We reached the southernmost point of our eight-day cruise Friday morning. It’s only ten miles from Greenport, but it feels like it’s 100 miles away.
No, actually it feels like it’s 3,000 miles away; it felt like we were traveling to Lake Winnipesaukee in New Hampshire ten minutes after we left Greenport.






This was our first visit to Sag Harbor, but it will not be our last; in fact, it has the potential to become one of our favorite destinations.
Mega Yachts Stacked Like Cordwood
As we approached the Village Marina, we were immediately struck by all the big yachts everywhere!





The last one is Freedom from Newport. It was built in 1926 and a quick search shows it belongs to some sort of fractional ownership group.
It’s not only beautiful, but the captain did a very impressive job exiting and returning to a very tight spot. I made a one-minute video capturing his skills.
As soon as we tied up, Jake and I gave Amazing Grace a good bath using the Unger DI system. It takes a little getting used to, but it really does make window cleaning much, much easier.
The Village Of Sag Harbor
Around noon we ventured into town to explore and find lunch. Unlike virtually everywhere we go, yelp was worthless at helping me find a place to eat.
We ended up at Lulu which was wonderful. When I looked it up on Yelp, I figured out why. Lulu is clearly a 4+ Star restaurant, but Yelp has it as a mere 3.2 (out of 5.0). I’m sure all the negative ratings were due to costs – Sag Harbor is a secret getaway for celebrities and billionaires and menus are priced accordingly.
Lulu
I also knew Yelp was off as soon as we started down Main Street and passed dozens of great-looking eateries. We started a short list of spots we might try, but as soon as we saw Lulu we tore up the list and grabbed a table.




Our server was a young German named Andre. I asked him if he had a hazy IPA and said “Oh yeah…”

He said what it was called, but I didn’t hear him. It was luscious and very hazy.
The Food
As mentioned earlier, a lot of the menu prices were astronomical.
DURYEA’S LOBSTER COBB SALAD (3PP) 97.00
GRILLED CHICKEN SALAD 38.00 “Cooks Venture Pasture” raised chicken breast, Gem lettuce cobb salad.
That said, I quickly spotted a true bargain…

I grew up digging quahogs and eating them like oysters on the half shell. Many restaurants offer Little Necks, which are so small that we’d have buried them again if we dug one up.
Topnecks, on the other hand, are the size of a plump oyster and we always considered them the perfect-sized quahogs. The only other place I’ve found them is Benjamins in Newport.
Here are some of the other delicious dishes we enjoyed:

GRILLED BROCCOLI SOUP – $15.00

8oz house mix (short rib & chuck), cheddar, Heirloom tomato, Gem lettuce, house-made rosemary brioche & fries

grilled baby artichokes, zucchini, bell peppers, tomato confit, pickled burned eggplant, shaved radishes, whipped tahini

Chives, house salad, Fontina cheese
Everything was wonderful and the open-air vibe really worked on the glorious late August day.
After lunch, we did a little shopping and general sightseeing.




This was our fifth day in a row exploring quaint seaside villages. Around Watch Hill, Jake said: “95% of these stores are women’s clothes”, and he was right.
Not so in Sag Harbor! Maybe 50% were women’s clothing and the rest were the kind of eclectics I love.
The first one I visited was called In Home.

Ironically, the owner’s name is David, and the younger fellow working for him is named Jake. David told me he’d been in Sag Harbor for 29 years.
The store has an endless supply of home goods that you would seldom see anywhere else.



Papi’s Booty
My second stop was the old-school 5 and 10-cent store.


When we were in Maine, I came up with an idea to treat our grandkids. I call it Papi’s Booty (they call me Papi and Booty refers to a Pirate’s Treasure Chest.)
As we travel, I buy little toys and games to fill a wooden box (treasure chest) and when the grandkids are here playing games, the winner gets to pick a prize from Papi’s Booty.
Another interesting sight was this miniature car gallery.


They sell exact replicas of classic cars that are about 50% the size of the original. They drive like the original and cost $125,000 each. Clearly a toy for the children of billionaires.

Back on the Skydeck, we enjoyed our first Bluebird Day with gentle breezes and temperatures in the high 70s.
As much as I wanted to try dinner at Page Sag, it was too nice an evening to leave the boat and we decided to eat onboard.
Getting DoorDash to deliver to a boat in a Marina is always challenging. My technique is simple.
- Locate a business very close to the marina and copy the address.
- Use that for the delivery address.
- Put an average tip on the order and then add a note to the driver explaining where we really are and promising a $20 cash tip if he comes and finds us.
I’m not sure what a DoorDash driver makes, but thus far, it seems they’ll walk through fire for $20.
Needless to say, he found us and we enjoyed a tasty meal from Fierro’s Pizza:

After dinner, Mrs. Horne and Peggy struck up a conversation with the couple next to us.

Their names are Stacey and Todd. They have a beautiful East Bay 60. Todd told me it’s basically the same boat as the Grand Banks 60 without the flybridge.

Interestingly enough, they are friends with Dave Northrop (President, Maritimo Americas) from his Grand Banks Day.

We almost caught the warm sunset.
This morning looks like a great day for the 70-mile run to Wickford.

I think Sag Harbor is a true gem and ill plan on skipping Greenport next time to spend 3-to 4 days here!
Next Up – Wickford, Rhode Island

Sag Harbor will dent the CC. Beautiful spot, Todd and Stacey are a special couple and family, great to see them enjoying their boat. Also a U of M Grad. – Go Blue.