The first portion of your trip is all about easing into the rhythms of Barbadian life before lifting anchor. You’re staying at Little Arches, Oistins, a laid-back, family-owned boutique hotel and a far cry from the islands’ larger, more developed resorts. You can kick back on the white sands of Enterprise Beach just across the road, and you’ll also have time to explore Oistins itself. This sleepy coastal village has a lively fish market, where you’ll see vendors bone their fresh catch. You could also attend a fish fry, where live music creates a jubilant, street-party atmosphere. 

Over the next seven days, you’ll sail between six islands, each with its own character and feel despite their relative proximity. You’ll stop at a different island every day but still have plenty of time to relax and absorb the experience of sailing on a five-masted square rigger, climbing to the crow’s nest, sea-gazing from the outdoor pool, or joining a knot-tying class. During the week, you could snorkel at the base of Saint Lucia’s twin Pitons, or take them in from above by helicopter. A Dominica, you’ll trade white sand for black and hike through forest trails to bubbling mud ponds and crater lakes. Antigua is a repository of British naval history, which you can probe into on a tour of Nelson’s Dockyard. And, you’ll explore a trio of lesser-visited islands, Saint Kitts has several well-preserved plantation houses, while Les Saintes and Martinique have their own French-influenced Creole culture. 

After disembarking, you can unwind in a beachside boutique property near Speightsown, perhaps visiting St Nicholas Abbey to sample its run.