Welcome to the LTD Sailing “Living the Dream!” BVI Flotilla
The British Virgin Islands are one of the world’s most beloved charter destinations—and for good reason. With short, scenic passages between islands, turquoise waters, and a mix of laid-back beach bars and natural wonders, this trip truly is Living the Dream. Occasionally we leave our own paradise to explore other parts of the world by sailboat. Here is our 7 day itinerary for British Virgin Islands Flotilla this spring:
Monday, May 26 — Hodges Creek to Cooper Island (4 NM, ~1 hr)
We begin our journey at Hodges Creek Marina, where we’ll board our Dream Yacht Charter catamaran. Settle into your private ensuite cabin and explore your new floating home. Breakfasts, lunches, snacks, and two dinners onboard are included, and we’ll help arrange onshore dining reservations—or you can explore local cuisine at your leisure.
🍾 Upon arrival: a welcome mimosa, quick trip briefing, and fun icebreaker.
After your captain’s safety briefing, we’ll cast off for Cooper Island Beach Club. You’re welcome to take the helm or simply relax—your level of involvement is totally up to you. Once anchored, take a swim or snorkel the nearby shipwreck before dinner ashore.
Tuesday, May 27 — Cooper Island to The Baths & Marina Cay (4 NM, ~1.5 hrs)
Start your day exploring The Baths, a labyrinth of granite boulders, hidden caves, and tidal pools. Climb ladders, splash through grottoes, and don’t forget your waterproof camera!
Then it’s on to Marina Cay where we’ll anchor for the night. Enjoy a cheeseburger-in-paradise dinner onboard and fire up your playlist.
🎯 Looking for adventure? Watersports like eFoils, hydrobikes, SUPs, and kayaks are available through Up and Under Watersports—or just inflate your floaty animal and lounge boat-side.
Wednesday, May 28 — Marina Cay to Leverick Bay (9 NM, ~3.5 hrs)
We head upwind today to Leverick Bay and the Bitter End Yacht Club. Settle in for a sundowner at the Harbor Master Lounge and explore the newly rebuilt club. Volleyball, anyone?
🎉 Tonight’s the Caribbean Shirt Party—bring your boldest, brightest attire!
Dinner will be ashore at the yacht club.
Thursday, May 29 — Leverick Bay to Anegada (13 NM, ~3.5 hrs)
Anegada is unlike the rest of the BVI—a flat coral island often compared to the Bahamas. You won’t see it until you’re nearly on top of it, and it’s surrounded by shallow reefs, so we’ll need all hands on deck as we approach.
🦩 Rent a scooter, visit the flamingos, and get ready for the Floaty Animal Parade! (Narwhal? Turtle? Giant swan? Bring your best.)
Tonight, we’ll feast on famous Anegada lobster at the Anegada Reef Hotel (pre-order recommended).
Friday, May 30 — Anegada to Jost Van Dyke (22 NM, ~5 hrs)
Our longest sail takes us to the legendary Jost Van Dyke. We’ll unwind with a round (or two) of Painkillers at the Soggy Dollar Bar—where they were invented!
Then it’s off to Foxy’s Tamarind Bar for more island vibes and dinner. Expect great food, great music… and possibly a rum squall or two.
Saturday, May 31 — Jost Van Dyke to Norman or Peter Island (10 NM, ~3 hrs)
We’re headed toward Willie T’s, the floating pirate bar that’s become the stuff of legend. It used to be that if you jumped off the top deck shirtless, you’d earn a Willie T’s shirt. Do they still do that? Only one way to find out…
⛱️ We’ll also snorkel, explore sea caves, and enjoy our final night with a “Chopped”-style onboard dinner—let’s see what we can whip up from what’s left in the galley. (Plank chicken, anyone?)
Sunday, June 1 — Return to Hodges Creek Marina
Pack your swimsuits and grab your flip-flops—it’s time to head back. We’ll return to Hodges Creek Marina by 9 AM to refuel and check out.
✈️ If you need ferry or airport transfers, please let us know by the day before. Plan extra time for travel, as airport lines can be slow (2–3 hours is typical).
And remember: it’s always smart to start planning your next vacation before this one ends. 😉
“Living the Dream!”
Let the memories begin.
