7 min read · Virgin Islands Itineraries · Updated Jun 8, 2026
Every charter is custom, but guests often ask for an example of what a four-night sail around St. John and St. Thomas can look like. Here is one version we love — weather permitting, of course.
Day 1 — Boarding & Christmas Cove
Board in the afternoon at the St. Thomas dock. Short sail to Christmas Cove. Dinghy over to Pizza Pi for the famous floating pizzeria, then back aboard for a quiet first night at anchor.
Day 2 — North Shore of St. John
Sail east along the south of St. Thomas, then up to the protected waters of St. John's north shore. Snorkel at Waterlemon Cay. Lunch aboard. Afternoon at the starfish flats. Anchor at Maho or Francis Bay for sunset.
Day 3 — Lime Out & the South Coast
Morning swim, then sail to Coral Bay on St. John's south side. Lunch at Lime Out, the floating taco bar — bring your appetite. Afternoon snorkel at one of the south-side reefs. Anchor at Salt Pond or a quiet cay nearby for the night.
Day 4 — A Bigger Day
Sail back west along St. John. If conditions are right, swing past the BVI border for the view, then anchor at a quiet spot like Hassel Island for the last night. Dinner aboard. A long evening on the deck.
Day 5 — Disembark
Coffee, a final swim, and back to the dock by late morning.
Notes
Real itineraries shift with weather, wind, and what you say you love most. The above is a starting point — the planning call is where it becomes yours.
Frequently asked
Common questions from guests
Is the itinerary fixed?
No — every itinerary is custom. The sample above is a starting point; the planning call shapes the real one around what you actually want and what the weather is doing that week.
Do we need passports if we cross to the BVI?
Yes. Passports are required for any BVI crossing, and BVI customs clearance is part of the planning. If you'd rather skip it, we'll stay USVI-side.
What's Pizza Pi?
A floating wood-fired pizza restaurant anchored in Christmas Cove on the east side of St. Thomas. You dinghy over, order from the boat, and bring it back to eat at your own anchorage.
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