5 Reasons to Charter a Boat in Massachusetts
Massachusetts offers a rich blend of New England charm, coastal beauty, and deep maritime heritage — and there’s no better way to experience it than from the water. Whether you're cruising past historic landmarks or casting a line in world-class fishing grounds, chartering a boat in the Bay State turns a regular day into a memorable one.
Here are five standout reasons to book a boat charter in Massachusetts:
1. Watch Whales Off Stellwagen Bank
Massachusetts is home to one of the best whale-watching destinations in the world: Stellwagen Bank National Marine Sanctuary, located just off Cape Cod Bay. Charter a boat from Provincetown or Gloucester, and you'll have the chance to see humpbacks, finbacks, minke whales, and even dolphins in their natural habitat.
Best time to go: May through October. Morning trips often offer calmer seas and better sightings.
2. Island-Hop Between Martha’s Vineyard and Nantucket
Massachusetts' southern coast is home to two iconic islands — Martha’s Vineyard and Nantucket — and chartering a boat is the most scenic, flexible way to explore them both. Depart from Falmouth, Hyannis, or New Bedford, and enjoy hopping between harbors, beaches, and waterfront restaurants.
Don’t miss: A quiet afternoon at Menemsha on the Vineyard or Brant Point Lighthouse in Nantucket.
3. Cruise Boston Harbor for Skyline Views and History
A Boston Harbor cruise offers a dynamic mix of city views and American history. Chartering a boat gives you a private view of the Boston skyline, USS Constitution, Fort Independence, and even the Boston Harbor Islands. Great for locals looking to see the city in a new way — or travelers wanting a nautical take on history.
Perfect for: Small groups, date nights, or sunset cruises with city lights as your backdrop.
4. Fish for Stripers, Fluke, and Bluefish in Buzzards Bay
If you're looking to reel in some fun, Buzzards Bay and Vineyard Sound offer top-tier inshore fishing. Charter boats out of Wareham, Marion, or Woods Hole head into waters loaded with striped bass, fluke, sea bass, and bluefish during the summer months.
Pro tip: Early morning charters often bring the best action — and calmer conditions.
5. Relax at Anchor in Padanaram Harbor or Cuttyhunk
Sometimes, the best boating days are the slow ones. Charter a boat and drop anchor in scenic, quiet harbors like Padanaram in Dartmouth or the laid-back island of Cuttyhunk. These are perfect spots to relax, enjoy a picnic on the boat, take a swim, or just soak up the salty breeze.
Ideal for: Families, couples, and anyone looking to unwind without the crowds.
Final Thoughts
From urban harbors and offshore whale zones to fishing hotspots and peaceful island retreats, Massachusetts offers boaters a little bit of everything. Whether you're after wildlife, history, or just a day on the water, there's no better way to see the state’s coastal treasures than by charter.
