History seeps between the weathered cobblestones still lining alleyways in downtown Boston. You can feel the legend of early America in the old Victorian homes of Dorchester, or the skinny meandering streets in North End—a place Paul Revere once called home, where today the Freedom Trail leads untold numbers of visitors through a fascinating narrative. Boston is a legendary city, which is why its expansive and picturesque harbors are best discovered in the boat that shares its namesake! Behind a GMC, you can trailer your Boston Whaler back to its legendary roots with this road trip itinerary that takes you through Boston and the surrounding area.
Before You Begin:
Follow these trailering tips from the experts at GMC to ensure your road trip goes smoothly.
Boston Harbor Islands:
Just oﬀ the coast of historic Boston Harbor, a chain of small islands dot the protected waterway, offering natural enclaves with stunning views of the city skyline. A free public boat ramp in the Dorchester neighborhood offers an ideal central location to explore. Pear-shaped Spectacle Island—a 15-minute cruise from downtown—holds hiking trails and sandy beaches. Farther east, the Civil War–era Fort Warren staunchly protects Georges Island. From the perch of your Boston Whaler, you can see the sweeping granite archways that once defended the city in the 19th century.
An hour trailering trek south of Boston, Falmouth offers visitors a taste of Cape Cod, where small coastal towns proﬀer a more relaxed pace with good food and good company. Launch your Whaler at the Falmouth Harbor Landing nestled between coastal cottages, boutique shops and world-class seafood restaurants. Once you cruise past the local charms, the open waters of the Vineyard Sound provide excellent fishing and options to navigate to Martha’s Vineyard.
Just an hour east, on the edge of the Cape, Chatham welcomes visitors with miles of sandy beaches, a historic lighthouse and traditional hospitality—not to mention some of the country’s best seafood. A public boat ramp provides access to Ryders Cove, one of Chatham’s many protected inlets. Head south to enjoy views of the town’s lighthouse, originally built in 1808.