Start in the city of Boston and walk in the footsteps of Revolutionary War heroes. Hear the story of Paul Revere’s Midnight Ride and relive the fight for American Independence with a self-guided walking tour of Boston’s Freedom Trail. Immerse yourself in the stories of the American Revolution, the Boston Tea Party, and the Sons of Liberty as you stroll along Boston’s scenic Harborwalk. Uncover Boston's historic and storied past while enjoying its beautiful harbor views between South Station and Long Wharf. Then, travel to the city of Cambridge outside Boston and explore the heart of Harvard University's campus at Harvard Square. Use the app to take a self-guided walking tour that covers must-see campus sights like the John Harvard Statue, Widener Library, and former dorm rooms of famous alumni like Bill Gates, Mark Zuckerberg, Natalie Portman, and more. Next, discover Cape Ann with a self-guided driving tour along the scenic waterfront. Enjoy the vistas, beaches, and natural beauty of the New England coastline at your own pace. Visit the famous Fisherman's Memorial, beautiful Beauport, all while diving into the stories of Massachusetts of days past. Continue to Cape Cod and see its quintessential lighthouses and sandy beaches. As you drive, learn more about the Cape’s seafaring traditions, Pilgrim history, and miles of beautiful beaches. From Barnstable to Provincetown, visit Nauset Lighthouse, First Encounter Beach, Marconi Station, and more.

Set sail from Boston Harbor first thing in the morning and enjoy the short ride to Provincetown, Cape Cod’s cultural capital. Step onto dry land just like the Pilgrims did when they landed here on the Mayflower in 1620, and begin your walking tour of the charming town with an expert local guide. Provincetown is still an important fishing colony, but it's also home to a number of rich cultural communities, including the oldest continuous artist colony in the US. Enjoy the unique art installations and murals all around you, see a replica 1905 schooner sunk by a German U-boat, and learn about the area’s culinary tradition that's closely connected to late celebrity chef Anthony Bourdain. After exploring a bit, it's time to hop onto a comfortable (and air-conditioned!) minibus to drive down to Wellfleet on the Outer Cape. A world capital for oysters, you’ll get to sample some for yourself, freshly caught right off the pier. After your fresh appetizer, it's time for a picnic lunch on the beach. Then you can walk down Main Street for a sweet Cape Cod specialty: homemade local ice cream. Get out your cameras—it’s time to see some lighthouses on Cape Cod National Seashore! Start with a visit to Nauset Light, a late 19th-century lighthouse that's still operational, which you may recognize from the logo found on bags of the popular Cape Cod potato chips. From there, you'll visit three more decommissioned lighthouses and hear the tragic story of the pirate captain “Black Sam" Bellamy. His ship, the Whydah Gally, was sunk off this very coast in 1717, and its remains weren't discovered until 1984. Moving away from the sea and further inland, it’s time to meet the pioneers of maritime winemaking at Truro Vineyards. Here you have the option to enjoy a tasting of their wines and spirits, and tour the gorgeous vineyard grounds. Even for non-drinkers in the group, the scenery alone will make this stop worthwhile. Time to end your journey where your day began, back in Provincetown. At this point, the town is your oyster! Sample more local cuisine, climb the Pilgrim Monument, or just explore before hopping on the return ferry home at your leisure.