Samui Regatta: Thailand's Premier Sailing Week off Chaweng Beach

For one week each May, the bay off Chaweng Beach turns into a racing arena. White sails fan out across the Gulf of Thailand, spinnakers bloom on the downwind legs, and the rhythm of life on Koh Samui shifts — briefly but unmistakably — to the wind.

The Samui Regatta is Thailand's longest-running international keelboat regatta and one of Asia's most respected sailing events. The 23rd edition runs from 23 to 30 May 2026, with racing organised by the Royal Varuna Yacht Club and the official Notice of Race published on samuiregatta.com.

Tim, who founded Mykeythai, is a passionate sailor himself — he grew up racing dinghies in Northern Europe and still spends a good part of every May tracking the Samui results from the host venue. This guide is written from that perspective: less press release, more notes from someone who genuinely loves the sport.

Why the Samui Regatta Matters

Founded in 2002, the regatta has built a reputation for serious racing in genuinely beautiful conditions. The fleet typically includes IRC racing classes, cruising divisions, multihulls and a small but competitive sport-boat contingent. Crews fly in from Singapore, Hong Kong, Australia, Europe and the Middle East, and the event is part of the AsianYachting Grand Prix series.

What sets Samui apart from regattas in Phuket or Hong Kong is the racing area itself. Courses are set in the sheltered waters between Koh Samui, Koh Phangan and Koh Tao, with the south-westerly monsoon delivering reliable 10–18 knot breezes and short, manageable seas. It's tactical sailing in postcard scenery — the kind of week that reminds you why you started racing in the first place.

The 2026 Format

While the final Sailing Instructions are confirmed closer to the event, the Samui Regatta traditionally follows a familiar structure:

• Day 1 — Registration and practice race at the host venue on Chaweng Beach
• Days 2–6 — Racing: a mix of windward-leeward courses and longer coastal races, including the popular passage race around Koh Phangan
• Day 7 — Final racing and prize-giving, followed by the closing party

Daily prize-givings are held beachside in the late afternoon. They are informal, generous with the rum, and one of the best places on the island that week to meet skippers, owners and trimmers from across Asia.

For Racers: Joining a Boat

Plenty of boats arrive in Samui short on crew. If you have racing experience — even modest — and can produce references, there is a real chance of picking up a ride. The classifieds on Asian Yachting and the regatta's own crew board are the obvious starting points, but informal introductions at the host venue often work better.

If you are an owner considering shipping or sailing your boat in, the regatta organisers maintain a logistics page covering arrival procedures, the Thailand Digital Arrival Card for crew, and recommended marinas. The closest deep-water moorings are at Bangrak and Big Buddha Pier, with overflow at Koh Phangan's Thong Sala.

For Spectators: Where to Watch

Unlike many offshore regattas, the Samui courses are set close enough to land that the racing is genuinely watchable from shore. The northern end of Chaweng Beach offers the best vantage point for inshore days. Bring binoculars and a cold beer.

Several local operators run spectator boats during race week — a far better way to see the action. Expect to motor out to the windward mark, watch the fleet round, then sail downwind alongside the racing yachts back toward the finish. It's a humbling perspective on just how hard these crews are working.

Sailing Charters on Koh Samui Year-Round

The regatta is a one-week peak, but Koh Samui's sailing season runs from roughly January through September. Three established operators stand out for sailors looking to charter under sail, in or out of regatta week:

• Samui Ocean Sports & Yacht Charter — the longest-running sailing operation on the island, with a small fleet of catamarans and monohulls including the cruising catamaran Dreamcatcher and the 44ft Geronimo. Day charters typically run Samui to Koh Phangan and back; overnight options reach Ang Thong Marine Park.
• Boutique Yachting — operating the 30-metre sailing yacht S/Y Naga. Pitched at the higher-end charter market, with full crew, four cabins and a chef. Ideal for a full-day Ang Thong cruise with serious comfort on board.
• Samui Island Explorer — runs sailing yacht charters in half-day, full-day, sunset and overnight formats, including multi-day itineraries to Koh Phangan and Ang Thong.

For sailors who want to keep their hand in, all three are happy to involve guests in trimming and helming if the conditions allow. Tell them when you book — most skippers are pleased to share the boat with someone who knows their way around a winch.

Beyond the Regatta: Other Sport on the Water

Race week brings a wider energy to the island, and several adjacent disciplines benefit from the same wind window:

• Kiteboarding picks up reliably from May onward, with the flat, shallow water off Bang Po and Maenam offering some of the best beginner conditions in the Gulf.
• Stand-up paddleboarding and ocean kayaking are best in the early morning, before the regatta breeze fills in.
• Free-diving and spearfishing charters operate out of Bophut for those wanting depth as well as wind.

For a wider overview of what the island offers on the water, see our guide to beach and water sports in Koh Samui.

Where to Stay for Regatta Week

The host venue and prize-giving sit on Chaweng Beach, so anything in Chaweng or Chaweng Noi puts you within a short drive of the action — and well clear of the crowd at the end of the night. Our Paradise Villa Eden and Paradise Villa Elysium in Chaweng Noi sit on the same headland with private pools facing the race course. Sky Dream Villa higher in the hills offers the best panoramic view if you want to track the fleet from a sun lounger between races.

Regatta week sells out early. If you are planning to come for the racing — or just for the atmosphere — we'd suggest getting in touch several months ahead.

Browse more in our Koh Samui events coverage, or read about the best time to visit Koh Samui to plan around the sailing season.