The Great Loop, the Downeast Loop, the Triangle Loop, Florida's Little Loop boaters seem to be quite loop happy. So here's one to add to your loopy list: the Nantucket Sound Loop, circling from Cape Cod in the north to Martha's Vineyard and Nantucket in the south. There are many well-protected harbors, the fishing is very good, beaches run for miles, and there are quintessential small towns everywhere.
Great place to start is in Woods Hole, just down the road from Falmouth on the Cape. It's less than 12 miles from the Cape Cod Canal and less than 25 from Newport, Rhode Island. From there, the loop runs east-southeast to Martha's Vineyard, east to Nantucket, north up to Hyannis, and west over to Cotuit Bay before heading southwest to return to Woods Hole. This route stays inside the Nantucket Sound, safe from large ocean swells. There are many shoals scattered around the sound, but they are well charted and marked, and there's plenty of room to avoid them. The longest run is about 25 miles, which means easy day trips for even the slowest of vessels. By going north from Nantucket to Hyannis, the trip takes advantage of the prevailing southwesterly winds that dominate here during the summer.
In Woods Hole, tie up in Hadley's Harbor, a very unique place. The Forbes family installed mooring buoys here in the inner harbor they are marked private but that seems to be a technicality, as cruising boats use the moorings regularly. Oh, and by the way, they're free. The only problem with that is that they're also often full. Your other options are to anchor in outer Hadley's Harbor or proceed to a mooring or slip in Woods Hole harbor. While you're in town, don't miss the tour at the Woods Hole Oceanographic Institute, it is excellent. And when you're motoring out of Woods Hole, pay attention to the current as you're maneuvering toward open water there are rocks all around!
Next up, Martha's Vineyard. This is a very big island with many ports to choose from. I like staying in Vineyard Haven Harbor. It's in the center of the island, is sheltered from the winds, has options for anchoring, mooring or dockage, and the excellent local bus system makes it easy to get around. Plus, the collection of classic yachts moored here is great fun to check out. To the east, Oak Bluff has moorings and dock space options and seems to be party central. Edgartown, farthest east, is an outstanding little village with anchoring, mooring, and some dock space as well. A walking tour of the many old sea captains' houses is a great way to stretch your legs. Take the ferry across to Chappaquiddick to explore the marshes and beaches.
After the Vineyard, it's on to Nantucket. This has to be the most New England of New England destinations. Many of the streets are cobblestone, and the buildings are postcard perfect. There is room to anchor, a large mooring field, and in the harbor is the excellent Nantucket Boat Basin (508-325-1350, nantucketboatbasin.com), which has earned the Marinalife Transient Marina Of The Year Award for three years running. George Bassett, the dockmaster for 28 years, has built up an 86 percent customer return rate, in large part because it's all about customer service at Nantucket Boat Basin. George and his 40-person staff keep everyone happy, and it's important to book your reservations early to make sure you get a spot. The wharf-like setting is charming and one-of-a-kind, with shops and restaurants just steps away. It has the appearance more of a fishing village than a marina, and it works very well. Arrange for a bike rental to venture along the island's paved bike trails past beautiful homes and pristine beaches. You can also run your dinghy five miles from Nantucket Boat Basin up to the Head Of The Harbor and the stunningly gorgeous Coskata-Coatue Wildlife Refuge.
There's nothing quite like Nantucket.Next, head 25 mile north to Hyannis. Don't lie, the first thing you think of when hearing Hyannis is Kennedy, and rightly so. That family made the town famous, and still has a compound there. You can anchor in the outer harbor not far from several of their moored boats. Visit the John F. Kennedy Hyannis Museum to learn even more about one of our best-known presidents. But there is also so much more to Hyannis. Well-protected Lewis Bay is accessed via a deep channel, and has a mooring field run by the Hyannis Yacht Club and a large area available for anchoring. Further into Hyannis' inner harbor you'll find the Hyannis Marina (508-790-4000, hyannismarina.com), a resort-like facility with all the usual extras plus 200 slips for yachts up to 200 feet, a pool, Trader Ed's Cabana Bar, Tugboat's Restaurant, three courtesy cars, and one of the best-stocked marina ships stores I've ever seen. Carla Sullivan, dockmaster for 18 years, runs a tight ship if you need it, she can get it. She regularly attends to the needs of the megayachts that frequently tie up, but gives the royal treatment to every boat that lands at her docks, no matter how large or small. If you can pull yourself away from the marina, there are all kinds of excellent restaurants and attractions to check out. The Black Cat Tavern has some of the best chowda around. Downtown there's a unique collection of waterfront artists' studios, a maritime museum, and plenty of shops to fulfill the need for retail therapy.
There are nice beaches on the inside and outside of Egg Island, just a quick dinghy ride from anywhere in the harbor.
The last stop on this loop is Cotuit Bay. The channel at the entrance to Cotuit Bay is quite shallow, so the preferred entry route is the channel into West Bay, followed by an immediate turn into the Seapuit River behind Dead Neck. This route gets dredged frequently and big sailboats use it regularly. There are marinas further up West Bay and a mooring field in Cotuit Bay, but I like to anchor behind Dead Neck in the no-wake zone. There is a sandy bottom with good holding behind the barrier-island bird sanctuary. You can walk around the beach to the sound to swim in the ocean, or just relax in the peaceful, quiet setting. From the West Bay channel, it's an easy day trip back to Woods Hole.
Falmouth Harbor, less than 10 miles west of Woods Hole, has plenty of marinas if anchoring out for a night is not your cup of tea. You can do this loop in a week, though it's better if you give it two weeks, and you could easily spend a month or two doing it, exploring all that the many islands and harbors have to offer. However long you go for, enjoy Nantucket Sound!