Foxy’s Cat Fight 2026: A BVI Halloween Regatta Guide

Somewhere around the full moon in late October, a fleet of catamarans, trimarans, and the occasional stubborn monohull sails into Great Harbour on Jost Van Dyke dressed for a costume party. That’s Foxy’s Cat Fight — the only race in the Virgin Islands built specifically around multihulls, hosted by the West End Yacht Club, and it hits its 30th year in 2026. We’ve ferried plenty of guests over for it, and it’s one of those events that photographs beautifully and feels completely unlike a formal regatta the moment you step ashore.

If you’ve never been, here’s what it actually is, when to expect it this year, and how to watch it from the water without getting in the way of the fleet.

What the Cat Fight Actually Is

The Cat Fight is sponsored by the West End Yacht Club, based out of Soper’s Hole on Tortola’s West End, and it’s run as the multihull-focused counterpart to the club’s more traditional racing calendar. Catamarans and trimarans get their own dedicated shootout, though the club opens entry to monohulls as well, so the fleet crossing the Sir Francis Drake Channel toward Jost Van Dyke on race day is a genuine mixed bag of hull shapes and racing pedigrees.

What sets the Cat Fight apart from most of the BVI’s other regattas — and there are a lot of them, which we cover in our BVI regatta calendar guide — is the timing and the tone. It’s scheduled to land near the full moon and Halloween, and it’s traditionally treated as the first race of the season after hurricane season winds down. That combination of relief, moonlight, and an excuse to wear a costume gives it a looser, funnier energy than a lot of the season’s more serious point-to-point racing.

The Bar Behind the Party: Foxy’s Story

It’s worth knowing what you’re actually walking into, because Foxy’s isn’t a bar that opened to cash in on the yachting crowd — it created that crowd. Philicianno “Foxy” Callwood set up a simple bar in the shade of a tamarind tree on Jost Van Dyke back in 1968, built to welcome the sailing yachts that were starting to discover these islands. His wife Tessa joined him in 1972, after meeting him on a schooner crossing the Atlantic from Gibraltar, and together they turned a shaded spot under one tree into what a lot of longtime sailors credit as the birthplace of BVI yachting tourism itself. Foxy went on to earn an MBE from Queen Elizabeth II for his contribution to Virgin Islands heritage and tourism — not bad for a beach bar that started with a guitar and a cooler.

That history matters here because the Cat Fight isn’t a corporate regatta bolted onto a random beach. It’s a community event thrown by a bar with fifty-plus years of relationship with the sailors who show up for it, and that shows in how loose and personal the whole afternoon feels compared to a lot of more formal racing calendars.

When It Happens in 2026

The Cat Fight is a West End Yacht Club event, and like a lot of BVI sailing dates, the exact day gets confirmed closer to the event rather than locked in a year ahead — expect it sometime in October 2026, timed around the full moon and Halloween. If you’re planning a trip specifically around it, check the West End Yacht Club’s current schedule or ask our crew when you book, since we track the local calendar closely and can help you time a charter around race day rather than guessing.

The race itself starts and finishes in the Sir Francis Drake Channel area before the fleet converges on Foxy’s Tamarind Bar in Great Harbour, Jost Van Dyke, for the party that’s really the main event for most spectators.

Watching From the Water: Where to Position Your Charter

You don’t need to be racing to get a good view. Great Harbour opens wide enough that a private boat can sit well clear of the starting and finishing lines while still watching the fleet come in, and the approach into the bay gives you a solid look at boats jockeying for position before they cross the line. A few notes from experience:

• Arrive before the fleet. Mooring space in Great Harbour fills up fast on event days — the earlier you’re anchored or moored, the better your view and the calmer your afternoon.
• Give racing boats real room. Multihulls close distance faster than most spectators expect; keep well outside the marked course.
• Bring cash. Jost Van Dyke’s beach bars run on a cash-first culture — the tradition goes back to the Soggy Dollar Bar’s origin story just around the coast at White Bay, where guests famously swam ashore with wet dollars in hand.
• Check current mooring guidance. Fees and availability shift season to season — our regatta calendar guide and local marine authorities are the best places to confirm before race week.

Beyond the Race: Foxy’s Halloween Party

Foxy’s has built its reputation on turning a beach bar into an island institution, and the Cat Fight’s after-party leans hard into that. Expect costumes that range from clever to genuinely bizarre, live music, and a crowd that includes as many spectators who never set foot on a racing boat as it does actual sailors. If this is your first Foxy’s event, it plays a little differently than the island’s other marquee night — our guide to Foxy’s Old Year’s Night covers the New Year’s version of this same venue, and the contrast is worth reading if you’re trying to decide which Jost Van Dyke night to build a trip around.

If costumes and racing aren’t quite your speed but you still want the Jost Van Dyke experience — White Bay, the beach bars, the swim-in culture — our full Jost Van Dyke day trip guide covers the island on a calmer day.

Making a Full Day of It

Most of our guests don’t come just for the two or three hours the race and party actually take up. Jost Van Dyke rewards a longer visit, and if you’re already making the crossing from Tortola, it’s worth building the whole day around it rather than treating the Cat Fight as a quick stop. A typical version of this looks like a late-morning departure, a couple of hours at White Bay or one of the island’s quieter coves while the fleet is still finishing its final prep, and then a slow drift over to Great Harbour as the boats start converging for the afternoon’s racing and the evening’s party. That’s the kind of itinerary a private charter handles well and a fixed ferry schedule can’t — you’re not racing a departure time back to Tortola while the party’s still going.

Practical Details

Location: Great Harbour, Jost Van Dyke, with the race organized by the West End Yacht Club out of Soper’s Hole, Tortola.
Timing: October 2026, timed near the full moon and Halloween — confirm the exact date closer to the event.
Getting there: private charter, ferry, or water taxi from Tortola; a private boat gives you the most flexibility to time your arrival before the fleet and your departure after the party winds down.
What to bring: cash for beach bar tabs, a costume if you want to join the spirit of it, reef-safe sunscreen, and a dry bag for your phone if you plan on swimming ashore.
Crowds: this is one of the busier nights on Jost Van Dyke’s calendar — book your transport in both directions ahead of time.

Frequently Asked Questions

Is the Cat Fight the same event as Foxy’s Wooden Boat Regatta?
No — they’re separate events on different dates. The Wooden Boat Regatta runs in late May, while the Cat Fight is a fall event timed near Halloween and the full moon.

Do I need to be a sailor to attend?
Not at all. Most of the crowd at Foxy’s that night is there for the party and the spectacle, not the racing.

Do boats other than catamarans race?
Yes. It’s built around multihulls, but the West End Yacht Club opens entries to monohulls as well, so the fleet is mixed.

What should I wear?
Whatever costume instinct strikes you — this is one of the more costume-friendly nights in the BVI’s event calendar, alongside the same venue’s New Year’s tradition.

How do we get from Tortola to Jost Van Dyke for the event?
A private charter is the most flexible option on a night this busy, since you control your own departure and return timing instead of working around a ferry schedule. Our full day charters can be built around race day, and our crew can help you time it right — reach out through our contact page to plan it.

Is the party family-friendly?
It’s a mixed crowd of sailors, spectators, and island regulars, and the daytime hours around the race tend to feel calmer than the evening party. If you’re bringing kids, plan your visit around the race itself and head back before the night really gets going.

Whatever your plan for the day looks like, tell us your dates and group size through our contact page and we’ll help you time a charter around the Cat Fight so you catch the race, the party, and everything in between without missing your ride home.