Life on Cape Cod kicks into high gear on Memorial Day weekend, and there is no better way to celebrate the start of the summer season than by checking out the Figawi, a wildly popular sailboat race from Hyannis Port to Nantucket. On the morning of Saturday May 28th, get up, grab a cup of coffee, and head down to Kalmus Beach, overlooking Lewis Bay, to watch the 200 plus sailboats gather by the race’s starting point at the Hyannis Port Jetty. Then, at 10 am, cheer on the 1000 plus sailors as they head off across Nantucket Sound, sailing 22 miles to their final destination at the entrance of Nantucket Harbor.

Figawi Race Weekend Activities

There are a whole roster of fantastic events surrounding this annual Figawi regatta that’ll please both sailors and landlubbers alike.

FRIDAY, MAY 27th: Starting at 3 pm on Friday, the Hyannis Yacht Club (located at 490 Ocean Street, Hyannis, MA) is throwing a kickoff party where competitors, friends, family, and Figawi fans can dance, drink, and buy some Figawi swag to show that they know how to celebrate the beginning of summer in style. Or you can hang with the sailors by grabbing a drink or two at Baxter’s, a Cape Cod institution overlooking the Hyannis Harbor and the watering hole of choice for the yachting crowd. Baxter’s has several events celebrating the Figawi all weekend long.

SATURDAY, MAY 28th: After watching the sailboats cut along Nantucket Sound, why not jump in the car to check out some of Robert Paul Properties’s spectacular listings in the area? Just a few minutes drive from the Hyannis Yacht Club is 23 Longwood Avenue, in Hyannis Port. This stunning property has 3 bedrooms, 2.5  baths, and a beautiful yard, making it a truly spectacular Cape Cod home.

For more information, call Linda Plunkett at 508.397.4894.

After exploring Hyannis Port, hop on a ferry and head to Nantucket for some post-race celebrations at the Race Weekend Tent Party, located at the corner of New Whale Street and Commercial Street in Nantucket.

SUNDAY, MAY 29TH: One of the weekend’s main highlights is the annual joke-telling session.It is an event with a long history. Since the 1970s, men and women have gathered at the Main Tent on Figawi weekend to tell dirty jokes to one another. According to Joe Hoffman, who wrote a book on the Figawi, the rules of the joke telling are strictly set forth: “No race, color, creed, or sex is safe from attack; no subject matter is off limits; a joke must be either a classic or fresh and funny.” So grab a drink, sit back, and get ready to laugh.

58 Pleasant Street

Stay in the Main Tent for a 12:30 pm Tasting and Tidbits party full of spirit samples and little bites to eat. Then take a quick drive down to see 58 Pleasant Street, which is a charming four bedroom house with one bedroom cottage at the edge of the Historic district. Then return to the Main Tent for more drinking and dancing. Or check out the Figawi Invitational, starting at 11:30 am, where high school sailing teams from across the Cape and Islands compete for the coveted Figawi Jr. Trophy. The races take place off the docks of Nantucket Boat Basin.

MONDAY, MAY 30TH: At 9:30 am, watch as the boats leave Nantucket to return to Hyannis. There is a post-race party at the Hyannis Yacht Club later in the afternoon for everyone to kick up their heels once more, and toast the Figawi.

Is there any better way to start summer?

For more information on any of our Cape Cod listings, check them out online, stop by our Mid-Cape Market Center, or call 508.420.1414 to speak to any or our agents. To find out more wonderful things to do around town, like us on Facebook.