Where to Dine:
1. The Homeport: Ran by DC Native Sarah Nixon, this restaurant is an extraordinary viewing place for the island’s dazzling sunsets on the water and serves quality traditional seafood in Menemsha’s peaceful and historic harbor.
The Homeport Restaurant
512 North Road, Menemsha, MA 02252
Tel: (508) 645-2679
2. The Black Dog Tavern: You’ve probably seen the infamous Black Dog imprinted on t-shirts scattered around DC. Grab a souvenir and order from the wide range of specialty dishes at the original restaurant located in Vineyard Haven.
The Black Dog Tavern
3 Water Street, Vineyard Haven, MA 02568
Tel: (508) 693-9223
3. Mediterranean Restaurant: This tasty Mediterranean cuisine tucked away on the outskirts of Oak Bluffs uses only the freshest ingredients cooked to perfection. Headed by executive chef Douglas Hewson, the unique, zesty recipes combined with the modern decor are aimed to please.
15 Island Inn Road, Oak Bluffs, MA 02557
Tel: (508) 693-1617
4. Lure Grill at the Winnetu Oceanside Resort : Hip and decadent, this restaurant serves delicious food and cocktails in a lively, yet relaxed ambiance overlooking the waterfront from South Beach. Tip: Take the complimentary water taxi from Edgartown to Lure at 6p.m–you’ll be glad you saw the stunning views of the harbor from the sea.
Lure Grill at the Winnetu Oceanside Resort
25 Dunes Road Edgartown, MA 02539
Tel: (508) 310-1733
5. Atlantic Restaurant: Fresh seafood, delectable cocktails, and dazzling views are boundless at this festive restaurant and bar situated in the heart of Edgartown’s harbor.
2 Main Street, Edgartown , MA 02539
Tel: (508) 627-7001
Where to Stay:
- The Harbor View Hotel & Resort: Recognized as a fortress overlooking Edgartown’s beautiful harbor, Chappaquiddick Island, and the Edgartown Lighthouse, this hotel in essence is the perfect location and resort for summer visitors. Spacious rooms and family friendly.
The Harbor View Hotel & Resort
131 North Water Street, Edgartown, MA
2. Mansion House Inn, Health Club, Spa: Offering a wide variety of spa and fitness options, Mansion House balances the right amount of activity with relaxation. Ideally located in the center of Vineyard Haven, this inn will leave you detoxed and wanting to linger on the island longer.
3. The Charlotte Inn: The elegant inn is nestled on one of Edgartown’s quaint side streets and exudes a traditional lavish New England decor in a comfortable and relaxed environment.
The Charlotte Inn
27 South Summer Street, Edgartown, MA, 02539
Tel: (508) 627-4751
4. Hob Nob: As an eco-friendy boutique hotel centrally located in Edgartown, this hotel’s luxurious rooms and houses available for stay strikes the right balance of relaxation and tranquility in a quiet environment.
Hob Nob Inn
128 Main Street, Edgartown, MA, 02539
Tel: (508) 627-9510
5. The Beach Plum Inn: A charming inn overlooking Menemsha’s stunning harbor. With outstanding facilities, hospitality, and spectacular views of the island, this inn reserves the status as a spectacular place to stay on the island. Don’t miss out on the inn’s specialty restaurant.
The Beach Plum Inn
50 Beach Plum Lane, Menemsha, MA 02552
Tel: (508) 645-9454
Where to Visit:
- Chappaquiddick (Chappy): Only a ferry ride away from Edgartown, this serene and charming island oasis provides the perfect harmony of relaxation and beauty for anyone in pursuit of seclusion from the busy island mainland. Be sure to check out Wasque, the quiet, natural beach tucked away at the end of the road.
- Aquinnah: Overlooking bellowing red-cliffs on the island’s edge, this historic reservation provides panoramic views of the island’s natural scenic landscape.
- Menemsha: Ideal for island fisherman, this town boasts the best view of the sunset on the beach. Be sure to get there enjoy a cup of Clam Chowder from the Homeport before the sunset.
4. Edgartown: Beautiful residential haven for sailors, islanders, and visitors alike, this town centered in the heart of the island features a unique boutique shopping scene and offers an interesting array of original stores including the Original Vineyard Vines. For a great cup of coffee before hitting the town (or beach), don’t miss Espresso Love.
5. Vineyard Haven: This lively and eclectic island town offers unique stores interlaced with a natural and refreshing laid-back island vibe. Among the many island stores, look out for Carly Simon’s eclectic home décor and luxurious clothing boutique: Midnight Farm and charming island bookstore: Bunch of Grapes.