Breakwater Yacht Club
Sag Harbor · Sag Harbor Village
Community sailing focus with adult and junior programs on Sag Harbor Bay.
- Sailing school / Yacht club
- All ages
- Beginner
- Lessons-only
- Summer-only
51 Bay Street, Sag Harbor, NY 11963
On the Water
Sailing, fishing, paddling, docking and boat-up beaches across the East End.
Harbor cams
Watch all on /live →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.
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- Sailing
- Powerboat rentals
- JetSki / PWC
- Kayak & paddleboard
- Fishing charters
- Yacht clubs
- Marinas
- Sunset cruises
- Boat-up beaches
- Junior sailing
- Whale & seal watching
58 listings
Sailing
Sailing schools, lessons, racing clubs and ASA-certified programs across the East End.
Sag Harbor · 2
$$
Sailacat Sailing Yacht Charters
Sag Harbor · Sag Harbor Village
Private sailing-yacht charters leaving from Sag Harbor's Long Wharf, including daytime and sunset outings.
- Captained sailing yacht charters
- Private groups
- Beginner
- Captained
- Season not published
1 Long Wharf, Sag Harbor, NY 11963
Powerboat rentals
Center-console and runabout rentals.
East Hampton · 1
Peconic Water Sports (East Hampton)
East Hampton · East Hampton
Inside Shagwong Marina on Three Mile Harbor - charters, boat rentals, leases, sales and service, with coaches who teach beginners…
- Wake-sports charter & boat rentals
- All ages
- Beginner
- Captained
- Summer-only
215 Three Mile Harbor Hog Creek Road, East Hampton, NY 11937
Montauk · 2
Uihlein's Marina & Boat Rentals
Montauk · Montauk
Montauk Lake rental fleet of 18 powerboats from 16 to 31 feet plus Wave Runners, water skis, wakeboards and tubes…
- Marina / Powerboat rentals
- All ages
- Beginner
- Bareboat
- Summer-only
444 West Lake Drive, Montauk, NY 11954
Peconic Water Sports (Montauk)
Montauk · Montauk
Wake boats out of the Montauk Yacht Club on Star Island - wakeboarding, water skiing, wake surfing and tubing on…
- Wake-sports charter & boat rentals
- Adults
- Beginner
- Captained
- Summer-only
Montauk Yacht Club, 32 Star Island Rd, Montauk, NY 11954
Sag Harbor · 2
Lily's Boat Club — Sag Harbor
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…
- Boat club / Membership
- Adults
- Beginner
- Bareboat
- May–October
1 Bay Street Town Pier, Sag Harbor, NY 11963
Show 82 more listings
Sag Harbor · 2
Peconic Water Sports (Downtown Sag Harbor)
Sag Harbor · Sag Harbor Village
Captained wake boat out of West Water Street, five minutes' walk from Main Street - wakeboarding, water skiing and tubing…
- Wake-sports charter & boat rentals
- All ages
- Beginner
- Captained
- Summer-only
50 West Water Street, Sag Harbor, NY 11963
Noyack · 1
Peconic Water Sports (Noyack)
Noyack · Noyack
Inside Mill Creek Marina on Noyack Road - wake-sports charters, boat rentals, fishing charters, a kids' water sports camp, Peconic…
- Wake-sports charter & boat rentals
- All ages
- Beginner
- Captained
- Summer-only
3253 Noyack Rd, Sag Harbor, NY 11963
Kayak & paddleboard
Kayak, canoe and stand-up paddle rentals, tours and lessons.
Southampton · 1
Hampton Watersports
Southampton · Southampton
Full-service wind and wave shop on County Road 39, formerly trading as Windsurfing Hamptons and Kiteboarding Hamptons.
- Windsurf, wing, kite & SUP lessons and rentals
- All ages
- Intermediate
- Lessons-only
- Summer-only
1688 County Road 39, Southampton, NY 11968
Bridgehampton · 1
Atlantic Board Sports
Bridgehampton · Bridgehampton
Private kiteboarding, wing foiling and e-foil lessons taught by Duotone team riders Drew Christianson and Hugo Baker, both Hamptons-based for…
- Kiteboarding, wing foiling & e-foiling lessons
- All ages
- Beginner
- Lessons-only
- Summer-only
425 Dune Road, Bridgehampton, NY 11932
Wainscott · 1
MBX Surf Camp (formerly Main Beach Surf & Sport)
Wainscott · Wainscott
Surf shop and camp founded in Wainscott in 1987 by Lars Svanberg; now trades as MBX Surf Camp, still run…
- Surf shop / Paddle rentals
- All ages
- Beginner
- Bareboat
- Summer-only
352 Montauk Highway, Wainscott, NY 11975
Amagansett · 2
SkyWalk Kiteboarding
Amagansett · Amagansett
The Northeast's longest-running kiteboarding school, founded 2000, teaching at Napeague Harbor - waist-deep for hundreds of yards, which the school…
- Kiteboarding lessons
- All ages
- Beginner
- Lessons-only
- Summer-only
Lazy Point, Napeague Harbor, Amagansett, NY 11930
Amagansett · 2
Amagansett Beach & Bicycle Company
Amagansett · Amagansett
Amagansett rental shop for kayaks, paddleboards and bicycles.
- Paddle and bicycle rentals
- Adults and families
- Beginner
- Bareboat
- Season not published
1 Cross Highway, Amagansett, NY 11930
Montauk · 2
East End Surf Club
Montauk · Montauk
Surf instruction at Ditch Plains for beginners and progressing riders.
- Surf lessons and coaching
- Children and adults
- Beginner
- Lessons-only
- Season not published
Ditch Plains Beach, Montauk, NY 11954
The Surf Continuum Montauk
Montauk · Montauk
Structured surf coaching at Ditch Plains from a programme focused on skill progression rather than a one-time board rental.
- Surf coaching
- Children and adults
- Beginner
- Lessons-only
- Season not published
Ditch Plains Beach, Montauk, NY 11954
Springs · 1
Paddle Diva
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…
- SUP & kayak rentals, lessons and tours
- All ages
- Beginner
- Bareboat
- Season not published
10 Boat Yard Rd, East Hampton, NY 11937
Fishing charters
Montauk's fleet — party boats, head boats, and private six-pack charters.
Montauk · 13
Viking Fleet
Montauk · Montauk
Montauk's big head boats, sailing all year from Montauk Harbor.
- Party boat & charter
- All ages
- Beginner
- Captained
- Year-round
462 West Lake Drive, Montauk, NY 11954
Lazybones
Montauk · Montauk
Two half-day open-boat trips daily out of Montauk Harbor, 8am to noon and 1pm to 5pm: fluke in summer, diamond…
- Head boat
- All ages
- Beginner
- Captained
- Summer-only
474 West Lake Drive, Montauk, NY 11954
Montauk · 13
Star Island Yacht Club Fishing Fleet
Montauk · Montauk
Nine-boat charter fleet from 28 to 77 feet for sportfishing and cruising, plus an annual shark tournament open to seasonal…
- Private fishing charters
- Adults
- Intermediate
- Captained
- Summer-only
59 Star Island Road, Montauk, NY 11954
Fin Chaser
Montauk · Montauk
Fin Chaser runs both ways: the operator's own site says it "operates primarily as an open boat" — where you…
- Montauk fishing charter
- All ages — open-boat seats or a private group
- Beginner
- Captained
- May in Greenport, NY; June through November at Star Island, Montauk
59 Star Island Road, Montauk, NY 11954
Susie E II
Montauk · Montauk
A private Montauk fishing charter based on West Lake Drive, offering a smaller-boat alternative to the harbor's party fleet.
- Montauk fishing charter
- Private groups
- Beginner
- Captained
- Season not published
352 West Lake Drive, Montauk, NY 11954
Gina Ann Fishing Charters
Montauk · Montauk
Private Montauk fishing charters from West Lake Drive, with trips tailored to current fishing and the group's ambitions.
- Montauk fishing charter
- Private groups
- Beginner
- Captained
- Season not published
352 West Lake Drive, Montauk, NY 11954
Kopis Charters
Montauk · Montauk
A Montauk private fishing charter operating from West Lake Drive.
- Montauk fishing charter
- Private groups
- Beginner
- Captained
- Season not published
408 West Lake Drive, Montauk, NY 11954
Push the Limit Sportfishing
Montauk · Montauk
Captain Ben McCarron runs a 31ft Downeaster out of Montauk Marine Basin: half- and full-day inshore trips for porgy, sea…
- Montauk fishing charter
- Up to 4 passengers (some charters up to 6)
- Beginner
- Captained
- Season not published
Montauk Marine Basin, 426 West Lake Drive, Montauk, NY 11954
Montauk · 13
Moondance Charters
Montauk · Montauk
Six-pack charter out of Marlena's Yacht Club: inshore trips for striped bass, sea bass, bluefish and porgies, offshore runs for…
- Montauk fishing charter
- Up to 6 passengers
- Beginner
- Captained
- Season not published
Marlena's Yacht Club, 408 West Lake Drive, Montauk, NY 11954
Lady Grace Charters
Montauk · Montauk
Captain Mario runs Lady Grace VI, a 38ft sportfisherman out of West Lake Fishing Marina, for full- and half-day trips…
- Montauk fishing charter
- Up to 6 passengers
- Beginner
- Captained
- Season not published
West Lake Fishing Marina, 352 West Lake Drive, Montauk, NY 11954
VitaminSea Voyages
Montauk · Montauk
Captain John Gagne, a retired USCG Chief Boatswain's Mate, runs a 28ft Steiger Craft out of Montauk Anglers Club &…
- Montauk fishing charter
- Up to 6 passengers
- Beginner
- Captained
- Season not published
Montauk Anglers Club & Marina, 467 East Lake Drive, Montauk, NY 11954
My Joyce III
Montauk · Montauk
Captain Ken Hejducek's 41ft custom Michael Fitz sportfisherman, out of West Lake Drive: inshore and offshore fishing charters and Montauk…
- Montauk fishing charter
- Up to 6 passengers
- Beginner
- Captained
- Season not published
462 West Lake Drive, Montauk, NY 11954
November Rain Charters
Montauk · Montauk
Captains Jill and Steve run the November Rain, a 43ft USCG-inspected Lowell out of Westlake Marina, for inshore and offshore…
- Montauk fishing charter
- Up to 20 passengers
- Beginner
- Captained
- Season not published
Westlake Marina, 352 West Lake Drive, Montauk, NY 11954
Sag Harbor · 1
Surfmaster Charters
Sag Harbor · Sag Harbor Village
Capt.
- Bay fishing charter from Long Wharf
- 1 to 6 passengers — children welcome
- Beginner
- Captained
- Season not published
Long Wharf, Sag Harbor, NY 11963
Yacht clubs
Members clubs and one public-access resort marina.
Amagansett · 1
Devon Yacht Club
Amagansett · Amagansett
Private member-owned club on Gardiner's Bay.
- Private yacht club
- All ages
- Beginner
- Lessons-only
- Summer-only
300 Abraham's Landing Road, Amagansett, NY 11930
Montauk · 1
Montauk Yacht Club
Montauk · Montauk
Resort marina on Star Island run by Safe Harbor Marinas, with transient and wet slips for vessels up to 300ft…
- Public marina / hotel
- All ages
- Beginner
- Bareboat
- Spring–fall
32 Star Island Road, Montauk, NY 11954
Sag Harbor · 1
Sag Harbor Yacht Club
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…
- Yacht club / Marina
- Adults
- Intermediate
- Bareboat
- April–Thanksgiving
27 Bay Street, Sag Harbor, NY 11963
Marinas & guest docking
Public-access marinas where transient boaters can tie up overnight or for a meal.
Southampton · 2
Strong's Southampton Peconic Bay Marina
Southampton · Southampton
Strong's South Fork marina on North Sea Harbor, and the one South Fork address the operator lists for RENTALS and…
- Marina / Powerboat rentals
- Adults
- Intermediate
- Bareboat
- Year-round
1810 North Sea Road, Southampton, NY 11968
Strong's Southampton Shinnecock Bay Marina
Southampton · Southampton
Dockage and nothing else — the operator lists this Shinnecock Bay address for slips only, no sales, service, rentals or…
- Seasonal dockage
- Adults
- Intermediate
- Bareboat
- Season not published
74 Little Neck Road, Southampton, NY 11968
East Hampton · 2
Strong's at Harbor Marina
East Hampton · East Hampton
Strong's only Three Mile Harbor address, inside Harbor Marina of East Hampton on Gann Road.
- Boat sales at a working marina
- Adults
- Intermediate
- Bareboat
- Season not published
41 Gann Road, East Hampton, NY 11937
East Hampton · 2
Shagwong Marinas — East Hampton
East Hampton · East Hampton
Roughly 40 slips on Three Mile Harbor for boats from 25ft to 45ft, in a protected part of the harbour…
- Full-service marina
- Adults
- Intermediate
- Bareboat
- Season not published
219 Three Mile Harbor Hog Creek Road, East Hampton, NY 11937
Montauk · 3
Montauk Marine Basin
Montauk · Montauk
Family owned and operated on Lake Montauk since 1955 — seasonal and transient dockage, ValvTect fuel, a 70-ton travel lift…
- Full-service marina
- Adults
- Intermediate
- Bareboat
- Year-round
426 West Lake Drive, Montauk, NY 11954
Gosman's Dock
Montauk · Montauk
Iconic Montauk harbor complex at the inlet — the Gosman family's seafood restaurants, fish market and shops on their own…
- Harbor complex / transient dockage
- All ages
- Beginner
- Bareboat
- Summer-only
484 West Lake Drive, Montauk, NY 11954
Star Island Yacht Club Marina
Montauk · Montauk
Club marina on Lake Montauk with dockage open to visiting boats, diesel fuel at every slip, one of the area's…
- Full-service marina
- Adults
- Intermediate
- Bareboat
- Year-round
59 Star Island Road, Montauk, NY 11954
Sag Harbor · 1
Sag Harbor Municipal Long Wharf
Sag Harbor · Sag Harbor Village
Village-run transient dockage at the foot of Main Street.
- Public transient dockage
- All ages
- Intermediate
- Bareboat
- Summer-only
Long Wharf, Sag Harbor, NY 11963
Springs · 1
Three Mile Harbor Marina
Springs · East Hampton
Year-round marina and boatyard at the head of Three Mile Harbor: seventy slips on floating docks with finger piers, power…
- Full-service marina
- Adults
- Intermediate
- Bareboat
- Year-round
6 Boat Yard Road, East Hampton, NY 11937
Sunset cruises & day charters
Captain-narrated harbor tours, sail-cat sunset cruises, and classic yacht charters.
Montauk · 2
Mon Tiki Largo
Montauk · Montauk
65ft Polynesian-inspired sailing catamaran, USCG-certified, running Montauk day sails and sunset cruises from Slip 501 off Resort Dock 2 at…
- Sail-cat sunset cruise
- All ages
- Beginner
- Captained
- Summer-only
Montauk Yacht Club, 32 Star Island Rd, Montauk, NY 11954
Island Girl Adventures
Montauk · Montauk
Captains Bill and Maggie, a combined 50 years on the water, run private charters out of Star Island Yacht Club…
- Private powerboat charter & sunset cruise
- All ages
- Beginner
- Captained
- Season not published
- Exact location to come
Star Island Yacht Club, Montauk, NY 11954
Sag Harbor · 8
Sag Harbor Sailing
Sag Harbor · Sag Harbor Village
ASA-accredited sailing school running since 1997 out of the Yacht Hampton Boating Center at 51 Pine Neck Avenue.
- Sailing school / Charter
- All ages
- Beginner
- Captained
- Summer-only
Yacht Hampton Boating Center, 51 Pine Neck Avenue, Sag Harbor, NY 11963
Sag Harbor Excursions
Sag Harbor · Sag Harbor Village
Captain Chuck Wade runs a 30ft Axopar out of Long Wharf, six passengers max.
- Private powerboat charter
- All ages
- Beginner
- Captained
- Season not published
Long Wharf, Sag Harbor, NY 11963
Yacht Hampton
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).
- Luxury yacht charters, boat rentals & water-toy add-ons
- All ages
- Beginner
- Captained
- Season not published
9 Long Wharf, Sag Harbor, NY 11963
True Sailing Hamptons
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…
- Captained sailing charters, sunset cruises & ASA lessons
- Up to 6 passengers
- Beginner
- Captained
- Season not published
Sag Harbor Village Marina, Sag Harbor, NY 11963
Sag Harbor · 8
SailHamptons
Sag Harbor · Sag Harbor Village
The largest crewed sailing capacity on this page.
- Crewed schooner and trimaran charters for larger groups
- Up to 41 passengers
- Beginner
- Captained
- Season not published
- Exact location to come
Sag Harbor, NY 11963
Yacht Kelpie (formerly Kelpie Yacht Charters)
Sag Harbor · Sag Harbor Village
Kelpie is a 78.8 ft gaff-rigged schooner built in Maine in 1928, which hunted U-boats for the Coast Guard in…
- Private sailing charters on a 1928 schooner: brunch, half day, sunset, full day
- Private groups up to 24
- Beginner
- Captained
- Memorial Day weekend to mid-September
- Exact location to come
Sag Harbor, NY 11963
Sag Harbor Charters
Sag Harbor · Sag Harbor Village
Captain Hagen — a Sag Harbor resident who has run these waters for over 40 years — charters The Marlinspike…
- By-the-hour lobster-yacht charters on the bay
- Small groups
- Beginner
- Captained
- Season not published
23 Marine Park Dr, Sag Harbor, NY 11963
Harbor Charters LLC
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…
- Captained powerboat charters & wake sports
- Up to 6 passengers per boat
- Beginner
- Captained
- Season not published
- Exact location to come
Sag Harbor, NY 11963
Boat-up beaches
Bay beaches and coves reached primarily by boat.
Amagansett · 1
Napeague Harbor sandbars
Amagansett · Amagansett
Shallow-draft boats beach on the sandbars inside Napeague Harbor.
- Boat-up sandbars
- All ages
- Intermediate
- Bareboat
- Summer-only
Napeague Harbor, Amagansett, NY 11930
Springs · 1
Cedar Point County Park (boat-up beach)
Springs · East Hampton
Protected anchorage off the spit on Gardiners Bay — Suffolk County park, camping and a lighthouse ashore.
- Boat-up beach
- All ages
- Intermediate
- Bareboat
- Year-round
Cedar Point County Park, East Hampton, NY 11937
Sailing junior programs
Summer programs for kids — Optis, 420s and Lasers on Sag Harbor, Gardiners, and Shinnecock Bay.
Amagansett · 1
Devon Junior Sailing
Amagansett · Amagansett
Member-access junior program on Gardiner's Bay teaching in Optimists, Sunfish, Lasers and Club 420s, racing PGJSA regattas on the East…
- Junior sailing
- Kids
- Beginner
- Lessons-only
- Summer-only
300 Abraham's Landing Road, Amagansett, NY 11930
Sag Harbor · 1
Breakwater Junior Sailing Program
Sag Harbor · Sag Harbor Village
Week-long Opti and 420 sessions from June through August at Breakwater YC.
- Junior sailing
- Kids
- Beginner
- Lessons-only
- Summer-only
51 Bay Street, Sag Harbor, NY 11963
Whale & seal watching
Naturalist-led boat trips — summer whale cruises out of Montauk, winter seal cruises on Shinnecock Bay.
Southampton · 1
CRESLI Seal Cruise
Southampton · Southampton
A CRESLI scientist leads roughly two-hour expeditions aboard the R/V Peconic out of Stony Brook Marine Station to view, photograph…
- Winter seal-watching cruise
- All ages
- Beginner
- Captained
- Winter-only (November-May)
Stony Brook Marine Station, 8 Little Neck Road, Southampton, NY 11968
Montauk · 1
CRESLI Whale Watching aboard Viking Fleet
Montauk · Montauk
CRESLI naturalists narrate aboard the Viking Starship out of Montauk Harbor — the pairing's 31st season in 2026.
- Whale-watching cruise
- All ages (6+ recommended)
- Beginner
- Captained
- Late May-September
462 West Lake Drive, Montauk, NY 11954
5 listings
Powerboat rentals
Center-console and runabout rentals.
Shelter Island Heights · 1
Peconic Water Sports (Shelter Island)
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…
- Wake-sports charter & boat rentals
- All ages
- Beginner
- Captained
- Summer-only
184 N Ferry Rd, Shelter Island Heights, NY 11965
Kayak & paddleboard
Kayak, canoe and stand-up paddle rentals, tours and lessons.
Shelter Island · 1
Kayak Shelter Island
Shelter Island · Shelter Island
Kayak and paddleboard rentals plus two-hour guided tours from a Burns Road departure point on Coecles Harbor.
- Kayak rentals & guided tours
- All ages
- Beginner
- Bareboat
- Summer-only
80 Burns Road, Shelter Island, NY 11964
Shelter Island Heights · 1
Venture Out Paddle Board & Kayak
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…
- Beach walk-up SUP & kayak rentals
- All ages
- Beginner
- Bareboat
- Summer-only
Crescent Beach, Shore Road, Shelter Island Heights, NY 11965
Marinas & guest docking
Public-access marinas where transient boaters can tie up overnight or for a meal.
Shelter Island Heights · 1
Dering Harbor Marina
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…
- Shelter Island transient
- All ages
- Intermediate
- Bareboat
- Summer-only
177 North Ferry Road, Shelter Island Heights, NY 11965
Sunset cruises & day charters
Captain-narrated harbor tours, sail-cat sunset cruises, and classic yacht charters.
Shelter Island · 1
Charters in the Hamptons
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…
- Private yacht day charters
- All ages
- Beginner
- Captained
- Season not published
63 Menantic Road, Shelter Island, NY 11964
11 listings
Powerboat rentals
Center-console and runabout rentals.
Hampton Bays · 1
Lily's Boat Club — Hampton Bays
Hampton Bays · Hampton Bays
Members-only shared-fleet boat club at 86 Foster Avenue in Hampton Bays — one of three Eastern Long Island locations alongside…
- Boat club / Membership
- Adults
- Beginner
- Bareboat
- May–October
86 Foster Avenue, Hampton Bays, NY 11946
JetSki / PWC
Personal watercraft rentals.
Hampton Bays · 1
East End Jet Ski
Hampton Bays · Hampton Bays
Forty years at the foot of the Ponquogue Bridge, opposite the Shinnecock Coast Guard station.
- JetSki / PWC rentals & guided tours
- All ages
- Beginner
- Bareboat
- Summer-only
91 Foster Avenue, Hampton Bays, NY 11946
Kayak & paddleboard
Kayak, canoe and stand-up paddle rentals, tours and lessons.
East Quogue · 1
Adventure Paddleboards & Kayaks
East Quogue · East Quogue
Woman-owned and operated on Dune Road since 2012, renting paddleboards, kayaks and motorised GoBoats on the calm bay side away…
- SUP, kayak & GoBoat rentals
- All ages
- Beginner
- Bareboat
- Summer-only
Dune Road, East Quogue, NY 11942
Hampton Bays · 1
P&L Watersports
Hampton Bays · Hampton Bays
Paddleboard and kayak rental and instruction operating since 2015, based at Meschutt Beach on the Shinnecock Canal with a second…
- Delivered SUP & kayak rentals
- All ages
- Beginner
- Lessons-only
- Summer-only
Meschutt Beach, Canal Road at Old North Highway, Hampton Bays, NY 11946
Tuckahoe · 1
East End Explorer
Tuckahoe · Southampton
Guided kayak and SUP tours out of Tuckahoe, plus an oyster-farm boat tour run with Conscience Point Shellfish and a…
- Kayak & SUP tours, oyster farm boat tours
- All ages
- Beginner
- Lessons-only
- Season not published
449 N Magee St, Southampton, NY 11968
Fishing charters
Montauk's fleet — party boats, head boats, and private six-pack charters.
Hampton Bays · 2
Hampton Bays Charters
Hampton Bays · Hampton Bays
Captain Dave has fished Shinnecock Bay for more than 40 years, and fluke is his specialty.
- Fluke fishing charters and sunset cruises on Shinnecock Bay
- Families, first-time anglers and experienced fishermen
- Beginner
- Captained
- Season not published
9 Sagamore Road, Hampton Bays, NY 11946
Hampton Lady Fishing
Hampton Bays · Hampton Bays
A private fishing charter departing from Oakland's Marina on Dune Road.
- Hampton Bays fishing charter
- Private groups
- Beginner
- Captained
- Season not published
Oakland's Marina, 373 Dune Road, Hampton Bays, NY 11946
East Moriches · 1
Silly Lily Fishing Station
East Moriches · Brookhaven
The parent location of the Lily's operation, on Moriches Bay — west of the Shinnecock Canal in Brookhaven Town, so…
- Fishing station / Rentals / Experiences
- All ages
- Beginner
- Bareboat
- Opens May 16 (Wed–Mon 8am–5pm)
- Exact location to come
99 Adelaide Avenue, East Moriches, NY 11940
Yacht clubs
Members clubs and one public-access resort marina.
Quogue · 1
Shinnecock Yacht Club
Quogue · Quogue
Member-owned club at Quogue with a junior sailing program that races in the Peconic Gardiners Junior Sailing Association.
- Private yacht club
- All ages
- Beginner
- Lessons-only
- Summer-only
43 Niamogue Ln, Quogue, NY 11959
Marinas & guest docking
Public-access marinas where transient boaters can tie up overnight or for a meal.
Hampton Bays · 1
Shagwong Marinas — Southampton
Hampton Bays · Hampton Bays
The largest of the four: about 175 wet slips on 5.12 acres taking yachts up to 120ft in summer, with…
- Full-service marina
- Adults
- Intermediate
- Bareboat
- Season not published
6 Teepee Road, Hampton Bays, NY 11946
Sunset cruises & day charters
Captain-narrated harbor tours, sail-cat sunset cruises, and classic yacht charters.
Hampton Bays · 1
Hamptiki
Hampton Bays · Hampton Bays
"The O.G.
- Captained tiki pontoon boat cruise (BYOB)
- All ages
- Beginner
- Captained
- Season not published
6 Tepee St Slip 16MB, Hampton Bays, NY 11946
14 listings
Sailing
Sailing schools, lessons, racing clubs and ASA-certified programs across the East End.
Cutchogue · 1
Peconic Bay Sailing Association
Cutchogue · Cutchogue
Racing association on the Peconic Bays.
- Sailing club
- Adults
- Intermediate
- Bareboat
- Summer-only
- Exact location to come
No published contact channel — see the operator's listing.
P.O. Box 1196, Cutchogue, NY 11935
Greenport · 1
East End Charters
Greenport · Greenport Village
Captained sailing charters from Greenport, adding a North Fork departure to a guide otherwise heavy on Sag Harbor and Montauk.
- Greenport sailing charters
- Private groups
- Beginner
- Captained
- Season not published
1100 Manhasset Avenue, Greenport, NY 11944
Powerboat rentals
Center-console and runabout rentals.
Mattituck · 1
Strong's Marine
Mattituck · Mattituck
Four-generation North Fork dealer and marina marking its 80th year, with rentals and a boat club out of Mattituck Bay…
- Powerboat rentals / dealer
- Adults
- Intermediate
- Bareboat
- Year-round
2400 Camp Mineola Road, Mattituck, NY 11952
Southold · 1
Peconic Water Sports (Southold)
Southold · Southold
The fleet's own flagship, on Main Road in Southold - boat rentals, wake-sports charters, fishing charters, a kids' water sports…
- Wake-sports charter & boat rentals
- All ages
- Beginner
- Captained
- Summer-only
64150 Main Rd, Southold, NY 11971
Kayak & paddleboard
Kayak, canoe and stand-up paddle rentals, tours and lessons.
Riverhead · 1
Peconic Paddler LI
Riverhead · Riverhead
Riverhead kayak and paddle outfitter beside the Peconic River, useful for an easy freshwater launch and for visitors who need…
- Kayak and paddle outfitter
- Adults and families
- Beginner
- Bareboat
- Season not published
89 Peconic Avenue, Riverhead, NY 11901
Orient · 1
Eagle's Neck Paddling
Orient · Orient
Kayak and paddleboard rentals inside Orient Beach State Park, on the sheltered Long Beach Bay side of the spit, plus…
- State park kayak & SUP rentals
- All ages
- Beginner
- Bareboat
- Summer-only
Orient Beach State Park, 40000 Main Road, Orient, NY 11957
Yacht clubs
Members clubs and one public-access resort marina.
New Suffolk · 1
Old Cove Yacht Club
New Suffolk · New Suffolk
North Fork member club at New Suffolk with a junior sailing program that races in the Peconic Gardiners Junior Sailing…
- Community yacht club
- All ages
- Beginner
- Lessons-only
- Summer-only
No published contact channel — see the operator's listing.
1400 Old Harbor Road, New Suffolk, NY 11956
Marinas & guest docking
Public-access marinas where transient boaters can tie up overnight or for a meal.
Mattituck · 2
Strong's Water Club & Marina
Mattituck · Mattituck
Strong's marina at the head of Mattituck Inlet — the only one of its North Fork addresses the operator lists…
- Full-service marina
- Adults
- Intermediate
- Bareboat
- Year-round
2255 Wickham Avenue, Mattituck, NY 11952
Strong's Yacht Center
Mattituck · Mattituck
The yard rather than the marina — Strong's refit and service centre on Mattituck Creek, listed for sales, service, dockage…
- Boatyard / Full-service marina
- Adults
- Advanced
- Bareboat
- Year-round
5780 West Mill Road, Mattituck, NY 11952
Cutchogue · 2
Strong's at Broadwaters Cove
Cutchogue · Cutchogue
Strong's marina on Broadwaters Cove off Little Peconic Bay, at the end of Skunk Lane in Cutchogue — sales, service…
- Full-service marina
- Adults
- Intermediate
- Bareboat
- Year-round
8000 Skunk Lane, Cutchogue, NY 11935
Cutchogue · 2
Shagwong Marinas — Cutchogue
Cutchogue · Cutchogue
Well over 100 deep-water slips across 3.82 acres on Cutchogue Harbor, with a ship store, a fuelling dock, and summer…
- Full-service marina
- Adults
- Intermediate
- Bareboat
- Season not published
3350 West Creek Avenue, Cutchogue, NY 11935
New Suffolk · 1
Shagwong Marinas — New Suffolk
New Suffolk · New Suffolk
One of the oldest marinas on eastern Long Island — over 60 slips across 2.3 acres in the middle of…
- Full-service marina
- Adults
- Intermediate
- Bareboat
- Season not published
6775 New Suffolk Road, New Suffolk, NY 11956
Greenport · 1
Mitchell Park Marina
Greenport · Greenport Village
Village-run marina in the heart of Greenport: 60 floating slips for boats to 80 feet plus a 640ft standing pier…
- Municipal marina
- All ages
- Beginner
- Bareboat
- Summer-only
115 Front Street, Greenport, NY 11944
Boat-up beaches
Bay beaches and coves reached primarily by boat.
New Suffolk · 1
Robins Island anchorage
New Suffolk · Southold
Privately owned, ~90% under a Nature Conservancy conservation easement since 1997 — anchor off the western shore.
- Boat-up anchorage
- Adults
- Advanced
- Bareboat
- Summer-only
No published contact channel — see the operator's listing.
Robins Island, Peconic Bay, NY
Where to actually go once you're out there
Day-sail routes, sunset paths and anchorages.
- Day sail
- Sunset cruise
- Anchorage
Show the 19 routes 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.
Day sail
Day sail
Sag Harbor to Shelter Island circumnavigation
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.
- Duration
- 4-6 hours
- Skill
- Intermediate skills
- Best wind
- SW / W
- Season
- summer, early fall
Day sail
Three Mile Harbor to Gardiners Bay and Cedar Point
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.
- Duration
- 3-4 hours
- Skill
- Beginner-friendly
- Best wind
- SW / S
- Season
- summer
Day sail
Lake Montauk to Block Island Sound and Montauk Point
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.
- Duration
- 5-7 hours
- Skill
- Advanced / exposed water
- Best wind
- W / SW
- Season
- summer, early fall
No cell signal on this route — download NOAA charts before you cast off.
Day sail
Sag Harbor to Greenport cross-bay passage
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.
- Duration
- half day
- Skill
- Intermediate skills
- Best wind
- SW / S
- Season
- summer, early fall
Day sail
Napeague Harbor to Gardiners Island anchorage
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.
- Duration
- 4-5 hours
- Skill
- Intermediate skills
- Best wind
- SW / S
- Season
- summer
No cell signal on this route — download NOAA charts before you cast off.
Day sail
Shinnecock Bay protected loop
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.
- Duration
- 3 hours
- Skill
- Beginner-friendly
- Best wind
- SW / S
- Season
- summer
Day sail
Mecox Bay and Sag Pond small-boat circuit
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.
- Duration
- 2 hours
- Skill
- Beginner-friendly
- Best wind
- SW / W
- Season
- late spring, summer, early fall
Day sail
New Suffolk to Robins Island west shore anchorage
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.
- Duration
- 3-4 hours
- Skill
- Beginner-friendly
- Best wind
- SW / S
- Season
- summer
No cell signal on this route — download NOAA charts before you cast off.
Sunset cruise
Sunset cruise
Long Wharf to Noyac Bay sunset cruise
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.
- Duration
- 2 hours sunset
- Skill
- Beginner-friendly
- Best wind
- SW / W
- Season
- summer, early fall
Sunset cruise
Three Mile Harbor to Cedar Point sunset
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.
- Duration
- 2-3 hours sunset
- Skill
- Beginner-friendly
- Best wind
- SW / S
- Season
- summer, early fall
Sunset cruise
Lake Montauk to Fort Pond Bay sunset
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.
- Duration
- 2 hours sunset
- Skill
- Intermediate skills
- Best wind
- W / NW
- Season
- summer, early fall
No cell signal on this route — download NOAA charts before you cast off.
Sunset cruise
Greenport Harbor to Shelter Island Sound sunset
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.
- Duration
- 2 hours sunset
- Skill
- Beginner-friendly
- Best wind
- SW / W
- Season
- summer, early fall
Anchorage
Anchorage
Cedar Point County Park anchorage
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.
- Duration
- lunch anchor
- Skill
- Beginner-friendly
- Best wind
- SW / S / W
- Season
- late spring, summer, early fall
Anchorage
Coecles Harbor anchorage, Shelter Island
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.
- Duration
- overnight
- Skill
- Intermediate skills
- Best wind
- any
- Season
- late spring, summer, early fall
Anchorage
West Harbor, Fishers Island
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.
- Duration
- overnight
- Skill
- Advanced / exposed water
- Best wind
- SW / W
- Season
- summer, early fall
No cell signal on this route — download NOAA charts before you cast off.
Anchorage
Plum Gut anchorage off Plum Island
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.
- Duration
- slack-water only
- Skill
- Advanced / exposed water
- Best wind
- light air
- Season
- summer
No cell signal on this route — download NOAA charts before you cast off.
Anchorage
Robins Island west shore anchorage
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.
- Duration
- lunch anchor
- Skill
- Beginner-friendly
- Best wind
- SW / S
- Season
- summer, early fall
No cell signal on this route — download NOAA charts before you cast off.
Anchorage
Gardiners Island east shore anchorage
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.
- Duration
- lunch anchor
- Skill
- Intermediate skills
- Best wind
- SW / W
- Season
- summer
No cell signal on this route — download NOAA charts before you cast off.
Anchorage
Fort Pond Bay south shore anchorage
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.
- Duration
- overnight
- Skill
- Intermediate skills
- Best wind
- W / NW
- Season
- summer, early fall
No cell signal on this route — download NOAA charts before you cast off.
Safety & rules
VHF 16 is hailing and distress. Every motorboat operator needs a NY boating safety certificate.
3 safety contacts
Reference contacts, not destinations, so they are kept off the map. Channel 9 is the alternative hailing channel. The safety certificate rule covers everyone born after 1996 and, from 2025, every motorboat operator.
NY State Boating Safety Certificate (Brianna's Law)
ReferenceBrianna'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.
Suffolk County Marine Bureau
ReferenceCounty marine police — boarding, safety inspections, and non-distress assistance across Suffolk waters.
150 River Road, Great River, NY 11739
USCG Sector Long Island Sound
ReferenceCoast 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