Routes/stopovers new rochelle, ny to sag harbor ny

[GreggL]

Planning my first trip of this length. Looking for a route and some stopovers from New Rochelle, NY to Sag Harbor, NY. Have about two weeks off in August to do this and am planning to stay in Sag Harbor for the majority of it. The sailing time for my speed and energy seems to be about 3 days each way so I have plenty of time to explore along the way.
Any great or must see destinations to stop overnight? Slips at marinas are preferred, I don't trust my anchoring for overnight stays yet.
Thanks!

[chef2sail]

Not a lot of Mainas and they are expensive, save your bucks for Sag. It's beautiful

Their but expensive for a slip. Make sure you stop at Schivonnies for provisions there. On the LI side we stop at Port Jefferson- Seatauket yacht Club for a mooring. Next creek out is Mt Sinai and the Mattiuk Inlet. Certainly doable for you. We also have stayed at Greenport City Marina-nice place.

On the Ct side, there are many nice moorings and marinas. Old Saybrooke, Mystic, for marinas. Fishers Island for moorings or anchorages. Many of the mooring files have water taxis if you don't have a dinghy.

We will be leaving the Chesapeake on August 15 and cruising the Sounf about the same time as one of your weeks. maybe we can share a beer or bottle of wine.

Dave

[Billberner]

If ur looking for a 3-4 day trip each way and you want slips rather than moorings, id suggest a ct route in 1 direction and long island in the other.
Actually I'd suggest that whether mooring or Goin dockside.
On the ct side I would go for southport ct on night 1 at Pequot yacht club. Beautiful club that takes transients. Beautiful location.
Night to, I'd go for Guilford yacht club. Again a great club with good facilities and another great spot.
Then you can jump across the sound and go straight to sag or stop at orient if current timing at plum gut makes it more sensible to make a last stop

[GreggL]

Thanks for the input, going to check those places out.

[Billberner]

The long island sound side:
Matituck inlet
Mt Sinai harbor or port Jeff
Old spring harbor or oyster bay

If you have an extra couple of days make the jump to to Block island great salt pond. You can do it from Guilford then great salt then peconic bay or vice versa

New Rochelle to southport is a pretty good haul. If you want to shave some miles off that day, there a 3 places in Westport. Town marina that takes transients at compo beach, saugatuck tact club, or cedar point yacht club.

Even oswe is zieglers cove in Darien. Moorings are private but no one minds if you pick one up. Crowded in the day on weekends, but empties out by evening. Pretty spot. Keep an eye on your chart, gps, and depth sounder o. The way in and out.

Good luxk