If you surf Dockwa, you’ve probably noticed that there are two venues offering slips in Edgartown – The Harborside Inn and The Edgartown Harbormaster.

Occasionally, I’ll use The Harborside on a day trip, but it’s very expensive ($245 for lunch – $672/night) and there is no power or water at the dock.

That leaves The Harbormasters Slip. Or should I say slips, because there are exactly two!

These are great slips located amongst the finest real estate on Martha’s Vineyard with great services and a reasonable price – $6/foot or $300 minimum no matter when you book.

With just two slips in one of the most iconic harbors on earth, you might imagine they’re a little tough to get.

And you’d be right…

The first time we stayed here was a lousy Sunday and Monday night and I’m fairly certain the original slip holders must have cancelled due to weather.

Last year, I leisurely went online on the morning of February 13 and every summer day was already taken (we ended up with a late June date).

This year, I marked my calendar for February 13, set my alarm clock of 7:00 AM PDT, and booked 7 nights. I got four nights for Labor Day weekend and 3 for the last weekend in July, which is the subject of this report.

The Harbormaster’s Slip is located a short walk from downtown…

It’s an unusual spot in that it’s away from the action on Main Street and actually sits in a neighborhood of spectacular homes.

New England’s Finest Neighborhood?

There are plenty of great neighborhoods in New England, particularly in and around the south coast. Being avid bikers, we’ve seen them all, but I think this end of Edgartown may well be the prettiest…

Although the side street the slip is on is a quiet neighborhood, the waterfront is anything but. I always dock bow-in to give us a perfect view of the Chappy Ferry, Seafood Shanty, and the harbor…

Our Weekend Adventure

Once we booked this magical slip, the question was, “who do we invite to join us?” It’s an incredible slip in a priceless spot, but it’s not a marina and after the Harbormaster’s staff goes home at 5:00, you’re pretty much alone – so it’s a good idea to bring your own fun!

It didn’t take long to decide it just had to be Gary and Amy…

Amy and Mrs. Horne

Gary was the one who first talked me into taking The Mean Kitty directly to Edgartown (rather than mooring in Oak Bluffs and taking the island bus.) It was also Gary who discovered the Seafood Shanty – a place I’ve eaten at at least 50 times since…

The Seafood Shanty (of course…)

It took Gary all of 5 seconds to suggest we head over to The Shanty for lunch.

The new normal at the Shanty isn’t much different than the old normal. You now check in downstairs and the tables are a little more spread out…

Of course, I had to order my favorite dish – Shanty Wings…

Shanty Wings

I’m a bit of a wing snob, I like them fried crispy, no breading, hot – but not diablo, and not too wet. The Shanty’s wings never disappoint!

Like many busy downtown areas, the Edgartown city elders have declared downtown a Mandatory Mask Zone. Not being a big fan of mild suffocation, we skipped our typical stroll in favor of an afternoon on Vigilant’s aft deck…

As we were lounging about, Captain Dave Hogan walked by and introduced himself…

Dave owns Elysian – a Sabre 48, out of Plymouth. He’s a regular fan of My Buzzards Bay and we’ve chatted many times on the Sabre Back Cove Facebook page, but this is the first time we’ve met face to face.

A Brown Bag Dinner

We had had a big lunch and we were planning a fancy dinner Saturday, so we opted for a light dinner on Friday night.

These days you never know what to expect in terms of Covid 19 protocols and safety service changes in restaurants. Right after restaurants reopened, everyone was taking reservations – even for cocktails and appetizers. But in Edgartown, all but the high end establishments seem to be back to walk-ins.

It was a hot day and we decided we wanted to eat indoors with a little AC. I called The Newes and the manager told me we’d have no trouble getting seated before 6:30, so that’s where we went.

The Newes is a nice alternative to the seafood restaurants and the high end restaurants in Edgartown. It’s good honest gastro pub fare, cold draft beer, with a friendly staff…

Sure it’s a tad dark, but that also makes it feel cool on a hot July night.

Our light dinner was great, but I didn’t take any photos because “the presentation” was so bizarre. All of our appetizers and entrees were brought to the table at the same time in a huge brown paper to-go bag. It was up to us to dig in, figure out what was what and who ordered what.

I’ve eaten in dozens of restaurants during the Covid era, but this was the most extreme protocol I’ve seen yet. Oh yeah, all the drinks came in plastic cups!

Still, the food was great…

Good Morning Edgartown

Saturday arrived being even more tranquil than Friday. I had done some research and discovered that Edgartown Bicycle rented eBikes and I reserved four for 9:00 AM.

eBiking Chappy

I did a full review of Edgartown Bicycle – click here to read.

Mrs. Horne has become quite adept at eBiking and showed Amy the ropes…

We headed across the Chappy Ferry and out to the Wasque Preserve and the Teddy Kennedy Bridge…

Petrified Trees
The New Bridge
The Scene of The Crime

It’s actually called the Dike Bridge and it’s sole purpose is to provide access to East Beach which runs north to Cape Poge…

The hearty can park their bikes and walk, but these are huge dunes and that’s a lot of work. I noticed a lot of jeeps heading over the bridge and did some research.

East Beach by Jeep

Locals have always been able to take jeeps out on East Beach and 5 years ago, the local operators of Avis/Budget secured the rights for rental customers to do the same.

In order to drive a Jeep on the beach, you must reduce the air in the tires to 15 pounds and purchase a permit. It’s not exactly cheap, but on par with what we paid to do the same on Nantucket.

I just booked a Jeep for when we visit in September. It’s fairly straight forward…

1. You can rent a Jeep at A-A Island Rentals.

2. You need to purchase an Over Sand Vehicle (OSV) permit from the Wasque Trustees online.

3. Pick up your permit at the Mytoi Gardens where you can reduce your tire pressure and reinflate upon your return.

We carry beach chairs and umbrellas on board, so it’ll just be a matter of packing lunches and perhaps a few cold ones.

UPDATE: The rental agent thought that The Trustees weren’t allowing rentals inside the preserve. I contacted them and he was right. I just got this from The Trustees:

The Trustees do not allow rental jeeps on the beach. Our governing committees decided many years ago not to allow for-profit companies to utilize the non-profit owned and managed beaches for commercial gain. That policy is also in keeping with the Edgartown By-Law which precludes commercial businesses from using lands on Chappaquiddick and Norton Point beach.

Although we didn’t venture out on East Beach, we did make a rather lengthy trek from the Harbormaster’s Dock to Lighthouse Beach with chairs, umbrellas, and a light cooler.

Mrs. Horne, Gary, and I lounged and watched the scenery, while Miss Amy ventured in and out of the water…


It was quite a nice spot, but Amy said it was a bit rocky on her feet. It may be a little far to walk on a hot July day, but probably very pleasant in the spring or the fall.

As we returned to the boat I heard someone call out “Hey Dave” and turned to a younger couple with a dog…

John, Izzy, and Amy

Turns out it was John Hanzl, another fan of My Buzzards Bay and Facebook friend from the Sabre/Back Cove group.

John and Amy are serious boaters having taken the trip from Florida to New England in their Sabre 42 Sequel


John named her Sequel because he decide to take up boating rather than write the second book (Sequel) following his first thriller Out of Hell’s Kitchen

Dinner at E’ETOILE

As you may know, I’m not a big fan of fancy (expensive) dinners while cruising, but I do like to indulge now and then. Saturday night we did and chose a wonderful old French restaurant on Main Street.

I have already published a full review (click here to read), but I’m happy to report that the entire experience was a pure delight.

Here are a few photos of our spectacular meal…

Bye Bye Vigilant

In case you didn’t hear, we sold Vigilant…

It all happened a little too fast for us, but we love the new owners (Mattapoisett Townies), and our new boat – RELENTLESS, will be arriving in a few days.

Stay tuned for the next couple of stories about selling Vigilant and buying Relentless.

Meanwhile, here’s the view from my final approach into Mattapoisett on Vigilant 😢…