There’s something a bit romantic about the notion of spending the winter sailing around the Caribbean, dropping into sailors’ havens that dot the islands. The reality of it can be far less romantic if you aren’t a seasoned boater who loves the confined spaces of a boat for long stretches of time. There are other ways to do it, though.
We recently spent a few weeks in the Caribbean—a few days in Barbados, a fourteen-day Seabourn yacht-harbour cruise, then a few more days back in Barbados. The Seabourn “yacht” allowed us to see yacht harbours that larger ships can’t go to, all while enjoying the lifestyle of a luxury cruise ship.



With only 296 passengers, the Seabourn Ovation anchored off places like Soper’s Hole in the west end of Tortola BVI, Trois Ilets in Martinique and Terre-de-Haut, Iles des Saintes in Guadeloupe, all places larger ships can’t even go near. But we still wanted that private yacht experience.







We’ve done it before, and we’ll do it again. We’ve done private charters in the past: private boats in Florida, St. Lucia, St. Martin, and the French Riviera. And even a private plane charter from Barbados to St. Lucia last year—an experience to remember. And we did a charter again this year.
While in Barbados, we enlisted the help of the young concierge at Waves Hotel and Spa (a Marriott property) to find the perfect charter. He came through for us with a half-day charter from Unseen Barbados.
The boat was called Princess Hope, a 58-ft Sea Ray yacht for just the two of us. (It can take up to 14 passengers.) The boat did a beach pick-up for us at our hotel—two crew members came ashore with the tender and motored us out. Onboard, the third crew member, a lovely woman with local culinary talents, had laid out a charcuterie board and told us lunch would be ready whenever we wished to eat. The captain took to the bridge, his first mate poured us rum and coke, and we were off to explore the island’s southwest coast.






The boat was truly lovely, and the captain and first-mate, Barbados-born and bred brothers, had the island in their veins. They were personable and polite to the core, knew every nook and cranny of the coast we motored by, and were more than willing to go wherever we wanted. Evidently, most passengers prefer the northern route because it’s calmer. We’d done that before, and since we’re pretty seasoned boaters, we preferred the road less travelled—so to speak!
The route took us south along the Platinum Coast of the island, past Bridgetown, to the Oistins area, the village best known for its Friday night fish fry.
We turned and made our way back toward Payne’s Bay Beach after a terrific authentic Barbadian lunch on board and a few more rum drinks!


The best thing about a private charter is that it is truly personalized. We have control over the itinerary without catering to the whims of other passengers or even the guide. This experience was one for the memory books as we look forward to our next private adventure. Newfoundland, here we come!
Now join us on the water!
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