5 of 6 spots reserved · 1 open
British Virgin Islands
October 25 - October 30, 2026
5 Days
The British Virgin Islands are easily one of the best and most accessible places to sail in the Caribbean. If you go in late fall or winter, you'll catch perfect 15-to-25-knot trade winds blowing across the Sir Francis Drake Channel. This deep-water stretch separates Tortola from a chain of smaller islands, offering incredibly smooth sailing. Since the channel is protected from the open ocean swell, you get easy 10-to-15-mile hops with plenty of calm anchorages to drop your hook for the night.
This plan depends on weather and conditions, routes and overnight stops can change day to day.
Planned Stops
1. Tortola
Meet at the boat dock in Road Town Harbour, settle into cabins, run through systems, stop at the grocery store for provisioning. Night one is spent on the boat in the harbor, we'll wake up early the next morning and sail away.
2. Norman Island
First real day out. We’ll head south to Norman Island and grab a mooring ball. From there we can dinghy over to the Willie T floating barge, then snorkel The Indians (the rocky islets just off Norman) that are one of the best underwater stops in the BVI.
3. Cooper Island
From Norman Island, we'll sail over to Cooper Island and stop by the Cooper Island Beach Club where we can post up at the bar and pick up any provisions we may have missed at the club store. This is a great spot for swimming and snorkeling.
4. Virgin Gorda, The Baths
Early morning run from Cooper Island to The Baths, we want to get here early to get a good spot to be able to explore and go hiking. This place is iconic for a reason. Massive granite boulders tumbled into caves, tunnels, and sea pools you can scramble and swim through. Hike to the top of the island for a view of the entire North Sound.
5. Guana & Great Camanoe
After the baths we can either stay overnight on anchor, or head up to Guana and Great Camanoe for a day of snorkeling and swimming. We'll spend the night in Trellis Bay, and possibly catch one of the beach parties on shore.
6. Virgin Gorda, North Sound
Early morning departure for the longest leg of upwind sailing of the trip, we'll sail up to Saba Rock and stay overnight near the resort. This is one of the more fancy places to go ashore, either at Saba Rock or Virgin Gorda itself. This is also a good opportunity for us to dock and get some fresh water..
7. Anegada
Check in on weather conditions and make our way to Anegada. This is a long open-water sail, you won't see land in any direction on the way. Anegada is the flat coral outlier in the BVI and really feels like you're in the middle of the ocean. On the island we can rent dirt bikes to explore the island and navigate to the north shore.
8. Jost Van Dyke
A long reach or downwind sail to Jost Van Dyke. If you've seen an iconic picture of a white sand beach and a bar with a dollar sign in the sand, this is the place. White Bay’s Soggy Dollar Bar is the classic stop, this is where we'll likely see the most other actual people on beaches relative to the rest of the trip.
The Boat · Beneteau 440
We'll be on a Beneteau 440, a 44-foot monohull with an open cockpit, galley, 4 cabins and two full bathrooms. If the wind is good, this boat is fast.
Trip Captain / Organizer
Patrick Costanzo
@patrick.coI grew up racing boats at Youngstown Yacht Club on Lake Ontario in upstate New York. I've captained many of my own charters in the Carribbean on both monohulls and catamarans ranging from 34 to 55 feet.
I owned and lived aboard a Neel 43 trimaran for several years out of Riviera Beach, Florida while working my engineering job from the boat and rebuilding the electrical systems onboard. Currently based in Austin, Texas and know my way around the British Virgin Islands well (on the water, at least).
If you come on this boat and do Trumpy shit I will dump you in the middle of the ocean.
Travel Planning
Fly into St. Thomas (STT) on October 24
The trip leaves the dock on Sunday, October 25, so land Saturday the 24th. If you can't get to the Charlotte Amalie ferry terminal before 5pm that day, fly in on the 23rd and spend the night on St. Thomas or Tortola.
Buy ferry tickets in advance, both ways
Book Charlotte Amalie to Road Town for Saturday, October 24. If you're flying out Friday the 30th, book the return for that day; if you stay the weekend on Tortola, book the ferry for whenever you actually leave. The last boat to Road Town is 5:30pm; companies rotate which boat runs which day.
BVI ferry schedulesCab from the airport to the ferry terminal
Cyril E. King to Charlotte Amalie is about a 15-minute ride. Leave a buffer on the 24th, you still need to make the ferry and clear customs into the BVI.
Saturday night is on the boat at the dock
We sleep aboard in Road Town Harbour on October 24. After you drop bags and settle into a cabin, we walk to the grocery store and provision as a crew. We sail Sunday morning.
Ferry back on the 30th, or stay the weekend on Tortola
The trip ends Friday, October 30. You can take the Road Town ferry back to Charlotte Amalie that day and fly out of STT that evening if you can. Road Town boats to St. Thomas run through mid-afternoon, so a morning or midday ferry gives you the best shot at an evening flight. Or stay a few extra nights at a resort on Tortola — it's the weekend, so it's a good excuse to linger before heading home.
