Thanks to all for the help. We got home last night after two weeks out. Here's what we did.
Day 1 - provisioning in RI, helping friend ready his boat to join us around week 2.
Day 2 - RI to Dering Harbor on Shelter Island. Longest cruise up front to get things going. Head current for much of it, so it took nearly 10 hours of beating into the wind/current. Moorings were $95 per night!! It was worth a visit, but I doubt we'll go back. People were nice and friendly. Well protected cove, except for northerlies.
Day 3 - Stayed on mooring in Dering, but took the dinghy over to Greenport and toured around Sterling Harbor. Greenport is a nice little town worth visiting. The famous Prestons chandlery is a bit over rated, but still worth browsing. I can occupy myself in just about any chandlery or hardware store.
Day 4 - Shelter Island to Three Mile Harbor. Circumnavigated Shelter Island in 20 kt winds with gusts near 30. Current runs pretty strong on the south side near the ferry. We skipped Sag, as the winds were staying up all night and wanted more protection in the harbor and we've been to Sag before.
The harbor is huge, but you need to cruise to the western side to get any protection from prevailing wind.
Day 5 - stayed in the harbor for a night, just to relax. We walked to East Hampton for exercise (3 miles away, that's where the harbor got its name). We were not impressed. Its just showy, with little to be showy about.
Day 6 - Three Mile Harbor to Fisher's Island West Harbor. Expected light winds, but got 15 kts on the beam and rocketed to FI in two and a half hours. Anchored in West Harbor, which has plenty of room and great holding. Took dinghy to Yacht Club, which has a bad reputation for guests, but couldn't have been nicer to us. We asked if they had a transient slip available for the following two nights and they did. Fixed dock, but water and power were welcome at $3 per foot.
Day 7 and 8 - Stayed in slip at Fishers Island. Family took the ferry to meet us there, as we used to vacation on the island as kids. Ran around to see the old sights, BBQ, lobster, all the old traditions. Picked up my daughter and her friend to come with us for week two.
Day 9 - Fisher's Island to Cuttyhunk. Cutty is a very familiar place for us. Great stop over or day trip. We used it to rendezvous with a friend to flotilla for the next week.
Day 10 - Cuttyhunk to Edgartown (Martha's Vineyard). Great weather, but made a big mistake. Slept in at Cutty, went back in to town with kids, then decided to look up the current through Vineyard Sound. Right on the nose all afternoon and it can be a brutal 3 knots. No wind and we had to motor the whole way. It took over 5 hours. Again, met more friends on the Island and had dinner. Edgartown is a great harbor and the town has plenty to do. Wish we had stayed longer.
Day 11 - Edgartown to Nantucket - Another long day with little wind. Planned to get out in time for favorable current, but getting everyone going was slow and we hit it again. Not as bad as prior day and we have a three day mooring reservation, so we know we'll just kick back once we get there.
Day 12 and 13. Very relaxing time, saw July 4th fireworks from boat in mooring field. We thought they might be too far away, but they were great. The best place to watch is about a mile from the dinghy dock. The thought of walking back at 10 pm with all the crowds was unappealing.
I have to say that Nantucket offers a lot, if you can get there. Moorings were $75 per night, but seemed to be in very good condition, with adjustable anti-chafing. A skiff meets you in the channel and escorts you to your mooring. Then another comes along with literature on the island and everything you need to know. Pump-out boat is very responsive. Everyone was very friendly. The launch is the only thing that will really get your attention, it is $5 per person each way. Not owned by same people. We took the dinghy.
Day 14 - Nantucket to Cuttyhunk. Again, our standard layover. Better current this way. It took less time than getting to Nantucket from the Vineyard and it was nearly twice as far.
Day 15 - Cuttyhunk to RI. This was the first day in two weeks that we saw seas over 2 feet. Some of those calm seas came with calm winds, but this day's were only 3 to 4 feet and occasional 5 feet. Reasonable seas with good wind to sail home on last leg.
All in all, we liked the Cutty, Vineyard, Nantucket tour much better than Eastern Long Island. We probably won't return to Gardiner Bay on Long Island anytime soon, but it was worth poking around.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.