3 Luxury Sailing Vacations to Go On Before You Die

Cuba

Cuba is, of course, much more than Castro, old cars, and fancy cigars. Passengers on G Adventures’ Sailing Cuba trip begin their journey in Havana before being whisked away to Cienfuegos to board a modern catamaran. The small ship tour (with a maximum of just 14 passengers) focuses on the Canarreos Archipelago, where visitors spend most of their eight-day journey leisurely exploring the beautiful island chain from the water. Relaxed days are spent sunbathing on deck, strolling pristine beaches, snorkeling, and checking out the archipelago’s more remote islands. Standard pricing starts at $1,999, including a twin-share room and most meals (booze is extra).

Italy

If you fancy your relaxation with a bit more luxury, Sailing Collective specializes in small ship cruising that includes whole cabin booking (no sharing with strangers), plus private chefs and unique land-and-sea itineraries. Most of the catalog features bespoke cruise itineraries where guests travel by flotilla with up to five ships together. The Sail Sicily itinerary, in particular, takes passengers on a week-long journey around Italy’s famous Aeolian Islands. The volcanic archipelago is both rugged and pristine, surrounded by impossibly blue waters. The fact that it’s UNESCO-protected makes it a worthwhile destination in its own right. The daily schedule blends sea- and land-based exploring, however, the crew leaves it largely up to the passengers to decide the specific excursions. Pricing starts at $2,200 per person double occupancy and includes most meals (booze is extra).

Fiji

If a four-cabin catamaran is a bit too claustrophobic for your liking, Captain Cook Cruises’ tall ships offer plenty of room to spread out. The company has a fleet of vessels, from a rustic, 88-foot pirate ship to the Fiji On, one of the area’s most luxurious charter boats capable of transporting up to 160 passengers. The Fijian islands are among the most exotic and beautiful in the world: pristine coral reefs, cobalt blue waters, and perfect tropical weather year-round. Captain Cook offers day and lunch cruises around the archipelago. However, the company specializea in custom, multi-day itineraries (with custom pricing) that allow passengers to explore as much of Fiji as they like.

If you prefer your travel experiences with less cocktail-sipping relaxation and a more hands-on approach, these sailing adventures put you in the captain’s seat in some of the world’s most beautiful waters.