Mark Twain said that twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do.
So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails.
This time of year ( anytime actually) I’m ready to drop it all and dive into silky water and powdered sugar sand.
Rum bars, seafood shacks, beach shanties, calypso music, salty pirates, sweaty dance floors, megayachts and boutique resorts galore….the Caribbean Islands are at top of mind and should be at the top of your list.
Here are some favorite islands…
U.S. Virgin Islands
My home away from home, the USVI is seared in my heart. Fair winds, blue skies, secluded beaches, off the beach reefs, national park, underwater monuments, hiking trails, petroglyphs, strong willed locals and even stronger drinks, I learned to sail these waters with a true pirate and comrade and lived, laughed, and loved well on these emerald volcanic rocks. St. John continues to be one of the most beautiful places in the world and a divers paradise.
Where to Stay in the U.S. Virgin Islands:
- Take to the water on The Ritz-Carlton, St. Thomas’ 60-foot catamaran, The Lady Lynsey II to Honeymoon Beach!
- Villas of Distinction in Peter Bay, St. John for the most beautiful sunsets and Chef prepared meals.
- My favorite is a St. Thomas Yacht Charter with Moorings!! A year-round balmy seas and fair winds, as well as the ability to experience the very best sights and sounds of the three beautiful main islands and the more than 50 smaller Caribbean cays and islets surrounding them is your best vacation bet.The turquoise waters and the Caribbean culture need to be explored by water! 7-10 day itineraries available.
Puerto Rico
PR was our stomping ground for real nightlife. Loading the Vueve Cliquot up and Beaches, Massage, Steam, Shake, Repeat. But Natural reserves such as El Yunque and Caja de Muertos, the old city’s colonial architecture, bio-luminescent bays, and music are on the docket too. If I were to pick my favorite about PR and the territory, it would be the soul food. The cuisine is distinguished by its abundance of flavorful meaty, crunchy, and fish dishes, with a healthy dose of herbs and spices and local flavor. While the massage’s effects are getting fuzzy, the vivid memories of the island and its people are not. Puerto Rico is so accessible right now and would love to welcome you with open arms.
Where to Stay in Puerto Rico:
- Don’t miss the Condado Vanderbilt Hotel’s historic pink-marble art deco lobby.
- Dorado Beach, a Ritz-Carlton Reserve has a great water-sports program and outdoor activities on its 1,400 acres.
- Post up at Fairmont El San Juan Hotel for its proximity to downtown and its perch on Isla Verde Beach.
- The Ritz-Carlton, San Juan is set on a two-mile stretch of beach 20 minutes east of Old San Juan.
- Tee off on The St. Regis Bahia Beach Resort, Puerto Rico’s Robert Trent Jones Jr.-designed golf course.
Nina Choi
Dominican Republic
It deserves all of the acclaim. Dominicans’ Spanish-African heritage distinguishes them in terms of music and food, as well as in their strong and recognizable accent and dialect. Music and dancing are an important part of their rich culture. And wouldn’t you know it, I will be there in a few weeks to dance, dance, and dance!! Squeal.
Where to Stay in the Dominican Republic:
- Eden Roc Cap Cana’s La Furnia is a natural cenote at the heart of the resort.
- Amanera makes an impression with its clifftop infinity pool overlooking Playa Grande.
- Test your polo skills at Casa de Campo Resort & Villas’ equestrian center.
- Indulge in all inclusive decadence at Hyatt Zilara Cap Cana.
Turks and Caicos
Of course, Turks is world-famous for their sugar sand beaches: Everybody goes to Grace Bay Beach for its shopping, restaurants, bars, and pristine stretch of sand. I spent seven glorious days in January and will be back in September 2021.
But quieter Long Bay Beach catches a stiff breeze and is popular with kite surfers; Sapodilla Beach, on the Caribbean side, has powdery white sand and calm waters ideal for Jet Skiing ( although I hard pass on the noise pollution). If you love water sports, as I do, you can do everything here from parasailing to deep-sea ( or near shore) fishing, diving, or chartering a yacht to island-hop. Nothing like sinking feet into a sand at the Conch Shack and Rum Bar in Providenciales after diving the reef. TAKE ME BACK!!
Where to Stay in the Turks and Caicos:
- Slip off to Como Parrot Cay for private island bliss.
- Amanyara has serene Indonesian vibes transplanted to the Caribbean for the high rollers.
- Book a palatial private villa at Grace Bay Club’s Estate, a resort within the resort.
- Treat yourself to a treatment at The Palms Turks and Caicos’ 25,000-square-foot spa.
- Escape crowds at The Shore Club, set on a secluded stretch of Long Bay Beach
Saint Lucia
An emerald island where nature’s wonders never cease: While driving the switchbacks and hairpin turns, you turn a corner and right there is a brilliant rainbow arching over an aptly named flamboyant tree (also known as royal poinciana). For divers, Soufrière Bay at the base of Petit Piton, is spectacular. It feels as though you are swimming in a glass of French champagne: On a calm day, there’s a mirror reflection of the piton rising straight up from the ocean. Coral juts out at you like trees in the water below and reggae sounds waft in the good clean living air. Flights are being added often and I have the contact for a helicopter transfer to whisk you away upon landing.
Where to Stay on Saint Lucia:
- For access to a secluded beach, check into Cap Maison Resort & Spa.
- Jade Mountain has suites without a fourth wall, bringing you closer to the lush landscape.
- Settle in at a prime perch between the two Pitons at Ladera Resort.
- Sugar Beach, a Viceroy Resort tempts guests with indulgent treatments in its treehouse spa.
Richard James Taylor
Anguilla
I wasn’t going to add this delicious island as the travel restrictions continue to be so rigid but if you have the time and money, it is a destination worth fighting for…For boating, Prickly Pear Cays and Dog Island are the special places – undeveloped! I love that. Locals come here with a cooler and swim ashore to hang out for a few hours, then get on their boats and head back to main land Anguilla. The sea breaking over the reefs on Prickly Pear is magical and the water divine.
Where to stay in Anguilla
- Belmond Cap Juluca’s whitewashed, Moroccan-inspired domed villas brighten moods on sight.
- Taste your way from Tokyo to Morocco to Greece and beyond at CuisinArt Golf Resort & Spa’s five restaurants and bars.
- Four Seasons Resort and Residences Anguilla’s glamorous interiors come courtesy of design maven Kelly Wearstler.
- Spread out at Malliouhana’s 25 oceanfront acres.
How Far Adventures is an independent affiliate of GTN, A Virtuoso Member. I LOVE to travel and indulge in the Caribbean and I love Travel Planning just as much. If you are curious about another culture and ready to dive in, I would love to help you get there, Soon Come.
