables, dance the night away at Disco Fever with a setup including a variety of colored disco lights, or book your very own private DJ. Whatever you choose, you’ll be sure to have a memorable experience you’ll be talking about for years to come at Necker Island. Book a getaway for two for $25,000 per week during Celebration Weeks or buy out the entire island for up to 50 people starting at $350,000 per week.
eustatiaEustatia Island, British Virgin Islands

The lush, self-sustaining, 35-acre Eustatia Island is an exclusive sanctuary for travelers seeking exploration and relaxation. Explore one of the world’s most beautiful islands which thrives with year-round ambient water temperature, over 300 days of sunshine per year and fresh trade winds. The island is one of the most exclusive water sports centers in the world, offering an impressive variety of activities using the most innovative equipment available. An elite supply of boats, superior water equipment, and experienced coaches will get you set with everything you need for an incredible adventure on the island’s clear turquoise waters. Experience the ideal private adventure by buying out the island for up to 30 people with rates beginning at $315,000 per week.
cayo espantoCayo Espanto, Belize

Live your best life at Cayo Espanto, a five-star world-class resort where paradise and luxury come together as one. This private island located three miles off the coast of San Pedro, Belize, is home to seven private villas, each engulfed in the Caribbean waters and offers all-inclusive, award-winning cuisine tailored to each guests’ tastes, along with custom excursions like scuba diving, fishing, mainland adventure tours, and private luxury yacht tours. You can even relax and rejuvenate in your own private oasis with spa treatments, including massages, facials, and spa therapies. Rent a villa for two starting at $13,270 per week or buy out the entire island for up to 14 people starting at $92,890 per week.
ray cayeRay Caye Island Resort, Belize

Ray Caye is situated off the coast of Placencia, Belize and offers a unique vacation alternative to the hubbub of the larger island and mainland beach destinations. Their private island caters to travelers looking for a getaway that’s as exotic and fun as it is authentic and natural. The three-bedroom Oceanfront Villas are the newest addition to the resort and offer an upgraded island experience—each featuring a personal plunge pool, private deck, spacious living area, and full kitchen. The private exterior entrances to each Villa Room and Suite mean that you can book them individually or choose to book the entire villa to create a spacious unit, perfect for families and guests. Outside your villa lies the Gladden Spit and Silk Cayes Marine Reserve where you’ll have access to some of the best scuba diving in Belize. Their PADI certified Pirate Reef Divers can help you navigate some of the healthiest and thriving parts of a reef that’s home to over 25 species of fish. Depending on the time of year, you might also spot a gigantic but gentle Whale Shark in the midst of migration. Enjoy a customized diving experience, take a lesson, and even get certified yourself. Ray Caye Island Resort is available to book for two people starting at $14,000 per week or up to 30 people for an island buyout starting at $30,000 per week.

bawah reserve

Bawah, Indonesia

Take a seaplane 80 minutes off the coast of Singapore and you’ll land in Bawah Reserve—an oasis enveloped by lush tropical greenery and azure blue water, sheltered in carefree seclusion in Indonesia’s remote Anambas Archipelago. This previously uninhabited marine conservation area features 11 overwater bungalows exclusively accessed by ironwood walkways and blessed with splendid vistas over the lagoon and outer islands. At Bawah, they cater to outdoor adventurers with an appetite for indulgence as well as paradise seekers looking for relaxation. No matter what you’re looking for, your vacation will be carefully curated to ensure that your stay in Bawah is nothing but perfect. Spend your days kayaking, snorkeling, sailing, trekking through the tropical forest, taking local cuisine cooking classes, going on picnics, dining on private beaches and enjoying open-air cinema nights. From your spectacular seaplane journey to endless experiences above and below the water, every detail is taken care of. Book an unforgettable vacation for two starting at $10,000 per week or buy out the entire island for up to 70 people for $609,000 per week.

5 Reasons Why Anguilla Wins World’s Best Island Every Year

Earlier this year, Anguilla was ranked the #1 island in the Caribbean, Bermuda, and the Bahamas for the third year in a row in the 2019 Travel + Leisure World’s Best Awards, honoring the top travel destinations and companies around the globe as rated by its readers. It also claimed the #6 position in the Top 15 Best Islands in the World. In 2018, the Anguilla Tourist Board launched its Beyond Extraordinary destination campaign, which aims to capture the diversity and richness of the Anguilla experience, and it’s certainly paid off. This slender length of coral and limestone fringed with green tucked away in the Northern Caribbean has managed to retain a charming character and appeal that have kept vacationers returning again and again. Here are just a few of the reasons we can’t recommend it enough.


Breathtaking Beaches

Anguilla is surrounded by more than 12 miles of stunning, powder-white sand sparkling-clear turquoise waters for visitors to enjoy. All of the island’s 33 beautiful beaches are public, uncrowded, and unspoiled, and every cove, bay, and stretch of sand is marked by unique characteristics like rock and coral formations and picturesque tropical plants. It’s actually not uncommon to get a beach all to yourself—especially those inaccessible by land as they require some effort to reach. From the super serene secluded coves of Little Bay and the gentle shoreline and sparkling sea of Rendezvous Bay to the popular and striking white sands of Shoal Bay East and the party atmosphere of the picturesque Sandy Ground, there is truly a beach for everyone and every mood.

Delectable Dining

If Anguilla’s beaches are the most enviable feature of the island, its world-class restaurants come in at a close second. The award-winning dining scene offers discerning travelers international sophistication and elegance with creative cuisine that fuses fresh local flavors from land and sea with elegant imports. The artistry of the island’s chefs—both Anguillan and international—is unmatched anywhere in the Caribbean and provides an opportunity to savor the culture. Stop by a roadside barbecue shack for a slab of jerk chicken or book a reservation at a beachside bistro and hear the sound of lapping waves in the distance. Presenting eclectic culinary techniques complemented by a touch of local flavor, Anguilla’s culinary scene is uniquely Anguillan and authentically Caribbean.


Renowned Resorts

Three Anguilla resorts are featured in the Top 25 Caribbean Resort Hotels category of Travel + Leisure’s World’s Best Awards: Frangipani Beach Resort ranked #2, Malliouhana, Auberge Resort Collection ranked #14, and Zemi Beach House Hotel & Spa ranked #24. The Frangipani Beach Resort is also the only property in Anguilla to be featured in the Top Hotels Overall category, ranked at #46. This Meads Bay hotel only has 19 rooms and suites and offers a luxury experience with a boutique feel—guaranteeing you’ll have attention and beachside access all to yourself. Our favorite hotel on Anguilla is the Four Seasons; we frequently book our clients for stays at this luxurious property. Many hotel rooms on the island provide a spectacular view of the island’s sensational sunsets where you’ll spot an elusive green flash as the sun kisses the water goodnight—but that’s just one of the many perks of Anguilla’s award-winning resorts.


Abundant Activities

Despite it being one of the smaller Caribbean islands, visitors are spoiled for choice when it comes to activities. Anguilla is chock-full of limestone caves to explore, wildlife to observe (like sea turtles and native birds), and sandy beaches to tan on. Take in the island’s natural beauty on a hike or learn more about the island’s heritage on a self-led or guided tour. Many hidden treasures are tucked away on unmarked roads, so it pays to have a knowledgeable guide by your side. Explore the island by sea and hire a boat and dock on some of Anguilla’s most scenic beaches or rent a snorkel and swim around the island’s massive coral gardens, which are home to pufferfish and squid alike. The island offers a variety of popular water-based activities, with the incredible sense of tranquility undoubtedly being Anguilla’s main attraction.


Humble Hospitality

Anguilla’s Ministry of Tourism credits the people of Anguilla and their longstanding tradition of warm hospitality for their recurring award win, and it’s not hard to see why. Anguillians are always willing to help if you need a hand and not because they expect anything in return. They do so out of the goodness of their hearts. True, life-long friendships have even been known to form between Anguillians and visitors. Long after vacations end and visitors return to the States, Canada, or the UK, there are many stories of people inviting Anguillian friends up north wanting to play host to them in their home. “The people here have been some of the friendliest that I’ve encountered in the Caribbean,” a Travel + Leisure reader wrote. “They’ve been hard hit by the latest hurricanes but haven’t lost track of what they consider important.”

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