The program consists of a wide variety of events from single day trips to extended cruises. Review the itineraries and sign-up for the events that interest you.  All members and their friends welcome. Come join the fun!


Friday, May 27th at 5:30pm

Watch Hill Yacht Club
Meet & Greet with the Cruisers

Join the Cruise Committee on the lower deck of the WHYC. Port Captains will share useful information regarding each port-of-call and the organized social activities.


June 25th & 26th

Weekend Rendezvous at Fishers Island

Port Captain Bill McKendree

Explore Fishers Island, tour the museum, then enjoy cocktails and a cookout on the lawn of the Fishers Island Yacht Club or a burger and a beer at the Pequot.

July 16th - 23rd

Mid Summer Cruise East
Elizabeth Islands, Martha’s Vineyard, and Nantucket with stops throughout Buzzards Bay

Saturday, July 16th

New Harbor, Block Island, RI

Port Captain: N/A
Rendezvous in harbor at our first overnight waypoint east. Enjoy a relaxing raft party aboard our yachts at the club’s mooring in the Great Salt Pond or head ashore for dinner.

Sunday, July 17th

Cuttyhunk Island, Gosnold, MA

Port Captain: Bob Kiel
Gather at the head of the dock at Cuttyhunk Marina for a docktail happy hour. Enjoy a short walk to the Cuttyhunk Fishing Club for a lobster boil dinner overlooking Vineyard Sound.
Monday & Tuesday, July 18th & 19th

Edgartown, MA with a day trip to Nantucket Island on July 19th

Port Captain: Gerry Gorman
Arrive Edgartown Harbor on Monday. Tour the town with its many shops and lunch spots. Gather at the Edgartown Yacht Club for cocktails and dinner. On Tuesday morning, embark a large yacht for a day trip to Nantucket.  Explore Nantucket Island and return to Edgartown late afternoon, relax and enjoy the evening. 
Wednesday, July 20th

Kingman Yacht Center, Cataumet Village, Bourne, MA

Port Captain Nick Durgarian
Cruise north from Edgartown, Martha’s Vineyard to Cataumet in Bourne, MA.  Arrive at Kingman Yacht Center.  From the yacht center, Falmouth is a 20 min Uber ride if you would like to explore the town or simply relax at the marina. A club group dinner reservation will be made at the Chart Room restaurant overlooking the water and the Kingman Yacht Center.
Thursday, July 21st

Padanaram Village, South Dartmouth, MA

Port Captain: David Grande
Tour the tiny village of Padanaram or simply relax at the New Bedford Yacht Club. A few dinner options include dining aboard boats, take-out from the New Bedford Yacht Club, at the Club, or visit the Farm and Coast Market in the heart of Padanaram Village.
Friday, July 22st

Sachuest Point, Third Beach, Middletown, RI

Port Captain: Dick Holliday
Sachuest, an overnight stop on our way home to Watch Hill. Located on the west side of the entrance to the Sakonnet River, Third Beach is a hidden gem.  What it lacks in amenities, it makes up with its beauty and charm.  Grab a mooring, take a deep breath and relax.  Jump in your dingy and motor or row ashore to enjoy an enchanting beach party! 
Saturday, July 23rd

Watch Hill Harbor, Homeport

After a night on the beach or your boat in Sachuest, get underway for a graceful cruise home through Rhode Island and Block Island Sounds.  Arrive home in Watch Hill Harbor or Avondale to offload and wash-down your boat.  Later in the day, gather at the Watch Hill Yacht Club at 6pm for a post-cruise shakedown social hour. Enjoy a cocktail and a sampling of Chief Sergio’s fabulous hors d’oeuvres while we all recall the week’s events, share fun stories and things we won’t do again next year!

August 5th

Lunch at Montauk Lake Club

Port Captain: Gerry Gorman
Cruise to the east end of Long Island and on into Montauk Lake. Enjoy a relaxing early afternoon lunch at the Montauk Lake Club.

August 19th – 21st

End of Summer Cruise West
Dering Harbor, Shelter Island & Sag Harbor

Port Captain: Bill McKendree
Cruise through Fishers Island Sound, Long Island Sound and Gardiners Bay to Dering Harbor, Shelter Island.  Visit the Shelter Island Yacht Club. Ferry over to Greenport, NY to visit the shops.  Enjoy camaraderie, cocktails and a cruise group dinner at the Shelter Island Yacht Club on Friday, August 19th.  On Saturday, August 20th, embark a large yacht for a day trip to Sag Harbor. Tour the town, grab some lunch and return to Dering Harbor for a free night to relax and prepare for your cruise home to Watch Hill Harbor the following morning.

September 23rd – 25th  

Fall Getaway
The Connecticut River, Essex, CT and beyond

Port Captain: Fred Prelle
Take in the fall scenery as we cruise the up the Connecticut River to Essex, CT.  Arrive Safe Harbor, Essex Island.  Jump on the ferry to the mainland for dinner at the Essex Yacht Club on Friday, September 23rd.  On Saturday September 24th, tour the shops in town or join a river cruise to Haddam, CT for lunch at the Blue Oar restaurant.  Afterwards, return to Essex Island for a cocktail as we watch the sunset and we prepare for our trip home to Watch Hill in the morning. 

Ports and Marinas

Skippers make your own slip or mooring reservations.
Reciprocal yacht clubs may ask to see proof of yacht club membership.  Be sure to carry your WHYC membership card aboard your vessel.
Most marinas provide COVID specific policies or updates on Dockwa.

Fisher's Island

Block Island

Cuttyhunk Island

FIYC Marina: Dockwa or (631) 788-7036. Mention you are with WHYC
FIYC Monitors VHF 10

Paynes Dock or Champlin’s Marina on Dockwa or the Boat Basin at
Moorings are first come, first serve via the harbormaster.
VHF 12

Cuttyhunk Marina on Dockwa
Moorings are first come, first serve upon arrival via Cuttyhunk Marina.
VHF 9. 

Edgartown, Martha's Vineyard

Cataumet Village

Padanaram Village

Edgartown Harbormaster and a variety of marinas on Dockwa
Edgartown Harbormaster
VHF 74.

Kingman Yacht Center on Dockwa.
Kingman VHF 71
New Bedford Yacht Club on Dockwa.  Mention you are with WHYC.


Sachuest Point

Montauk Lake

Shelter Harbor

Moorings can be reserved through the Town of Middletown Harbor Master on Dockwa or (401) 871-6544 
Harbormaster VHF 9
Montauk Lake Club at
Mention you are with the WHYC
Montauk Lake Marina VHF 12.
SIYC at (631) 749-0888; Mention you are with WHYC.
Marinas in Dering Harbor and Greenport, NY on Dockwa

Essex, CT

Safe Harbor Essex Island or Safe Harbor
Dauntless on Dockwa
Moorings or Slips may be available from EYC at (860) 581-4612
or (860) 767-8121 ext. 1.  Mention you are with WHYC.
Essex Island VHF 9. Dauntless & EYC VHF 68

Registered participants will receive event details and updates throughout the season.