Carefree Boat Club of Southern CT is conveniently located on Connecticut's Gold Coast only minutes
from many popular boating destinations in Connecticut, Long Island and New York. Whether you want
to explore a new village, soak up some sun on the beach, or try out a new restaurant; there is sure to be
a local spot to meet your needs. We highly suggest purchasing a Long Island Sound Embassy Guide
(available to members t a discounted price). This guide will give you all the information you need, from
where to dock to what you can see or where you can eat, to plan a great boat trip. Our Dock Staff are
also happy to offer suggestions on where to go and will advise you of any obstacles you should avoid
while you are in transit.
Stamford is a bustling city and home to one of Carefree Boat Club of Southern CT's locations. Boating out of, or visiting Stamford you will find some great restaurants, both on the water and a short walk from the docks, where there are also many shops. We highly recommend that you visit The Crabshell Restaurant, where you can tie up on their private docks. Members can contact the Carefree's Stamford Dock Master and will be welcome to free dockage while visiting.
Black Rock Harbor is home to Captain's Cove Seaport and another of Carefree Boat Club of Southern CT's locations. Captain's Cove is one of the CT Shoreline's hidden gems where there is always something happening. They have live music every night, a great restaurant and bar, and plenty of cute shops. Members can contact Carefree's Black Rock Dock Master for free dockage during while visiting.
There is not much transient dock space available in Greenwich but there are some amazing anchorages around the Captain Islands and in Greenwich Cove. There are also shallow waters for fishing and the pristine Island Beach, although you must buy a beach pass from the Town Hall.
Cos Cob has plenty of transient docking, allowing you to take advantage of all the provisions and restaurants that you can find ashore. There is plenty to explore ashore, as well as a great waterside park to stretch your legs.
Comprised of 16 islands, the Norwalk Islands are an anchorage paradise, even in the height of the season it is not unusual to find an unoccupied place to anchor. Ashore, around Norwalk harbor, you can access the impressive Calf Pasture Beach, as well as explore South Norwalk, home to many restaurants and attractions.
Historic Westport and the Saugatuck River is a great boating destination and also home to one of Carefree Boat Club of Southern CT's locations. Cruise the river passing by multi-million dollar homes, and explore the great shops downtown. There are also many great restaurants that will cater to any taste and budget. Members can contact Carefree's Westport Dock Master for free dockage while visiting.
Milford boasts the longest coastline in CT, and just a short walk from Milford Harbor, the second longest Green in the country. Just behind Boston Common, Milford's Green is flanked by restaurants, shops and other attractions. Just off shore, connected by a sandbar, is Charles Island home to Silver Sands State Park.
Branford's Stony Creek is a gorgeous waterway that meanders through the great town. You will also find the Stony Creek Brewery right on the water with their own dock. This trendy brewery has outdoor games, food trucks (on certain days) and, of course, a great beer tasting bar with a deck overlooking the water.
Long Island, North Shore
Mt. Sinai Harbor
Mount Sinai Harbor is a busy little harbor with plenty to see and do. Cedar Beach offers a gorgeous sandy beach flanked by a dense growth of cedar trees. There are a number of local restaurants right on the water, as well as others within local villages.
Port Jefferson is a deep water, protected boating destination on the North Shore of Long Island, almost straight across from Black Rock Harbor and Captain’s Cove Seaport. There are many attractions in the area including waterfront and inland restaurants, shopping, art galleries, markets, a children’s museum, and parks. .
Smithtown Bay, just to the west of Port Jefferson, is a great boating and fishing area. The Sunken Meadow State Park with its pristine coast and beautiful beaches makes up a majority of Smithtown Bay’s shoreline. There are a few marinas tucked in the shallow Stony Brook, and in the village center there are some great places to eat.
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.
Huntington Bay houses beautiful anchorage bays on Long Island’s northern coast. On shore, Huntington Bay offers visitors places to shop and grab some food.
Cold Spring Harbor
Cold Spring Harbor is now a thriving summer community and the home to a whaling museum and aquarium. 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.
New York Shoreline
Larchmont & Mamaroneck
These locations are so close to each other that they are typically referred to as one. Both boast numerous harbors, home to some impressive yachts, as well as quaint villages to explore. On shore you will find many attractions, including Rye Playland, an impressive amusement park that you might recognize from the movie Big. There is also some great fishing in the area.
City Island offers some great on shore attractions. You'll find ample shopping and many restaurants on City Island Avenue. Transient docking is plentiful on City Island.