Situated just west of downtown, Shelter Island is connected to the mainland by a thin sliver of land — but feels like worlds away. Ships and yachts bobbing in the colorful marina characterize the quaint seaside village, known also for its serene parks, buzzing food scene, and outdoor events. Toward the end of the island sits the historic Yokohama Friendship Bell, given as a gift by San Diego’s sister city of Yokohama, Japan.

Many nautical adventures launch from here, attracting sailors, sea-loving explorers, and marine animal lovers. Travelers flock to Shelter Island for sea cruises, featuring dolphin watching, sea lion scouting, and yacht gazing. Stay awhile and relax at one of the island’s many hotels or resorts, or bask in the sunshine during summer Concerts By The Bay.