Carefree Boats Club of Southern Connecticut’s Westport location is on the beautiful Saugatuck River in the heart of historic Westport at Bridgebrook Marina and Bridge Square. Only a block away, from each other, both locations are on Riverside Ave.
Bridgebrook Marina is one of the few privately owned marinas in Westport and will be home to half of the Westport fleet. Bridge Square will house the other half of the fleet and our sales office; it is also the location of restaurants, small shops, and offices. Having these two, close proximity, locations allows variety in the fleet as the waterway between the two locations is divided by the low Saugatuck River Bridge.
Within walking distance is all that downtown Westport has to offer including several restaurants with dishes ranging from fresh seafood to Mexican food. Grab some Pad Thai from Rainbow Thai, treat yourself to a hot pressed wrap from Roly Poly Sandwiches, or relax after boating with a cocktail at Rizzuto’s Oyster Bar and Restaurant.
The location of Bridgebrook marina on the Saugatuck River offers a scenic journey to Long Island Sound. The Saugatuck River contains some of the purest water in southwestern Connecticut along with the Saugatuck River Bridge, the oldest surviving movable bridge in CT, built in 1882.
Take your time cruising from Bridgbrook marina, past multi-million dollar waterfront homes, and out to the Long Island Sound. The Saugatuck River, with its shallow, calm waters, is also perfect for cruising with family and friends, and for a variety of watersports including kayaking and paddle boarding. While the sound can get a bit choppy, the harbor is perfect for learning how to wakeboard or for taking the kids tubing,
Long Island Sound (LIS) is a saltwater tidal estuary that lies between the north shore of Long Island and Connecticut and New York. The LIS is 110 miles long and 21 miles at its widest point, with depths up to 230 feet. It is a great body of water for everything from water sports, fishing, to just cruising around exploring, and everything in between. There are a handful of small islands to visit just outside of the river, and the north shore of Long Island is only a 14 mile trip.
The Long Island Sound is home to many species of aquatic life, and, most of the year, presents anglers with excellent surface conditions for fishing. Please see our related Fishing in Connecticut for details on what you can hope to catch in the sound.
The Norwalk Islands is a chain of sixteen islands stretching for six miles along the coast of Connecticut. A majority of these islands are privately owned, so coming ashore is discouraged, however, anchoring in these islands’ coves and bays offers plenty of opportunities for relaxation. Sheffield Island offers a lighthouse tour and picnic areas, and the coves and reefs sheltered by the islands offers great fishing.
Port Jefferson is a deep water, protected boating destination on the North Shore of Long Island, pretty much straight across from Black Rock Harbor and Captain’s Cove Seaport. There are many attractions in the area including shopping, art galleries, markets, a children’s museum, and parks. There is also a great selection of waterfront and inland restaurants.
Smithtown Bay, just to the west of Port Jefferson, is a great boating and fishing area. The Sunken Meadow State Park makes up a majority of Smithtown Bay’s shoreline, making for a pristine coast and beautiful beaches to visit. There are a few marinas tucked in the shallow Stony Brook, and in the village center there are some great places to eat.
Huntington Bay, where Connecticut patriot Nathan Hale was captured by the British, houses beautiful anchorage bays on Long Island’s northern coast. Steeped in a rich history and the hometown of poet Walt Whitman, Huntington Bay’s shoreline is dotted with both seaside mansions and working fishing boats and boat yard. On shore Huntington Bay offers visitors places to shop and grab some food.
On Long Island’s gold coast is the charming Northport Bay. Northport village is made up of shops, restaurants, and ice cream parlors and visiting boaters will find dockage at one of the friendliest town docks on Long Island.
The former whaling port, Cold Spring Harbor is now a thriving summer community and the home to a whaling museum and aquarium. There are many free public beaches and parks on the shore of Cold Spring Harbor. Once ashore, visitors will also find a handful of restaurants and local attractions such as the Cold Spring Fish Hatchery.
Oyster Bay is the home to an ample population of bluefish, as well as ideal waters for cruising and exploring the shoreline. On shore visitors will find beautiful sandy beaches and a plethora of restaurants and shops. Centre Island shelters the waters of Oyster Bay and provides boaters with calm conditions and gorgeous anchorages.