Cape Cod: 16 Sweet Escapes

Boaters based on the south shore of Cape Cod — or those who trailer their vessels to the South Cape area—have it pretty good. After all, few places offer such ready access to a variety of fun, exciting places to visit by water—many in the same day!

Here are 16 great day trips or weekend destinations worth checking out, all of them accessible from South Cape ports.

1. CUTTYHUNK

This isolated outpost at the end of the Elizabeth Islands chain is within reach of many South Cape boaters launching from points west of Hyannis (distance from Falmouth Harbor is 16 nm). Duck inside the peaceful, protected harbor and contact Cuttyhunk Marina at the town wharf for short-term dockage. For moorings, contact Jenkins Moorings (VHF 9) or Frog Pond Marine (VHF 72).

Once ashore you can wander the hilly slopes of town for amazing views of Vineyard Sound and Buzzards Bay, play in the surf at Barges Beach, grab a hot dog at Bart’s Cart, or cast a plug for stripers or bluefish in one of the greatest surfcasting venues in the world. If you choose to spend the night, be sure to hail Cuttyhunk Shellfish Farms, which will deliver ocean-fresh oysters and other raw-bar items direct to your boat.

2. WASHBURN ISLAND

This unique island inside Waquoit Bay—part of a state park—offers a rustic ocean escape for all types of boaters, from kayakers to fishermen. Washburn Island features sandy beaches, walking trails and campsites, which can be reserved from May to October. The surrounding waters are warm in season and ideal for swimming and kayaking, and the island makes a good base camp for fishing trips in Vineyard Sound and beyond.

3. MENEMSHA

Few Northeast harbors compare to Menemsha. Located some 14 nm from Falmouth Harbor, Menemsha Harbor is Martha’s Vineyard’s most isolated and picturesque port—a working harbor that remains home to a stalwart commercial fishing fleet.

Once you arrive, contact the harbormaster (508) 645-2846, to arrange a slip, mooring, or space alongside Dutcher Dock. If conditions allow, you can also drop the hook outside the harbor and dinghy (or swim) to the gorgeous white-sand beach. Grab a stuffed quahog or lobster roll at Larsen’s Fish Market. Local artists sell copper fish weathervanes and sculptures at The Copperworks. For ice cream, lobster rolls and more, head for the Menemsha Galley.

4. HYANNIS HARBOR

Centrally located, Hyannis Harbor is an easy run from most any South Cape port, plus it boasts a variety of restaurants, shops, and other attractions. Contact the harbormasters office at 508-790-6273 or VHF 9 to see about free dockage along Bismore Park. If there’s room, you can go ashore and visit local artists displaying their work in the park, or grab lunch at Spanky’s Clam Shack or the Black Cat Tavern. Both are kid-friendly.

Drop by the Cape Cod Maritime Museum for a look at the Cape’s nautical past and watch wooden boatbuilding in action. On the eastern side of the harbor, you can arrange for a slip at the Hyannis Marina while you enjoy a drink or something to eat at Tugboats or Trader Ed’s. Baxter’s Boat House, next to the Steamship Authority docks, is yet another dock-and-dine option on the harbor.

5. VINEYARD HAVEN

Vineyard Haven is short run from Hyannis (18 nm), Falmouth (5 nm), or Wood’s Hole (6 nm) and offers boating amenities galore. You can drop off passengers at the Owen Park town dock then anchor in the outer harbor or secure a mooring for the day, night or weekend (reservations are recommended in summer). Call the harbormasters, who are always ready to help. Once ashore, there are many shops and restaurants to explore nearby. Don’t miss the homemade ice cream at Mad Martha’s, harborside dining at The Black Dog Tavern, or the fresh seafood-in-the-rough at the Net Result on Beach Road.

6. MONOMOY

Monomoy is one of the great natural wonders of New England—a world apart from the rest of Cape Cod, or anyplace else. Surrounded by Bahamas-clear sand flats, it’s an amazing place to visit by boat, as long as you respect the tide. Many a careless mariner has anchored here, only to find himself (and his family) high and dry for the entire afternoon. Study the charts and tide tables, and make sure you have a GPS in case the fog rolls in, as it often does here, being so close to the chilly open Atlantic. Once anchored, break out the kayaks or a dinghy and explore the wonderland of flats and channels. The crystalline water teems with crabs and baitfish, as well as predators such as striped bass and bluefish. And you’ll likely see a harbor seal or two cruising the shallows.

7. SAMPSONS ISLAND

This long barrier island (also known as “Dead Neck”) off Osterville and Cotuit is managed by Massachusetts Audubon, whose staff may ask for a donation while you use the beach. You can access the protected backside of Sampsons Island via the narrow channel that connects Cotuit and West Bays then gently nose your bow onto the sand to offload passengers and gear. This is a wonderfully protected place for small children to splash around, and there’s a nifty tidal pool on the western end of the island to explore. Note that much of the island’s interior is off-limits to protect nesting shorebirds.

8. NANTUCKET HARBOR

This trip isn’t necessarily for small-boats, but ACK is certainly within easy striking distance of many South Cape ports. The distance from Hyannis, Bass River, and Falmouth Harbor is 21 nm, 21 nm, and 27 nm respectively. Once inside Nantucket Harbor, hail Nantucket Moorings or the Nantucket Boat Basin for a place to secure your vessel while you go ashore. The quaint, cobbled streets of downtown are flanked by shops and galleries. If you’re looking for a local spot to anchor and beach it for a while, a safe bet is Dioness Beach, just west of the harbor.

9. LAKE TASHMOO

This lovely salt pond on Martha’s Vineyard is accessed via a small inlet on Vineyard Sound (MLW depth 5.5 feet) just south of West Chop. Boaters in shallow-draft vessels can pull up onto the sand flat just inside the inlet and let the kids frolic in the warm water. Or you can anchor in the southern part of the pond, with permission from the harbormaster. Leave your dinghy at the dock at the foot of Lake Street then stroll the mile or so into Vineyard Haven. Moorings on Lake Tashmoo are also available through the Tashmoo Boatyard, (508) 693-9311.

10. CHATHAM

Downtown Chatham isn’t directly on the water, but that shouldn’t stop you from visiting by boat. Set a course for Chatham Roads then head north towards Stage Harbor. At the truncated lighthouse, you have 2 options: continue into Stage Harbor and grab a mooring or slip at Stage Harbor Marine, Oyster River Boat Yard, or Chatham Yacht Basin, or bang a right and follow the winding channel east to Outermost Harbors, where you can rent a slip before strolling the mile or so into town. The marinas in Stage Harbor can arrange lift to Main Street, but it’s more fun to take a dinghy up either the Oyster River or Mitchell River. Both feature public landings close to Main Street. Enjoy dinner, a beverage and live music at the famous Squire Tavern or Red Nun, or spend a romantic night at the Chatham Inn on Main Street. No matter how you get there, Chatham is a special place.

11. OAK BLUFFS

Oak Bluffs Harbor may be small, but it’s the main party spot on the Vineyard. Oak Bluffs Marina welcomes visiting boaters with slips and moorings, available on an hourly or nightly basis. On shore is a cornucopia of restaurants, shops, and the Flying Horses Carousel. This vintage ride, complete with brass rings to grab, was built in 1884 yet continues to thrill new generations of kids. Adults can grab a cold beverage and burger at Coop de Ville overlooking the harbor, or order sashimi at the Sand Bar & Grill, also on the water. A short walk will bring you to the Offshore Ale House and Sharky’s Cantina, which serves up tasty Mexican fare in a fun family atmosphere. Check out the colorful Victorian cottages of the Revival Campground nearby, or play on the beach along Seaview Avenue.

12. EGG ISLAND

This low-lying and ephemeral island at the entrance to Lewis Bay off Hyannis is a wonderful spot to drop anchor and go ashore for a few hours to frolic in the shallows or picnic on the beach. It also offers good protection from the prevailing southwest wind in summer. Try to plan your trips around the low tide, however, as there isn’t much dry land available at high water. Egg Island is also a popular anchorage if you’re thinking of spending the night while visiting Hyannis.

13. EDGARTOWN

Edgartown (17 nm from Hyannis; 10 nm from Falmouth Harbor) is widely considered the most “upscale” of Martha’s Vineyard ports, boasting a wonderfully protected inner harbor and a rich variety of restaurants, boutiques, galleries and shops along its well-groomed and architecturally interesting streets. In terms of daytrip access, however, simply popping into town for a few hours is not as cheap or easy as places such as Hyannis or Menemsha. Many boaters offload passengers at Memorial Wharf when the ferry is not tied up, then cruise around or fish while their family and friends explore the town or get something to eat. If you’re lucky, you may be able to find a short-term berth at Mad Max Marina or a transient mooring through the harbormaster at (508) 627-4746 or VHF 74/16. You can get a lift into town via Oldport Launch, VHF 68.

14. TARPAULIN COVE

Veteran cruisers know Tarpaulin Cove, about midway along the Vineyard Sound side of Naushon Island in the Elizabeth Islands, as a well-protected anchorage and all-around aquatic gathering spot. It’s also one of the few places on the privately owned island where you can go ashore and enjoy the lovely sand beach. Just don’t wander into the island interior. Note that there are no public bathrooms on shore.

15. EAST BEACH (MARTHA’S VINEYARD)

Aside from the occasional surfcaster in a 4-wheel-drive vehicle, boaters can have this sprawling beach on Chappaquiddick Island all to themselves. And once you get past the rocks off Cape Poge, there are no underwater hazards to hinder your approach to shore. East Beach, which is managed by the Trustees of the Reservations, is an especially nice spot when the southwest wind begins to honk on a summer afternoon, plus the water bordering the beach is deep enough for large boats to offload crew and gear before setting bow and stern anchors.

16. MADAKET

If you love Nantucket, but are looking to get away from the bustle of downtown Nantucket Harbor, plot a course for laidback Madaket, on the west end of Nantucket and roughly 20 nautical miles due south of Hyannis. Make your way through the winding channel and you’ll see why Mister Rodgers (remember him?) made Madaket his summer neighborhood for over 30 years. Madaket Harbor’s shallow waters are ideal for kids to romp in, and there’s food and beverages in a pleasant atmosphere to be enjoyed at Millie’s. Boaters can drop off crew at one of local landings then anchor inside Smith Point and dinghy ashore. Contact the harbormaster at 508-228-7261 if unsure of protocol.

Written by Tom Richardson
A Massachusetts native and past editor of New England Boating & Fishing, Tom has spent time working for Salt Water Sportsman,
Offshore Magazine and was a founder of BoatingLocal. You can now find Tom as the Host, Executive Producer at Explore New England TV.