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.

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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Lazy Lizard

Introducing a new Caribbean Destination – Anguilla

This year we are fully dedicated to expanding our presence in the Caribbean and are proud to present a new destination we invite our guests to check out – the island of Anguilla. This little Caribbean island has everything you are dreaming of – azure blue waters, a laid-back atmosphere, white sand beaches, warm tropical breezes, and five-star resort services and accommodations. Come here to escape the hustle and bustle of life and enjoy the numerous activities the island offers to its visitors.

The island of Anguilla has 33 beautiful beaches, and most of them are quite remote. Even popular beaches like Shoal Bay East are often empty, so don’t be surprised if you have the beach all to yourself. The best way to hop from beach to beach is by car, so if you plan to do beach exploring we recommend renting a car. Another popular water activity is to spend the day on a sailboat. A popular tour will take you to Little Bay, only accessible by boat. There you can enjoy swimming and snorkeling in crystal clear waters. For just a $10 boat ride your island adventures will continue with a trip to Sandy Island, a very suitable name for this island because there is only sand and one restaurant serving seafood here.

In addition to the abundance of water activities and adventures we recommend you to take a day and explore the popular historic site of Fountain Cavern National Park, which is home to numerous petroglyphs created by the Arawaks around AD 300. The most impressive petroglyph is the head of Jocahu, the Arawak God of Creation, carved from a stalagmite. The Fountain Cavern National Park is believed to have been a major regional worship site and a place of pilgrimage for the Amerindians.


Sold on visiting the island? Ok, let’s talk about where to stay. Most of the accommodation options on Anguilla are private villas, so we recommend avoiding hotels because they can get quite busy. Staying at a private villa will give you resort-like services and amenities in a private setting. Our first choice of accommodation is the villas at Four Seasons, set along the island’s northwest shore, atop coralline bluffs overlooking two of Anguilla’s most pristine beaches. The resort has 3 to 5 bedroom villas that can accommodate up to 13 guests.

If you are interested in visiting Anguilla and need help arranging your vacation, please let us know 🙂


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