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2026 & 2027 sailing adventures with Captain Tim & Admiral Donna.

Private Sailing Charters  ·  Premier Waters Worldwide

This Just In We've confirmed a new Last-Minute Escape — July 26, 2026 in the British Virgin Islands.
Scroll down, or click here for details →
★ 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

BVIs & USVIs

Completed
March 19 – April 2, 2026
Road Town, Tortola, BVI — with crew pickup and drop-off at St. Thomas, USVI on March 26, returning to Road Town April 2. Aboard the Irish Wake (42-foot, 3-cabin sailing catamaran).
Sailing the British Virgin Islands and USVI

Agana (Split), Croatia

Completed Sold Out
May 30 – June 6, 2026
Departing Agana Marina on the afternoon of May 30 (first night at marina), sailing the Dalmatian islands and returning June 5 afternoon. Disembarkation by 9 am June 6. Leopard 45, 4-cabin sailing catamaran.
Sailing the Dalmatian islands, Croatia

French Polynesia

Sold Out
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.
Sailing French Polynesia — Taha'a and Bora Bora View Sample Itinerary

2027

Belize

★ Featured Charter Available Just 2 guest cabins — both open
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.
Sailing the cays of Placencia, Belize Reserve a Cabin Why Belize? →

British Virgin Islands

Available Only 1 of 2 guest cabins left · week 1 Only 1 of 2 guest cabins left · week 2
April 22 – May 6, 2027  (1 or 2 weeks)
Starting Road Town, Tortola, BVI (boarding around 6 pm April 22, casting off morning of April 23), returning and disembarking Road Town by 9 am May 6. Option to join or depart from Tortola airport (EIS) on April 29 for a 1-week sail. 42-foot, 3-cabin sailing catamaran.
Sailing the British Virgin Islands from Tortola Reserve a Cabin

Ionian Islands, Greece

Sold Out
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.
Sailing the Ionian Sea, Greece

British Virgin Islands

Available Just 2 guest cabins — both open
October 28 – November 8, 2027  (11 nights / 12 days)
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 8. 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).
Sailing the British Virgin Islands Reserve a Cabin

Hold Your Cabin Today

1
$300 deposit to hold your cabin
2
$700 six months before sailing
3
Balance (typically $1,000) ninety days before sailing
(Balance may be less than $1,000 for Last-Minute Escapes and more for sails lasting more than one week.)
Total: $2,000/cabin/week
Plus post-charter reconciliation for shared expenses (~$900/cabin for BVI)

Deposits are generally non-refundable. In case of compelling circumstances like illness, we're reasonable and will work with you.

Reserve a Cabin — $300

Estimated Total Cost — BVI

Cabin fee$2,000
Provisions, mooring, fuel, insurance, fees~$900
Estimated total (BVI)~$2,900

Includes open bar, breakfasts, some lunches, one dinner aboard. Does not include dining out or boat toys.

Full expense breakdown →
Flexible & discounted

Last-Minute Escapes

Several times a year, our sailing calendar opens up on short notice — dates we can only lock in 16 days before sailing for most destinations (and 10 days for most of the Med). The upside for you: these sails come with a $500 discount and are often prime weeks. If your calendar has some give, this is the best value we offer.

British Virgin Islands

Available 💰 $1,500 Off — Just $500/cabin Just 2 guest cabins — both open · week 1 Just 2 guest cabins — both open · week 2
July 26 – August 9, 2026  (1 or 2 weeks)
A short-notice summer escape to the islands. Starting Road Town, Tortola, BVI (boarding around 6 pm July 26, casting off morning of July 27), returning and disembarking Road Town by 11 am August 9. Option to join or depart from Tortola airport (EIS) on August 2 for a 1-week sail. 42-foot, 3-cabin sailing catamaran.
Just $500/cabin/week — a special deep discount on this trip ($1,500 off the usual $2,000). Sail either week or both.
A summer escape to the British Virgin Islands Reserve a Cabin

Join the Last-Minute List

Tell us roughly when and where you could sail on short notice. When a matching date opens, we'll email you first — no obligation, ever.

We'll only email you when a short-notice date actually opens. No spam, no obligation.

Don't wait too long

Cabins fill quickly.

We keep our groups intentionally small — just two or three guest cabins per trip. If a date catches your eye, the surest way to hold it is a $300 deposit. Not quite ready? Ask us anything first — we write back personally.

Reserve a Cabin — $300

Questions first? We write back personally →