Day 1 Sag HarborEmbark on your yacht in Sag Harbor and take a short cruise to Shelter Island where a tender can rendezvous with your yacht to bring you onshore for lunch at Sunset Beach. This East End staple feels more like St. Tropez than Long Island with it’s yellow and white parasols and Mediterannean vibe. After a relaxing post-lunch swim or a jet ski ride, take a sunset cruise back to Sag Harbor where you can dine aboard your yacht or head into town and have farm-to-table fare at Wölffer Kitchen.
Day 2 MontaukAfter breakfast onboard, head to the North Fork of Long Island, home to dozens of vineyards and charming small towns. Make sure to pay a visit to the lavender fields at Lavender by the Bay before heading into town for lunch at the Frisky Oyster in Greenport. After embarking on your yacht, head to the hip surf town of Montauk. Cruise to the famous Montauk Lighthouse and then drop anchor at Navy Beach where you can take in the breathtaking sunset before heading back to Montauk for dinner at the Crow’s Nest where you’ll have some of the freshest local food with a lake front view.
Day 3 Block IslandKnown for its protected beaches, Block Island was named by the Nature Conservancy as one of the sites in the list of “last great places” in the Western Hemisphere. Visit the Mohegan Bluffs, and take the staircase to the bottom of the clay cliffs, and make sure to try a bowl of New England clam chowder at the National Hotel.
Day 4 NantucketFrom Block Island take a morning cruise to Nantucket, made famous by the Kennedy family for their family compound in Hyannis Port. Originally a whaling port, Nantucket has been named a National Historic District and little has changed since the 17th century with its old fashioned lamps still lining the streets. Nantucket is better known for its pristine dune-backed beaches, cobblestone streets and is famous for its 4th of July fireworks. Spend the day exploring this unique New England island.