The Sydney

Please note: The Sydney opens for the season mid-May and has a 2 night minimum stay requirement on weekends.

The island of Martha’s Vineyard, off the southern coast of Massachusetts, is well known in the Northeast as a summer playground for affluent New Englanders. That’s a demographic that’s not always known for being on the stylistic cutting edge, but the Sydney takes a classic whaling captain’s house, marries it to a second, brand-new structure, and presents itself to the world as a thoroughly contemporary boutique hotel.

The location is central, on compact Edgartown’s tony North Water Street, two blocks from the water’s edge. The newer building contains 14 rooms, decorated in a colorful contemporary style with just the right amount of Victorian influence — they feel like nothing else on the island, but they still feel like they belong. Meanwhile the Captain’s House is scarcely more traditional, its Colonial Revival architecture contrasting vividly with modern colors and bold patterns.

Also in the Captain’s House, on the ground floor, is the Sydney’s restaurant, the delightful L’Etoile, owned and operated by chef Michael Brisson. It’s not just a “hotel restaurant” but a local favorite as well, though it’s far from the only game in town — Edgartown is extremely walkable, and there’s plenty to see and do within a short walk from the hotel’s front door.