Written by Doug Simmons
September 2018

Exploring new places and events is a big part of owning or chartering a boat. Calendar these great escapes for sports fans, art lovers and festival goers, then plan your cruise and join the fun.

Boston Calling Music Festival

Boston, MA
May 24-26, 2019

Bean Town’s premier pop-rock fest isn’t all about the music — well, mostly it is — but there’s also a food lab, film screenings, comedy shows and a high-flying Ferris wheel. Taking place over Memorial Day weekend, multiple stages host headliners like The Killers, Jack White and Eminem as well as a curated list of regional and hometown bands. The overall vibe is controlled, relaxed and delightfully diverse.

Where to Dock: Constitution Marina and Boston Yacht Haven

Preakness Stakes

Baltimore, MD
May 19, 2019

As one-third of the venerable Triple Crown, the Preakness deserves a visit for the excitement of the 14-horse stampede. But there’s the spectacle, too. The storied grounds of Pimlico Race Course are a kaleido-scope of activity, part corporate retreat and part state fair. Cocktail parties, velvet ropes, rock concerts, a bikini contest, fried dough vendors — it’s all here and then some.

Where to Dock: Harbor East Marina and HarborView Marina

Spoleto Festival USA

Charleston, SC
May 24-June 9, 2019

This annual 17-day performing arts celebration, held in a dozen locations on the downtown peninsula, was voted by Southern Living readers as the

“South’s Best Festival” in 2018. The fete presents renowned names and emerging artists in classical and popular music, jazz, dance, opera, theater and more. Each of the 150 individual events is ticketed, so do your homework prior to setting course for the creative cultural event.

Where to Dock: Charleston City Marina

RBC Heritage

Hilton Head Island, SC
April 15-21, 2019

Whether you’re a golf nerd or just hate northerly winter weather, the RBC Heritage awaits in April. It’s played in Sea Pines Plantation, a gated community on the toe end of the foot-shaped island, and the course fringes the iconic, candy-striped lighthouse in Harbour Town. From there, you can watch one of the signature holes on the PGA tour while sipping an Arnold Palmer and planning your sunset walk on the beach.

Where to Dock: Harbour Town Yacht Basin

Georgia Elvis Festival

Brunswick, GA
March 8-10, 2019

We like our Elvis one of two ways: emerging star oozing with rockabilly swagger or blinged-out King of Rock and Roll dressed in a sequin jumpsuit. This jivey event promises plenty of both during an opening ceremony, two headlining shows, the Ultimate Elvis Tribute Artist Contest and a Sunday morning Elvis gospel music revival. Word has it the after-hour parties are enough to make your knees shimmy and shake.

Where to Dock: Brunswick Landing Marina

Petanque Amelia Island Open

Amelia Island, FL
November 9-11, 2018

A mashup of horseshoes and bocce, petanque (pronounced “pay-TONK”) becomes the talk of the town each November when the sport’s largest U.S. tournament hits the shores of this beautiful, French-inspired island. Beginners, amateurs and champions all play together in one big contest with lots of laughter and plenty of food and drink within walking distance of the waterfront.

Where to Dock: Amelia Island Marina

Daytona 500

Daytona Beach, FL
February 17, 2019

No event captures the raucous excitement of a NASCAR race better than the Daytona 500. Ticket holders take in the action from the tops of motor homes, tailgate near the perimeter of the speedway or watch the 500-mile sprint from the grand-stand or infield, where you can meet your favorite drivers before the flag. Another highlight: you can bring your own food and drink, and kids 12 and under are free in the University of Northwestern Ohio (UNOH) Fanzone.

Where to Dock: Halifax Harbor Marina

U.S. Open Polo Championship

Palm Beach, FL
April 20-22, 2019

Ask anyone on the street what they think of polo, and they’ll likely tell you it’s swank and well-behaved and some-thing most of us don’t watch on TV. But to see the sport live is intense, the matches thrilling and dangerous, more like hockey than croquet on horse-back. Mounts are ridden at speeds up to 35 mph while players in helmets and knee pads use mallets to strike the ball into the opposing team’s goal. Settle in for a chukker or two at this annual tourney in April.

Where to Dock: Palm Harbor Marina

Delray Beach Open

Delray Beach, FL
February 15-17, 2019

This “ace” is the only combined ATP World Tour/ATP Champions Tour event meaning it draws from both current, and past legends of tennis. The 25-year-old Delray Beach Open features 10 days of single-elimination singles and double matches, plus special happenings to entertain fans. Sign up for clinics with Grand Slam legends, VIP parties, Pro-Am matches, kids’ activities and more.

Where to Dock: Seagate Yacht Club at Delray Beach

Art Basel Miami Beach

Miami, FL
June 12-16, 2019

One of the biggest events in the contemporary art world turns the  Miami Beach Convention Center into a melting-pot of North American and Latin American masterpieces in  March. More than 250 of the world’s leading galleries and 4,000 artists  from 31 countries participate,  displaying paintings, sculptures, installations, photographs and  editioned works in the main exhibition hall. Be inspired, then attend artist talks, panels and discussions.

Where to Dock: Miami Beach Marina and Sunset Harbour Yacht Club

Uncorked: San Diego Wine Festival

San Diego, CA
August 11, 2018

Uncorked Wine Festivals excels at creating fun wine-tasting events that blend live music, gourmet food trucks, and both familiar and new wineries from all over the world. Its San Diego Wine Festival is held at the Embarcadero Marina Park North overlooking Coronado Island and the Pacific Ocean beyond. Sample the select vintages and then spend an evening supping and shopping in nearby Seaport Village.

Where to Dock: San Diego Marriott Marquis & Marina