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OUT OF FALMOUTH
Where We Cruise
Flying Bridge Marina puts us within reach of some of the best water in the Northeast — Martha’s Vineyard in under an hour, the Elizabeth Islands and Woods Hole just minutes away, Cape Cod Bay in every direction. Every charter is custom, so where we go is up to you.
Why Falmouth Is the Right Starting Point
Charter location matters more than people realize. Boats based further up-Cape spend the first hour of every trip just getting somewhere worth being. Out of Flying Bridge Marina in Falmouth, we’re already there.
In under twenty minutes we can reach Woods Hole, the Elizabeth Islands, or Vineyard Sound. Martha’s Vineyard is a short cruise across — closer from Falmouth than from any other major Cape town. Cape Cod Bay opens up to the north. Protected anchorages, lighthouses, and quiet sandbars sit in every direction. Your charter time is spent on the water, not in transit.
Martha's Vineyard
The most popular destination we run to, for good reason. Martha’s Vineyard is close enough for a half-day trip, big enough to spend a full day exploring, and varied enough that the version you experience depends on which harbor you choose.
We run to all four major harbors — each with its own character. Here’s how to think about them:
Oak Bluffs
Gingerbread cottages, walkable Circuit Avenue, the carousel. The Vineyard’s most social harbor and the best first-visit choice for groups who want food, shops, and atmosphere within a few blocks of the dock. About 35–45 minutes from Falmouth.
Vineyard Haven
The Vineyard’s working harbor. Quieter and more local than Oak Bluffs, easier in and out. Good for groups who want a cleaner shore stop without restaurant scrums. About 35–45 minutes from Falmouth.
Edgartown
The polished side of the island. Whaling-captain architecture, brick sidewalks, upscale boutiques, and classic harbor views. The best lunch reservations are here — book them when you book the charter. About 45–60 minutes from Falmouth.
Menemsha
A working fishing village on the Vineyard’s west side, famous for sunsets and lobster rolls eaten on the dock. The quietest of the four harbors, and the one most Cape and Vineyard tourists never reach. Slightly longer cruise — worth it. About 60–75 minutes from Falmouth.
Any of these harbors can be a shore stop on a longer day charter, or the destination of a dedicated Martha’s Vineyard trip. Captain Elliot can also coordinate split-harbor charters — drop at one harbor, pick up at another — if your group wants to spend the day walking the island.
Woods Hole & the Elizabeth Islands
Some of the best cruising water on the East Coast sits within sight of our dock. The current that runs through Woods Hole is unlike anywhere else — fast, deep, alive — and the Elizabeth Islands stretch west from the mouth of the harbor, a string of mostly private, remote, and stunning islands most Cape visitors will never see up close.
Naushon Island is the largest of the Elizabeth chain, privately owned by the Forbes family since the 1800s and off-limits to the public. But from the water, its beaches, meadows, and stone walls are some of the most photogenic coastline in New England.
Pasque Island and Nashawena Island sit further west — smaller, quieter, and rarely visited. We cruise past them on the way to Menemsha or as part of scenic charter routes.
Cuttyhunk Island is the outermost and the only one with public access. A working fishing village, a handful of full-time residents, and one of the most under-the-radar shore stops on the East Coast.
Great for: scenic cruising, lighthouse loops, swim stops in protected coves, and shorter charters that don’t require a full Vineyard crossing. It’s the route we recommend for groups who want a real day on the water without committing to island shore time.
Sandbars & Anchorages
Drive-by tourists never see them. Sandbars only show themselves at the right tide, and the best ones aren’t on any map worth checking. Captain Elliot knows where they are and how to time the trip to catch them at their peak.
Sandbar stops are the part of the charter most groups end up loving most. Anchored in two feet of water, swimming off the back of the boat, music playing, lunch spread out on the bow — it’s the Cape Cod day people picture when they book. Kids can walk off the boat. Groups can spread out. Photos come out unreal.
The specific sandbar depends on the tide, the wind, and how busy the water is that day. Captain Elliot makes the call the morning of your trip. Some of our regular spots include:
- Middle Ground and the shoals off Nobska Point
- Protected anchorages along the Falmouth south coast
- Quiet coves on the Elizabeth Islands’ southern shore
- Vineyard Sound sandbars accessible only at specific tides
Great for: day charters, celebration charters, family trips, anything where you want serious time on the water and in the water.
Lighthouse Routes & Scenic Cruising
Some of the best photo days we run don’t really have a destination at all. The Cape’s coastline reads differently from the water — the old lighthouses, the dunes at Sandy Neck, the Vineyard’s bluffs at golden hour, the working harbors and quiet coves in between — and a slow scenic cruise is often the most memorable thing a charter can offer.
Nobska Lighthouse sits on the point where Vineyard Sound meets Buzzards Bay. From the water, it’s the classic New England lighthouse view — white tower against the bluff, the Sound stretching out behind it. One of the most photographed lighthouses in Massachusetts.
West Chop and East Chop Lighthouses frame the entrance to Vineyard Haven harbor. A common photo stop on Martha’s Vineyard runs.
Tarpaulin Cove Light on Naushon Island — quieter, less visited, and often the highlight of an Elizabeth Islands cruise.
Cleveland Ledge Light in Buzzards Bay — a working caisson lighthouse, easy to reach on a scenic day.
Great for: sunset cruises, anniversaries, engagement cruises, and groups who want the camera-roll version of the Cape without any specific stop in mind.
Cape Cod Bay
North of Falmouth, Cape Cod Bay opens up into protected, glass-flat water on the right day — the spot we recommend for first-time charter guests, families with younger kids, or anyone who wants a smooth ride and quiet anchorages. Day charters that stay in the Bay tend to be the most relaxed trips we run, and the easiest to extend if the group decides they want more time.
The Bay is also home to some of the Cape’s best wildlife — seals hauled out on rock ledges, occasional whale sightings during migration season, and seabirds working the shallows. On calmer days, we can push further north to hit remote anchorages that get very little charter traffic.
Great for: first-time charter guests, families, celebration groups that want calm water, and anyone who doesn’t want to commit to open-water conditions.
Custom Routes
Every charter is custom. If there’s a spot on the Cape or Islands you’ve been wanting to see from the water, or a route you’ve taken before and want to repeat, tell us — we’ll build the day around it. The locations on this page are the ones most groups choose, not the only ones we run.
We’ve done custom charters to Nantucket, private drop-offs at specific Vineyard beaches, photo shoots at remote lighthouses, and multi-stop days built entirely around a client’s itinerary. If it’s on the water within reach of Falmouth, we can probably do it.
OUR HOME DOCK
Flying Bridge Marina, Falmouth
Every charter departs from Flying Bridge Marina at 220 Scranton Avenue in Falmouth — easy to reach from anywhere on the Cape, accessible from Boston in about ninety minutes, and located next to one of Falmouth’s best waterfront restaurants if you want to start the day with brunch or end it with dinner. Parking is available at the marina. We recommend arriving 15–20 minutes before your scheduled departure.
Private boat charters out of Flying Bridge Marina in Falmouth. One captain, one boat, one charter at a time.