Enjoy a cruise through Vineyard and Nantucket Sounds before the summer crowds arrive. The consistent June prevailing winds will fill your sails to each port. Each destination is timed to take advantage of the currents in the sounds. 

If a weather day forces us to stay in port the currents remain favorable the next day. No need to make mooring/dockage reservations in advance as there will be plenty of last minute availability. If 10 or more boats are interested in Nantucket slips I’ll look into an incentive.  Friday, June 19th would be the alternative cruise start date should foul weather bear down on us on the 5th.

Friday - June 5th - Edgartown

Meet in Edgartown Harbor on the 5th (or show up a day or two early to enjoy the Vineyard!) 
The morning current is favorable pushing you towards Edgartown from Buzzards Bay. Try to get through Woods Hole by 11:30am

• sun downers at 5PM on sv Christina. Dinner on your own. Past years a few of us head to Rock Fish for dinner.

Saturday and Sunday - June 6th and 7th, 

lay over to explore Edgartown and the island. 

• Saturday or Sunday (pending weather outlook) we’ll ride bikes to Oak Bluffs and gather at Off Shore Ale for lunch.

• Sundowners location will be announced each day.

Monday, June 8th - Nantucket

Set sail at 8:30AM for Nantucket, 25nm, ~5 hours. Current is favorable all the way. 

Use Dockwa to reserve your slip at the Nantucket Basin and take advantage of early season rates.

• Monday the 8th: sun downers at 5, on the dock at sv Christina. Dinner on your own.

• Tuesday the 9th: rent a bike and meet for lunch at Millie's Restaurant next to Madaket Beach.
  Sun downers at 5, boat/dock to be announced. Dinner on your own.

• Wednesday the 10th: Free day to explore on your own
  Sundowners at 5, boat/dock to be announced. 

Thursday, June 11th - back to the Vineyard

~9AM departure. Captains choice: head back to Edgartown or to Vineyard Haven if it looks like a calm evening. Edgartown is always a calm harbor. Vineyard haven can be nasty with Northerly winds.

Friday, June 12th - Cuttyhunk

Set sail at 10am for Cuttyhunk. 
EFFECTIVE 2026 - CUTTYHUNK NOW REQUIRES MOORING RESERVATIONS USING DOCKWA

• BBQ at Martha and Winn Sanfords home, 5pm

• We’ll provide chicken and pork loin for grilling. You bring an appetizer, side, or dessert. 

Saturday and beyond

• Draft fellow cruisers and head to Block Island or Newport

• Alternatively head to your home port or your next destination

Participants responsibilities: 

• You’re responsible for your respective dinner checks and mooring/dockage fees. 

• You’re requested to host one sundowner gathering at 5pm. 

• Please bring an appetizer to share at sundowners,  and of course BYOB. 

NOTES

• Registered Captains cell phone will be added to a WhatsApp Messaging Group to receive updates during the cruise. WhatsApp is the primary means of sharing cruise updates. As always, monitor VHF 16/72 

Photo Scavenger Hunt 

Capture these moments during the cruise! Each photo earns points. Post your photo real time to the WhatsApp group.

1. A picture of a perfect tack

2. Someone hoisting a sail

3. A crew doing a synchronized wave

4. A funny hat spotted on the dock

5. A signal flag message (decoded or displayed)

6. A boat with a unique name

7. A creative knot arrangement

8. A photo of the sunset with a sail silhouette

9. A dinghy on a plane full speed

10. A sailor tying a bowline knot

11. A colorful spinnaker

12. A boat passing Nantucket light house

13. A sailor wearing stripes

14. A life jacket in action

15. A humorous moment on the dock

16. A signal horn being used

17. A creative crew pose

18. A sailor costume in action

19. A photo of the club burgee

Prizes presented at Cuttyhunk