Tours in Old Saybrook

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From their waterfront post on Southold Bay, the seasoned mariners of Eagle's Neck Paddling Company rent kayaks to facilitate adventures through the estuaries and arteries of Long Island's North Fork. Daily kayak tours depart in the morning and evening, whereas lessons with certified instructors equip explorers with the skills to serenely navigate waters populated by herons, egrets, turtles, and former CEOs who have decided to live off the grid.

62300 Route 25
Southold,
NY
US

The US Coast Guard–licensed captains with Peconic Water Sports tow customers through the water using all of the 400 horses inside their Malibu Wakeboats' Indmar engines. Before launching from the dock in Greenport Harbor, they wield their coaching experience to train each participant in the techniques necessary to ride their selection of Liquid Force wakeboards, Connelly Marine water skis, tubes, and kneeboards. These captain-coach hybrids emphasize safety as much as technique, and each is annually certified in CPR and First Aid. Captains also conduct seasonal fishing charters through the bay or open sea, as well as sightseeing cruises along Eastern Long Island.

102 Main St.
Greenport,
NY
US

Specializing in the art of chardonnay, Chamard cultivates varietal grapes on 20 acres of gently rolling vineyards, unleashing an assortment of palate-pleasing wines. Bring a guest and relish the ambrosial aromas and mouth-uplifting flavors of chardonnay, cabernet sauvignon, pinot noir, merlot, and cabernet franc blends created with time-honored winemaking methods and state-of-the-art graping equipment. Grasp a Riedel glass and try five wines while overlooking the pond on the deck, warming up by the tasting room's fire, or hiding in one of the cellar's wine barrels. After sampling fermented grape serums, customers can activate the power of a 15% discount to purchase a bottle of wine ($12.99–$24.99) for enjoying at home or christening a new caravel.

115 Cow Hill Rd
Clinton,
CT
US

The crew at Reel Mania Charters customizes fishing trips for anglers of all abilities. As tunes blast from iPods and drinks emerge from coolers, groups cast out lines and reel in fish that range from flounder and porgy to striped bass and sea bass. After a full day of fishing and watching the sun glisten off rolling waves, coolers transport fish home for eating, trophy mounting, or displaying to neighbors to prove that the ocean exists.

Niantic Bay
Niantic,
CT
US

East Hampton lies on the far eastern coast of New York's Long Island, which boasts white sands and lush green spaces. The idyllic natural surroundings have long drawn notable out-of-towners. In 1945, husband-and-wife painters Jackson Pollock and Lee Krasner bought a wood-frame house here. Pollock used the barn as his studio. Both buildings are still standing and have been added to the National Register of Historic Places. Other historical structures of note include some holdovers from the colonial era and a handful of wooden windmills. Along Montauk's rocky coast, popular pursuits include fishing and treks to observe seals as they come ashore in colder months to warm up over hot toddies.

272 Old Montauk Hwy
Montauk,
NY
US

Shoreline Segway's well-trained, friendly staff ushers segway-equipped and helmet-clad visitors on excursions through Guilford. A friendly tour guide leads a half-hour segway riding practice session before starting the one-hour ride. Feet weary after leap-frog marathons can rest aboard the environmentally conscious, two-wheeled vehicle while their optical counterparts feast on local landmarks such as the Agricultural Fair grounds, Faulkner's and Grass Island, Guilford Marina, Long Island Sound, and Connecticut's oldest house. A mobile lesson in regional history provides Jeopardy-bound brains the knowledge to survive the Connecticut category.

260 River Street
Guilford,
CT
US