Shelter Island attracts visitors with its lively but laid-back atmosphere. You can hop on a boat for a fishing tour or whale-watching cruise or enjoy a meal at one of the eateries along Shelter island Drive. Head to the southern end of the island to see the Pearl of the Pacific fountain at Pacific Rim Park and the Friendship Bell, given to San Diego by its sister city of Yokohama, Japan. From the water, you can admire the island on a bay cruise, a sailing adventure, or a “seal tour” by amphibious vehicle.
From downtown, head toward Point Loma on North Harbor Drive, turning south to round the bay and reach the island. Or catch bus 28 from the Old Town Transit Center.
Locals flock to Shelter Island during the Concerts by the Bay music series at Humphreys Restaurant and Inn. From roughly April to October each year, the outdoor theater seats 1,400 people for shows that range from rock ‘n’ roll to jazz.
Not to be confused with Shelter Island, Harbor Island is a neighboring not-really-an-island that’s slightly larger and easier to reach from downtown. It offers a similar combination of restaurants, hotels, marinas, and a waterfront park.
