Ballards Beach, Block Island (24 miles) This is where to go to see and be seen. Ballard’s Inn serves sushi, barbecue, and drinks on the waterfront and the beach party atmosphere attracts a young, hip crowd. Anchor out and swim in to enjoy the scene, you’re guaranteed a great downwind run home the next day.

Great Salt Pond, Block Island (24 miles) Dock, moor, or anchor in the Great Salt Pond and cross to the East side of the island for a great family beach. Rent surfboards, go horseback riding, or explore further inland on rental bikes or mopeds. Water rides will keep the kids happy when they’ve tired of swimming and building sand castles.

Cuttyhunk (26 miles) Cuttyhunk has managed to stave off commercialism over the years and still has the charm of a remote and unspoiled island. The island is dry, so bring your own alcohol if you plan to drink, you can bring extra and trade it to the locals for a fresh lobster dinner delivered to your boat.

Menemsha Basin, Martha’s Vineyard (34 miles) Several scenes from Jaws were filmed in this quaint fishing town and it still retains its salty ambiance. Bring your own booze and go to the nightly fish market for fresh fish cooked on the spot and served up on fish crates stacked nearby.

Gay Head Cliffs, Martha’s Vineyard (34 miles) Beautiful sunsets come standard as the sun’s last rays highlight the sandy cliffs, you won’t want to stay the night, but Menemsha—just around the corner—provides plenty of protection.

Fisher’s Island (36 miles) Dock, moor, or anchor in West Harbor, since the eastern 2/3 of the island is part of a gated community and off limits to visitors. Rent bikes to explore the island and keep an eye out for celebrities and politicians who frequent the downtown. For dinner, have lobster dinners delivered to your boat or hit the Pequot Inn, a “hopping” restaurant and nightclub with live music and pool tables.

Montauk, Long Island, New York (43 miles) You won’t run out of things to do if you make the trek to Montauk. The city prides itself on its sportfishing and you can pick up fresh tuna, marlin, and shark as the catches come in. Montauk also boasts horseback riding at the country’s oldest cattle ranch and rental bikes, kayaks, surfboards, and more.