Coast With the Most: This Cape Cod Vacation is Perfect For a Girls Trip

There’s no best time for a Cape Cod vacation, only the best people – and that’s got to be your girlfriends. Traveling to this part of the world on a girls trip means you’ll never have a dull moment, whether you’re tucking into the region’s world-famous seafood, walking along its stunning coastline, or exploring the towns and cities, each with their own unique architecture and history.

When should I travel to Cape Cod?

Like many destinations Cape Cod gets very busy in summer, its peak season. But luckily it’s not the only time to visit – in fact, shoulder season is particularly magical in this part of the world. Shoulder season in Cape Cod runs between from May to June (late spring), and September to October (early fall). These months are not only quieter, allowing you to soak up the sights and sounds of this scenic area in peace, but the weather is often better for exploring, avoiding the heat of the summer.

In spring Cape Cod comes to life with sunshine, as the flowers begin to bloom and more outdoor activities start to emerge, from coastal hiking to bike rides, and of course al fresco dining. Meanwhile, fall is known as Cape Cod’s ‘second summer’ thanks to its warm weather, bringing with it a multitude of festivals from oyster contests, beer and wine festivals, and live music.

But where to start when planning your girls trip to Cape Cod? Our Boston, Cape Cod & The Islands Women-Only Tour is an 8-day Cape Cod vacation, taking you from Massachusetts to Rhode Island, across the shores of Cape Cod Bay and to the seaside city of Newport, from historical buildings to cruising on a catamaran. 

With a female Travel Director always on-hand, you’ll also get to experience a range of unique women-led interactions exclusive to this tour, from meeting your captain on an 80-foot schooner ship to taking a Notable Nantucket Women guided walking tour.

Discover our perfect girls trip itinerary below for a Cape Cod vacation to remember.

The perfect girls trip Cape Cod vacation itinerary

Day 1-2: Boston 

Day 1: You Cape Cod vacation begins in Boston, one of the oldest cities in the U.S. and often described as the most European. You’ll have some time to take in its thriving art scene, charming architecture, and maybe even sample its well-known seafood before joining your Travel Director for dinner, where you’ll meet your fellow guests. 

DISCOVER MORE ON

Boston, Cape Cod and the Islands, a Women-Only Tour TOUR

View Tour

Day 2: Wake up and explore Boston with your Travel Director, learning about the city’s transformative past. You’ll follow part of the red-brick Freedom Trail, bringing the story of the American Revolution to life. Catch sight of the iconic Boston Waterfront, the Old State House and the Bunker Hill Monument in Charlestown, passing through colorful neighborhoods of Back Bay and historic North End (also known as Boston’s Little Italy). No trip is complete without trying the local delicacies; leave time to try the neighborhood’s famous cannoli with an espresso.  

Later, with Insight Choice you can choose to visit Fenway Park, America’s oldest baseball stadium and home of the Boston Red Sox, or tour The John F. Kennedy Presidential Library and Museum dedicated to the memory of the nation’s 35th president. 

Day 3: Plymouth & Sandwich 

Day 3: Today brings a wealth of adventures – it’s goodbye Boston and hello Plymouth, where you’ll discover the town’s history as the first pilgrim settlement. Join your first MAKE TRAVEL MATTER® Experience, visiting the Plimoth Patuxet Museum learning about the relationship between English and Wampanoag women of the 17th century.  

Catch sight of Plymouth Rock, the historical disembarkation site of the Mayflower Pilgrims, and a full-scale replica of the Mayflower II – the ship that made the initial voyage to the Americas in 1620 – before indulging in a lunch hosted by the Museum Educator, dining on traditional English and Indigenous foods including Naussamp cornmeal, Native stewed squash, cheate bread, colonial carrot soup, and mint tea with blueberries. 

Next, travel down the coast to the coastal haven of Sandwich, home to the Sandwich Glass Museum. Get up close and personal to this colorful treasure trove, while also hearing from a skilled craftswoman about not only the glassblowing technique itself, but her personal glassmaking story. 

Tonight, you’ll rest and recharge in the Dan’l Webster Inn and Spa hotel in Sandwich, the centerpiece of the oldest town on Cape Cod, which has provided lodging for weary travelers for over 300 years. You’re treated to the romance of the past with all the amenities of today’s conveniences. 

Day 4: Cape Cod & Sandwich  

Day 4: Get out into nature today as you head to Salt Pond on Cape Cod’s National Seashore which, since 1961, has preserved these 40 miles of dunes, beaches and marshes along the eastern side of Cape Cod. Learn about the natural wonder and human history represented on the Cape, from its First People and European settlement to modern lifestyles.  

If you’re feeling a little adventurous, you have the chance to join a Local Expert for an Optional Experience driving through the historic Sand Dunes to catch sight of Pilgrim Lake and the famed artists’ dune shacks, home to American artists and writers from the 1920s to present day including Tennessee Williams and Jack Kerouac. 

Day 5: Martha’s Vineyard 

Day 5: Get your sea legs on, as in the morning you’re boarding a ferry to Martha’s Vineyard. You’ll feel right at home on this charming island, with its pristine sandy beaches and harbor views drawing countless presidential visits, from the Clintons to the Obamas.  

Once you arrive on the island you’ll make your way to Oak Bluffs, known for its rainbow-colored, gingerbread-like cottages with gothic storybook decorations, high-peaked roofs, and dainty verandas. You’ll also find the oldest operating platform carousel in America here. Tuck into local delicacies at a sea-to-table dinner in the evening, where you’ll savor the season’s freshest offerings from local farms, fishing boats, foragers and markets. 

Day 6: Nantucket & Newport 

Day 6: Depart Martha’s Vineyard in style on a high-speed catamaran as you head for the picturesque island of Nantucket. This exclusive coastal community is beloved for a reason, and you’ll see it all on your Notable Nantucket Women walking tour. Take in the beauty of its cobblestone streets and historic architecture (which dates back to its whaling days) with your Local Expert, hearing tales of notable Nantucket women and their impact on the island from the fishing industry to local lifestyles. 

Day 7-8: Newport 

Day 7: The sights of Newport are waiting for you on a scenic drive along the city’s famed Ten Mile Drive, where you can marvel at opulent mansions from America’s Gilded Age – you’ll even enjoy a visit to one of Newport’s renowned landmarks, The Vanderbilt’s Breakers Mansion.  

Then, meet your female captain and board the Adirondack II for a leisurely sunset sail on Newport Harbor and Narragansett Bay on the 80-foot schooner ship. You’ll sail out and pass nearby islands, old historical buildings and homes of the rich and famous, as you learn about the region’s exciting history, including its pirate activity. 

Your final dinner is one to remember; savor a delicious meal at the historic La Forge Casino Restaurant, reminiscing about your trip with your newfound friends, before spending your final night in Newport’s charming, tranquil seaside setting.  

Day 8: Goodbye, New England 

Your Cape Cod vacation comes to an end, as you travel back to Boston for your flight home with countless new memories.

Ready to plan your next girls trip? Discover our Boston, Cape Cod & The Islands Women-Only Tour now.