Southern Connecticut - Local Boating

Local Boating Guide

Exploring the waters of the area offers endless opportunities for adventure, sightseeing, and dining. Check out our local guide for inspiration on where to go, what to see, and the best spots to eat and drink on your next boating trip.

Places to See

Things to Do

Places to Eat & Drink

Places to See

Port Jefferson

Port Jefferson is a deep water, protected boating destination on the North Shore of Long Island, almost straight across from Bridgeport Harbor. There are many attractions in the area including waterfront and inland restaurants, shopping, art galleries, markets, a children’s museum, and parks.

Black Rock Harbor

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.

Milford Harbor

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.

Stamford Harbor

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.

Oyster Bay

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 Oyster Bay and provides boaters with calm conditions and gorgeous anchorages.

Huntington Bay

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.

Captain's Little & Big Island

Following your gps and charts closely you will enter Captains Island. Near the island is a good spot to drop an anchor and go swimming. If you do enjoy fishing it also is a great spot to catch stripped bass and fluke.

Address: GPS coordinates: 40°58′57″N 73°37′24″W

Greenwich Harbor

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.

Statue of Liberty

People have gone past the Statue of Liberty for over a century. This boat ride will be unlike any other. You will pass under the white stone and Throgsneck bridges and see planes land into La Guardia airport. The beautiful skyline of NYC will be a sight to see! Come check out our lady of liberty today!

Rye Playland

A short boat ride from the mouth of Rye Harbor you will find Playland. You are able to pick up a mooring and have a launch boat bring you directly to the boardwalk. From there you will be able to enjoy Charley’s Pier Restaurant & Tiki Bar for some delicious food and drinks. A short walk from the restaurant you will be able to enter Rye Playland's amusement park.

Website: Visit Website

Things to Do

Watersports

Watersports

Steelpointe HarborRye City Boat BasinBridge Square

Westport – Saugatuck River: This scenic river location is perfect for trying your hand at wakesurfing. The sheltered coves and gentle currents make it easy to carve smooth waves behind the boat, ideal for both beginners and experienced surfers looking to catch a fun ride. Bridgeport – Long Island Sound: For adrenaline seekers, the open waters of the Sound provide ample room for high-speed wakeboarding and aggressive tricks. Wide, unobstructed areas make it easy to practice slalom skiing or push your wakeboarding skills to the next level. Rye – Milton Harbor: Milton Harbor offers a mix of calm and open water, perfect for mixing activities in one trip. Start the day with wakesurfing or wakeboarding in the wider sections, then slow down for tubing or casual waterskiing closer to the sheltered coves.

Fishing

Steelpointe HarborBridge SquareCrabshell Side

Carefree Boat Club of Southern Connecticut offers incredible fishing opportunities across some of the region’s most productive waters. Members can target striped bass, bluefish, flounder, porgies, sea bass, and even blackfish at prime spots like Marker 32A in Stamford, Stamford Reef, and The Cows in Stamford Harbor. For fluke and flounder, Todd’s Point offers sand-bottom fishing ideal for squid or spearing baits, while the Noaa Weather Buoy delivers world-class striped bass action in late spring and early summer, and big bluefish throughout the summer months. Smithtown Bay, near Port Jefferson, provides a scenic backdrop with marinas, beaches, and calmer waters perfect for a more relaxed fishing day. For adventurous anglers, Execution Rock Lighthouse in the middle of the Sound offers challenging rocky fishing, though it’s strictly for experienced boaters due to its location. With a mix of inshore coves, reefs, and open water, Carefree Boat Club members have access to some of the best fishing in Southern Connecticut and Long Island Sound.

Fishing
Swimming

Swimming

Bridge SquareCrabshell Side

Carefree Boat Club members have access to some of the best swimming spots in the area. Calf Pasture Beach and Sand City offer classic sandy shores ideal for a refreshing dip, while Ziegler’s Cove is a protected, family-friendly spot perfect for anchoring and spending the day in calm waters. For a more scenic experience, Shippan Point allows you to enjoy a swim right in Stamford Harbor while taking in beautiful waterfront homes from the water. These locations provide safe and enjoyable options for every boater that's looking for an easy and fun way to take a dip.

Places to Eat

The Turn

The Turn at Port Jefferson Country Club, expertly managed by Lessing’s Hospitality Group, serves up a laid-back yet refined dining experience just steps from the golf course. Perched 100 feet above the Long Island Sound, it offers panoramic waterfront views and a welcoming menu that ranges from classic breakfast fare to hearty burgers, crisp salads, and satisfying handhelds.

Address: 44 Fairway Drive, Port Jefferson, NY

Website: Visit Website

Phone: 631-473-1440

Dockside Brewery

This large indoor/outdoor brewery and restaurant is located on the Housatonic River and sporting about 60 boat slips. Their beer and food selection is immense and there is also a full bar. During the summer there are outdoor games and activities to keep the whole family entertained. To reserve a slip you can go to their website or call the restaurant.

Address: 40 Bridgeport Ave, Milford CT

Website: Visit Website

Phone: 203-693-3900

Joey C's Boathouse

This waterfront gem focuses mainly of seafood, but also covers many other culinary bases from BBQ to Mexican fare. Located across the Housatonic River from Dockside Brewery you can grab a transient slip and enjoy some great food in a fun atmoshpere.

Address: 955 Ferry Blvd, Stratford, CT, 06614

Website: Visit Website

Phone: 203-870-4838

Rowayton Seafood

Rowayton Seafood, set in what was once the oldest lobster co-op on Long Island Sound, is a beloved family-run restaurant and market that perfectly captures coastal New England charm. Situated on the scenic Five Mile River in Norwalk, Connecticut, it has earned high praise—from Zagat’s “Excellent” rating to multiple “Best Seafood” awards—thanks to its outstanding seafood dishes, waterfront views, and warm, attentive serviceDiners rave about standout offerings like lobster rolls, roasted oysters, and raw bar selections, paired with a stellar wine and cocktail program. Whether you're enjoying a leisurely brunch river-side or grabbing fresh seafood to take home, Rowayton Seafood delivers exceptional flavors, a relaxed atmosphere, and a memorable dining experience.

Address: 89 Rowayton Ave, Norwalk, CT 06853

Website: Visit Website

Phone: 203-866-4488

Prime

For high-end waterfront dining, look no further than Prime. Their Stamford restaurant is right next to our Stamford docks, and their Huntington location is located, waterside on Huntington Harbor. Both restaurants are open for lunch and dinner, and reservations are recommended.

Address: 78 Southfield Avenue, Stamford, CT 06902 | 117 North New York Avenue Huntington, NY 11743

Website: Visit Website

Phone: Stamford: 203.817.0700 | Huntington: 631.385.1515

Sunset Grille

Sunset Grille offers a relaxed waterfront dining experience at Norwalk Cove Marina. The restaurant provides a variety of seafood dishes, including New England-style clam chowder, artichoke crab dip, and linguine with white clam sauce. Guests can enjoy meals on the outdoor deck or under a canopy, with views of the scenic Norwalk Harbor.

Address: 52 Calf Pasture Beach Rd, Norwalk, CT, 06855

Website: Visit Website

Phone: (203) 866-4177

Crab Shell

Crab Shell is Stamford's premier waterfront dining experience and they care very much for their boating customers. So much so that they have 11 transient slips just for their diners! The restaurant is located just a few docks away from our Stamford location. To reserve a slip you can reach the restaurant on channel 9 on your VHF or call the restaurant.

Address: 46 Southfield Ave Harbor Landing, Stamford, CT, 06902

Website: Visit Website

Phone: 203-967-7229

The Wheel

The Wheel offers a modern American dining experience with a focus on seasonal, locally sourced ingredients. Located in The Village waterfront complex, the restaurant features an open hearth oven for roasting meats, fish, vegetables, and baking Neapolitan-style pizzas. With a menu crafted by Executive Chef Chris Shea and a rooftop garden supplying fresh herbs, guests can enjoy flavorful dishes paired with handcrafted cocktails, wines, and local craft beers. Its industrial-chic atmosphere and commitment to quality make it a standout spot for both locals and visitors.

Address: 4 Star Point, Suite 101, Stamford, CT 06902

Website: Visit Website

Phone: (475) 270-1300

Tiki Beach Pier Restaurant

Tiki Beach Pier Restaurant in Rye, New York, offers a vibrant beachfront dining experience on the historic boardwalk of Playland Amusement Park. With breathtaking ocean views, the restaurant serves a diverse menu featuring American, seafood, and sushi dishes. Guests can enjoy live entertainment from local bands and performers, creating a lively atmosphere. Tiki Beach Pier Restaurant is a popular destination for both casual dining and special occasions.

Address: 1 Playland Pkwy, Rye, NY, 10580

Website: Visit Website

Phone: 914-274-4211

Louie's Grille

If you’re looking for a great place to dine, Port Washington has just the spot. Louie’s offers delicious food paired with stunning bayside views, making it the perfect setting to enjoy a meal with family or friends.

Address: 395 Main Street, Port Washington, NY

Website: Visit Website

Phone: 516-883-4242

Bartaco

Bartaco is located upriver in Port Chester Harbor and offers dock-and-dine service on a first-come, first-served basis. The restaurant has only two dock slips, so plan accordingly. It’s a great spot for a quick bite or takeout.

Address: 1 Willett Ave, Port Chester, NY 10573

Website: Visit Website

Phone: 914-937-8226

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