US Virgin Islands Sailing Itinerary

Chart your course with confidence and explore our handcrafted US Virgin Islands sailing itinerary.

Our suggested week-long USVI yacht charter itinerary assumes a start in the Charlotte Amalie area on St. Thomas, where most of the charter bases are located. I take you on a figure eight around the islands, beginning with the north shore of St. John.

Why does this plan work?
  • With prevailing easterly trade winds, we get our upwind leg out of the way on the first day by motoring (or sailing) around the south side of St. Thomas, and then NE to St. John. You’ll have some protection in the lee of St. John to avoid a bumpy ride
  • Further upwind passages on the north shore of St. John are short and protected as you hop between the fantastic beaches and bays of the Virgin Islands National Park
  • It gives you a chance, mid-trip, to make a pitstop in Cruz Bay for re-provisioning, if needed
  • Cruising around the north shore of St. Thomas should be a beautiful, downwind sail under normal conditions
  • It leaves you for your last night at Water Island, a short motor back to the charter bases on St. Thomas

Day 1: Hawksnest Bay

After your charter briefing motor or sail for the north shore of St. John and the Virgin Islands National Park. You can pick from any of the many bays where mooring balls are provided by the NPS.

Hawksnest Bay is a great choice! A sea turtle sighting is almost guaranteed. Stroll the beach, snorkel the many reefs, or go in search of the Mermaid’s Chair. Pour yourself a sundowner and get ready for an epic Virgin Islands sunset. You’ve arrived in paradise!!
Great sunsets from the Maho Bay mooring field

Day 2: Beaches, snorkeling, repeat

That’s the plan for the next couple days as you make your way east. I like Maho Bay as a 2nd night overnight, but don’t get there until the afternoon.
 Take your time. You have plenty of special bays to explore along the way.

Check out the underwater snorkel trail at Trunk Bay and gaze at the luxurious villas hanging to the cliffs at Cinnamon Bay.

Onwards to Maho Bay. Spend the afternoon lounging on the wonderful beach. Back on your yacht, get ready for an unobstructed sunset over the cays to the west.

Ram Head and the Salt Pond Bay mooring field

Day 3: Enjoying solitude at Salt Pond Bay

In the morning, you have plenty of time for more snorkeling and exploring of the area, if you wish. Around the corner is Leinster Bay and Waterlemon Cay. Many people claim this is where you can find the best snorkeling in all of St. John. 

Raise the sails and continue south towards your overnight mooring ball at Salt Pond Bay. Along the way, consider a stop in Coral Bay from some shopping or dining. Lime Out is a popular floating taco bar attraction.

With just a handful of NPS mooring balls at Salt Pond, enjoy the beautiful scenery in (relative) solitude. If it’s crowded, other options are Great and Little Lameshur Bays, just to the west.
Cruz Bay

Day 4: Cruz Bay for a night out

Before you leave, a great excursion is the short hike to Ram Head. On a clear day, you might be able to see all the way to St. Croix. Sail around the south side of St. John to the moorings at Caneel Bay. We’re headed for Cruz Bay, but it’s off limits by some charter companies. From Caneel Bay, it’s a short(ish) dinghy ride into town.

Head ashore to Cruz Bay for an afternoon or evening of shopping, bar hopping, or dining. You can also find several grocery stores here where you can stalk up on provisions. The Visitor Center for the Virgin Islands National Park is also located here.
Spectacular Magens Bay

Day 5: Onwards to St. Thomas US Virgin Islands

Raise your sails for an easy downwind passage around the north shore of St. Thomas. Consider checking out the uninhabited Hans Lollik Islands for a day stop on the way.

Enter Magens Bay at marvel at the spectacular setting. It really is special with a large crescent-shaped beach and long peninsula, which forms the bight. Drop the hook (no mooring balls here) in the areas marked on charts.
Magens Bay

Day 6: Beach day optionality

I always like to plan a day where we don’t move the boat. Today’s that day!
Dinghy ashore to enjoy a relaxing day on this wonderful beach. Magen’s Point Beach Bar and Grill whips up some good pizza and serves up drinks from the bar.

Other options? You can rent kayaks and stand up paddleboards, or put on your shoes for a short hike up the hills in the area.

Magens Bay could also be a good jumping off point for excursions ashore. Phantasea Botanical Garden or Mountain Top are popular attractions, nearby. It's easy to arrange a taxi from the beach.
Honeymoon Beach, Water Island

Day 7: Wrap up the trip at Water Island

Continue your downwind sail along the north shore of St. Thomas and enjoy the coastal scenery. Head for Honeymoon Bay at Water Island. This anchorage can be crowded, and the mooring balls are private, so try and arrive early if you can.

You can’t go wrong just relaxing on Honeymoon Beach while liming away the afternoon. Dinghy’s Beach Bar is a popular spot, or you can walk up the road for a drink at Heidi’s Honeymoon Grill.

Unobstructed epic sunsets are almost guaranteed here – not a bad way to end your USVI sailing itinerary! You’re just a short 15 minute motor to return your charter yacht the next morning.

US Virgin Islands charter planning?

Consider booking with the Yacht Warriors.