Head north early to get a jump on the season and avoid crowds.

The annual summer cruise is one of your family's favorite traditions. Most years, you head north from Long Island, New York, in early August, but this summer you've decided to get a jump on the season and beat the crowds. Instead of docking at the usual spots, you also decided to poke into some alternative anchorages and drop the hook.

Coming north from Long Island, you ducked into Block Island's Salt Pond but decided against anchoring in the notoriously hard bottom of the pond and were instead fortunate enough to find a vacant town mooring for the night. Though the crowds were moderate by midsummer standards, it was still nice to spend the night out on the water rather than rafted into a group of dockside revelers.

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Lobster in the Pond
The day starts off slowly as you linger in the bunk, listening to the water gently lapping against the hull. A sudden call "andiamo" drifts across the anchorage, but by the time you are dressed and on deck, the pastry delivery boat from Aldo's has moved on to the other end of the pond. Memories of fresh pastries purchased from that same delivery boat in years past soon have you salivating, and you inform the crew there will be a delay in the morning departure. Taking the dinghy ashore, everyone heads to Aldo's restaurant to enjoy the daily breakfast buffet.

Later, after securing the tender, you put Block Island behind you as you ride a calm sea northeast toward the Rhode Island coastline. First Point Judith then Beavertail Point come into view, with the faint but unmistakable profile of the Claiborne Pell Bridge in the background. But Newport's tony waterfront is not on today's agenda; instead, you alter course slightly to starboard to pass east of Brenton Reef, making for Gooseberry Island. With no appreciable swell running, conditions seem favorable to drop the hook off the eastern end of the island for lunch and a midday swim.

By the time the afternoon sea breeze kicks in, you are once again under way, motoring east toward the Elizabeth Islands. Passing the north side of Cuttyhunk Island, Massachusetts, you follow the markers past Middle Ledge. While passing through Cuttyhunk Harbor, you flag down a local lobster fisherman, who gives you a good price for a pair of 2-pounders just out of the trap. With dinner in hand, you idle into the protected waters of the pond. Even though it's mid week, mid afternoon and mid-June, there are a fair number of boats at anchor. After a couple of turns through the fleet, you find a good place to set your own hook. Once you are satisfied the anchor is holding, you head ashore for a pre-dinner hike up the hill to catch the sunset. Later you'll put the cockpit grill to good use with those lobsters.

The Alternative Anchorage
Today's destination is less than 10 miles away up Vineyard Sound, which means you have plenty of time to poke around Cuttyhunk and the Elizabeths. For starters, you can break out some spinning tackle and join the charter guides who ply the tidal rips for striped bass and bluefish. If the weather stays nice, you can also duck into Quick's Hole on Nashawena Island for a swim and some beach time.

Eventually, you'll want to head over to Martha's Vineyard, where you'll stop short of West Chop and look for the single beachside marker that leads into Lake Tashmoo. This tidal lagoon is connected to the sound by a narrow cut that requires some careful navigation at the mouth then opens into an expansive body of water that could accommodate a small armada of sailboats were it not for limiting depths of 4 to 5 feet. Since your cruiser draws just under 4 feet, you can join the handful of other powerboats that choose to drop the hook here rather than next door in busy Vineyard Haven Harbor.

The lake provides a pleasant degree of isolation and privacy, but you are actually quite close to the onshore attractions of Vineyard Haven. Getting into town is as easy as motoring the dinghy to the Lake Street landing then walking a half-mile or so into the village. Tonight, you'll come ashore for dinner at the Blue Canoe.

One night isn't nearly enough time to enjoy all the pleasures of Martha's Vineyard. Fortunately, you have allowed ample time to explore the island. With the boat sitting pretty on the hook, you can head into town to fortify yourself with a hearty breakfast at the Artcliff Diner before renting bikes for a ride into Oak Bluffs and around to Edgartown. After all that pedaling, you might want to take a taxi for the trip out to Gay Head for an afternoon at the beach.

Into the Bay
After a couple of days on the island, you are ready for a change of scenery. A quick trip across the sound brings you to Woods Hole, where a modest outgoing tide actually helps you maintain steerage as you power your way through the twists and turns of the strait. A final turn to starboard brings you around the Penzance headland and on to the markers that will guide you safely past the rock shoals guarding the entrance to Quissett Harbor.

Rather than attempt to squeeze among the moorings of the inner harbor, you set the anchor near the entrance then deploy the dinghy to go ashore at the Quissett Harbor Boatyard, were you can stretch your legs on a hiking trail that leads through a grove of towering oaks and up to the outcropping known as the Knob. 

The beach just below is an option or a bit more walking can take you in to East Pont, where you can nip into the Captain Kid for a tavern lunch.Quissett can be a peaceful place to spend the night, but you have other plans. By 4 p.m., you are back aboard and ready to start exploring Buzzards Bay. Tonight, you've set your sights on one of the most picturesque coastal villages in southern New England. Though it takes a few passes, you find swinging room in Marion's town harbor, just north of Ram Island. The staff at the venerable Beverly Yacht Club allows you to secure your dinghy at the club docks, and you stroll down tree-lined water street to the town green, then over to the Moonfish Restaurant.