Hawkins Island

On a small private island that's just a quick trip from Hamilton and Long Island by boat, this unique property can accommodate up to 16 people in two small houses with a private chef, beach, dock and water sports options.

• The proximity to Hamilton and the ease of a private island experience that's close to home for those on the East Coast.
• The prime viewing location for sailing regattas (VIPS spent time here during the America's Cup in 2017).
• The island's history as a Boer War prison camp makes it great for history buffs and for independent children who love to get outside and explore.

This 26-acre-island reserve, just a short boat ride from Hamilton, has a full-service villa (including a dedicated chef and water sports instructor available upon request). The main villa sleeps eight in a two-bedroom master suite and two one-bedrooms that are modern in feel, with contemporary décor and a sand and white color scheme. Bathrooms have deep soaking tubs and rain showers; there are also two outdoor showers. The Guard House is a bit more no-frills and can accommodate eight more (two in one bedroom and six in a tight bunkroom) for a total of 16 guests, though 10 to 12 would be preferable. (This would work best for kids over eight, traveling with a nanny/babysitter or a family). Be advised that there are steep ladders leading to loft areas for rainy day reading or hanging out in the main house. The Guard House also has a hot tub on the viewing deck upstairs. There is a private dock and a small beach and terrace. A pool and outdoor entertaining spaces are being added to the property. The island was once a Boer War prison camp from 1901-2, holding 1,300 prisoners. Though the property on-site is still a work-in-progress, it's an unusual option for anyone looking for a private island escape from New York in just a few hours.

Families with children or friends who enjoy spending time on the water and are looking for a private island experience. It could also work for a small wedding.