Turquoise waters, white sands, and a private villa – magic!

Greetings travelers!!  I was born a planner which comes as no surprise since any travel advisor worth their salt needs to excel in the ability to plan.  When it comes to traveling myself, I plan my itinerary in detail (easily accessible on an app on my phone) but leave room for spontaneity. I recommend the same to my clients. One of the joys of traveling is the amazing surprises you come across, whether it be a restaurant, experience, or people you meet along the way.  These experiences also make for the best stories and memories!  For example, when we were on the Hana side of Maui, we got a tip from another guest at our resort about beach-hopping and spent an afternoon discovering hidden gem red and black sand beaches that weren’t on our map.  Also highly memorable was the villa we stayed in, described as a plantation-style ocean bungalow, complete with a direct ocean view and hot tub.  It was one of the most amazing paradises I’ve ever experienced.  Today, private accommodations are highly sought after for any destination and come in a range of price points. 

In this newsletter, I’ll be highlighting some Caribbean resorts where you can find private accommodations in the ‘villa’ or ‘cottage’ type categories.  Remember, you have clout as a VIP and will receive perks when booking with a travel advisor, so I don’t recommend DIYing an upscale (4-star and above) hotel reservation.  For example:  when I was in Bermuda last fall, I not only earned an upgrade to a larger cottage upon arrival but received breakfast (in this case an extensive brunch buffet) for two people every day of the trip ($40 per person per day x 5 days = $400 total savings).  Breakfast for two is one of the standard inclusions when you book a Virtuoso network hotel. 

Important note about our current times – each island has its own requirements and process for entering tourists and those requirements can change.  For example, the Bahamas changed their reopening policy twice in less than one week. Reach out to me directly for the most current information and guidance. 

Also, some people are considering a Caribbean getaway for this coming holiday season (with fingers crossed).  If you’re in the same boat, now is the time to look and book, and cancellation policies are typically more flexible than they have been before. 

This newsletter is a two-parter, and I’ll highlight more islands and resorts next week!  Read on for future inspiration about six Caribbean islands with resorts that offer private accommodations like villas and cottages…

A private villa outdoor space at Half Moon in Jamaica


This month, Travel+Leisure magazine published their list of the 25 best islands in the Caribbean (based on reader rankings of activities and sights, natural attractions and beaches, food, friendliness, and overall value), and Anguilla sits at #1 on the list.    

Anguilla is all about relaxing in a paradise-like setting.  The snow-white sands and clear, turquoise waters will hypnotize you.  Water activities will keep you moving through exploring limestone cliffs, underwater caves, and hidden coves. 

Belmond Cap Juluca is only 10 minutes from the airport and offers 42 suites perfect for families or couples.  One to three-bedroom suites or villas with direct ocean views, private terraces, and private pools dot the coastline.  Belmond resorts always exceed expectations, and they VIP Virtuoso travelers. Have an upcoming celebration like a milestone birthday or anniversary?  This is your place. 


Finding quiet and private places in the Bahamas is very doable on the smaller islands in particular.  Abaco Island, Harbour Island, Exuma, and Eleuthera took places 2, 3, 8, and 12 respectively on Travel+Leisure’s list.  Hidden Gem tip – we love Eleuthera and one of our team spent a term at The Island School and Cape Eleuthera Institute studying marine biology and sustainability which was an amazing experience (anyone who knows a teen interested in these subjects, reach out for more info). 

As you likely recall, the northern Bahamian Islands were severely affected by hurricane Dorian last year, especially Abaco Island.  Eleuthera wasn’t similarly affected.  The Bahamas are essentially closed right now for leisure travel from the US (it’s wacky – I’m happy to explain if you’d like to know the details), but some lovely properties offer private accommodations in smaller, boutique type resorts when it reopens:

The Cove Eleuthera is an intimate, mellow 57-room resort with stylish seaside cottages and villas.  Spend your days in the turquoise ocean waters and hilltop infinity pool and your evenings at the open-air sunset bar and gourmet restaurant.  You won’t want to leave!

Coral Sands on Harbour Island, sometimes referred to as the ‘Nantucket of the Caribbean,’ is off the northeast coast of Eleuthera.  Newly refurbished, Coral Sands has added new beachfront cottages.  Take a stroll on a pink sand beach and venture into quaint Dunmore Town and its charming mix of pastel cottages and 18th-century buildings. 

The fishing is incredible in the Bahamas so if you love to drop a line, these islands are your nirvana.  Try bonefishing with a private guide.  Also, be sure to visit the scenic Glass Window Bridge and at least one of the incredible Blue Holes


Everyone who has been to Bermuda knows it’s an incredibly special place; Mark Twain expressed his passion for the island by saying, “You can go to heaven if you want.  I’d rather stay in Bermuda.”  Easily accessible from the US’s east coast, travelers visit repeatedly. 

For adults, the place to vacation away from the crowds and in your own pink cottage is Cambridge Beaches Resort & Spa.  Cambridge Beaches is located away from bustling Hamilton on the western end of the island and is its own private paradise. I enjoyed five days of tranquility there last year and am ready to return!  If you’re a golfer, they have a relationship with the gorgeous Port Royal Golf Course and will gladly secure you a tee time with transportation to and from the course. 

For families, the Rosewood Bermuda offers luxurious suites and residences and will keep the kids entertained with the Rosewood Explorers program and junior golf and tennis academies.  The resort is a “low-density setting” which allows guests to feel the spaciousness of Tucker’s Point and its 240 coastal acres.  All ages will love their stay at Rosewood Bermuda. 

Dominican Republic

Some fun facts about the Dominican Republic:  the national sport is baseball, it offers the highest peak in the Caribbean, and has the oldest city in the Americas.  Add 750-miles of postcard-perfect coastal beaches, and you know that the DR is an amazing destination. 

If an oceanfront villa in a resort with three private beaches, a marina, equestrian center, and top-ranked golf appeals, then Casa de Campo is the place for you.  And if you’re sporty, you will LOVE this resort.  Not just for golfers who flock to the top-rated “Teeth of the Dog” course, you can play tennis, ride horses, sail/boat, sport fish, dive, shoot clays and even attend Real Madrid soccer school!   

Private villas range from 3-10 bedrooms (up to 24 people) and include a private pool and dedicated concierge. Villas with 4 bedrooms and above receive a golf cart for use during their stay.  If there are fewer than 4 of you, consider a superior casita at the hotel which sleeps up to 4 people and includes a golf cart and private terrace.

A full-luxury, more private experience your thing?  Eden Roc Cap Cana will deliver!  Nestled in the exclusive, beachfront community of Cap Cana, Eden Roc is secluded on the eastern tip of the DR.  Couples and families have a choice of only sixty private suites and villas decorated to reflect the Italian and French Rivieras.  We love their private ecotourism safari experience where you take a speedboat ride through mangroves and caves, mountain bike and zipline in the Anamuya Mountain area, and immerse yourself in the local flavor of the island. 


Jamaica is home to some amazing resorts where you never have to leave the property!  The reggae comes to you.  A gorgeous resort that’s family-friendly, close to the airport, and Hidden Gem favorite is Half Moon (pictured above).  It offers the largest spa oasis in the Caribbean, an 18-hole championship golf course, tennis and squash, The Sugar Mill (considered a top restaurant in Jamaica), equestrian center, and a children’s village and program to delight your kids.  Rose Hall Villas offer 4 to 7 bedrooms and are perfect for families, groups, and golfers.  Each villa features a living room, dining room, outdoor living space, private pool, butler, housekeeper, and cook.  What more could you ask for?  Perfect for families who love a country club lifestyle. 

Round Hill Hotel & Villas is a former pineapple and coconut, 100-acre plantation on a peninsula eight miles outside of Montego Bay. Elegantly understated, past guests include Johnny Cash, Paul Newman, and Paul McCartney.  In fact, JFK and Jackie honeymooned in Villa 10!  The villas have spectacular views and private swimming pools.  Come as a couple or family – the Pineapple Kids Club is fun for young children through teenagers.  Many travelers vacation at Round Hill year after year. 

Turks & Caicos Islands

Anyone who has been to Turks & Caicos knows the water and beaches are beyond spectacular!  If you haven’t been, it’s an easy flight and you must go – enough said.  Grace Bay Club is located on the western end of the island of Providenciales, only 15 minutes from the airport, and on a prime location of iconic Grace Bay beach.  This all-suite resort is a haven for beach-side relaxation.  Couples and families alike will feel at home with a choice of family-friendly suites or even a private home.  The Private Villa Collection offers two to nine-bedroom villas with all the resort amenities. 

COMO Parrot Cay is secluded on Parrot Cay which is a 25-minute ride by speedboat from the main island.  The 1,000-acre propertyoffersvillas and houses with private pools, and many have direct beach access with 24-hour butler service.  The resort takes wellness seriously; guests 16 and older can enjoy the COMO Shambhala’s award-winning, Asian-inspired programs, and spaces including an airy yoga room and jacuzzi garden.  Healthy, delicious cuisine compliments the wellness vibe for the ultimate in personal rejuvenation.

Ready to pack your beach bag?  Do you know someone who is contemplating a Caribbean getaway and would appreciate some professional advice?  Hit reply to schedule a  call/virtual coffee chat or jump over to www.facebook.com/hiddengemtravelconsulting and comment on today’s post about this newsletter. 

Hidden Gem Tip: Not sure which island is right for you but know you want a private accommodation like a villa?  We work with a top-rated villa supplier that offers breathtaking properties around the world.  The villas range from 2 to 24 bedrooms and every one is amazing in its own way!  They make sure that the villa you select is perfectly matched to your needs.  Their inventory in the Caribbean is impressive!

Wishing you and your family continued good health,


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Hi, I'm Susan Wilson

I’m the founder of Hidden Gem Travel Consulting. As your personal travel advisor, I craft custom worldwide itineraries that astound and inspire you.


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