Cape Cod Vacation Itinerary Day Five

If you have enough time during your Cape Cod vacation, and you’re up for another jaunt to an island, head to Martha’s Vineyard where each of the island’s six charming towns boasts its own personality and charm. To get there, you can take one of two ferry lines – Steamship Authority out of Woods Hole, abut an hour and a quarter from the Captains House Inn and a 45 minute ride on the high speed ferry, or Hy-Line Cruises out of Hyannis, about a 40 minute ride from the inn and an hour on the ferry. You may also choose to fly out of Hyannis airport, which saves time, but is a bit more expensive and not ideal for anyone prone to fear of flying as the aircraft between the mainland and island are rather small! While there is the (quite pricey) option to take your car on the Steamship Authority ferry with advance reservations, we do not recommend doing this as the island has plenty of public transportation, cabs, and even rentals if you do prefer your own wheels.

Once there, many folks find a brief bus tour of the island is helpful in understanding the layout and getting a thorough overview before setting out on their own. Martha’s Vineyard Transportation and Tours offers several different tour options, the most popular of which is a one hour overview of the island. Next, take your pick of towns to explore – you may be inclined to head to Chilmark, a rural, unspoiled town, home to a small fishing village and a working sheep farm. Or, if you prefer more hustle and bustle, Edgartown, Oaks Bluff, and Vineyard Haven are the most popular destinations among tourists. Edgartown is renowned for its impressive ship owner and whaling captains’ mansions lining North Water Street. The downtown area offers upscale shops and gourmet restaurants, and nestled beside Memorial Wharf is the Chappaquiddick ferry transporting passengers to the “island within and island” where highlights include Mytoi, Japanese gardens, and a vast expanse of coastal nature preserves.

Vineyard Haven is the port where most ferries drop passengers and is home to a naturally protected harbor which was once one of the busiest in the United States and along which Gannon and Benjamin boatyards, one of the finest manufacturers of wood yachts, is located. Downtown, grab lunch at the Black Dog Tavern, a well known eatery attracting tourists from all over (though Vineyard Haven is a dry town, so despite its name, alcohol is not served here).

Don’t miss Oaks Bluff, the island’s liveliest town, particularly in the wee hours during the summer months. Take a ride on Flying Horses, the nation’s oldest operating carousel and explore Union Chapel dating back to 1870. For animal lovers, a visit to Island Alpaca, is a must. Here, the alpacas are bred, raised, and sold and visitors can enjoy a self guided tour and learn all about the gentle, unique creatures.

Clearly, Martha’s Vineyard is packed with sightseeing and activities that can easily fill a day, but be sure to head back to the Cape with enough time to get ready for dinner because tonight, you’re heading to the Impudent Oyster – an unfailing crowd pleaser and landmark in Chatham for over thirty years. Here, the fresh seafood and bustling atmosphere consistently earn rave reviews from guests. Finally, snuggle into our 600 thread count sheets with a full belly and visions of Martha’s Vineyard architecture, harbors, and alpacas dancing in your head.