The waters of southeastern Connecticut and southern Rhode Island flow together seamlessly to create a cruising corner packed with maritime history, soft beaches, classic New England dining and activities for all ages. Plan ahead if you want a slip or mooring, as summer attracts many a mariner to these waters.
Fisher’s Island, NY
Nine-mile-long Fisher’s Island has a backstory of grand estates and resort amenities. Although private summer residences still dominate, a hearty year-round community and a small village preside over the island’s western end.
West Harbor, outside the moorings, offers the best anchorage. You can also reserve a slip at Fisher’s Island Yacht Club Marina. (They even deliver lobster, cooked or not, to your boat.) Pirate’s Cove Marine has a few moorings, but they fill up quickly.
In the village, you can rent a bike, enjoy libations at the oft-lively Pequot Bar & Grill or dig into the history of this New York hamlet at the Henry L. Ferguson Museum. Simply strolling and enjoying the outdoors are popular pastimes here. East of Flat Hammock is a good place to drop the hook, take an afternoon swim or anchor in quiet Chocomount Cove or East Harbor. The island’s ocean side has plentiful fishing grounds.
Day 1: Mystic, CT
West Harbor, Fisher’s Island to Mystic Harbor 3 NM
Boating runs through the veins of Mystic, past and present. From the approach at Mystic Harbor and all the way up the main artery of the Mystic River, outstanding facilities line the shores.
At the pulse of it all is the renowned Mystic Seaport. Streets of the 19th century village come alive with re-creation. Watch figurehead carvings, sing sea chanteys, listen to sea stories, learn celestial navigation in the planetarium and so much more. Among the line of seaport vessels is the Charles W. Morgan, the last wooden whaleship in the world. The June Sea Music Festival is one of a plethora of lively events throughout the year.
Former sea captains’ homes dot the streets of the town, which teems with summer visitors. For dining, The Captain Daniel Packer Inne is an 18th century mainstay. Mystic Pizza gained fame in the 1980s in the movie of the same name starring Julia Roberts. Grab an ice cream at Mystic Drawbridge Ice Cream Cafe and be mesmerized by the exposed cement counterweights lifting and lowering the Mystic River Bascule Bridge. Mystic Aquarium and the shops of Olde Mistick Village are located a mile and a half north of town.
If you want a quiet base close to the mouth of Mystic Harbor, stay in Noank or just crack open a lobster at one of the village’s legendary dock and dines: Abbott’s Lobster in the Rough or Ford’s Lobsters.
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Day 2: Stonington, CT
Mystic Harbor to Stonington Harbor 4 NM
Walk up Water Street in Stonington Borough, and you’ll see boats dancing in the gaps between Saltbox, Federal and Greek Revival buildings. This pleasant town fills the peninsula that reaches from northeastern Connecticut.
The Captain Nathaniel B. Palmer House
lets you step into the history of a Victorian mansion and climb to the cupola for sweeping views. (Palmer is renowned for discovering Antarctica at 21 years old in a 47-foot sailboat.) At the foot of Water Street, the Old Lighthouse Museum details the past of the 1840 beacon that served mariners for 50 years. Across the street, purchase a day pass at duBois Beach to enjoy swimming in gentle surf or crabbing off the jetty.
Dodson Boatyard has slips and moorings (which start inside the west breakwater) and operates a launch. The boatyard’s Dog Watch Café is a Stonington signature; another waterfront favorite is Breakwater on Water Street. The annual Blessing of the Fleet in July ranks high as a colorful nod to the longstanding fishing fleet located here.
Day 3: Watch Hill, RI
Stonington Harbor to Watch Hill 3.5 NM
Many boaters dream all winter of pointing their bow toward this lovely resort town and its street of small pleasures. Watch Hill Docks in the heart of Watch Hill Cove has highly coveted slips, or you can stay on the Pawcatuck River. The go-to anchorage is north of Napatree Point, with dinghy access to shore to enjoy serene beaches and a happy little village.
At the foot of town, riders on the antique Flying Horse Carousel “fly” out from a center frame suspension and squeal with the delight as they try to grab the brass ring for a free ride. You’ll want to get an ice cream at St. Claire Annex or fudge at the Candy Box, as it seems everyone on Bay Street has one or the other. Boutique shops and eateries round out the lane with a classic choice being the Olympia Tea Room, which is known to serve Watch Hill’s most famous resident, Taylor Swift.
Napatree Beach, a long sandy spit, puts you aside a bird sanctuary and leads to the scant remains of 19th century Fort Mansfield. For a stunning ocean view, walk out to the Watch Hill Lighthouse
or stroll down East Beach, where you can see the re-created Ocean House Resort. The yellow exterior of the magnificent hotel stands out even amidst the Watch Hill mansions.
