Memorial Day on Nantucket

Are you ready to kick off the summer season this upcoming Memorial Day Weekend? We, at Hotel Pippa, are excited for the months to come and thrilled to welcome guests for high season on Nantucket. We still have a few rooms available for the holiday weekend – three days of sailing races, strolls on the beach, on-island explorations, delicious local meals, and fun activities.
There are many on-island traditions on Memorial Day Weekend – seasonal visitors make their way to the island among thousands of sailors hailing from all over the country for the Figawi race. The historic cobblestone streets of Nantucket are vibrant with locals and travelers taking advantage of the mild weather, bustling shops and countless events.
Explore the island’s gray-shingled cottages, manicured gardens and blooming hydrangeas by taking a bike ride through the island’s villages and visit Cisco Brewery for beer and wine tastings and local live music.
On Saturday, get up early to watch the Skippers and boat owners prepare their boats, gather their crews, and head out to the start line. Beginning around 8 am, the parade of sailboats head out of Lewis Bay, pass by Kalmus Beach, and gather off the Hyannis Port jetty. The pursuit regatta officially starts at 10 am and finishes at the entrance of Nantucket Harbor, with a parade into Nantucket Boat Basin. Standing on the beach at Brant Point Light is a great spot to watch all the action.
On Sunday, walk the docks at Nantucket Boat Basin and watch the local high school teams from across the Cape and Islands compete in the annual regatta called the Figawi invitational. On your way back to downtown Nantucket, stop for a delicious ice cream at The Juice Bar and collect local souvenirs at the shops. On Monday, the Memorial Day Parade passes through Main Street, an occasion to honor local and visiting military veterans.
Throughout the weekend, enjoy New England cuisine and eclectic foods are Nantucket’s restaurants – most of them reopen for the summer season on Memorial Day weekend and offer the freshest seafood and local produce. We highly recommend making reservations in anticipation of your visit, and our front desk team can assist once on-site as well.
As high season approaches, Memorial Day weekend on Nantucket is the perfect time to reconnect with family and friends, enjoy the island’s beautiful beaches and perfect summer vibes.