18 min read · Virgin Islands Itineraries · Updated Jun 8, 2026
This is the working map I'd hand a friend planning their first week in the US Virgin Islands. It's not a top-ten list — it's the actual logic a captain uses to assemble a charter week: which bays sleep well in which wind, which reefs are at their best before the day boats arrive, which beaches reward a dinghy landing, and which crossings are worth the paperwork. Save it, share it, and use it as a starting point for the conversation we'll have when you book.
How a USVI charter week actually fits together
A normal seven-night charter sails six legs and visits five to seven anchorages. The first night is close to the home dock so guests can settle in after a travel day. The middle of the week is the variety — a national-park morning, a snorkel reef, a quiet cay, a beach with a dinghy-up bar. The last night is back near St. Thomas to make the morning departure painless. Everything else is preference.
St. John, north shore: the postcard coast
The north shore of St. John is the centerpiece of most charters. Hawksnest, Trunk, Cinnamon, Maho, Francis, and Leinster line up west-to-east along Virgin Islands National Park. Maho Bay is the easiest day: shallow, calm, sea turtles grazing in the seagrass, mooring balls maintained by the park. Francis Bay sleeps quieter than Maho and has a better sunset angle. Trunk Bay is the famous one — a snorkel trail and a beach that's earned every photo — but the day boats descend by mid-morning, so we visit at first light or skip it on a holiday weekend.
St. John, east end: Coral Bay and Hurricane Hole
The east end is where the island gets quiet. Coral Bay is a sleepy harbor with a few dinghy-up restaurants (Skinny Legs, Indigo) and the kind of feel St. John had thirty years ago. Hurricane Hole, just inside Coral Bay, is a protected national-park anchorage ringed by mangroves — a fascinating snorkel for the curious. It's a 40-minute sail from the north shore and a meaningful change of pace.
St. John, south shore: Lameshur and Salt Pond
The south shore is the wild side. Lameshur Bay (Great and Little) is national park, undeveloped, and almost always empty. Salt Pond Bay has a salt pond you can walk to and one of the best snorkel reefs on the island at Booby Rock. These aren't on the day-boat circuit; they reward charters that want at least one day away from the crowds.
St. Thomas-side anchorages worth a night
Christmas Cove at Great St. James is a favorite first-night anchorage: 20 minutes from the dock, a Pizza Pi boat for dinner, and a reef worth a swim. Honeymoon Bay at Water Island is another easy first night, with a small beach bar and a sunset that earns the name. Magens Bay is famous but exposed; we anchor there on settled days only.
The snorkel reefs in order of when they're best
Waterlemon Cay (off Leinster Bay) — early morning, before the day boats. Booby Rock (off Salt Pond) — anytime the south-shore swell is down. The Caves at Norman Island (BVI) — first thing in the morning, before the swim mob arrives. Carval Rock (off the north shore of St. John) — a captain's-pick spot, deep water, big fish, conditions-dependent. Buck Island (off St. Thomas) — turtles, easy entry, family-friendly.
When the BVI crossing is worth the paperwork
If you have four or more nights and the weather cooperates, a BVI day or overnight is one of the highlights of the week. The Indians (snorkel pinnacles), the Caves at Norman Island, the Soggy Dollar Bar at White Bay on Jost Van Dyke, and the Baths at Virgin Gorda are the bucket-list stops. A two-night BVI loop is the sweet spot. A single-day round-trip burns more time at the customs dock than it earns. If you only have three nights, stay in the USVI and use that time well.
Reading the wind and what it means for your week
USVI winds are easterly trades almost year-round, usually 12–20 knots. That means east-facing anchorages are exposed and west-facing anchorages are protected. When trades are up (above 20), we shift to Francis, Maho, and Leinster (all west-facing). When trades are light, we open up the east-facing options like Salt Pond and the BVI's Anegada. You don't need to learn this; it's the captain's job. But it explains why your itinerary may bend day-to-day — and why it should.
Building your own week from this atlas
Tell us what you care about most — snorkel, beach, quiet, food ashore, BVI bucket list — and we'll assemble a draft itinerary that hits the right anchorages in the right order for your dates and the forecast. Most guests start with three priorities; we work from there. The atlas is the menu. The week is yours.
Frequently asked
Common questions from guests
What's the single best anchorage in the USVI?
There isn't one — and any captain who tells you there is hasn't sailed it in different conditions. Maho Bay is the easiest answer for first-timers (calm, scenic, turtles in the seagrass). Francis Bay is the better answer for a quiet night. Leinster Bay is the best snorkeling base. Pick by conditions and what you want that day.
Do you need to clear customs to cross to the BVI?
Yes. A BVI crossing means clearing out of the USVI and into the BVI (and back). It's a half-morning of paperwork, fees, and time at a customs dock — worth it for a full day or overnight, not for a quick lunch.
When are anchorages most crowded?
Weekends and holidays bring the day-boat traffic, especially to Trunk Bay, the Caves at Norman Island, and the Soggy Dollar. Sunday through Wednesday is meaningfully quieter. We plan the famous stops for off-peak days when the calendar allows.
How far apart are these anchorages?
Most legs between USVI anchorages are 30 minutes to two hours under sail. A USVI-to-BVI crossing is two to three hours depending on wind angle. Nothing in a normal charter week is a long day at sea.
What about hurricanes / storm season?
Peak season is December through April. May–June and November–early December are shoulder seasons (good value, generally settled weather). August–October is hurricane season; we don't charter then.
Keep reading
Virgin Islands Itineraries
A Sample St. John and St. Thomas Sailing Itinerary
Christmas Cove, Pizza Pi, the starfish flats, Lime Out, and the sunset anchorages we love most.
USVI Term Charters
USVI Term Charter Guide: What to Expect Aboard a Crewed Catamaran
From boarding to disembarking — a day-by-day look at what life looks like on a Virgin Islands term charter.
USVI Term Charters
What Is a Caribbean Term Charter?
A plain-English guide to multi-night, fully-crewed yacht charters in the Caribbean — and why couples and small groups love them.
