Welcome to the WHYC cruising season. The cruise committee has been hard at work this winter planning five exciting trips. This season introduces three single harbor trips and two long-cruises with a relaxed itinerary. The east and west cruise itineraries include multiple days in a single port as well as lay days that offer Skippers the flexibility to remain in port an extra day or venture to destinations of their choice. Register and join the fun!

Skippers make all transient slip or mooring reservations on Dockwa, with the exception of a town mooring in Vineyard Haven or a SIYC mooring in Dering Harbor. For a town mooring reservation as part of the WHYC group reservation in Vineyard Haven, be sure to select a Vineyard Haven mooring when registering for the cruise. For a mooring reservation in Dering Harbor, contact the Shelter Island Yacht Club, email or call the SIYC office at (631) 749-0888.

Click here to register for cruise events.


Cruise Kickoff Cocktail Hour and Dinner

Thursday, June 15th 5:30pm at the WHYC

Skippers and their crew will gather in the dinning room for cocktails, dinner and discussion of the summer cruise season.


One Harbor Trips

Fishers Island, NY
Family Picnic at FIYC
Saturday, June 17th

Back by popular demand, an afternoon Picnic at Fishers Island, NY. At noon gather on the lawn of the Fishers Island Yacht Club for a fun family style BYO picnic. FIYC offers a great venue for families and children to relax and enjoy the scenery of the Club grounds and West Harbor. A yacht tender will be available to shuttle cruisers to/from their boats located in the West Harbor mooring field or anchorage. The FIYC marina starts reserving slips through Dockwa beginning April 15th. Book your stay at FIYC on Dockwa or call the FIYC at (631) 788-7036.


Block Island, RI
Dinner at The Barn at Spring House
June 27th – 28th

A short reach to Block Island from Watch Hill Harbor, join this one harbor event in the Great Salt Pond. Reserve a slip at Payne’s Dock, New Harbor Boat Basin, or Champlin’s on Dockwa. Town moorings are first come, first serve upon arrival. Hail the Harbor Master on VHF CH 12. A group dinner event is in the works for June 27th at The Barn at Spring House. Event details are forthcoming.

Mattituck, NY
Strong’s Water Club and Marina
July 10th – 12th

Cruise west in Long Island Sound, enter the Mattituck inlet and arrive at Strong’s Marina. Informally gather on boats for cocktails and conversation. Explore the town of Mattituck or venture further to local area Long Island vineyards, breweries or distilleries for tours and tastings. Strong’s water club and marina is open on Dockwa for reservations.


Go East through Narragansett Bay with an excursion to Martha’s Vineyard – Skippers choose your ports…

Newport, RI
For Boaters and Land Cruisers alike
August 7th & 8th

Skippers can book slip or mooring reservations on Dockwa. Gather in Newport on Monday, August 7th for a cruise group dinner at 41 North, 351 Thames St.  Dinner will be a 4 course meal served family style. Food and beverage minimum is $110.00 per person plus tax and tip.  


Bristol, RI
Bristol Yacht Club
August 9th & 10th

Explore the town of Bristol, rent bikes, tour Colt State Park, Coggeshell Farm, or visit the many museums in the area. On Thursday August 10th, gather at Bristol Yacht Club for a BYO picnic style BBQ - bring your favorite food items for the BBQ grill and don’t forget your favorite sides. The Bristol Yacht Club offers a relaxing bar, lounge and porch overlooking the harbor, gas BBQ and picnic areas.

Bristol Yacht Club is open on Dockwa for mooring reservations and offers launch service to visiting guests. Slips can be reserved at area marinas on Dockwa.

On Friday August 11th, travel down the Sakonnet River to points south and east such as Cuttyhunk and Martha’sVineyard. Along the way, raft off Fogland Beach for lunch and a swim.


Island rendezvous

Cuttyhunk Island
The Fishing Club
August 11th

Cuttyhunk is the outer most of the Elizabeth islands. A truly unique spot, a throwback place, and a great stop over to Martha’s Vineyard. Cuttyhunk has a museum of the Elizabeth islands, Church’s beach, a nice hike to the World War II bunkers and Lookout Park. For the adventurous, you can hike on nearby Penikese Island, and visit the ruins of the leper hospital! Cuttyhunk pier has a small takeout restaurant and fish market. Up the hill is a small grocery store and gift shop. Arrangements are in the works for a traditional shore dinner on the
Island. Details for this event are forthcoming.

The Cuttyhunk fishing club has rooms available for those who do not want to stay on their boats. Contact Rudd and Julie Mason, 508–992–5585.  Cuttyhunk Marina is open on Dockwa for slip reservations. Moorings are first come, first serve on day of arrival (50 total). Contact the harbormaster upon arrival 508-990-7578. Ch. 9/10. There is no launch service.


Lay Day
August 12th

Skippers choice: Remain in Cuttyhunk for a second night, head
for Hadley Harbor, Martha’s Vineyard or any destination of your

Martha’s Vineyard
Vineyard Haven or Edgartown
August 13th

Book your slip or mooring reservation on Dockwa. Black Dog Wharf is open on Dockwa. Edgartown Harbor Master opens for mooring reservations on Dockwa February 15th. Vineyard Haven Town Moorings are first come, first serve and can only be reserved as a group reservation. Vineyard Haven Harbor Master assigns the mooring upon arrival and will likely raft you with other boats.

If you would like a town mooring in Vineyard Haven as part of the WHYC group reservation, be sure to request a mooring reservation in Vineyard Haven when registering for the WHYC cruise be sure to select a Vineyard Haven mooring when registering for the cruise.

Plans are in the works for an informal Docktails happy hour in Vineyard Haven on Sunday 13 August. Skippers make their own dinner reservations.  Details to come. Skippers can remain on MV for as long as they like and individually plan their return home or elsewhere.

Cruise Cocktail Hour
Thursday, August 17th 6:00pm at the WHYC

Gather on the lower deck to visit with fellow cruisers and enjoy your favorite beverage as we share stories from this season’s events.


Late Summer Cruise West

SAG Harbor
Wednesday, September 13th

Priority Marinas for Sag Harbor should be Waterfront Marina or Sag Harbor Yacht Club - both should be accessible through Dockwa or by directly contacting the facilities.

Arrive in Sag Harbor and explore shopping and eats along Main Street and Division Street, which are immediately adjacent to the harbor. Opt-in for a group dinner at Lulu Kitchen and Bar,, for great drinks, amazing cuisine with a range that will suit any pallet, and a casual rustic ambiance perfect for kicking back after a day on the water.

Lay Day
September 14th

Skippers choice: remain in Sag, head to Coecles Harbor, West Neck, or Dering / Greenport, NY.
Dering Harbor / Greenport, NY

Dinner at the Shelter Island Yacht Club
Friday, September 15th

Relax in Dering Harbor or explore the town of Greenport, NY. Gather for an informal cocktail hour aboard our boats and opt-in for a group dinner at the Shelter Island Yacht Club. Transient dock or mooring reservations in Dering Harbor or Greenport, NY can be made on Dockwa. To reserve a mooring at Shelter Island Yacht Club, email or call the SIYC office at (631)749-0888.


Day-Boating events

Day-boating is best done on fair weather days. Once in season, if the weather looks good for a couple days, we might announce an afternoon trip or two to lunch destinations such as Montauk Lake Club, Red 36, Ford’s Lobster, Costello’s, The Oar, or City Dock Restaurant & Oyster Bar. You can subscribe to the day-boating email list on the cruise registration page.

Click here to register for cruise events.