• Juliet Weller

What To Do & Where to Stay on Five of Our Fave Islands

Updated: Sep 20, 2021


We’re having an adventure at my house. Here are a few hints – packing, cleaning, staging, storing, showing. Get it? Yes, our home is on the market. There will more to this story, but for now, sound bites and mini-clues are all I’m divulging. Thanks goodness I can distract myself from the tedium of this “adventure” with the joy of planning my clients’ real adventures in luxury, relaxation, and exploration; I can inspire your travel with my article; and next week I'll participate in a travel symposium. Somehow it will all get done, and I’m not worried because it always does!

Based on last week’s article, some of my readers requested “more Caribbean!” As I mentioned in that article, I know this isn’t everyone’s travel love. So let me take the opportunity to remind you that if there is a topic you’d like me to explore, do not hesitate to let me know. I do take requests, and this week the request if for smaller island hideaways that a person might not think of when seeking the Caribbean vibe. To do this I am risking the ire of my Jamaican readership who will wonder why I didn’t include Jamaica. Let me put it this way: nobody DOESN'T think of Jamaica when the word “Caribbean” is mentioned. That is a wonderful blessing, but it’s just not the topic of today’s article. Irie?

Rum bars and seafood shacks, music, mega-yachts and boutique resorts galore. In a sea of tempting white sands, it’s my job to help you choose from among the gorgeous destinations and still steer you clear of tourist traps.

Please note that I’m not including any of the Covid travel restrictions/requirements for these destinations as they change frequently and are best reviewed as part of the trip planning process.


Saint Bart’s - St. Bart’s immerses you in an easy tempo. It’s a nice feeling of freedom amid the beauty of the landscapes, the brightness, the cleanliness, the absence of car horns. Maybe that’s why, at one point, the oldest person on earth was an inhabitant of Saint Bart’s (a nun named Eugenie Blanchard, who lived nearly 115 years!). Take in the small market in Lorient for its fruits and vegetables and spices , or the fish market in Gustavia, where you’re likely to run into any one of a number of celebrities who call the island home. One of the biggest spectacles of the year is the St Barths Bucket Regatta, held in March. It is a ‘bucket’ regatta in name only. This mega-yacht race is as formidable as the America’s Cup.

Where to stay:


Saint Lucia - where nature’s wonders never cease: for lovers of things botanical, a rainbow of flowers and flowering trees like the aptly named flamboyant tree (also known as royal poinciana). For divers, Soufrière Bay at the base of Petit Piton, is spectacular: 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. At Latille Falls, a Rastaman named m Selai, has tended a garden around the waterfall for more than 20 years; he offers a fish pedicure that’s more like fish tickling your feet – which translates into forgetting all your worries. You have no choice but to laugh. Gros Islet’s Irie Bar, a remarkably chill and unpretentious spot where the owner, serves cold beers and rum with fish from his daily catch – with soothing reggae or film screenings in the background.

Pro Tip: Check in three hours prior to departure as suggested– which is totally not necessary, as the airport is never that busy – then head back out to Island Breeze Bar & Grill on Vieux Fort’s Sandy Beach, across from the airport. It is the coolest airport lounge. You can even go for a swim, since the airport the terminal is literally a two-minute drive away.

Where to stay:



U.S. Virgin Islands - A diver’s dream. Even if the typical marine life is quite similar across the Caribbean, the diversity of diving sites around Saint Thomas is remarkable. From ancient coral reefs that grew steadily for centuries to giant granite boulders and from tunnel and canyon formations to the numerous shipwrecks, the visual impact is amazing. Boating and cruising past some of Saint Thomas’ neighboring islands provides constant visual pleasure.

Saint Thomas’ sheltered deep-water harbor made it a big colonial trading center. Main Street’s fancy shops are partitioned from the old days’ large warehouses – their original walls still show the many coral chunks used as bricks. The capital, Charlotte Amalie, is an extended relic of Danish colonial architecture with much to explore: pirate museums full antiques, shipwreck artifacts, and exhibits. After seeing the town, take the gondola to Paradise Point, at the top of a high hill, for the best view of the city and the harbor.

Where to stay:



British Virgin Islands - Two words: Smuggler’s Cove. When driving on the western end of Tortola along the Sir Francis Drake Channel, the ocean is about ten feet away (which sounds a lot like Palisadoes Spit on Kingston Harbor – there I said it). Nearby, on Carrot Bay, head to D’CoalPot for unmatched conch chowder and grilled lobster. Tortola has non-touristy villages and untouched, natural shoreline. They are tranquil, but full of life.

Where to stay:

  • Virgin Gorda’s Rosewood Little Dix Bay has an open-air rum room

  • Retreat to Sir Richard Branson’s Moskito Island for a memorable family reunion.

  • Necker Island is a 74-acre sustainable, unspoilt private island paradise, complete with flamingos and lemurs. a stunning and unspoilt area of the Caribbean. surrounded by coral reefs and fringed with beautiful white sandy beaches.


Grenada - You can always find something to do in Grenada. Saint George’s, the capital, is lively and is where everything happens. The House of Chocolate has a café and small museum about the history of chocolate on the island, and will let you make your own cocoa balls. The island’s food in general will surprise you. Weekly Fish Fridays with steel pan music or live shows. Kelly’s Hot Spot is a local favorite for fresh seafood from the nearby fish market. In Sauteurs, Petite Anse serves fantastic barbecue with a wonderful view of some of the smaller islands from its balcony. Visit Annandale or Concord waterfalls. They’re secluded and very calming – if you’re lucky, you might see a monkey. Wherever you go, you’ll discover that the country’s most positive attribute is the very down-to-earth, very laid-back, friendly people

Where to stay:

And for a bonus...

Anguilla - What’s special about Anguilla is its sense of freedom and intimacy that 15,000 people share. It’s easy to know everybody; there’s a familiarity and an egalitarian feel. It has a stunningly beautiful marine environment and beaches with a sea breeze most of the year.

Where to stay:

Make sure you click on the links I've included; the photos are stunning. Sift through them just to take a break from your day; there are hundreds of them - cool pools, turquoise beaches, high-end cuisine, friendly faces awaiting your arrival, top-notch accommodations and relaxing spas.Then let me know which of these destinations entices you. Or at least let me know what you'd like to read about next.


'til next week!

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