★ Featured Charter
Belize, February 2027 — the trip we picked for ourselves, and the flattest water we'll sail all year.
Get the insider scoop on why we chose it →
We run two kinds of trips: Plan-Ahead Charters with firm dates you can reserve today for charters months or years away, and Last-Minute Escapes that open up on short notice at a discount, several times a year. Scroll down for details on Last-Minute Escapes.
Plan-Ahead Charters
A note on timing: most of our crew reserve twelve to eighteen months ahead. For trips like these, booking that far out isn't overcommitting — it's simply how it works, and the sooner you reserve, the better your pick of dates and cabins.
2026
French Polynesia
September 30 – October 8, 2026
Starting at Marina Apooiti (5-min cab from Raiatea Airport—RFP), sailing to Taha'a, nearby small islands, and Bora Bora (26 nm away) and return. Disembarkation at Marina Apooiti by 10 am October 8. Leopard 42, 3-cabin sailing catamaran.
2027
Belize
February 6 – February 13, 2027 (1 week)
The one we picked for ourselves. A week among the 450 cays of the Placencia coast, sailing entirely inside the world's second-largest barrier reef — steady trade winds, flat calm water, and snorkeling right off the stern. If you've ever been curious about a sailing week but worried about seasickness, this is the gentlest big-water sailing anywhere. Boarding in Placencia (PLJ) around 5 pm Feb 6, casting off the morning of Feb 7, disembarking by 11 am Feb 13. 42-foot, 3-cabin sailing catamaran. Getting there is easy — a nonstop to Belize City, then a spectacular 35-minute hop down the coast — and we'll help arrange it.
British Virgin Islands
April 22 – May 6, 2027 (1 or 2 weeks)
The Jewel of the Caribbean and Sailing Capital of the World! (There's a reason we hang here so much!) Starting Road Town, Tortola, BVI (boarding around 6 pm April 22, casting off morning of April 23). Dropping off week 1 guests and picking up week 2 guests at Trellis Bay dinghy dock on April 29 (just steps from the EIS airport main door — we'll meet you there and walk with you to the boat), returning and disembarking Road Town by 9 am May 6. 42-foot, 4-cabin sailing catamaran.
Ionian Islands, Greece
May 22 – May 29, 2027 (1 week)
Starting from Lefkas Marina on Lefkada Island (21 min cab from Aktion airport—PVK). Boarding around 6 pm May 22, casting off morning of May 23, returning to the marina May 28, and disembarking by 9 am May 29. 42-foot, 4-cabin sailing catamaran. Sailing the crystal-blue Ionian Sea and visiting beaches and islands straight from ancient myths (like Ithaca, home of Odysseus) while savoring unforgettable wine and food at waterfront tavernas.
British Virgin Islands
October 28 – November 7, 2027 (10 nights / 11 days)
A return to the sailor's happy place! Hard to beat the BVIs — right at the beginning of the sailing season. Starting Road Town, Tortola, BVI (boarding around 6 pm Oct 28, casting off morning of Oct 29), returning and disembarking Road Town by 11 am Nov 7. 42-foot, 3-cabin sailing catamaran. (Mid-charter pick-up or drop-off at the airport possible for a shorter trip.)
$3,000/cabin booking fee for the full trip (due to the extra length of the sail).
2028
Just Added
Croatia
May 27 – June 3, 2028 (1 week)
Back to the stunning Dalmatian coast and islands of Croatia, where we had an unforgettable time — the very same week — in 2026! Amazing towns, history, food, people… and sailing. Starting from the charming town of Marina Agana (about 12 miles by cab from Split Airport (SPU) and 25 miles from beautiful and historic Split), boarding around 3 pm May 27, spending the night aboard and casting off the morning of May 28, returning to Marina on June 2, and disembarking by 9 am June 3. 42-foot, 3-cabin sailing catamaran. Visiting incredible islands like Brač, Šolta, Hvar, and Vis and their picture-perfect towns, villages and beaches.
