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.

Chartering A Yacht in the British Virgin Islands

The British Virgin Islands (BVIs) are a very popular destination for sailors—and with good reason. Near-constant trade winds, all-year-round warm temperatures and dazzling white sandy beaches surrounded by clear and tranquil turquoise waters and lined with striking coral reefs make these islands the perfect place to test your sea legs and create lifelong memories with your family and friends. Whether you want to explore the breathtaking, secluded anchorages, see tropical aquatic life by snorkel or scuba, hop between uninhabited islands, or head to the palm-fringed beaches and enjoy the bars, chartering a yacht in the British Virgin Islands gives you the option to do all of that and more. However, there are a few things you should know before making the big decision to charter a bareboat, crewed, by-the-cabin, or skippered yacht.

Passports and Visas

Everyone in your party, including U.S. and U.K. citizens, requires a passport that is valid for another six months upon arrival when entering the BVIs. Most visitors who stay for less than six months don’t need a visa if they possess a return or onward ticket depending on your country of citizenship. For the latest travel advice including security and local laws, plus passport and visa information check and follow @TravelGov and Talk to your British Virgin Island yacht charter company to make sure you have all of the correct documents for your seafaring vacation and make copies and/or take pictures of them.


Insurance and Deposits

Take out appropriate travel insurance before setting sail and make sure it covers you for all the activities you want to do. Every British Virgin Islands yacht charter company is going to have different insurance options, however, you’ll definitely have to buy (or at least, want to consider buying) yacht insurance. This may or may not cover trip cancellations, boat or dinghy damage, or lost items. Some special types of charters will require additional insurance or deposits, such as the racing deposit required for yachts chartered for entry into regattas or a cell phone deposit for a direct line of communication between your boat, your charter company, and their mechanic.


Temperature and Sailing Conditions

Temperatures in the BVIs are around 77°F to 82°F all year round. August is the hottest and sunniest month and sea temperatures are warmest in September. The hurricane season is between June and October, which is also the wettest month, however, there is a very low chance of a hurricane affecting your vacation. If you’re looking to be alone in an anchorage with the pristine beach to yourself, this is the perfect time to come. The BVIs are also known for the tradewinds season between November and June and the famous Christmas winds in December/January. Winds are mainly from the east or northeast and blow from 10 to 20 knots, depending on the time of year. Groundswells can occur between December and March after particularly strong winds. If you like a bit more action on your British Virgin Islands yacht vacation, this is when you’ll want to set sail.

Moorings and Marinas

Most of the bays in the BVIs have overnight moorings. A lot of sailors prefer the safety and comfort of an overnight mooring instead of anchoring. Expect to pay $30 per mooring per night. You can use the app BoatyBall to reserve and pay for mooring balls located in prime locations throughout the BVIs. If you would like to get your land legs back, spend the night in one the BVIs’ full-service marinas. Hook up to the shore power, run your shoreside AC if you have it, and make use of a little luxury onshore. Expect to pay from $1.50-$2.50 per foot for the night.

Bon voyage!


Where to Go Fishing in the U.S. Virgin Islands

The US Virgin Islands are located right at the edge of the six-mile deep Puerto Rico Trench, an area known for having some of the best game fishing in the world. Twenty-one world records in fishing have been set in the Virgin Islands including the still-standing IGFA Women’s ‘All-Tackle’ world record for Blue Marlin back in 1982—a whopping 1073 pounds! Monumental catches such as these are a testament to the excellent fishing opportunities anglers of all ages and experiences levels will find both inshore or offshore in the US Virgin Islands and we at Blue Sky Luxury Travels are here to make your trip one you certainly won’t forget.

Red Hook

St. Thomas is home to several fishing tournaments throughout the year such as the Dolphin Derby in April, the Bastille Day Kingfish Tournament in July and the Wahoo Windup in November. It’s also one of the most renowned locations to catch Atlantic Blue Marlin and while Marlin fishing is fine year-round, the most optimal months are May through October. One of the best places to go fishing on the island of St. Thomas is in Red Hook. Offshore, you’ll find Mahi Mahi, Tuna, Wahoo, Sailfish and of course, Marlin. Stay closer in and you’re looking at the perfect place to catch some King Mackerel, Snapper, Grouper and Jacks. Red Hook also has some great snorkeling where you can swim alongside turtles, stingrays, a variety of colorful fish and amazing coral of all shapes and sizes.

Just twenty minutes west of Red Hook is where you’ll find another great fishing spot in St. Thomas—Charlotte Amalie. Thanks to its proximity to the North and South Drops, you’ll find waters rife with Blue Marlin, Wahoo, Mahi Mahi and Tuna. Some charters even allow you to snorkel with turtles and dolphins. Spend a day here and you’ll be able to say that you fished some of the best sports fishing grounds in the world.


Cross the Pillsbury Sound and you’ll reach the smallest of the three main US Virgin Islands, St. John. Without a doubt, the best place to go fishing on this island is in Cruz Bay and with Offshore Adventures Charters, you can depart from either The Westin St. John, Resort & Villas or the National Park Dock in Cruz Bay (along with all of the resorts and public docks back in St. Thomas). Choose between a custom 32ft Diesel Inboard Center Counsel Fishing Boat with Marine Head and a 41ft Custom Open Salon-Style Ronin Sportfisher and spend four, six or even ten hours live bait fishing to your heart’s desire.

There’s another fun spot to fish in St. John and this one’s particularly underrated. For a completely different experience, head over to Leinster Bay for classic flats fishing. Here, you’ll find the easily-spooked and hard fighting bonefish. These fish can weigh as much as 19 pounds and measure as high as 30 inches or more.

ChristianstedFinally, we turn our attention to the largest US Virgin Island, St. Croix. This island is surrounded by a drop which is .5 to 4 miles north or south. Migrating schools of small fish gather in these areas so you’ll find a lot of fish similar to St. Thomas here—the Billfish, Tuna, Wahoo, Marlin, and Mahi Mahi. However, unlike St. Thomas, St. Croix has a narrow under-water shelf off its shores which makes fishing from small boats close to the shoreline very rewarding. On the northern side of the island is the town of Christiansted where you’ll find some of the best charters and tours. It’s also a great sight-seeing spot for whales, porpoises, and turtles.

What are you waiting for? Give us a call and let Blue Sky Luxury Travels provide you with a legendary experience in one of the best places to fish in the world.


Recommended Caribbean Villas

Villa Flower
Over Yonder Cay

A Day In the Life: What Does a Luxury Concierge Service Actually DO?

Blue Sky Luxury Travels is based in the Caribbean and creating vacation experiences for clients in stunning destinations all over the world. We make a point of visiting each property that we represent, and we love to share our discoveries so we post photos every day of beautiful destinations and luxury experiences. We know it may all look like fun and games, island-hopping in Fiji, Hawaii, the US Virgin Islands, and the British Virgin Islands, but we promise, we are actually hard at work! Since so many people have asked, we wanted to share what a day in the life is for Shanna Dickerson, the CEO of Blue Sky Luxury Travels. Shanna stays in different islands and towns all over the world, but wherever she is, she makes sure to keep to her schedule and make sure that all of her clients’ needs are cared for.

So here’s what a day in the life of Shanna really looks like:


Shanna rises early and meditates for twenty minutes to get her head straight for the day. Next, she heads straight for the coffee machine for a nice hot cup of coffee. She checks her phone for any urgent client messages and looks over her schedule for the day, always making a point of picking a beautiful spot with a view to start the day off right.



Workout time! It’s so important to keep energy high and muscles strong, so Shanna gets her exercise done, either with a hike in the hills, a trip to the local gym, or her 25-minute at-home workout routine.


Client messages. Clients and vendors communicate with Shanna through many different means: text messages, Facebook and Instagram direct messages, emails and phone calls. When a new client comes in, Shanna sends them a Concierge document outlining the services that Blue Sky Luxury Travels has available, and clients usually email her with their specific needs. Shanna keeps track of client requests for upcoming trips on a gigantic spreadsheet, so she refers to that and fills in details as she gets new requests. She makes notes of what needs to be done for the day and answers questions for clients who are coming to the islands.



Vendor phone calls. In the Virgin Islands, most car rental services, grocery delivery services, and BVI Yacht Charters operate primarily by phone. This is why it’s so essential to have a travel concierge service handle planning when you’re visiting St. John, St. Thomas, St. Lucia or the Bahamas- it’s hard to get in touch with someone who can set things up. It’s not like other trip planning where you can just go online and do it all yourself. Internet service can be spotty on the islands, so Shanna makes most of her arrangements with vendors over the phone. They’re all accustomed to hearing her cheerful voice and she makes sure they stay organized and keep to the arrangements she’s made for her clients coming to the islands. Shanna makes arrangements for Caribbean villa rentals, yacht rentals, catamarans, fishing trips, grocery delivery, snorkel gear rental, kayak and paddleboard tours, and dining reservations so her clients can relax and enjoy their Caribbean vacations.


Shanna takes a break for lunch, usually a big salad or veggie bowl, at a restaurant on the island. She makes sure to try all the different dining options on each Caribbean island where she stays, so she can offer the best recommendations.


Back to work on emails and phone calls, making arrangements with clients and vendors.


Client meetings. Shanna handles housing for hundreds of hurricane recovery workers through her Blue Sky Global Logistics division. She often meets with top-level officials to understand their needs and find the appropriate solutions. Some days, she’ll take a boat to another island to meet with visiting corporate clients to plan their upcoming corporate events on the islands. Other times, she’ll offer a quick island tour to visiting friends, to show off her favorite spots for paddleboarding and beach time. Face to face is always best, so Shanna makes the time to meet in person with her clients.

Dinner time. Sometimes it’s a dinner meeting with clients, or a meetup with friends staying in a Caribbean villa nearby, or even a quick sandwich at home when the work schedule is intense.


Shanna checks her messages one more time to make sure everything is handled, then the phone goes OFF for a little meditation and quiet time before bed.


Bedtime! Early to bed, and early to rise, keeps Shanna energized, cheerful and ready for anything!

We hope this window into Shanna’s world has helped you understand a little more of what Blue Sky Luxury Travels really does. We take care of every trip planning detail for you from start to finish. Our goal is to make your vacation relaxing, fun and incredibly memorable. If you’d like to put our concierge team to work for your next vacation, please email us at


New Hot Additions to our St. John Island Villas Collection

The island of St. John is undergoing a complete restoration after the destruction caused by Hurricane Irma, the Category 5 storm that hit the island in 2017. More than a year later the island is coming back to life and is ready to welcome visitors in newly upgraded villas. Here is a sneak peak of three new villas we recently added to our St. John villas collection. We have personally checked them out and highly recommend these Caribbean villas to all of you looking for luxurious comfort and style in the Caribbean.

Mare Blu

Located on the hillside of one of the most prestigious locations on the island at Rendezvous Bay, this villa offers six luxurious bedrooms with majestic views of St. John’s south shore. The villa is suitable for 12 guests and provides seclusion for each party since it features four separate buildings linked together by tropically decorated outdoor paths. All bedroom suites boast unique Caribbean furnishings, air-conditioning, flat screen 24 inch televisions with cable and have bathrooms with double vanities, showers, and are tiled in grey granite from floor to ceiling and many other custom features. For your entertainment there is an outdoor sitting space with a huge 55 inch flat screen television with cable and DVD player. The covered outdoor area flows directly into the sundeck and the infinity edge pool. The lounge also has refrigerator drawers for drinks and snacks, a closet filled with floats and pool toys, and a powder room for convenience. In addition to this luxurious outdoor entertaining area you can also enjoy a fully equipped outdoor kitchen with with awesome ocean views from everywhere you turn.

Taylor House

This newly constructed villa sits proudly on a hillside overlooking the world-famous north shore of St. John. This spacious 4,000 square foot villa is ideal for groups of up to eight guests. All four bedrooms are air-conditioned with private balconies and private bathrooms. One special characteristic about Taylor House is that is is very bright inside. You will get full sun exposure from sunrise to sunset. Outdoors you and your party can enjoy a heated swimming pool with comfortable loungers overlooking views only mother nature can create. The outdoor area is very eco-friendly and features tropical gardens with banana, mango, lime, coconut and papaya trees.

Villa Sunspot

Villa Sunspot is your ultra luxury property located within exclusive Lower Peter Bay featuring modern architecture with island charm. This majestic villa has a two level Main House with the living room, dining room and kitchen on the first level and the master bedroom on the second level. The Sunspot master bedroom has a private deck with views of Cinnamon Bay Beach. In case you don’t feel like getting out of bed, you can enjoy this dramatic view right from your pillow. The guest bedrooms are located next to each other in a semi-exterior hallway with a tropical garden area and are luxuriously designed with an old world Spanish décor. Each bedroom has its own en-suite bath, air-conditioning and a balcony with ocean views. Despite all amazing indoor amenities you will be tempted to spend most of your time in the outdoor pool cabana, an elegant outdoor living area for Caribbean entertainment. A few steps below it is the infinity pool with a pool bar and tropical garden gazebo overlooking magnificent Caribbean panoramas.


For a complete list of St. John villa accommodations, please visit our page –

Recommended St. John Villas

A La Mer
Caribbean Palm Villa
Estate Solenborg
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