We first started doing the Island Tour six years ago. The idea was simple: visit the southern islands of Massachusetts on the historically hottest weekend of the summer.
In 2022, we expanded it by creating the Cuttyhunk Progressive Dinner and inviting the Flotilla on the Island Tour.
Not only does the tour bring a group of good friends to the coolest islands in southern New England, but the marinas involved have low dockage fees for midsummer and decent cancellation policies:
- Menemsha: $3.50/ft – 48 hour cancellation
- Cuttyhunk: $4.50/ft – 7 day cancellation
- Oak Bluffs: $6.00/ft – 7 day cancellation
The trick is you really need to mark your calendars and book these Marinas the day they open for booking on Dockwa.
- Menemsha – 5/1 @ 11:00 AM EST
- Cuttyhunk – 1/15@ 8:00 AM EST
- Oak Bluffs – 2/1@ 8:00 AM EST
I mention this because the Flotilla would have been much larger, but many members didn’t attempt to book until May, and every weekend was sold out.
Menemsha
The forecast for this four-day cruise could not have been better: light winds, relatively low humidity, and temperatures in the low 80s.
The ride over was silky smooth. Just as we entered the channel, I heard a guy on channel 16 report the sighting of two killer whales a mile offshore.
This weekend, we had a new guest: Carol, Mrs. Horne’s childhood friend.
Although I had confirmed a bulkhead dock for Menemsha, it turned out to be a very tight spot that required me to parallel park all 100,000 lbs of Amazing Grace.
Menemsha is a beautiful little boat basin, but it’s far more popular than its 16 dedicated transient slips can accommodate. I literally set my alarm clock to book this slip on May 1st.
The dining options in Menemsha are pretty limited. There’s take-out from the various fish houses and The Galley. I had a very pedestrian Crab Cake sandwich from the Gallery last year and suggested Peter, and I collaborate on lunch aboard Amazing Grace,
Lunch On The Barbie
One feature of all Maritimos is an electric flat top built into an outdoor kitchen just off the swim platform.
The fact that it’s electric proved key since Menemsha doesn’t allow gas grilling.
Peter made smash burgers and I did a cucumber pickled salad and smashed potatoes for sides.
We are still experimenting with the temperature settings and cleaning protocol, but it’s an excellent addition to the onboard galley.
Of course, everything was excellent, with two culinary powerhouses at the Barbie. I made the Pickled Cucumber Salad up on-the-fly, but it’s definitely a keepa from now on.
The transient slips in Menemsha are about 100’ from their beautiful town beach. We planned to go to the beach, but it was getting hot, there was no wind, and the greenhead flies were lurking everywhere.
Surprisingly, there were none on the Skydeck. I’m guessing they don’t fly that high. Add it all up, and we spent the afternoon near the beach but not on it!
Around six, we headed to Homeport for dinner.
There is a shortcut through a few backyards, but it does involve a steep hill.
Homeport Restaurant
The Homeport is a little like The Chartroom. It’s iconic, and it has some great dishes and some of which you might want to avoid.
When we sat down, we were delighted that Spencer from South Africa was our server, and Spencer was even more excited that I remembered him after six years.
It’s quite a feat for Spencer to be working at Homeport six years later. In 2020, Homeport closed due to COVID restrictions barring foreign workers.
Then in September, the owner – Will Holtham died.
Meanwhile, the labor shortage in 2021 and the lack of affordable housing on Martha’s Vineyard kept the restaurant closed until 2022.
When Homeport finally reopened, it had a whole new look. There was an oyster bar on the deck and a brilliant Prix Fixe menu.
Chilmark is a dry town, so make sure you bring your beverage of choice.
There is a nominal setup charge for corkage and glasses.
Since there were seven of us, we sampled a great cross-section of the menu.
Jalapeño Lime Slaw, Remoulade Sauce & Lemon Wedges
Soft Shell Clams, Aromatics, & Drawn Butter
Cucumbers, Butter Beans, Tarragon, & Dijon Vinaigrette
Island Succotash, Truffle Corn Emulsion & Sweet Basil
Drawn Butter, Baked Potato, Summer Corn, and Slaw
Vanilla Ice Cream
Whipped Cream, Zest & Sea Salt
BURNT S’MORES CHOCOLATE PIE
Milk Chocolate, Torche Fluff & Crushed Graham
Most everything was great. The steamers and scallops were perfect, as were the desserts. Everyone loved their lobster, but mine was about a minute underdone (dark green, wet tomalley), and Peter wasn’t crazy about having his hot Salmon presented on a cold summer salad.
The Homeport is a must-do if you’re staying in Menemsha. Of course, it’s even better on a perfect midsummer evening.
Saturday – Cuttyhunk
The short ride from Menemsha to Cuttyhunk allowed us to cruise at a leisurely 15 MPH.
We docked at the town wharf and decided to try some of the local pop-ups for lunch.
I’ve been hearing about The Godnold Grill on the Cuttyhunk Chatter Facebook page, so I was excited to try it.
I wish I could tell you it was great, but sadly it was not.
Not only was my linguica overcooked, but none of the sandwiches were prepared the way we ordered them
I ordered a linguica dog loaded with bacon, cheese, and onion on a toasted bun.
Instead, I got a plain burnt split dry linguica dog on a cold bun. We have mustard and relish onboard, but even that could not make this meal edible.
Similarly, no one got exactly what they ordered.
The Cuttyhunk Progressive
Although we planned a progressive, Jon was making lamb chops, and I was doing tacos and Elote, so we thought we’d do everything on Amazing Grace, where we could comfortably serve nine.
At 4:00 I served a few appetizers…
We’ve only known Rick and Christine for a few years but may never see them again. They decided to sell everything, get on board their 40’ Sea Ray, and spend the next ninety days cruising to Charleston, then figure out what to do with the rest of their lives—amazing.
The evening was perfect for a cocktail party on the Skydeck.
Around 7:00 dinner was served.
Oak Bluffs Sunday
It’s about 25 miles from Cuttyhunk to Oak Bluffs. Our slip wasn’t scheduled to be available until noon, so we once again departed at a leisurely pace.
We arrived in OB around 11:00 and decided to try bow-in docking for a change. The vibe from Skydeck is dramatically better than backing up to the parking lot.
I suspect we will do this from now on, but the finger pier is only 60’ long, so we cannot get the e-bikes from lazarette.
Edgartown Bound
Mrs. Horne was looking forward to a bike ride to Edgartown, but it was not in the cards. I pointed out that taking the bus would likely result in 2-3 miles of walking on either end, so we headed up the hill to the bus stop.
MV Transit still uses old-school ticket vendors at every major stop. In OB, it’s Debbie, and she is a hoot.
I sat on the left side of the bus and created a short video of leaving OB along the way to Jaws Bridge.
The Atlantic
Of course, we had to visit our favorite restaurant in Edgartown.
The timing was perfect as we watched the end of The British Open at the bar.
After lunch, we stopped at Portabella Road for a bit of shopping.
After another fun bus ride back to OB, we enjoyed some serious people-watching from the Skydeck. Oak Bluffs in the summer is absolutely nuts with boats rafting, people swimming around the moorings, and people jumping off of flying bridges.
And yes, naps were also involved!
Mikado OB
Of course, we also had dinner at my favorite restaurant in Oak Bluffs with Doc Ruel, Joan, and Jean.
Mongolian Beef – $20
As always, everything was prepared perfectly. Although it was owner Kevin’s day off, he was there keeping an eye on things.
We considered the Ritz for the Holy Rock and Roll Revival, but at 8:00, the stage was empty.
Instead, we returned to the boat, enjoying the gorgeous midsummer evening.
Hadley’s Gunkhole
Monday was a splendid day to be on the water, so we waited until 11:00 to depart and then proceeded to Hadley’s for our first Gunkhole Lunch on Amazing Grace.
I wanted to go through the entire anchoring process on the new boat and, in particular, test the hold and the ratio of Rode to Depth.
Relentless had a rode that was about ten feet of chain and the rest 5/8” line. I’m not sure why the original owner did that, but it was very flakey. If we’d kept her, I think I would have replaced it all with chain.
I let out 50’ of chain in 10’ of water and set the anchor with a burst of reverse throttles. I marked the spot with a waymark on the chart and watched it fit for ten minutes.
We never slipped, and I joined the crew on the Skydeck for a cold one before lunch.
The wind direction gave us a perfect view of Buzzards Bay with shade on the hot and humid afternoon.
Meanwhile, I whipped up Carnitas Tacos for the crew.
When we pulled the anchor, Mrs. Horne and Peter discovered a giant grass and mud ball on her. They then spent about twenty minutes surgically removing the mudball with a boat hook.
The chain went almost straight down off the bowsprit, so I probably didn’t need to reverse the engines to set the anchor with our all-chain rode.
I’m not sure we’ll anchor there again anytime soon.
The ride home was increasingly choppy, and when we entered the Cape Cod Canal, we were surrounded by six-foot chop.
Next up – Family Time!
Our daughter and her family are coming to town on Friday. They are very private when it comes to social media so we will have limited reports for the next two weeks.
Glad you like “nose-in” in Oak Bluffs. We prefer it to give us some privacy from the sidewalk and it also gives a good view of the harbor (people watching).
Yes, but the finger pier is too short to get the bikes out of the lazzerette!
Classic New England cruising stops. Good fun, good food (for the most part). If you dock in Pt. Judith, be SURE to go to the Matunack Oyster Bar. Incredibly good seafood, killer key lime popsicle dessert.