• Mobile App For Android Now Online!

    Download it here. The app is searchable in the Google Play Store under Sailboat Owners.

    Sorry iPhone/iPad users, we are still waiting on Apple. :(

    Click the X in the upper right corner to make this go away

Overnight Trips From GSB, Fire Island NY

Jun 11, 2020
Hunter 29.5 Northport
New sailor (Catalina 25) in the Great South Bay of Long Island. Does anyone have any recommendations for overnight trips from GSB? Is it terribly difficult to get out and around to Sag Harbor? NYC? Obviously we can do some overnights in marinas along Fire Island, but would like to go beyond that.

Next year we will move her to the LI Sound closer to where we live which will obviously open up a lot of options. But would like to get in some overnights this year.

Oct 22, 2014
CAL 35 Cruiser moored EVERETT WA
Hi @kjdoyle1 . Welcome to the Forum.
Congrats on your Catalina 25. Nice boat.
I guess your "New Sailor" identity causes me pause to say "Go for it"
What is the worst that could happen? I think it was Captain Ron who stated "If it is going to happen, It's going to happen out there..."

Perhaps you might want to test the waters before jumping into the deep end. I suspect that the boat (if in a sound condition) will be capable of handling the waters beyond Fire Island Inlet, I have no idea if you are capable. It will be different sailing in the ocean than sailing in the bay. What is the worst weather conditions have you sailed your boat in the bay? In the ocean it can be 5-10 times worse. Then there are days when it can be like a big bathtub.

How are your weather skills? Can you predict the weather? Captaining a boat out into the ocean means you want to know the tides, wind and sea state before you go and how long it will be nice so you cansafely get home before any change.

Fortunately you can give yourself some tests. Sit at home on a Thursday and looking at weather charts identify the tide and currents at Fire Island Inlet. Check the winds, sky and general sailing weather conditions for the bay, inlet and coastal area 5 miles on either side of the inlet.
Then on Saturday go for a drive and see if your Thursday predictions were good. You can drive across the Inlet on the Fire Island Inlet Bridge. Spend a day on the Beach checking out the ocean, have a picnic at the Robert Moses Tower and validate your weather planning capabilities.

Next step is to do a Thursday plan and then venture out the Inlet in your Catalina 25. Of course you'll ask the CG Auxiliary too Inspect your boat before you go, getting a 100% on the "Vessel Inspection". Acquiring any missing safety equipment recommended during the inspection. The Inspector is usually an accomplished boater and you can ask the inspector what are their experiences out in the ocean.

Then proudly sail out the inlet into the ocean and return through the inlet back to your home port, a day sail.

As your confidence builds there are other bays on the East side of Long Island that you can possibly explore. Moriches Bay (28NM), Shinnecock Bay (41NM) to the north of Fire Island Inlet. Note from outside the inlet at 5 knots boat speed they are 5.6 hours or 8.2 hours of cruising from the ocean marker for Fire Island Inlet. This would mean the first would be one day and the second would be 2 days of focused cruising each way. That is why testing your weather planning skills becomes critically important.

Looking forward to hearing about your adventures on your Catalina 25.
Jan 22, 2008
Hunter Catalina 400 PORT JEFERSON, NY
When I returned to sailing, I sailed a Macgregor 26 out of Patchogue on the GSB. First sails were to the Connetquot River, The Sore thumb by Gilgo, a trip into Morriches Bay and Shinnecock Bay and thru the canal into the Peconic. NYC may be a long haul in the best of circumstances( fuel, weather) but is do able. Start with small steps, gain confidence.

Alan J S/V Skol C400 #130
Dec 19, 2006
Hunter 36 Punta Gorda
Hi hope you enjoy your new to you and I sailed LI Sound Peconic and great South Bay with a Hunter 29 for many years living LI and your boat is smaller so just always check weather before going out and a few times got caught out when weather changed.
I also sailed to Block Island and moved up to Hunter 36 and sailed to Florida where I now live and sail many times to the Keys.
Weather weather always check weather before going out sailing and keep a eye on the weather and my wife
does not like bad weather and she will not go sailing with me if she is scared.
We go out here in Florida for 3 weeks at a time

Last edited:
  • Like
Likes: jssailem


Jun 2, 2004
Island Packet 31 stony point,ny
For years i sailed long island sound and to newport and block island on a catalina 25. If the weather report was iffy as it often can be in the summer, we stayed where we were either at anchor, a mooring or a slip. Other than that the boat was pretty comfortable and sailed well. We looked forward to the trip every summer. One year my foul weather pants were home in the garage- that was a very wet day on the water!


Dec 1, 2009
Sabre 402 Southport, CT
We plan cruises based on us averaging about 5 knots and sailing about 6 to 8 hours a day to keep the crew (me included!) from getting tired and cranky. This is on a J/36, a relatively quick racing sloop. This means we plan hops of 30 to 40 miles each day. A Catalina 25 might average 4 knots - and possibly less, because of the wind and current- so you might want to figure out destination harbors 20 to 30 miles apart. From East Islip to Montauk is about 90 sailing miles, and the "hops" you might make en route involve getting in through inlets that can get really nasty and be dangerous in bad weather (note insistance on checking weather in other posts). Taking weather into account, It might take you three or four days to get to Montauk, and another to get from there to Sag Harbor. This year might be good for to exploring the Great South Bay and venturing into Moriches Bay, while saving Sag Harbor, Greenport and Shelter Island for next year.