Two-Week Sailing Adventure

No format is better suited for exploring the Virgin Islands than sailing. It makes it easy to get around and captures the real natural attraction of the place. It is also exciting and fun. Plan as long a sailing trip as you can—you will lose a day on each end to checking in and checking out.

This two-week itinerary includes a few land-based days on Anegada and St. Croix, and many short sails between bays and cays. Plan your sailing vacation early—get a chart and plan your course at home—and be sure to get a skipper if necessary. You don’t want to spend your vacation worried about wrecking a multimillion-dollar boat.

DAY 1
Fly to Terrance B. Lettsome International Airport, Beef Island. Check in with your charter boat company, provision your yacht, and plan your itinerary.

DAY 2
Set sail to Norman Island. Snorkel at the Caves and pick up a mooring at the Bight for the night.

DAY 3
Rendezvous with the dive boat, and dive the RMS Rhone. Nondivers in your party can dinghy ashore to Norman Island and hike to the top of Spyglass Hill.

DAY 4
Sail to Salt Island. Go ashore and hike around the salt pond. Sail to Manchineel Bay, Cooper Island, for the night.

DAY 5
Pick up a day-use mooring at Fallen Jerusalem, where you can snorkel and hike over the rocks. Sail to North Sound, Virgin Gorda, for the night.

DAY 6
Dinghy around North Sound. Pack a picnic and take it ashore to Prickly Pear Island for a day of exploring.

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DAY 7
Sail to Anegada. Treat yourself to a real bed at Neptune’s Treasure Guesthouse.

DAY 8
Take a taxi tour of the island and stop at Loblolly Bay on the North Coast for the best snorkeling on the island.

DAY 9
Sail to St. Croix. Pick up a mooring in Christiansted Harbor. Celebrate your successful sail at a waterfront eatery.

DAY 10
Sail to Buck Island for the day. Return to Christiansted at night, and come ashore for a night of live music.

DAY 11
Sail to Coral Bay, St. John. Eat dinner at a seaside café and swap sailing stories at the bar.

DAY 12
Sail to Francis Bay, St. John. Swim ashore to the beach, and hike the Francis Bay Trail.

DAY 13
Sail back to Road Town, Tortola, and come ashore for dinner at a beachfront restaurant. Dance under the stars at Cane Garden Bay.

DAY 14
Check out with your charter boat company and travel to Beef Island for your flight home.