Top 5 Off the Beaten Path Caribbean Cruises

Philipsburg, Sint Maarten, Dutch Antilles cityscape at the Great Salt Pond.
Philipsburg, Sint Maarten, Dutch Antilles cityscape at the Great Salt Pond.

Caribbean ports can get crowded in peak season, so why not join a cruise to some of the less visited islands?

The Caribbean certainly has its parade of “Greatest Hits” ports. And, while they have lovely beaches and plenty of rum punch, they can also be quite crowded, particularly in the wintertime. If you’re looking to get away from it all, consider one of these five cruises.

1) Azamara Journey, Azamara Club Cruises

st john island

Why we love it: This 686-passenger ship sails from St. John in the U.S. Virgin Islands. From there, you’ll see Guadeloupe, Dominica, Nevis, St. Barth, St. Maarten, and Virgin Gorga before returning to Miami. It’s the best of both worlds: a great route that ends in an easy flight home.

Book it: The 12-night sailing departs December 11, 2015, and starts at $3474 per person double occupancy.

2) Sagitta, Island Windjammers

sagitta caribbean cruise

Why we love it: This casual sailing yacht – complete with wood-lined cabins and tall masts – accommodates only 24 passengers at a time. The itinerary includes St. Barts, St. Kitts, Anguilla, Nevis, Iles des Saintes, Dominica, Guadeloupe, and Martinique. The rum punch flows freely and snorkeling gear is provided.

Book it: The 12-night sailing departs May 10, 2015, and starts at $2,775 per person double occupancy.

3) SeaDream II, SeaDream Yacht Club

sea dream caribbean cruise

Why we love it: This 112-passenger ship likes to think of itself as a yacht – they have daybeds for two on deck, a watersports platform, and the captain’s allowed to change the route based on weather. This round-trip out of St. Thomas takes in a variety of small islands, including Anguilla, St. Barth, Virgin Gorda, Anegada, and Jost Van Dyke.

Book it: The 5-night sailing departs November 22, 2015, and starts at $2,999 per person double occupancy.

4) Royal Clipper, Star Clippers

Why we love it: This 227-passenger tall ship is a dream if you love sailboats, with knot-tying classes, visits to the bridge, and a bowsprit net, which may just be the best spot on the ship to sunbathe. This round-trip out of Barbados visits Grenada, a couple of small spots in The Grenadines, St. Vincent, Bequia, and two ports each in Martinique and St. Lucia.

Book it: The 7-night sailing departs November 28, 2015, and starts at $3,310 per person double occupancy.

5) Wind Star, Windstar Cruises

st lucia


Why we love it: This 148-passenger ship sails round-trip out of Barbados to Grenada, three spots in the Grenadines, and two ports in St. Lucia, offering a taste of both the rainforest and the beaches. Watching the sails being unfurled for the first time is a highlight.

Book it: The 6-night sailing departs December 12, 2015, and starts at $1,799 per person double occupancy.

Top Tips

Here are three ways to carve out some island time for yourself:

1. Get in a taxi. Before you leave home, research the nicest beach on the island that’s within a short drive. Then, once you’re in port, grab the beach towels from your cabin, a snack from the breakfast buffet, and hop in a cab.

2. Have a nice, long lunch. If you’re in a port you’ve already seen, or you have had your fill of beach days, make a reservation at one of the nicer restaurants on the isle. Often, you’ll find these at luxury resorts.

3. Plan a run. There’s no better way to get to know an island than by throwing on your sneakers and plotting out an ideal route. You’ll get your workout in, see the island and work off the big dinner you had the night before.

Insight Guides | Sherri Eisenberg