Sailing, fishing, paddling, docking and boat-up beaches across the East End.
Everything on the water beyond surfing and swimming. East End Guide does not broker rentals or charters — call or visit the operator's own site for pricing, reservations, and season updates.
58 listings
Sailing schools, lessons, racing clubs and ASA-certified programs across the East End.
Sag Harbor · 2
Sag Harbor · Sag Harbor Village
Community sailing focus with adult and junior programs on Sag Harbor Bay. A member club of the Peconic Gardiners Junior Sailing Association, run by the registered 501(c)(3) Breakwater Sailing Center Inc.
51 Bay Street, Sag Harbor, NY 11963
Sag Harbor · Sag Harbor Village
Private sailing-yacht charters leaving from Sag Harbor's Long Wharf, including daytime and sunset outings. This is Sailacat, an active operator, not the unrelated former Sailaway business.
1 Long Wharf, Sag Harbor, NY 11963
Center-console and runabout rentals. NY's boating safety certificate (Brianna's Law) is required for every motorboat operator.
East Hampton · 1
East Hampton · East Hampton
Inside Shagwong Marina on Three Mile Harbor - charters, boat rentals, leases, sales and service, with coaches who teach beginners to wakesurf, waterski, wakeboard and tube. New equipment each season. Onsite parking and bathrooms.
215 Three Mile Harbor Hog Creek Road, East Hampton, NY 11937
Montauk · 2
Montauk · East Hampton
Montauk Lake rental fleet of 18 powerboats from 16 to 31 feet plus Wave Runners, water skis, wakeboards and tubes, alongside a full-service marina. No special license is needed to rent a boat; renters must be 18 with a driver's license.
444 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Wake boats out of the Montauk Yacht Club on Star Island - wakeboarding, water skiing, wake surfing and tubing on Lake Montauk, with pick-up at Navy Beach or any home or marina on Lake Montauk and Fort Pond Bay. Coaches teach beginners to get up on a board or skis. Bathrooms, showers and changing rooms on site.
Montauk Yacht Club, 32 Star Island Rd, Montauk, NY 11954
Sag Harbor · 2
Sag Harbor · Sag Harbor Village
Members-only shared-fleet boat club at the Bay Street town pier — one of three Eastern Long Island locations alongside Hampton Bays and East Moriches, with easy reach of Peconic Bay and Shelter Island. Membership pricing is not published; hands-on training is included and the club handles cleaning, maintenance and storage.
1 Bay Street Town Pier, Sag Harbor, NY 11963
Sag Harbor · Sag Harbor Village
Captained wake boat out of West Water Street, five minutes' walk from Main Street - wakeboarding, water skiing and tubing on Sag Harbor Bay, run by Captain Austin Langston. Bathrooms, showers and changing rooms on site. Boat rentals and private charters from the same dock.
50 West Water Street, Sag Harbor, NY 11963
Noyack · 1
Noyack · Noyack
Inside Mill Creek Marina on Noyack Road - wake-sports charters, boat rentals, fishing charters, a kids' water sports camp, Peconic Boat Club memberships, and kayak/paddleboard rentals through the marina. Customer parking, bathrooms and showers on site.
3253 Noyack Rd, Sag Harbor, NY 11963
Kayak, canoe and stand-up paddle rentals, tours and lessons. No licence needed, and most operators deliver.
Southampton · 1
Southampton · Southampton
Full-service wind and wave shop on County Road 39, formerly trading as Windsurfing Hamptons and Kiteboarding Hamptons. Sells, repairs and rents gear and teaches windsurfing, kiteboarding, wing foiling, e-foiling and stand-up paddle - the only place on the East End teaching all five. Rental locations on Peconic Bay at Cold Spring Road and at Napeague; the shop publishes its own guide to local launches and when each is worth the drive.
1688 County Road 39, Southampton, NY 11968
Bridgehampton · 1
Bridgehampton · Southampton
Private kiteboarding, wing foiling and e-foil lessons taught by Duotone team riders Drew Christianson and Hugo Baker, both Hamptons-based for over 5 years. Beginner, private-two-person and advanced/intermediate tiers for kite and wing; custom-built lesson plans rather than a fixed curriculum.
425 Dune Road, Bridgehampton, NY 11932
Wainscott · 1
Wainscott · East Hampton
Surf shop and camp founded in Wainscott in 1987 by Lars Svanberg; now trades as MBX Surf Camp, still run by Svanberg at the same address and phone. Rents surfboards, kayaks, canoes and stand-up paddleboards, launching on Georgica Pond, Sagg Pond and Northwest Creek. No jet skis or powerboats.
352 Montauk Highway, Wainscott, NY 11975
Amagansett · 2
Amagansett · East Hampton
The Northeast's longest-running kiteboarding school, founded 2000, teaching at Napeague Harbor - waist-deep for hundreds of yards, which the school says makes it ideal for learning, with White Sands nearby for advanced riders once they're up. Beginner, intermediate and advanced lessons, each with radio-helmet chase-boat coaching and gear included. Two-person max per instructor. Book by text or WhatsApp.
Lazy Point, Napeague Harbor, Amagansett, NY 11930
Amagansett · East Hampton
Amagansett rental shop for kayaks, paddleboards and bicycles. It is not itself a waterfront launch, so confirm transport and launch logistics when reserving water gear.
1 Cross Highway, Amagansett, NY 11930
Montauk · 2
Montauk · East Hampton
Surf instruction at Ditch Plains for beginners and progressing riders. The beach meeting point is the useful distinction: confirm the session and exact sand-side meetup with the instructor before arriving.
Ditch Plains Beach, Montauk, NY 11954
Montauk · East Hampton
Structured surf coaching at Ditch Plains from a programme focused on skill progression rather than a one-time board rental. Reserve ahead and use the operator's session instructions for the meetup.
Ditch Plains Beach, Montauk, NY 11954
Springs · 1
Springs · East Hampton
Stand-up paddleboard and kayak outfit at Three Mile Harbor Marina: one-hour and multi-hour board/kayak rentals, group and private SUP lessons, and guided tours. FareHarbor booking, no walk-up rates published on the plain page.
10 Boat Yard Rd, East Hampton, NY 11937
Montauk's fleet — party boats, head boats, and private six-pack charters.
Montauk · 13
Montauk · East Hampton
Year-round Montauk fishing: four-hour half-days from $75 with rod, reel and tackle included, full-day porgy and sea bass trips, and 30-hour-plus offshore runs from $550. Also runs the seasonal fast ferry, whale watches and sunset cruises.
462 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Two half-day open-boat trips daily out of Montauk Harbor, 8am to noon and 1pm to 5pm: fluke in summer, diamond jigging for bass and blues in fall. $75 adults, $70 seniors, $55 children 12 and under, all tackle and bait included. Reservations by phone only.
474 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Nine-boat charter fleet from 28 to 77 feet for sportfishing and cruising, plus an annual shark tournament open to seasonal dockage holders with no entry fee.
59 Star Island Road, Montauk, NY 11954
Montauk · East Hampton
Fin Chaser runs both ways: the operator's own site says it "operates primarily as an open boat" — where you book an individual seat — but "is also available and easily accommodates large private group charters." The boat docks at Star Island, Montauk from June through November and in Greenport in May.
59 Star Island Road, Montauk, NY 11954
Montauk · East Hampton
A private Montauk fishing charter based on West Lake Drive, offering a smaller-boat alternative to the harbor's party fleet. Call the captain to match the trip to the season and the group's experience.
352 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Private Montauk fishing charters from West Lake Drive, with trips tailored to current fishing and the group's ambitions. A direct-booking alternative to the harbor's large open boats.
352 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
A Montauk private fishing charter operating from West Lake Drive. Contact the captain for the seasonal target species, trip length and exact dock instructions.
408 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Captain Ben McCarron runs a 31ft Downeaster out of Montauk Marine Basin: half- and full-day inshore trips for porgy, sea bass, fluke, striped bass and bluefish, night striper trips, and offshore runs 10-80 miles out for shark, mahi-mahi, marlin and tuna.
Montauk Marine Basin, 426 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Six-pack charter out of Marlena's Yacht Club: inshore trips for striped bass, sea bass, bluefish and porgies, offshore runs for bluefin and yellowfin tuna, and sunset cruises along the Montauk coastline.
Marlena's Yacht Club, 408 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Captain Mario runs Lady Grace VI, a 38ft sportfisherman out of West Lake Fishing Marina, for full- and half-day trips after striped bass, fluke, bluefish, shark, tuna, blackfish, sea bass and porgies. All tackle and bait provided, six passengers max.
West Lake Fishing Marina, 352 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Captain John Gagne, a retired USCG Chief Boatswain's Mate, runs a 28ft Steiger Craft out of Montauk Anglers Club & Marina: light-tackle drift and bottom fishing for black sea bass, striped bass, tautog, cod, porgy, flounder and bluefish, plus sunset cruises.
Montauk Anglers Club & Marina, 467 East Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Captain Ken Hejducek's 41ft custom Michael Fitz sportfisherman, out of West Lake Drive: inshore and offshore fishing charters and Montauk sunset cruises.
462 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Captains Jill and Steve run the November Rain, a 43ft USCG-inspected Lowell out of Westlake Marina, for inshore and offshore fishing (striped bass, fluke, seabass, tuna, shark), sunset cruises and private parties — up to 20 passengers, a six-time TripAdvisor Travelers' Choice winner.
Westlake Marina, 352 West Lake Drive, Montauk, NY 11954
Sag Harbor · 1
Sag Harbor · Sag Harbor Village
Capt. Tom Federico's charter boat The Surfmaster departs daily from Long Wharf — the bay-fishing counterpart to the Montauk ocean fleet. Federico has been licensed since 1983, fishing these waters since the 1970s, and is a member of the Montauk Boatmen & Captains Association; the boat is licensed and insured and takes one to six passengers, with trips of almost any length at almost any time of day. The grounds are the bays themselves: Noyac Bay, Cedar Point, Jessup's Neck, the Ferry Slip, out to Gardiner's Island — weakfish through the summer, stripers in the fall, plus fluke, porgies, sea bass and blackfish. The dockside sign says it plainly: families welcome.
Long Wharf, Sag Harbor, NY 11963
Members clubs and one public-access resort marina. Membership policies vary.
Amagansett · 1
Amagansett · East Hampton
Private member-owned club on Gardiner's Bay. Instruction in the club's 23ft Sonars, Sunfish and Lasers, with a junior program in Optimists, Sunfish, Lasers and Club 420s. Weekly one-design racing runs June through September.
300 Abraham's Landing Road, Amagansett, NY 11930
Montauk · 1
Montauk · Montauk
Resort marina on Star Island run by Safe Harbor Marinas, with transient and wet slips for vessels up to 300ft, shore power, fresh water and pump-out, plus resort pools, spa and restaurants. Transient slips book through Dockwa.
32 Star Island Road, Montauk, NY 11954
Sag Harbor · 1
Sag Harbor · Sag Harbor Village
Members club on Sag Harbor's inner harbour, a five-minute walk from Main Street, with transient dockage for visiting boats from 20 to 200+ feet and drafts up to 12 feet.
27 Bay Street, Sag Harbor, NY 11963
Public-access marinas where transient boaters can tie up overnight or for a meal. Hail the harbormaster on VHF 9 before approaching.
Southampton · 2
Southampton · Southampton
Strong's South Fork marina on North Sea Harbor, and the one South Fork address the operator lists for RENTALS and the boat club as well as dockage, service and storage — so it is the one a visitor without a boat can actually use.
1810 North Sea Road, Southampton, NY 11968
Southampton · Southampton
Dockage and nothing else — the operator lists this Shinnecock Bay address for slips only, no sales, service, rentals or storage, which is why it reads shorter than every other Strong's on this page.
74 Little Neck Road, Southampton, NY 11968
East Hampton · 2
East Hampton · East Hampton
Strong's only Three Mile Harbor address, inside Harbor Marina of East Hampton on Gann Road. The operator lists SALES here and nothing else — do not turn up expecting a transient slip from Strong's; the dockage at this site is the marina's own.
41 Gann Road, East Hampton, NY 11937
East Hampton · East Hampton
Roughly 40 slips on Three Mile Harbor for boats from 25ft to 45ft, in a protected part of the harbour with dockhands on staff in season and a wide lawn above the docks. Slips are held back for boaters arriving by water, and the operator's EHP Resort sits half a mile down Three Mile Harbor Road.
219 Three Mile Harbor Hog Creek Road, East Hampton, NY 11937
Montauk · 3
Montauk · Montauk
Family owned and operated on Lake Montauk since 1955 — seasonal and transient dockage, ValvTect fuel, a 70-ton travel lift with mechanics on staff, bait and tackle, and charter boats.
426 West Lake Drive, Montauk, NY 11954
Montauk · East Hampton
Iconic Montauk harbor complex at the inlet — the Gosman family's seafood restaurants, fish market and shops on their own docks.
484 West Lake Drive, Montauk, NY 11954
Montauk · Montauk
Club marina on Lake Montauk with dockage open to visiting boats, diesel fuel at every slip, one of the area's largest tackle and ship's stores, and the Star Island Grill. Marina hours Mon–Thu 7am–6pm, Fri–Sun 7am–7pm.
59 Star Island Road, Montauk, NY 11954
Sag Harbor · 1
Sag Harbor · Sag Harbor Village
Village-run transient dockage at the foot of Main Street. Contact the Sag Harbor Harbormaster on VHF 9.
Long Wharf, Sag Harbor, NY 11963
Springs · 1
Springs · East Hampton
Year-round marina and boatyard at the head of Three Mile Harbor: seventy slips on floating docks with finger piers, power and water, hauling for vessels from 17 feet to 40 tons, and indoor and outdoor storage.
6 Boat Yard Road, East Hampton, NY 11937
Captain-narrated harbor tours, sail-cat sunset cruises, and classic yacht charters.
Montauk · 2
Montauk · Montauk
65ft Polynesian-inspired sailing catamaran, USCG-certified, running Montauk day sails and sunset cruises from Slip 501 off Resort Dock 2 at the Montauk Yacht Club. Sister boats Mon Tiki (40ft) and Mon Tiki Mini (26ft) sail from the same dock.
Montauk Yacht Club, 32 Star Island Rd, Montauk, NY 11954
Montauk · East Hampton
Captains Bill and Maggie, a combined 50 years on the water, run private charters out of Star Island Yacht Club: sunset and champagne cruises, harbor tours with mimosas, fishing-and-champagne combo trips, and custom outings.
Star Island Yacht Club, Montauk, NY 11954
Sag Harbor · 8
Sag Harbor · Sag Harbor Village
ASA-accredited sailing school running since 1997 out of the Yacht Hampton Boating Center at 51 Pine Neck Avenue. Family-run, with USCG-licensed captains: lessons, ASA 101 certification, day sails and sunset cruises on a 23ft Pearson Ensign.
Yacht Hampton Boating Center, 51 Pine Neck Avenue, Sag Harbor, NY 11963
Sag Harbor · Sag Harbor Village
Captain Chuck Wade runs a 30ft Axopar out of Long Wharf, six passengers max. Sunset cruise 2h $800, lighthouse cruise 3h $1,200, day charter 7-8h $1,800, and a whale-watching charter at $2,000 - humpback, fin and minke. Also a private water taxi to Shelter Island, Montauk and Block Island.
Long Wharf, Sag Harbor, NY 11963
Sag Harbor · Sag Harbor Village
A yacht brokerage-style charter and rental operation with two Sag Harbor locations (9 Long Wharf and 51 Pine Neck Ave). Beyond the boat itself, charters can add jet skis, an electric hydrofoil (Fliteboard e-foil) or an electric surfboard as on-the-water extras.
9 Long Wharf, Sag Harbor, NY 11963
Sag Harbor · Sag Harbor Village
Private sailing charters out of Sag Harbor on Elizabeth, a 42ft Catalina, with an experienced captain and crew aboard and a maximum of six passengers. Charters run two, three, four or eight hours, so a sunset sail and a full day are the same booking at different lengths. A 20ft centre console, Hummingbird, works out of Swan's Marina in East Hampton for swimming, paddleboarding and fishing. Lessons are taught by an ASA instructor.
Sag Harbor Village Marina, Sag Harbor, NY 11963
Sag Harbor · Sag Harbor Village
The largest crewed sailing capacity on this page. Luna is a Coast Guard-certified Bermudian schooner the operator describes as having "the largest decks and passenger capacity of any charter sailboat in the Hamptons", carrying 41 guests with three to four crew aboard. Cosmos, a Coast Guard-certified mahogany performance trimaran, is certified for a capacity over 20 and reads as more intimate for smaller groups. A third boat, Starlight — a 57' French sailing yacht designed by Bruce Farr, "the queen of the fleet since 2016" — is not Coast Guard-certified for Hamptons waters and so carries at most six passengers, is booked Monday through Thursday only, and starts at $3,200 for a 3-hour sail with captain and mate. Charters sail from Sag Harbor, Shelter Island and Greenport, from a couple of hours to a full day. Booking is by phone or email only, not an online calendar.
Sag Harbor, NY 11963
Sag Harbor · Sag Harbor Village
Kelpie is a 78.8ft traditional gaff-rigged schooner, designed by Francis Sweisguth and built in 1928 at the Harvey Gamage Shipyard, once used by the U.S. Coast Guard in WWII before a 2014 refit. Sold as four named charters — brunch sail, half day, sunset sail and full day, up to 24 guests — each booked by emailing or calling the crew rather than through a rates page or online calendar. The operator publishes no price, so call before planning a group around it.
Sag Harbor, NY 11963
Sag Harbor · Sag Harbor Village
Captain Hagen — a Sag Harbor resident who has run these waters for over 40 years — charters The Marlinspike, a 36-foot wooden lobster yacht with a swim ladder, real shade, and a full kitchen and bathroom, by the hour or by the day. Design your own outing or take one of his tours: pristine beaches, celebrity houses from the water, or just an hour on the bay. Cancellation is $100 unless it rains.
23 Marine Park Dr, Sag Harbor, NY 11963
Sag Harbor · Sag Harbor Village
Two captained boats out of Sag Harbor: a Sea Ray Sundancer 340 at $595 an hour including fuel for cruising, swimming and lunch or dinner runs, and a 23-foot Malibu at $525 an hour for wakeboarding, wake surfing, tubing and water skiing — plus sunset and fireworks charters, and stand-alone professional captain services at $125 an hour if you have the boat and need the license. USCG-licensed captains, fully insured, US DOT drug-and-alcohol program — the operator leads with the paperwork, which on the water is the right instinct.
Sag Harbor, NY 11963
Bay beaches and coves reached primarily by boat. No-discharge zones apply across the Peconic Estuary.
Amagansett · 1
Amagansett · East Hampton
Shallow-draft boats beach on the sandbars inside Napeague Harbor. Watch the tide, and note that East Hampton Town Marine Patrol is the enforcement authority for the waterways, beaches and shellfish areas here.
Napeague Harbor, Amagansett, NY 11930
Springs · 1
Springs · East Hampton
Protected anchorage off the spit on Gardiners Bay — Suffolk County park, camping and a lighthouse ashore.
Cedar Point County Park, East Hampton, NY 11937
Summer programs for kids — Optis, 420s and Lasers on Sag Harbor, Gardiners, and Shinnecock Bay.
Amagansett · 1
Amagansett · East Hampton
Member-access junior program on Gardiner's Bay teaching in Optimists, Sunfish, Lasers and Club 420s, racing PGJSA regattas on the East End and in Connecticut.
300 Abraham's Landing Road, Amagansett, NY 11930
Sag Harbor · 1
Sag Harbor · Sag Harbor Village
Week-long Opti and 420 sessions from June through August at Breakwater YC.
51 Bay Street, Sag Harbor, NY 11963
Naturalist-led boat trips — summer whale cruises out of Montauk, winter seal cruises on Shinnecock Bay.
Southampton · 1
Southampton · Southampton
A CRESLI scientist leads roughly two-hour expeditions aboard the R/V Peconic out of Stony Brook Marine Station to view, photograph and document seals in Shinnecock Bay — the 8th season in 2025-26, co-sponsored by the South Fork Natural History Museum. Cruises run roughly monthly, November through May; registration is required and spaces are limited. CRESLI also runs a free (donation-suggested) walking Seal Walk at Cupsogue Beach the same season — see /wildlife for both.
Stony Brook Marine Station, 8 Little Neck Road, Southampton, NY 11968
Montauk · 1
Montauk · East Hampton
CRESLI naturalists narrate aboard the Viking Starship out of Montauk Harbor — the pairing's 31st season in 2026. Sailing Sunday, Monday, Wednesday and Friday, with Saturday trips added in peak season, late May through September, for humpback, fin and minke whales offshore. Same dock and operator as the Viking Fleet fishing charters listed under Fishing charters.
462 West Lake Drive, Montauk, NY 11954
5 listings
Center-console and runabout rentals. NY's boating safety certificate (Brianna's Law) is required for every motorboat operator.
Shelter Island Heights · 1
Shelter Island Heights · Shelter Island
A pickup-only dock in the hamlet of Shelter Island Heights - the operator's own site says there is no on-site staff, so book online or by phone and the boat is waiting at the dock. Same rental fleet and wake-sports charters as the other Hamptons and North Fork locations.
184 N Ferry Rd, Shelter Island Heights, NY 11965
Kayak, canoe and stand-up paddle rentals, tours and lessons. No licence needed, and most operators deliver.
Shelter Island · 1
Shelter Island · Shelter Island
Kayak and paddleboard rentals plus two-hour guided tours from a Burns Road departure point on Coecles Harbor. Singles $35 for two hours to $65 all day, doubles $55 to $100, paddleboards from $35 an hour; guided tours $60 an adult in groups of five or more. Two-hour minimum on every boat. Co-runs the Coecles Harbor Marine Water Trail with The Nature Conservancy and the Town of Shelter Island.
80 Burns Road, Shelter Island, NY 11964
Shelter Island Heights · 1
Shelter Island Heights · Shelter Island
Walk-up paddleboard and kayak rentals from a white tent on Crescent Beach, no reservation needed, running on the island since 2011. Free delivery and pick-up anywhere on Shelter Island. Beach yoga and SUP yoga at weekends by appointment. Summer hours Mon-Thu 10am-7pm, Fri-Sun 10am-8pm; call or text before you go, since the beach operation moves with the weather.
Crescent Beach, Shore Road, Shelter Island Heights, NY 11965
Public-access marinas where transient boaters can tie up overnight or for a meal. Hail the harbormaster on VHF 9 before approaching.
Shelter Island Heights · 1
Shelter Island Heights · Shelter Island
Transient and seasonal slips and moorings inside Dering Harbor for boats up to 160 feet, with a fuel dock, pump-out and hot showers, a short walk from the Shelter Island Heights shops and the North Ferry.
177 North Ferry Road, Shelter Island Heights, NY 11965
Captain-narrated harbor tours, sail-cat sunset cruises, and classic yacht charters.
Shelter Island · 1
Shelter Island · Shelter Island
Charters in the Hamptons, LLC runs full-day private yacht charters from its Shelter Island home dock to Montauk and the rest of the Hamptons — a fleet that includes Pershing yachts, with USCG-licensed captains and an upfront quote before booking rather than a published rate card.
63 Menantic Road, Shelter Island, NY 11964
11 listings
Center-console and runabout rentals. NY's boating safety certificate (Brianna's Law) is required for every motorboat operator.
Hampton Bays · 1
Hampton Bays · Southampton
Members-only shared-fleet boat club at 86 Foster Avenue in Hampton Bays — one of three Eastern Long Island locations alongside Sag Harbor and East Moriches, launching members into Shinnecock Bay and out through the Shinnecock Inlet. Membership pricing is not published; hands-on training is included and the club handles cleaning, maintenance and storage.
86 Foster Avenue, Hampton Bays, NY 11946
Personal watercraft rentals. PWCs are prohibited inside Sag Harbor Village waters and restricted in Mecox Bay.
Hampton Bays · 1
Hampton Bays · Southampton
Forty years at the foot of the Ponquogue Bridge, opposite the Shinnecock Coast Guard station. Jet ski rentals, a guided local tour, a tour with a lunch stop, a full-day experience and an ocean wave-jumping tour. Staff fit every rider with a life jacket and run an instruction class first; the rental water is under five feet everywhere with a spotter on the water and on shore. Open seven days, reservations required and cancellable up to 48 hours ahead.
91 Foster Avenue, Hampton Bays, NY 11946
Kayak, canoe and stand-up paddle rentals, tours and lessons. No licence needed, and most operators deliver.
East Quogue · 1
East Quogue · Southampton
Woman-owned and operated on Dune Road since 2012, renting paddleboards, kayaks and motorised GoBoats on the calm bay side away from boat traffic. Group classes, water yoga, scheduled sunset and full-moon paddles, and a dog dock add-on. Open daily 10am to about 6pm, weather and tide permitting.
Dune Road, East Quogue, NY 11942
Hampton Bays · 1
Hampton Bays · Southampton
Paddleboard and kayak rental and instruction operating since 2015, based at Meschutt Beach on the Shinnecock Canal with a second stand at Indian Island Park in Riverhead. Delivers equipment to wherever you are paddling and teaches everyone from first-timers to SUP racers.
Meschutt Beach, Canal Road at Old North Highway, Hampton Bays, NY 11946
Tuckahoe · 1
Tuckahoe · Southampton
Guided kayak and SUP tours out of Tuckahoe, plus an oyster-farm boat tour run with Conscience Point Shellfish and a separate kids' day camp (eastendexplorercamp.com). Booking runs through a Peek widget rather than a published price list.
449 N Magee St, Southampton, NY 11968
Montauk's fleet — party boats, head boats, and private six-pack charters.
Hampton Bays · 2
Hampton Bays · Southampton
Private charters from Hampton Bays for fishing, cruising and sunset time on the water. A useful western option when a Montauk departure would add an hour to the day.
9 Sagamore Road, Hampton Bays, NY 11946
Hampton Bays · Southampton
A private fishing charter departing from Oakland's Marina on Dune Road. The Hampton Bays base makes it practical for western Hamptons families who want a captained fishing day without driving to Montauk.
Oakland's Marina, 373 Dune Road, Hampton Bays, NY 11946
East Moriches · 1
East Moriches · Brookhaven
The parent location of the Lily's operation, on Moriches Bay — west of the Shinnecock Canal in Brookhaven Town, so outside the East End itself. Boat, sailboat, kayak and paddleboard rentals, plus a sunset canopy-boat dinner in Tuthill Cove, an oyster and sugar-kelp farm tour with bayman's daughter Sue Wicks, an ecologist-guided Eco Bay paddle and Curated Beach Day skiff trips. Lily's Sailing School and Lily's Seaside Eats are on site.
99 Adelaide Avenue, East Moriches, NY 11940
Members clubs and one public-access resort marina. Membership policies vary.
Quogue · 1
Quogue · Quogue
Member-owned club at Quogue with a junior sailing program that races in the Peconic Gardiners Junior Sailing Association.
43 Niamogue Ln, Quogue, NY 11959
Public-access marinas where transient boaters can tie up overnight or for a meal. Hail the harbormaster on VHF 9 before approaching.
Hampton Bays · 1
Hampton Bays · Southampton
The largest of the four: about 175 wet slips on 5.12 acres taking yachts up to 120ft in summer, with winter storage for over 125 boats, a fuelling dock and three 75-ton lifts. A ship store and yoga studio on site, and direct access to the Atlantic, Shinnecock Bay and Peconic Bay. Formerly Prime Marina; the address is in Hampton Bays, in the Town of Southampton.
6 Teepee Road, Hampton Bays, NY 11946
Captain-narrated harbor tours, sail-cat sunset cruises, and classic yacht charters.
Hampton Bays · 1
Hampton Bays · Southampton
"The O.G. Tiki boat of the Hamptons," out of Jackson's Marina in Hampton Bays: a slow (rarely over 7 mph), BYOB pontoon cruise with a Bluetooth sound system, run by a licensed captain. Two boats — the original 12-passenger Hamptiki and the newer 35-passenger La Sirena.
6 Tepee St Slip 16MB, Hampton Bays, NY 11946
14 listings
Sailing schools, lessons, racing clubs and ASA-certified programs across the East End.
Cutchogue · 1
Cutchogue · Southold
Racing association on the Peconic Bays. Its New Suffolk Series is eight weekend races off New Suffolk, scored on PHRF of Eastern Long Island ratings, and it runs the Whitebread, a 32-mile race around Shelter Island. Membership is encouraged but not required; some races charge a fee.
No published contact channel — see the operator's listing.
P.O. Box 1196, Cutchogue, NY 11935
Greenport · 1
Greenport · Greenport Village
Captained sailing charters from Greenport, adding a North Fork departure to a guide otherwise heavy on Sag Harbor and Montauk. Book directly with the operator for the boat, duration and current meeting instructions.
1100 Manhasset Avenue, Greenport, NY 11944
Center-console and runabout rentals. NY's boating safety certificate (Brianna's Law) is required for every motorboat operator.
Mattituck · 1
Mattituck · Southold
Four-generation North Fork dealer and marina marking its 80th year, with rentals and a boat club out of Mattituck Bay and Southampton's Peconic Bay Marina.
2400 Camp Mineola Road, Mattituck, NY 11952
Southold · 1
Southold · Southold
The fleet's own flagship, on Main Road in Southold - boat rentals, wake-sports charters, fishing charters, a kids' water sports camp, Peconic Boat Club memberships, and new and used boat sales, storage, service and repair. Onsite parking and bathrooms.
64150 Main Rd, Southold, NY 11971
Kayak, canoe and stand-up paddle rentals, tours and lessons. No licence needed, and most operators deliver.
Riverhead · 1
Riverhead · Riverhead
Riverhead kayak and paddle outfitter beside the Peconic River, useful for an easy freshwater launch and for visitors who need equipment rather than a guide.
89 Peconic Avenue, Riverhead, NY 11901
Orient · 1
Orient · Southold
Kayak and paddleboard rentals inside Orient Beach State Park, on the sheltered Long Beach Bay side of the spit, plus delivery to North Fork addresses. The only paddle operator on the site east of Greenport. Park entry fee applies separately.
Orient Beach State Park, 40000 Main Road, Orient, NY 11957
Members clubs and one public-access resort marina. Membership policies vary.
New Suffolk · 1
New Suffolk · Southold
North Fork member club at New Suffolk with a junior sailing program that races in the Peconic Gardiners Junior Sailing Association.
No published contact channel — see the operator's listing.
1400 Old Harbor Road, New Suffolk, NY 11956
Public-access marinas where transient boaters can tie up overnight or for a meal. Hail the harbormaster on VHF 9 before approaching.
Mattituck · 2
Mattituck · Southold
Strong's marina at the head of Mattituck Inlet — the only one of its North Fork addresses the operator lists as taking TRANSIENT boats, alongside seasonal dockage, sales, service and storage.
2255 Wickham Avenue, Mattituck, NY 11952
Mattituck · Southold
The yard rather than the marina — Strong's refit and service centre on Mattituck Creek, listed for sales, service, dockage and storage. This is where the big boats go out of the water.
5780 West Mill Road, Mattituck, NY 11952
Cutchogue · 2
Cutchogue · Southold
Strong's marina on Broadwaters Cove off Little Peconic Bay, at the end of Skunk Lane in Cutchogue — sales, service, dockage and storage, and the guide's first record in that corner of the North Fork.
8000 Skunk Lane, Cutchogue, NY 11935
Cutchogue · Southold
Well over 100 deep-water slips across 3.82 acres on Cutchogue Harbor, with a ship store, a fuelling dock, and summer dockage plus winter storage for boats up to 60ft. Formerly New Suffolk Shipyard — Cutchogue Harbor.
3350 West Creek Avenue, Cutchogue, NY 11935
New Suffolk · 1
New Suffolk · Southold
One of the oldest marinas on eastern Long Island — over 60 slips across 2.3 acres in the middle of North Fork wine country, a short walk from New Suffolk's beach and its handful of restaurants. Formerly New Suffolk Shipyard.
6775 New Suffolk Road, New Suffolk, NY 11956
Greenport · 1
Greenport · Greenport Village
Village-run marina in the heart of Greenport: 60 floating slips for boats to 80 feet plus a 640ft standing pier for vessels to 250 feet, booked through Dockwa. The carousel ashore runs year-round.
115 Front Street, Greenport, NY 11944
Bay beaches and coves reached primarily by boat. No-discharge zones apply across the Peconic Estuary.
New Suffolk · 1
New Suffolk · Southold
Privately owned, ~90% under a Nature Conservancy conservation easement since 1997 — anchor off the western shore. No landing inland; respect the easement.
No published contact channel — see the operator's listing.
Robins Island, Peconic Bay, NY
Every other Hamptons site tells you which charter to book. This is the next question: where is it actually beautiful?
Day-sail routes, sunset paths and anchorages — each with duration, skill level, best prevailing wind, and where the bars drop out. Coordinates are approximate; cross-check NOAA charts before you cast off.
Sag Harbor Long Wharf → return to Sag Harbor
The classic Hamptons day sail. Leave Long Wharf on a building SW, carry the breeze through Noyac Bay, thread the North Ferry channel, duck into Coecles for a lunch anchor, then run the Mashomack shore back through Shelter Island Sound. Four legs, four different points of sail — this is the one you plan the whole summer around.
Three Mile Harbor, East Hampton → return to Three Mile Harbor
Protected-water sail that works for families and first-timers. Head out Three Mile on the outbound tide, reach across Gardiners Bay to Cedar Point Lighthouse, drop an anchor on the sand bar, lunch ashore at the county park, then run home on the returning breeze. Easiest big-water day on the South Fork.
Lake Montauk inlet → return to Lake Montauk
Exposed-water passage around the most dramatic coastline on Long Island. Exit the Lake on slack water, run the north shore under the cliffs, round Montauk Point under the lighthouse, then tack home with the afternoon SW in your teeth. Not a beginner day — the rip off the Point stacks up fast and the cell bars disappear a mile off the beach.
No cell signal on this route — download NOAA charts before you cast off.
Sag Harbor Long Wharf → Greenport Harbor
Popular weekend passage across the Peconics. A building SW reaches you the whole way, Shelter Island opens on your starboard beam, and Greenport's transient dock puts you a block from oysters and a beer. Tie up, spend the night, ferry back — or run it as a round trip if the wind is polite.
Napeague Harbor, Amagansett → anchorage off Gardiners Island east shore
Lunch-hook trip to the edge of the most storied private island in the Atlantic. Anchor in 15 feet off the east shore, watch the ospreys work the cliffs, stay in the boat — Gardiners is private, no landing, no exceptions. Bring charts: cell signal drops to nothing once you clear the Napeague breakwater.
No cell signal on this route — download NOAA charts before you cast off.
Shinnecock Canal, Hampton Bays → return to Shinnecock Canal
The most forgiving big-water sail east of the canal. Shinnecock Bay stays flat in a blow, the western end opens toward Cupsogue's barrier-beach sweep, and you can reach back to the canal in almost any wind. Good first-day-out-of-the-slip sail.
Mecox Bay town launch, Bridgehampton → return to Mecox launch
Small-boat and paddle scale — Sunfish, cat, kayak, SUP. Mecox and Sag Pond are coastal ponds barely separated from the ocean by a dune, so the wind is honest and the fetch is short. Quiet, glassy, and exactly the right place to learn to read a shifting SW on a small boat.
New Suffolk town dock → anchorage off Robins Island west shore
A short reach across the western Peconic to the lee of privately owned Robins Island, protected by a conservation easement with no public landing. Anchor off the west shore in flat water, swim off the stern, and watch ospreys in the cliff-top pines. Cell signal here is spotty; load charts in New Suffolk before you cast off.
No cell signal on this route — download NOAA charts before you cast off.
Sag Harbor Long Wharf → return to Long Wharf after sunset
The classic. Leave Long Wharf an hour before sunset, carry the dying SW west into Noyac Bay, let the sky burn over North Haven to starboard and the Shelter Island hills to port, drift home on the light evening thermal. The sunset cruise everyone else is trying to copy.
Three Mile Harbor, East Hampton → Cedar Point anchorage, return after dark
Sunset sets behind Gardiners Island from this angle — you get the silhouette of the private island's cliffs stamped against an orange sky. Short reach from Three Mile, anchor off Cedar Point, watch the light go, motor home on glass. Best on a dying SW.
Lake Montauk inlet → Fort Pond Bay south shore
The only sunset on the South Fork where you watch it go down over the water from the east end of Montauk, with the silhouette of Gosman's and The Crow's Nest dock carving up the foreground. Short run out the Lake, swing west along the north shore, drop the hook off Fort Pond Bay.
No cell signal on this route — download NOAA charts before you cast off.
Greenport Harbor, Mitchell Park → Shelter Island Sound, return to Greenport
The North Fork sunset — unobstructed west-facing light across Shelter Island Sound with the spire of Greenport village behind you. Reach south out of the harbor, flatten off in the Sound, drift home on the evening thermal. Good even on a light-air day because the Sound is short-fetch.
Cedar Point County Park → Cedar Point bar and lighthouse
Protected sand-bottom anchorage off the Cedar Point bar with the stone lighthouse ashore. Drop in 8–12 feet, row in to walk the spit, the county beach is a public landing. The go-to lunch hook for anything out of Three Mile or Sag Harbor.
Coecles Harbor, Shelter Island → Coecles Harbor
Deep, quiet, and protected on all sides — one of the best natural harbors on the East End. Holding is good in mud, the inner anchorage stays flat in a blow, and the Ram Island beach is a short dinghy ride from most hooks. Book the mooring field early in season or tuck into the west lobe.
West Harbor, Fishers Island → West Harbor
If you have the range, this is the most pristine New England water inside a day-sail of the Hamptons. Cross Block Island Sound, thread Plum Gut or Race Rock on the fair tide, tuck into West Harbor. Clear water, rocky New England shoreline, zero Hamptons crowd. The passage is the hard part — this isn't a beginner's run.
No cell signal on this route — download NOAA charts before you cast off.
Plum Gut, off Orient Point → Plum Gut
Current-tricky — Plum Gut runs 4+ knots on a spring tide and the rip builds with any wind against the ebb. Anchor only on slack water in the lee of Orient Point, stay aboard (Plum Island is federal, no landing). For experienced boaters who want to see one of the wildest tide races on the East Coast from the water.
No cell signal on this route — download NOAA charts before you cast off.
Robins Island west shore, New Suffolk → Robins Island west shore
Lee-shore lunch hook in the western Peconic with a view straight up Great Peconic Bay. Robins Island is privately owned and protected by a conservation easement, so there is no public landing. The anchorage is flat, and in August it fills with the New Suffolk weekend fleet. Cell signal is thin; load charts before you leave.
No cell signal on this route — download NOAA charts before you cast off.
Gardiners Island east shore
The most historic private island in America, viewed from 100 yards off the east bluff. Anchor in 15 feet of sand, osprey nests line the cliff, the old manor is just visible through the trees. No landing — this is and has been private for nearly 400 years — but the anchorage itself is legal and unforgettable.
No cell signal on this route — download NOAA charts before you cast off.
Fort Pond Bay, Montauk → Fort Pond Bay south shore
Quiet anchorage distant from the village crowds, with The Crow's Nest and Navy Beach both a short dinghy ride ashore. Bay is exposed to the north but protected from the prevailing SW, holding is fair in sand. The sleeper-pick of the Montauk anchorages.
No cell signal on this route — download NOAA charts before you cast off.
Reference contacts, not destinations — these are kept off the map. VHF channel 16 is hailing and distress; 9 is the alternative hailing channel. Everyone born after 1996 needs a NY boating safety certificate, and by 2025 it applies to every motorboat operator.
Brianna's Law requires every operator of a motorized vessel or PWC in New York to hold a state-approved boating safety certificate. One exception matters for visitors: anyone 18 or over may rent and operate a motorboat from a livery without one. Classroom fees vary by instructor and the certificate is bought separately; online course fees include it.
County marine police — boarding, safety inspections, and non-distress assistance across Suffolk waters.
150 River Road, Great River, NY 11739
Coast Guard sector covering Long Island Sound and the East End. Distress on VHF channel 16; dial 911 on land.
120 Woodward Avenue, New Haven, CT 06512