A mix of swift-sailing production yachts and equally speedy West Indian workboats is what makes the Anguilla Regatta something special. Set for May 11-13, the event is based out of the beautiful Sandy Ground anchorage on the west end. “The Anguilla Regatta is produced 100 percent by volunteers, with all monies donated to the Anguilla Youth Sailing Club,” says Regatta Officer, Steve Donohue. “After nine regattas, we are proud to have taught the sport of sailing to over 200 youngsters with half on full scholarship.”

Visiting sailors are welcome to enter in spinnaker, non-spinnaker, open and multihull classes. It’s also possible to jump aboard as crew on an island-crafted Anguilla race boat (get ready to hoist the sandbag ballast on tacks) or wooden workboat after chatting up one of the owners at registration or the kick-off blast at Roy’s Bayside Grill.

All races are round-the-buoys. Sailors can expect 13-18 knots of breeze in May, with some challenging wind shifts when rounding offshore keys and marks located close to some of the island’s Five-Star resorts. Spectators can join in ‘Land Race’ where locals and visitors alike pile into pick-up trucks and drive to various vantage points to watch the racing from shore. “Sandy Ground is home to some of Anguilla’s best nightlife,” says Donohue. “Enjoy burgers, tapas or a sit-down meal just five minutes from your mooring. anguillaregatta.com

New name for Cap Cana Billfish Tournament

Stay on your vessel in the largest inland marina in the Caribbean, or in one of the new stunning Mediterranean-style villas at the Fishing Lodge at the Cap Cana Resort in the Dominican Republic for this year’s Fishing Lodge International Cap Cana Billfish Shootout May 17-22.

“The Chivas Regal Division has its set of team and individual angler awards for boats participating in the Calcuttas, while the Brugal Rum Division is similar, but with no money,” says Tournament Director, Rick Alvarez. “It’s like two tournaments in one!”

Over 30 vessels from the U.S., Dominican Republic, Puerto Rico, St. Martin and Aruba are expected to compete. Last year, it was Watson Canivess’ boat, the 59′ Caroline, built by Paul Spencer, that won by releasing 15 white marlin and 1 blue marlin in three days of fishing. The marlin fishing grounds are as close as three miles from the Marina Cap Cana’s entrance.

Nightly parties include the Beach Caribbean Rum Bash featuring the 28-piece Brugal Rum Orchestra, a ‘Golf Scramble’ on the lay-day morning at the Jack Nicklaus-designed course in Punta Espada, followed by the Cap Cana Cook-Off where anglers and crews can show off their galley skills. intlbillfishtourns.com/currentEvents/capCanaShootout2012.htm

Classic Plastics welcome at 

Foxy’s Wooden Boat Regatta

Fishing lodge at Cap Cana in the Dominican Republic. Richard Gibson photo

It’s not just wooden boats that are welcome at Foxy’s Wooden Boat Regatta, set for May 25-27 on the British Virgin Island of Jost Van Dyke. “We’ve included a Classic Plastic open fleet for boats of a design over 30 years old to swell the participation and make a good party,” says Mike Kirk, one of the West End Yacht Club (WEYC) organizers. “Foxy (Callwood) was suspicious at first, but he hasn’t complained at the increased bar take!”

Two races daily leave ample time for daily partying and prize-giving. Everyone wins something.

The WEYC will again run its Goslings Cup Series, which kicks off with Foxy’s regatta and includes the Firecracker 500 in July, Gustav Wilmerding in December, and Dark & Stormy in March 2013. For more information, email: martin@sailsistership.com.