There is an old adage – If you want to make God laugh – Tell him your plans!

After decades of boating on Buzzards Bay you’d think I’d learn that you really can’t make plans for boating, but I still do.

Due a mass of weddings and other family commitments, we have a bunch of one-day weekends where only Saturday or Sunday are available (but not both). This means that we only have one possible day to take our working guests out on Vigilant.

In case you missed it, this has not been a very good summer weather-wise. Sure, we’ve had plenty of beautiful days, but a lot of messed up weekends with one nice day and one marginal one – like last Saturday. And of course, Saturday was our boating day.

We all had a great dinner Friday night at The Brew Fish in Marion and discussed our options for Saturday — I told everyone that we wouldn’t just have a Plan A and a Plan B, but Plans A through D!

Plan A – It looks decent in the morning, the forecast calls for improvement and we go somewhere for lunch by boat.

Plan B – Not so nice in the morning; we eat at home or at The Inn at Shipyard Park and then if it looks good, go out for an afternoon of boating.

Plan C – Start with Plan B and if it’s still not good after lunch wait and go to The Chartoom for dinner.

Plan D – Fagettabout boating and stay home, play cards, and make some music.

I can hear God belly laughing in my head as I’m laying out all these options.

It’s Plan A!

I watched NECN weather at 5:00 AM and looked out the window to see clouds breaking. It was much lighter out towards the Islands and as our house full of guests awoke, I told them we were going for Plan A with a 10:00 AM departure. The destination was still unknown.

As the morning went on, I started checking my weather app for Sandwich, Newport, Martha’s Vineyard, even Nantucket. It was clear that the sun would be be emerging on the Vineyard or Nantucket first, so once at sea, I used my special captain prerogative and made Martha’s Vineyard our destination.

I was thinking Black Dog Wharf to test out Vineyard Haven serving liquor starting June 16, but a quick call to the Black Dog revealed they couldn’t take a 45′ boat until 2:00, we we diverted to Edgartown.

The Harborside Inn

With 8 passengers, moorings and launch service can get pretty pricey in Edgartown so I decided to give the Harborside Inn a try. It’s a great place to tie up, but it’s expensive ($75 plus tip) and you never really know if you’ll be able to get in until you get inside Edgartown Harbor.

harborside edgartown
Harborside sits just behind the Edgartown Yacht Club

Barry Harborside
Barry The Friendly Dockmaster
Although you can call the Harborside (508-627-4312) and reach the Dockmaster Barry at extension 117, I don’t think he’s ever answered the phone for good reason — he’s almost always out on the dock helping people.

He does come in quickly if you hail him on Channel 10.

I’ve found that the issue at Harborside isn’t dock space, but rather the limits in how many boats Barry can handle at one time – ONE.

I frequently get “sit tight and let me look around and figure out where I can put you” when I reach him. Of course by then, we’re already past the Edgartown Yacht Club and we can see Barry scurrying up and down the dock.

Although Harborside is a fixed dock, it extremely well padded and I never bother with fenders. Barry will take your lines and tie you up.

Vigilant Harborside

I like pulling in bow first so we can hang out on the back deck of Vigilant and enjoy the view of Edgartown Harbor before heading in to town.


Harborside Gate
The dock at Harborside is literally 300 feet from downtown Edgartown
Another great thing about The Harborside Inn is the location.  The greenery covered walkway from the Harborside exists right next to Backwater and across the street from the Black Dog making it a perfect spot for shoppers who don’t went to lug their purchases too far.

Although my “go to” restaurant in Edgartown is The Seafood Shanty , virtually every guest we bring to the Island wants to stop at the Black Dog Store before leaving.

Of course, we exited right on Main Street, took a quick left onto Dock Street and headed to the Seafood Shanty for lunch and a brew!

The Alex Show at The Shanty

Although it was still a little gray outside, Mrs. Horne insisted on sitting outside. The wait for a table for 8 was a 30 minutes (1:00 PM on a Saturday in July), so we settled for two tables for 4. I spotted 4 bar stools around the back of the horseshoe bar and grabbed them before anyone else saw them.

CB Seafood Shanty
An always happy face at the Shanty – CB
I love the bar at The Seafood Shanty. The doors that go out to the deck open completely “Maui Style” and I think the view from bar height chairs is actually better than down low on the deck.

It was great to see our old bar keep CB and all eight of us huddled around the 4 stools and enjoyed a variety of beverages.

Today’s report is about people not food, but just in case you’re interested, the food was great (you can find a more detailed review in this report of the Seafood Shanty.)

The Alex Show at The Shanty

The servers at the Seafood Shanty turnover frequently, but most are first class. On Saturday, we may have had the best server eva  – a very amicable young lady named Alex.

Alex - Seafood Shanty
Alex – very friendly and smart too!
Mrs. Horne’s sister Janet decided she’d have some fun with Alex and started asking her questions. The first was “some of us are brothers and sisters, can you guess who they are?”

Alex immediately got in the game and gave it a guess. She made a good effort, came up goose eggs, and left to grab our drinks.

Next up Janet said “we’re all couples – can you guess who’s married to who?”

More valiant efforts and another strike out followed by Alex quickly returning with our entrees.

Seeing how much fun this game was going, Janet goes for the trifecta and asks Alex “can you guess who’s oldest, who’s youngest, and put us all in order of our ages?”

This is when I knew Alex was perhaps the smartest server on earth. She said “no, but I have a quiz for all of you – if you can guess the exact amount of the bill, I’ll pay it and you’re lunch will be free.”

I was the closest, but still $10 off. It was great fun and it made it very easy to give Alex an exceptional tip.

Before we left, Alex brought her boss Jeff over to join in on the fun.

Jeff and Alex Seafood Shanty

It was a great day, great food, and really wonderful people. As we left Edgartown and headed to Hadley’s for a 2 hour gunkhole, the sun came out.

Hadley's Sue and Janet
Mrs. Horne and her sister Janet