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There’s nothing wrong preparing before you leave, make sure you have these items on your travel bag, items such as sunscreen, sunglasses, portable music player (if you like some music), swimsuits, slipper (sometimes its provided as complimentary on some hotels), or some books for reading.
Enjoy.

My proposed remedy for his suburban stress was the somewhat unoriginal recipe of a Caribbean island, gorgeous weather, a seaworthy vessel, and copious amounts of rum. His unexpected response after six years of rewarding lock-down, was, “I’m in!”

After arriving at the Moorings marina in Road Town, the capitol of Tortola, home to our sleek 55-foot monohull, we were introduced to our captain and chef, Australian couple Tom and Jaquie. But shortly after we toured our elegantly appointed cabins, Barry started with queries of cell phone availability and Internet service. Mildly discouraged, I still had faith that the sun, the sand, the cool island breeze and life, in general, on our new floating villa would soon dismantle his daily worries of life back home.

Our seven-day voyage began on the island of Tortola, the largest of the 60 islands that comprise the British Virgin Island chain. Located in the northern Caribbean, Tortola is chock-a-block with soft, white sandy beaches and lush mountains. It also has a protected harbor strewn with a multitude of yachts in all shapes and sizes.

Our first visit was the Bright at Norman Island, just seven nautical miles south of Tortola. Helping to form the Southern perimeter of the Francis Drake Channel, Norman Island is often referred to as Treasure Island because of the vast number of pirates that once claimed these waters. One of its unique features is an area called The Caves, rumored to be the inspiration for Robert Louis Stevenson’s book Treasure Island. Now if the beauty of the British Virgin Islands isn’t enough to loosen the knots of suburban life, I’m not sure what is.

However with the balmy breeze offering a most refreshing relief to the beating sun, Jaquie’s uncanny timing as she delivered a cold rum and Ting with some of our favorite bites, I could see Barry beginning to unravel. We launched ourselves overboard into a turquoise sea, swimming and snorkeling in and around the rock formations called the Indians, easily imagining what glorious treasures might have been sunken in the depths beneath our treading toes. Just below was the Rhone, a British steamer, which sank in 1867 during a hurricane and is now considered to be one of the very best wreck dives in all of the Caribbean.

We made our next stop at a floating bar/restaurant called the Willie-T. Yeah, this one’s hard to describe without sounding shameless and irresponsible. Take yourself back, if you will, to your junior year of college. You’ve been drinking, life’s pretty good, and no dare seems unreasonable. Got it? Now stick this local, anything goes-watering hole on a boat in the middle of the Caribbean and there you have it – the Willie-T. This I knew, of all things, would peak my brother’s interest. You see the Willie-T has only one way to obtain the bar’s famed t-shirt, and no, not with your credit card. You have to earn it by taking a topless dive off the top deck and strolling back across to collect your clothes. He may be a lawyer but he’s still a guy and lucky for him there were some eager takers.

Sailing approximately 11 nautical miles from Norman Island, we reached Jost Van Dyke, a small and picturesque harbor protected by 1000 foot peaks, and home to the world famous Foxy’s beach restaurant and bar. As fate would have it, Foxy himself was “in the house” as we anchored for a visit. It was an open-air, picnic table meets cabaret type party. We sat next to strangers, ate freshly caught Mahi Mahi, drank rum-inspired cocktails and shopped shamelessly at Foxy’s beach-side boutique. Before we knew it, the magic hour began to fall upon us, and Foxy, with guitar in hand, lit up the night. We danced in our bare feet and celebrated life and the glorious sense of freedom before falling into hammocks hitched to coconut palms that lined the beach.

It was now and new and glorious morning filled with exceptionally blue skies. It must have been 11 a.m. when my brother surfaced from his mahogany cocoon below, which was a telling sign that my plan was working. The day ahead was filled with adventures at sea. The Caribbean was like a giant, wet wonderland where we would kayak, windsurf, swim and snorkel. Barry kayaked over to a tiny island known as Sandy Spit, which couldn’t have been more than a few acres from end to end. He carried with him only a book, a towel and suntan oil. Yes oil, not block or screen. This was an ongoing comedy routine throughout the trip. He wanted a tan – refusing to consider that he might benefit from starting off with a higher screen, allowing the sun to do its thing slowly and methodically but instead he chose SPF 8 oil on day one of our trip. At Sandy Spit, we were down to a mere SPF 4. Two hours later I found an electric red Barry snoring beneath a lone palm.

Considered to be one of the most beautiful anchorages in all of the BVI, our next stop was Cane Garden Bay. We whiled away the hours, frolicking in the sea before happy hour at Myettes, a lively hotel, restaurant and bar. Starting off slow, the bar had just a few guests, and we could see that there was a wedding taking place down by the water. A band arrived, sort of Jimmy Buffet meets Bob Marley meets Motown kind of thing. I vaguely remember a rum-tasting session, becoming the official tambourine player for the band, and Barry, now two sheets to the wind, on the microphone with our Jimmy Buffet look-alike, singing his own special version of Mustang Sally. It was official. He was de-stressed. The eventful happy hour was followed by a feast of fresh crab and lobster, then a dinghy ride back to our bobbing home under the stars.

Our mornings were refreshing and lucid. Next stop: Marina Cay, located near Guana Island. This cay is roughly 10 nautical miles from Cane Garden Bay and is a picture postcard island, just minutes from Trellis Bay and the airport, making it a wonderful pit-stop for island shopping at Pussers company store, refueling, or buying a drink and taking in the sunset. We opted to grab a bite at Monkey Point then carry on to Virgin Gorda, which gets its name from its shape. Columbus described the island as resembling a plump woman with her belly in the air. There, our journey called notice to the luxury resorts of Little Dix Bay with its incredible spa and Biras Creek, an elegant bungalow style resort; the Bitter End Yacht Club, which offers a wonderful sailing school; and Baraka Point Villa, which comes with its own chef and crew.

Our last stops before heading back to Road Town were Cooper Island and the private island resort of Peter Island, where we took a swim at Deadman’s Bay. But it was the mysterious Baths at Spanish Town, back on Virgin Gorda, which melted away the last faded wrinkles of city stress. At the Baths, giant granite boulders strewn throughout the beach and along the water’s edge create stunning grottos, caves, wading rock pools and trails that lead to magnificent beaches. Believed to have been a spiritual and physical cleansing place for the Amerindians, the Baths remain a calming place that calls for meditation. On our way back to the boat, we discovered the Mad Dog bar. We ordered their famous frozen pina coladas and pondered the meaning of life, love — and with a chuckle, how well Barry’s law firm might do based on Tortola.

As I dropped a very dark, funny red version of Barry at the airport, I noticed that he was also a much more relaxed, looser version. We joked about leaving empty handed with all the talk of buried treasure. But teary-eyed and full of laughter we both knew where to find the treasures in our lives, and he was heading home to his.

If your answer is “yes,” as mine invariably is, have you revisited? Perhaps.

But more than likely, not.

Well, no more. I recently discovered Royal Caribbean’s Cruisetours — billed as an addendum “designed to make a vacation for clients a complete vacation.” Offered in conjunction with cruises in Alaska, South America, Asia, Australia/New Zealand and Europe, it’s a pre- or post- multi-day escorted land segment that will immerse you into the land and its lore.

A Cruisetour is optional and it takes your on-water adventure inland for 3 to 7 additional days through a transportation combo of luxury motorcoaches and/or trains.

It’s simply the best way to minimize the hassles and maximize being there.

I speak from experience. Prior to a Mediterranean sailing from Rome, I opted for the Cruisetour — it commenced in Venice (2 nights), continued to Florence (1 night) and concluded in Rome (2 nights).

Highlights: A professor of art’s lecture on the work of Michelangelo at the base of sculptor’s famous statue of David in Florence’s Accademia Gallery; an insider’s visit to the Vatican and Sistine Chapel, again guided by an historian insider (additional perk: we were ushered to the front of the admission line that wrapped around the perimeter of Vatican City) and a private dinner in the cellar of a Tuscan winery after a personal vineyard tour.

The best part: I didn’t deal with luggage (my eternal Achilles travel heel); I made no hotel arrangements (they were pre-made, prepaid, upscale and centrally located); local transportation, transfers, city tours, some meals and tickets to famous sites were handled (as were VIP admissions); tips were included; free time was ample and an escort (and acting concierge when requested) was ever-present.