Gone Fishing & Sailing with Dad: Father’s Day Fun on the East End Water

Go fishing with dad for Father's Day
Go fishing with dad for Father’s Day
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With waters as wonderful as the East End’s, what dad wouldn’t want to spend Father’s Day at sea or bay? Here are some of the many options available to dads looking to fish, sail or otherwise enjoy their special weekend on the water.


Montauk waters are ideal for fishing, which would explain why there are fishing charters aplenty. Winning the 2021 award for Dan’s Best of the Best South Fork Fishing Charter, My Mate Charters (mymatecharterboat.com) offers half and full days fishing on the shore, shark fishing, Block Island excursions, sunset cruises and more, courtesy of Captain Pete Casale.

Whether trolling the waters off Shagwong Point for striped bass or heading further offshore for big tuna, marlin and sharks, Montauk Sportfishing on the ADAH-K (hookerfishingmtk.com) is a solid option, thanks to Captain Dave Kohlus’ nearly 50 years of experience fishing these waters. Captain Michael Potts’ Blue Fin IV (bluefiniv.com) is another popular pick among Montauk fishing charters and is considering an exciting adventure for the whole family.

Other great Montauk fishing options include Captain Ron’s Famous Fishing Charters (captronsfishing.com), Blue Crush Charters (bluecrushcharters.com), Grand Slam Charters (montaukstriperfishing.com), Double D Charters (doubledmontaukfishing.com), Lady Grace Charters (ladygracecharters.com), Lazybones (lazybonesmontauk.com), The Sea Wife IV (seawife.com), Susie E II (susiee.com), Miss Montauk II (missmontauk.com) and Weejack Charters (weejack.com).

Next to Montauk, the Hampton Bays area offers some of the South Fork’s best fishing charter opportunities. Families can set sail with Captain James Foley of Hampton Lady Fishing (thehamptonlady.com), Captain John Capuano of the Shinnecock Star (shinnecockstar.com) or Captain Peter Stassi the “canyon specialist” of the Sea Venture (seaventure44.com).

The Surfmaster Charters boat docked in Sag Harbor
David Taylor

For anyone looking to fish in Sag Harbor, Captain Tom Federico’s Surfmaster Charters (sagharborfishing.com) are the way to go. They provide bait and tackle, rods and reels, fish cleaning and prep, and an unforgettable experience for up to six passengers.

Across the Long Island Sound, the Captain Bob Fishing Fleet (captbobfishingfleet.com) was crowned Dan’s Best of the Best North Fork Fishing Charter for its popular Mattituck monster flukes, sea bass, stripers, porgies and blues charters. North Fork Adventures (northforkadventures.com) in Southold provides bottom fishing, sightseeing and offshore fishing aboard their Parker 25, while the Prime Time 3 (631-323-2618) in Orient offers a summer roadbender special that combines drift fishing with bottom fishing for fluke, porgy and sea bass.

Other North Fork fishing charters include Sundowner Charters (sundownercharters.com) and Monty Man II Charters (631-363-2020) in Orient, as well as Peconic Star Fleet (peconicstarboats.com) and Nautic Lady (captjoe19.com) in Greenport. And for fishing and sunset cruises on Shelter Island, Tubby Charters (tubbycharters.com) is your best bet.


Once again, Montauk is tough to beat in terms of scenic sailing, and best among the options is Dan’s Best of the Best South Fork Sailing Charter Mon Tiki (sailingmontauk.com), which offers adventures on Polynesian-inspired catamarans certified by the U.S. Coast Guard. They offer charters for small groups, 1–6 people, and large groups of up to 100, as well as soul sailing with Captain David Ryan.

Sail Montauk (sailmontauk.com) also offers exquisite charters on private sailboats, each manned by a Coast Guard licensed captain and packed with pool noodles, water guns, a cooler and a bluetooth speaker for whatever sea shanties are on your phone. Viking Fleet (vikingfleet.com) is another safe charter option in Montauk, as well as a prime candidate for whale watching.

Charles Charters (charlescharters.com) has quite a large fleet in tow, with two vessels providing charters in Sag Harbor and three in East Hampton. Those looking to set sail in pristine Sag Harbor can also do so with Dove Charters (631-901-8928) or Sag Harbor Sailing (sailsagharbor.com). As for those setting a course for Westhampton waters, they can set sail from Westhampton Beach with Pontoon Paddlers (pontoonpaddler.com) or from East Moriches with Moriches Island Sailing (morichesislandsailing.com).

Setting sail on the North Fork is the most luxurious with Dan’s Best of the Best North Fork Sailing Charter Layla Sailing (laylasailing.com) in Greenport. Guests can lounge on comfy beanbag chairs while sipping rosé and letting the highly trained crew work their magic. The female-owned-and-operated business was founded by now Southold Town Trustee Liz Gillooly and supports One Percent for the Planet, Group for the East End and other environmental

Also launching out of Greenport, check out East End Charters (eastendcharters.com) and Nautical Dreamers Sailing Charters (nauticaldreamercharters.com).

Long Island Aquarium's Atlantis Explorer Tour Boat , Photo: Courtesy Long Island Aquarium
Long Island Aquarium’s Atlantis Explorer Tour Boat Courtesy Long Island Aquarium

Over on the beautiful Peconic River, the Atlantis Explorer Tour Boat (longislandaquarium.com/explorer-boat-tour) provides guests with a two-hour excursion led by Long Island Aquarium educators. It’s a delightful way to learn about the Peconic Estuary.


In addition to fishing and sailing charters, the East End also offers some more unique boating experiences, many of which take the fun outside of the vessel.

Global Boarding (globalboarding.com), with locations in Noyac and Sag Harbor, provides plenty of wild water sports options including wakesurfing, waterskiing, wakeboarding, kneeboarding, tubing and wakeskating. Professional instructors will ensure that no one is left floundering as they develop a radical new skill.

Get Salty Adventures (getsaltyadventures.com) starts off with a refreshing boat ride on Moriches Bay, which leads to a tiny island inhabited only by seabirds that families are free to explore. Next, they’re given a paddleboarding lesson in the shallow waters around the island, making for a comforting first step into the relaxing-once-you’re-good-at-it water sport.

With pick-up locations in Montauk, Sag Harbor, Shelter Island and Southold, you’re never far from a Peconic Water Sports (peconicwatersports.com) charter. Each boat is stocked with wakeboards, waterskis, wakesurfers and three-person tubes. Fishing charters are also available.

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