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Massachusetts Summer Getaways: Cape Cod & the Islands

Based out of Boston, FlipKey may have an affinity for Massachusetts, but not without good reason. New England showcases the four seasons like no where else in the United States. Vacationers come from all over the world to survey New England’s fall foliage, apple pick in Central Massachusetts, or hike in the Berkshires. As winter arrives, New Englanders trade their hiking boots for skis as people flock to the mountain slopes. In springtime, Boston becomes a hotspot for vacationers eager to experience Colonial history through Duck Tours and walking the Freedom Trail.

But when it comes to summers in Massachusetts, there’s no place better than Southeastern Massachusetts. So if you’re planning a summer retreat, look no further than Cape Cod and the Islands.


 ProvincetownAt the utmost tip of the Cape Cod Peninsula lies Provincetown, or more affectionately known as “P-town”. While the population may seem desolate during colder months, from Memorial Day to Labor Day, Provincetown becomes a nonstop soirée of vacationers. In true summer style, vacationers can kayak around P-town Harbor, sail the Cape Cod Bay and partake in a whale watching tour, peruse the busy shopping district of Commercial Street, or simply enjoy the ocean breeze on its sandy, pristine beaches, all within eyeshot of the famous, 252-foot Pilgrim Monument. Provincetown also features a variety of festivities to honor the arts, such as the International Film Festival in June and the Provincetown Jazz Festival in August. Of course, Provincetown is best known as a gay village. The majority of its events and festivals are centered around the LGBT community, perhaps of which no event proves more popular than the annual Independence Day celebration.


 ChathamIf you want to experience the true old world charm of the Cape, look no further than Chatham. The town has managed to avoid the urban sprawl that has pervaded many parts of Massachusetts, and still features a variety of mom and pop shops along the picturesque Main Street. Chatham’s appeal comes from its antiquity. You can tour the old Atwood House, built in 1752, or pay a visit to the Chatham Lighthouse, established by Thomas Jefferson in 1808.


HyannisFor a slightly more urban appeal while still on the Cape, head over to Hyannis, home to the Cape Cod Mall. As one of the largest towns on the Cape and a designated commercial and transportation hub, Hyannis has earned the nickname, “The Capital of the Cape”. Hyannis offers something for all ages, from a family-friendly tour of the Cape Cod Potato Chip Factory, to the much more adult tour of the Cape Cod Beer brewery. Don’t forget to pay homage to one of our most beloved political families, the Kennedy’s, by visiting the John F Kennedy Memorial and Museum.


 FalmouthTo witness the natural beauty of the Cape, visit Falmouth, whose southern shore boasts a series of ponds and rivers indicative of the Cape’s topography. Enjoy the finer things Falmouth has to offer, like a day trip to the Cape Cod winery, or a visit to the Cornelia Carey Sanctuary, which features nature trails that run alongside Buzzard’s Bay and offers spectacular views of the Elizabeth Islands and seaside sunsets. Perfect for a family trip or a romantic date, the Shining Sea Bikeway winds along the Vineyard Sound shoreline, ending in Woods Hole. From there, you can catch the ferry over to Martha’s Vineyard.

Martha’s Vineyard

 MarthasVineyardThe once home of Jackie Onassis, Martha’s Vineyard has attracted the attention of celebrities, politicians, and artists for decades. The Vineyard boasts temperate summers rarely exceeding 90 degrees, features ample beaches and cliffs, and offers plenty of scenic ocean views and places to eat and shop. Be sure to stop by The Black Dog, a restaurant and tavern that has become a Martha’s Vineyard icon, known throughout New England by its souvenir tee shirts featuring its eponymous Black Dog logo. Another popular destination, the Wesleyan Grove in the town of Oak Bluffs features 350 gingerbread cottages. Or check out the town of Aquinnah to view the scenic Gay Head Cliffs. Proceed with caution, however, as below the cliffs lies Lucy Vincent Beach, one of the few remaining nude beaches left in the US.


Nantucket2A place of serene beauty, Nantucket has become known as a center for the visual and performing arts, but not without a price tag. Nantucket possesses the highest median property value of anywhere in Massachusetts, but for good reason. It hosts a variety of world-class museums, including the Maria Mitchell Association, featuring observatories, an aquarium, a natural history museum, and a science library. While you’re there, plan a visit to the Whaling Museum, the Nantucket Vineyard, Cisco Brewery and Triple Eight Distillery, or the Brand Point Lighthouse, America’s second oldest lighthouse.