Plan a Sailing Trip Around 15 Caribbean Islands

·5 min read
Photo credit: ANDERS OVERGAARD
Photo credit: ANDERS OVERGAARD

Private yacht charters spell travel freedom. You can use them to explore many islands or to have maximum time on the water (helpful if borders suddenly close). You can be as active (mountain biking) or laidback (onboard spa treatments) as you like. You can leave an anchorage earlier than planned, or linger. And let's not forget water toys--most vessels come with a full array of them, motorized and not. So consider this Leeward Islands itinerary one excellent example of what is possible. When can you go? Now, but you may need to adjust some ports of call if protocols change—no big deal. For details, see "How to Book It" at the end of this article.


DAYS 1–2: HAVE SOME HISTORY WITH YOUR HEDONISM—ON ANTIGUA.

Photo credit: Daisuke Kishi - Getty Images
Photo credit: Daisuke Kishi - Getty Images

Where Antigua. Why The largest of the English-speaking Leewards has plenty of secluded anchorages and beaches, and a major historic site: Nelson’s Dockyard, the British Royal Navy’s 18th-century Caribbean base and now home to Antigua’s sailing and yachting events. How A private car will whisk you from the airport to the yacht, where the crew awaits. Laze aboard, visit the dockyard, or take a tender to swim and snorkel. Cocktails and dinner are onboard, and the yacht relocates in the morning to either Green Island (private, lots of reef fish) or Five Island Harbor and its beautiful coves.

DAY 3: WALK WITH HAMILTON—ON NEVIS.

Photo credit: Mark Meredith - Getty Images
Photo credit: Mark Meredith - Getty Images

Where Nevis (daytrip). Cruise time from Antigua 4.5 hours. Why It’s small and scenic (dominated by the Nevis Peak volcano) and untouched by mass tourism. It’s also the birthplace of Alexander Hamilton. How Your captain will choose the best location for swimming and water sports (there’s diving at Monkey Shoal), as well as for rum punches and live reggae. There’s a beautiful botanical garden, and the golf course designed by Robert Trent Jones II at the Four Seasons is tops in the Caribbean; tee times can be reserved.

DAY 5: VANQUISH A VOLCANO—ON ST. KITTS.

Photo credit: Andreas Pietsch / EyeEm - Getty Images
Photo credit: Andreas Pietsch / EyeEm - Getty Images

Where St. Kitts (which is part of the same country as Nevis). Cruise time from Nevis 1 hour. Why It’s one of the most unspoiled, tranquil, and beautiful islands in the Caribbean, much of it national parks with rainforests and mountain ranges. How After picking an anchorage, you can go hard (hiking the Liamuiga volcano) or easy (exploring on a 4X4—flowers, birds, and waterfalls—an onboard fitness class, or a tour of the colorful town of Basseterre).

DAY 6: FLEX YOUR PADI CREDS—ON SABA.

[

Photo credit: Brandi Mueller - Getty Images
Photo credit: Brandi Mueller - Getty Images

Where Saba (daytrip). Cruise time from St. Kitts 3.5 hours. Why It’s just 5 square miles, most of it occupied by the dormant volcano Mount Scenery, and a wonderland both above water and below. How After anchoring, experienced divers have Saba National Marine Park to play in: coral formations, underwater mountains, sharks, turtles, dolphins. Non-divers can hike, snorkel, or play with the water toys—wakeboards, water skis, kayaks, Seabobs—you name it. (Inflatable slide, anyone?)

DAYS 7–8: PRACTICE YOUR FRENCH—ON ST. BARTS.

Photo credit: Donald Nausbaum - Getty Images
Photo credit: Donald Nausbaum - Getty Images

Where St. Bart’s. Cruise time from Saba 2.5 hours. Why Need you ask? The fun part of arriving at St. Bart’s by yacht is that you’re immediately smack in the middle of the action. How You’ll wake up in the port of Gustavia and have two full days. When you’re not trying to guess which yacht is whose, you can beach-, restaurant-, and spa-hop; you can also shop till you drop. And, yes, there’s all that other stuff: hiking, diving, and water sports, including deep sea fishing and a tour in a little yellow submarine. Et voilà.

DAYS 9–10: BECOME A BEACH BUM—ON ANGUILLA.

Photo credit: Maremagnum - Getty Images
Photo credit: Maremagnum - Getty Images

Where Anguilla. Cruise time from St. Barts 2 hours. Why We have the flat little island’s coral base to thank for its superb beaches: blinding white sand, turquoise water—the best. And hardly any people on them. How Picking beaches—there are 33—is serious business on Anguilla, as all have their special aura (and some have restaurants). Your captain will go over the charts with you to assist in the wrenching choices—Rendezvous Bay Beach, Meads Bay, Maundays Bay, Little Bay, Shoal Bay East, Shoal Bay West, Long Bay, Barnes Bay, Cove Bay, Crocus Bay, Captain's Bay, Junk's Hole Bay.... You get the idea.

DAYS 11–14: CHANNEL YOUR INNER BUCCANEER—IN THE BVI.

Photo credit: cdwheatley - Getty Images
Photo credit: cdwheatley - Getty Images

Where The British Virgin Islands. Cruise time from Anguilla 7.5 hours. Why Its multitude of green isles, some uninhabited, is a yachting paradise. How You’ll clear into the BVI in Tortola (from which, on day 15, you’ll also depart for home) and have four days to explore. In your sights: Peter Island, Cooper Island, Virgin Gorda, Great Camanoe, Little Camanoe, Guano Island, Jost Van Dyke, and Norman Island—which inspired Robert Louis Stevenson’s Treasure Island. Castaway picnics will be provided, and the mothership—here’s the beauty of it—is always standing by.

HOW TO BOOK IT:
Private yachting expeditions are of course highly personalized. You can book exactly this one, developed with long-time yachting specialist Mary Crowley of Ocean Voyages, or work with her to customize it to your wishes and budget. Crowley has access to all the boats that are up for charter and her speciality is knowing the right vessels and best crews. Pricing depends on the number of people in your group as well as the type of vessel you choose. Contact Crowley at sail@oceanvoyages.com

Click here for more travel inspiration from T&C

You Might Also Like