Welcome to SailNut Chris.
You have a nice boat to start out your cruising adventures. Your itinerary sounds infinitely do-able and you'll probably have a blast doing it. The is a whole great world out there beyond the GSB.
You probably already know this but timing your exit at FI Inlet to the tides is a good idea. You probably also have anchors and all the rest of required safety gear.
Be safe, have fun.
Toughest part of that trip is the first leg. Once you exit the Fire Island inlet, there's really no easy place to stop in bad weather until you get to Montauk.
Enjoy the trip.
The wind, prevailing from the SW will undoubtedly swing around and be on the nose for the duration of your trip out. Your return trip will undoubtedly encounter winds from the WSW.
Make all your plans, prayers, chants, set all your tide and weather apps, chart plotters, etc. as if you are headed to Atlantic City then turn left as you exit the harbor. It's your only chance of sailing when cruising.
I'm a little confused - are you planning on doing this trip in one short, or over the entire summer? The circumnavigation of Long Island as you have listed it is probably around 300 nm. How long do you think this will take?
The Long Island sound is a very rich cruising ground. Between the CT and LI sides there are probably harbors every 5-10 miles. The only real exception to this is the Long Island side between Mt. Sinai and Mattituck - thats about 20 nm with no harbors in between. On the CT side there are still plenty of harbors.
Anyway, if you haven't been there, you should look into Active Captain. The problem with the LIS is that there are SO many marinas and harbors that making a decision on which ones to see is the real challenge. You can anchor out, hang on a mooring, stay in a bare bones marina, or one that is more like a country club.
hi Chris your new itinerary sounds much more doable. Ive done the Block Island and Montauk runs from Babylon at different times and my favorite format now is to cruise near the inlet the evening before leaving and sleep on the hook inside Sore Thumb or grab a berth in the State Park boat BASIN AT Robert Moses. The boat basin is rarely busy often nearly empty.
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Sounds like you've got a good adventure planned. It looks like your modified plan still has you doing a lot of sailing, which is what it is all about, but like an earlier post, I've been tending to put my long sails in at the beginning and end and stay/cruise in sort of a defined area. I don't know LI yet (I sail out of New Bedford), but I went to a wedding out in Sag Harbor area and it seems to me there is a good week's worth of sailing/cruising in that Gardiner's Bay, Peconic Bay, Montauk, Greenport area alone. I sail with my wife, who has limited interest in long passages. Earlier this summer, we sailed down to Newport. It took about 7 hours with the conditions. Once we got to Narragansett Bay, she was not participating in anything but hops between harbors in the bay for a week. It seems we could spend a summer in that bay and not see it all. My only point is, I've been there with the need to get out there put the miles in and see as many places as possible, but that east end of Long Island might satisfy your first long trip and not burn anyone out. By the way, almost no one ever reports back after a post like yours, so if you are inclined, let us know how it went.
Sounds like a great trip! very jealous, if you ever need a crew Im 26 and in the construction industry also. Live in massapequa , boat is in Napeague Harbor. Enjoy the trip and post pictures when you return.
Always looking to meet new sailors and enjoy the bay! PM me and we'll set something up! Napeague is far! I've windsurfed there a few times.
When the time is right you will move your homeport... 2 hrs out and 2 hrs will be better spent driving a bit to the north shore. Most harbors on the Sound take some time to get out... but nothing like that!
Going west from BI... my suggestions are:
Sail a lovely reach to Watch Hill and they stop for the night in Stonnington. Fabulous little town.
From Stonnington... you can visit Mystic... a short way to the west and West Harbor is nice anchorage on Fishers. Good holding bottom in these three (BI has a lot of eel grass!)
From west end of FI sound... sail along the north side... perhaps duck in to Saybrook and you can sail up to Essex. Old Lyme has a fabulous boat yard... small and all sailboats. Walk to a shopping center.
Sail on the north side of LI shoal and head for the Thimbles... you can anchor or take one of the 5 or 6 moorings. Very cool anchorage... between a bunch of tiny private islands.
Next sail to Port Jef. Anchor on the east or west side of the channel. (I anchor on the east up close to the beach) good holding too. If you have a dink... check out Seatauket... or motor over to the Pt Jef town pier and tie along side (free) and visit Pt Jef. Nice town. Too bad they sited their power plant in the harbor.
Next you can check out Northport and Huntington and maybe anchor inside of Eaton's neck for a lunch stop. Great spot. You can anchor far out at NPT or pay for a transient mooring... or tie over night at the town pier... cheap. Super town lots going on there. Copenhagen Bakery is fabulous...
Next Huntington... transient moorings only IIRC.
Next Cold Spring Harbor and Oyster Bay. CSH is nicer to stay on the hook.
10 miles across the sound is South Norwalk... and the islands where you can anchor...
Then you might want to visit port Washington after rounding Sands Point... or anchor off (or rent a mooring at City Island.) The west side you can see the Throgs neck and Manhattan beyond.
Plan you run down the East River... You have to go in a fair or slack tide... There are a few docks on Manhattan and in Queens if you want.
Then you sail out of NY Harbor to the Atlantic and back to the GSB. Maybe anchor in Staten Island (never done it).
You can use Navionics on a mobile device... works fine.
Just wanted to check in and thank you all again for all your help with what became an epic adventure for my girlfriend and me! Here's a summary of our trip:
We left the dock in Babylon last Saturday (8/28) evening, sailed out of the Great South Bay, and spent the night at Sore Thumb- a small anchorage just inside the inlet. We left Sore Thumb Sunday morning just after sunrise and exited Fire Island inlet with an outgoing tide in super calm conditions. The wind, as RobGallagher predicted, was out of the east at around 5 knots as we were leaving, so we motor-sailed for the first few hours until the wind shifted and picked up a bit out of the SE. We originally planned to stop for the night at Shinnecock Bay, but as we approached the inlet, the wind was too perfect to stop sailing and the forecast for the next day called for practically no wind, so we decided to sail straight through the night to Block Island. Best decision ever! We sailed under the milky way and shooting stars with a beautiful 10-12kt South breeze for the entire night until the wind completely died between MTK and Block. We motored for the final 10 NM and at around 4am we were in 130 feet of water between Montauk and Block! By first light we were approaching land and entered Block Island inlet to New Harbor just at sunrise on Monday, after 24 hours of sailing. Found a great spot in the anchorage with plenty of room even though it was the most crowded when we arrived. After cleaning up the boat and eating a nice meal, I slept like a baby for a few hours and we just relaxed on the boat for the rest of the day/night. That night, I took some long exposure shots of the stars as the boat was swaying on the hook and they came out pretty cool. The next few days we were able to explore the island a bit, make friends with a liveaboard couple who needed our help changing an anchor light on their 48' Hatteras Trawler, and just relax and enjoy the scenery on the boat. However, on the first day, it was obvious that we would need to cut the trip short and head home early due to TS Hermine approaching. The forecast for Thursday called for rain and light winds in the morning, but clear skies and steady northeast winds gusting to 15kts with east swell for the evening and through the night into Friday. So, we decided to sail straight home through the night and it was unbelievable
!! I couldn't have asked for more favorable conditions! Fair winds and following seas!! I reefed the main and used my 130 jib for the entire ride and it was a delightful sleigh ride! I was averaging 6.5kts for a while and even hit 7kts at one point which is a record for me and my boat! The thrill of the ride kept me awake through the night, but the toughest part was the period between 3am and 5:45am (first light). Once the sun rose and warmed us up, we were greeted with schools of dolphins jumping next to and all around us! The steady offshore winds and following seas made for a fast and smooth ride home and we actually made it back to Fire Island inlet 6 hours ahead of schedule! Took us 24 hours to get to Block and only 18 hours to get home which was nice and all, but I was hesitant to enter the inlet during an outgoing tide. I was ready to just sail around and kill time for 3 hours until the tide turned, but I figured the strongest time of the current has already passed and it would only be a slight outgoing current, so I decided to motorsail in and it worked out just fine
Since we cut the trip short, we decided to spend the night at Atlantique anchorage in Fire Island near the inlet and met our friends on land for some drinks that night. At that point, the joyous feeling of accomplishment had sent in and it was just pure bliss sailing in to my home port.
It was truly an unforgettable experience and I learned so much from it. I will always be grateful for all the help and encouragement I received from you guys on this forum. As a token of my gratitude, I have posted a bunch of photos from our trip for you all to view in this Dropbox link in my next post (#11).
I can't wait to start planning our next sailing adventure and will be sure to reach out to you guys for advice again when I do!