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2024 Long Island Cruise

The first time I cruised Long Island waters in June I felt alone – and (almost) guilty for having these waters to myself.
Before school breaks for the summer and families take their vacations, June is the ideal time to visit these busy harbors.

Saturday, June 15th

     Sail to Cuttyhunk from Edgartown.  Rise and shine for a 25-mile sail. Depart Edgartown by 8 AM and sail with a favorable current for the 5-hour trip to Cuttyhunk. Timing should allow you to pass through Quicks Hole by 1pm which is when the current turns against us.

Cuttyhunk Town Moorings are first come first serve. Just pick up an empty mooring and the harbormaster will be by in the evening to collect the fee (~$50). There has been some light shoaling of the inlet.
We’ll send out navigational guidance before the cruise to those who registered.

Sunday June 16th

     Sail to Block Island – Our 35-mile sail tends to be against the prevailing south westerly breeze. If you leave about 8AM the currents will be in your favor for a mid-afternoon arrival.

Cuttyhunk Town Moorings are first come first serve. Just pick up an empty mooring and the harbormaster will be by in the evening to collect the fee (~$50). The anchorage has a questionable bottom.
Harbormaster monitors VHF 12

            Perhaps we will meet at The Oar on the lawn for drinks at 5.

 Monday June 17th

     Lay day on Block island. Rent bikes we’ll pedal around the island.  Dinner on shore at a restaurant TBD.

Tuesday June 18th

     Depart around noon for Lake Montauk where we anchor for the night. There will be a bit of a current against us but it will subside as we work to Montauk.
About an 18 mile sail.

Wednesday June 19th

     Pick up anchor and head ~23 miles east to Sag Harbor.
Call ahead or use Dockwa to reserve a mooring inside the breakwater. 
Let’s head into town for drinks and dinner.

Thursday June 20th

     Cast off the mooring and we’re heading east ~10 miles to Derringer Harbor aka. Shelter Island Heights.
Reserve your mooring at Derring Harbor Marina. +16317490045

Friday June 21st (two nights)

     We’re off again and sailing across Long Island Sound to Mystic Ct. The morning currents in the sound are favorable.

We’re going to the Mystic Seaport Museum – I love this dockage. It's such a cool place to be.

Reserve your dockage ASAP for two nights June 18th and 19th. If you miss reserving a spot here search for a nearby dockage so you can socialize with the group.

It’s about 15 miles across Block Island Sound through Watch Hill Passage. There’s a W to E current in the morning. Leaving Block around 11AM would get you across to find slack current at 2 PM which is ideal for traveling along the north side of Fishers Island to the Mystic River.

Traveling up the Mystic River. Mind the navigation markers as there are many. It can be confusing if its your first time – just pay attention.
There are two bridges to pass under. You will have to announce your vessel to the bridge operator and ask for an opening.

The Amtrak Mystic Railroad Bridge opens on demand when no train traffic is present.
The Mystic River Highway Bridge opens 40 minutes after the hour when requested.
Both bridges can be hailed on channel 13. The distance between the two bridges is half a mile.

Saturday June 22nd.

     Lay over in Mystic. Group tour of museum

Sunday June 23rd

     Head to your homeport or next destination.
Those eastbound consider Newport or Block Island as the current will be in your favor.

Saturday, June 15, 2024 to Saturday, June 22, 2024

Additional Info:
Event Contact(s):
John Garner
Registration is required before Monday, June 10, 2024 at 12:00 AM
Payment In Full In Advance Only
No Fee
No Fee