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Greetings travelers and happy August?!  If you live in Connecticut, you know that last week I was unable to send out this newsletter thanks to widespread power outages resulting from Tropical Storm Isaias which hit on Tuesday.  We waited a looong time for the power company to get its act together. 

Now that we’re back in business, we can refocus on the priorities we had before the storm.  For those of us with kids, we’re in the throws of figuring out back-to-school plans during this crazy time.  It’s so stressful dealing with it all – I’m sure you’ll agree.  What we all need is a safe getaway in the future when we can unplug and relax from the craziness of daily life.  When that might happen is up in the air and a personal choice for all of us.  I was able to take a short vacation to mid-coast Maine in July, and not only did it feel safe, but it was 100% rejuvenating.  We stayed at a truly lovely coastal resort (perfect for families and couples), and I’m happy to share the details with you if you’re interested.  Note – Maine has had an exceptionally low number of cases, and they are taking precautions very seriously (masks everywhere and social distancing).  We live in the northeast travel bubble so were allowed into Maine without testing or quarantining. 

Continuing our popular topic from the last newsletter, I’m highlighting more Caribbean resorts where you can find private accommodations in the villa-type category.  Remember, you have clout as a VIP and will receive perks when booking with a Virtuoso 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 received 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. 

Repeating last week’s important note about our current times – each island has its own requirements and process for entering tourists and those requirements can change.  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. 

Read on for future inspiration — a curated list of seven more Caribbean islands with resorts that offer private accommodations like villas and cottages…

Ladera, St. Lucia

St. Lucia

If you haven’t been to St. Lucia, you’re in for a treat.  Travel+Leisure magazine named it a top Caribbean Island this year and for good reason.  It’s gorgeous, and you can have any kind of vacation you want – relaxing, active or a combination of both styles. 

For couples, I love Ladera (pictured here!) which is nestled high with views of the Pitons. The resort is set on a forested ridge, 1,100 feet above the water overlooking the iconic piton mountains and Caribbean Sea.  Yes – a WOW view while you’re treated like a true VIP in one of their 32 suites with private pools and panoramic views.

I recommend Sugar Beach, A Viceroy Resort for families, because not only is it a gorgeous resort right on the white sand beach, but parents get a vacation too with the kids clubs (Sugar for ages 4-12 and Spice for tweens and teens) plus the babysitting service.  If you have a larger family or even a small wedding party, there are some amazing residences on property where everyone can stay together in luxury! 

Cap Maison Resort & Spa is terrific for families, couples, and foodies, with its top-rated restaurant called The Cliff.  It’s located on the opposite side of the island from Ladera and Sugar Beach so offers another view of the island’s culture.  A unique and WOW experience is a private dinner on a deck perched above the sea, and a Champagne zipline that whisks drinks to you.  Perfect for a special celebration!

Have an anniversary coming up?  A Hidden Gem experience for couples – split your week between Ladera and Cap Maison for the best of both worlds which includes VIP upgrades thanks to our strong relationship with these two resorts. 


Picture yourself surrounded by lush tropical gardens overlooking the Caribbean Sea.  Curtain Bluff is on 20 acres and considered a best value for an all-inclusive luxury resort.  Along with 72 oceanfront rooms and suites, the signature Hulford Collection of suites feature private infinity-edge pools. The on-property amenities include a spa and world class wine cellar, and loads of activities range from scuba diving, paddle boarding, windsurfing, putting green, tennis, squash, yoga, and Pilates.

If a private island is more your speed, Jumby Bay Island is a fantastic choice.  The 300-acre island has two white-sand beaches and 40 oceanfront guestrooms, villas, and private residences.  Four restaurants will keep you fueled as you snorkel, sailboard, and cycle around the island.  A hidden gem experience is to wake up to see the turtles lay or hatch their eggs! 

St. Kitts

Located in the West Indies, The Park Hyatt St. Kitts spans the entire beach of Banana Bay and is situated on the virtually untouched Southeast Peninsula, an area of natural beauty.  This newish luxury resort, opened in late 2017, receives accolades for its gorgeous design and 126 accommodations and suites with individual pools. Only 20 minutes from the airport and luxury dining and shopping at Marina Village, the Park Hyatt is ideal for a relaxing getaway for families and couples.  Hidden Gem clients are always treated like VIPs and will receive an upgraded room, if available!  I’ve heard great things about it so plan to check it out myself!


A short boat ride from St. Kitts, Nevis made Travel+Leisure’s top islands list this year, and the Four Seasons Resort Nevis does an amazing job for families in particular!  With 50+ luxury, 1-7-bedroom villas that overlook either the volcano or the sea, you have plenty of space for your family or extended family.  The kids will love the Kids For All Seasons program (ages 3-9) and there is babysitting as well.  Kids can also participate in the Sea Turtle Conservancy program for an educational experience they can share with their classmates once back home.  For older kids and adults who scuba, the Dive & Dine program let’s you slip into a wetsuit and join a Four Seasons chef and a dive master where you explore local dive sites and can lasso your own lobsters – that’s a hidden gem experience! 

Grand Cayman

It’s been a number of years since I vacationed in Grand Cayman but remember it well from its expansive Seven Mile Beach, amazing snorkeling, Stingray city experience, and hammock nap on Rum Point.  Award-winning, Virtuoso Best Of The Best Kimpton Seafire Resort + Spa is ideal for families and foodies who want a vacation with a full compliment of options and activities.   Camp Seafire kids club has day and evening programs (so the kids can have a blast while the parents get time off to reconnect).  The three restaurants have weekly foodie nights (sign me up for Taco and Tequila Tuesday on the beach!) For more privacy, consider an Oceanfront Bungalow complete with kitchenette. 

Puerto Rico

As an island, Puerto Rico has had a very tough time over the last few years, as you know.  However, it remains a popular destination for US tourists due to its proximity and variety of experiences.  Dorado is a gorgeous area of the island, and I remember it well from my last family trip.  Dorado Beach, a Ritz Carlton Reserve resort with a history dating back to the 1950s, offers luxury and privacy with 114 beachfront suites and Su Casa, a five-bedroom villa for extended families.  Wine lovers will enjoy the restaurant, COA, which has the largest wine cellar in Puerto Rico with 690 labels and 3,200 bottles!  Private wine tastings can be arranged for that extra-special experience.  Foodies will want to explore the Culinary Center offerings for cooking classes. 

British Virgin Islands

If you’re looking for a haven of tranquility and unspoiled paradise with a colorful history dating back to Christopher Columbus, Virgin Gorda and Rosewood Little Dix Bay is worth your consideration.  Renowned for its tranquil location where you can unplug, this resort recently went under a four-year renovation.  Suites and villas are tucked amid vibrant gardens along a half-mile stretch of sandy beach.  You can keep busy with water sports and activities from snorkeling to sunfish sailing that are on-property as well as garden tours and hiking.  The Rosewood Spa and kids club keep parents and children happy and relaxed.  The resort also offers complimentary Beach Drops which are water taxis to seven local beaches.  Take a picnic lunch for a memorable day!  In the evening, check out the 107 aged and rare rums in the Rum Bar.

Love boats? Our friends at the world’s premier yacht charter company, The Moorings, have a large base in Tortola and you can sail or power boat yourself around this Caribbean paradise or hire their skipper/entire crew.  If you’re interested, let’s talk! 

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 and comment on today’s post about this newsletter. 

Hidden Gem Tip: If you love the idea of chartering a boat with or without a skipper, The Moorings also has Caribbean itineraries in Antigua, Grenada, Martinique, St. Lucia, St. Martin, and St. Thomas.  Their newest location is St. Petersburg, Florida so you don’t have to leave the country if you’d rather stay closer.  I am happy to give you the full scoop as I spoke to them just yesterday.

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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