As you may well know, I love hitting the outer islands this time of year. The marina’s are reasonably priced and the crowds aren’t bad either. When I booked last week’s trip on Dockwa months ago, little did I know that the entire East Coast would be socked in a stifling heat wave.

Not only did we pretty much beat the heat, but we also enjoyed the great company of our old neighbors from California Kay and Steve.

Kay and Steve

Our journey began at Menemsha on Friday, then off to Cuttyhunk on Saturday, wrapping up in Oak Bluffs Sunday. And while OB is on an island southeast of Massachusetts, it is in no way an break from tourists – just the opposite, but it was our destination in 2001 when Kay and Steve joined us for the most harrowing boat trip ever (see Does Anyone Know Where The Love of God Goes…) so in a way we were returning to the scene of the crime.

Day One – Menemsha

The other nice thing about my little island tour is the distances traveled are all pretty short. All three legs were less than 20 miles and with relatively flat seas, I was able to comfortably power Vigilant at 25 MPH which meant about an hour between ports.

Since the tide was high, I decided to give the narrower Robinson’s Hole a shot. It was absolutely no problem and very scenic. I had Steve shoot some video as we passed through and I think it really captures the beauty of this strait as well the perfect conditions last Friday morning.

It was just about 80 degrees when we reached Menemsha with a fairly light breeze. We decided to head to town, grab a take-out lunch, and head back to Vigilant and eat there.

By the way, I just published a report on the Menemsha Marina which includes a map with slip numbers.

Lunch Options in Menemsha

Although dining options are limited in Menemsha, there are four that each have something to offer. Probably the best is the back deck at Home Port, but since we were having dinner there, it didn’t make sense to have lunch there as well…

Photo courtesy of Home Port

Our first stop was the Menemsha Fish Market. Although they are a serious seafood shop, they have a pretty attractive take-out menu…

We decided to walk down the road and check out the menu at the Deli before deciding what to eat.

We all spotted sandwiches at The Deli that looked tasty, so we placed our order there. Of course take-out is on “island time” (25 minutes), so we took a stroll why they were being prepared.

That’s when I came across the 4th dining option – one that I had forgotten about called the Menemsha Gallery…

I think we might have ended up eating here if we hadn’t already paid for out sandwiches at The Deli – it has a great lunch menu.

On the way back to the boat, I ran across something that Mrs. Horne said I just had to share…

Yep, that’s “Menemsha 5-0”, probably the first police golf cart I’ve ever seen.

Life’s A Beach

As I’ve mentioned before, I think the best attribute of docking in Menemsha is the beach that’s just a few hundred feet away.

In the summer I carry 4 beach chairs, 2 umbrellas, and Bose Micro Soundlink speaker on Vigilant. Steve and I had no trouble lugging it all over the jetty (along with a cooler full of beer) and after a 5 minute set-up we were enjoying one of the best beach experiences on the East Coast.

As we were packing up to go back to Vigilant, a fog bank slowly rolled in over the harbor – very cool…

Prior to the fog, it was in the low 80’s, once it passed through we dropped 5 degrees. It was still warm, but thankfully, Vigilant’s cockpit was facing Northeast and we were in the shade.

Vigilant has a SureShade retractable canopy over the cockpit, which creates a very comfortable spot for an afternoon cocktail party with live music…

Here’s a good tip for hot weather – when I saw the forecast a few days earlier I contacted all of our scheduled marina’s and requested slips where our bow would be facing southwest. This meant we’d have shade in the cockpit for cocktail hour. Thankfully all complied!

On Friday afternoon, a follower of My Buzzards Bay from Monroe Connecticut had come aboard and introduced himself. His name was Victor and he was aboard 31′ Tiara named Lady J.

Victor – Captain Lady J

Dinner At Home Port

Friday night we dined at Home Port, which is the only serious restaurant in Menemsha. I noticed earlier that all the windows were open – a clear sign that there’s no AC, but it was very comfortable inside.

The best way to describe the interior might be Cape Cod Shabby Chic. There are lots of fish on the wall, but the open windows wafting through the gentle sea breeze is perfect.

As is the food…

I did a review earlier in the year and I’ll likely update it with the wonderful dishes we enjoyed that night.

I began Day 2 with a lovely morning walk around the Boat Basin.

Just before we left, Victor’s wife Sheremy stopped by, introduced herself, and thanked us for publishing My Buzzards Bay…

Sheremy, Victor Eberily, and Colton

It turned out that this was the first of many followers to stop by and introduce themselves on this trip – so fun, when you all come by and say hello – it makes it all worthwhile!

Day 2 – Cuttyhunk

I generally like to avoid travelling every day at sea – preferring to stay 2-3 nights an exploring each port, but I already know all these spots and they’re not far apart.

Menemsha to Cuttyhunk is about 10 miles or about 20 minutes at 25 MPH. The autoroute suggested going through Quick’s Hole, but I wanted to take some photos of Gay Head and the southern tip Cuttyhunk, so I ran due south along Martha’s Vineyard and approached Cuttyhunk from Rhode Island Sound.

Monument on the Southern Tip of Cuttyhunk

It was 84 degrees when we left Menemsha, but the water in Rhode Island sound was a cool 66 degrees, so we were down to 78 when we hit Cuttyhunk.

We ended up in Slip 55, which is on the first finger pier facing Southwest.

New Food Option on Cuttyhunk!

We got take-out sandwiches from the deli at the General Store and went back to Vigilant to dine on the docks. After lunch we went over to the Fish Pier to order lobsters for dinner and noticed a hip Taco Stand just before the dock starts.

It’s called Isla Taco. They don’t open til 2:00, but stay open til 7:00, which made me think it might make for an great afternoon cocktail cruise. Cuttyhunk has a special rate for 4 hour tie-ups and it’s pretty close to most ports on Southern Buzzards Bay.

I can envision a noon departure and 1:30 arrival in Cuttyhunk. Maybe some oysters or Cherrystones – with ice cold beers at the slip followed by tacos with a 4:00 PM return home!

After lunch we made the trek to the top of the hill. That hill always seems steeper than I recall, but the simultaneous view of Vineyard Sound, Buzzards Bay, Rhode Island Sound never gets old.

When we got back to the boat, our second follower stopped by and introduced himself.

His name was David, his boat was Calypso, and his home port was Marion – the next town over from Mattapoisett.

About an hour later, we met our third follower Bruce and his big sweetheart dog Bodie…

Mrs. Horne gave Bodie her standard “What good dog you are…” and Bodie dove from the dock and into Vigilant. It was cool and scary at the same time. Bruce had quite a time picking up 80 lb. Brodie and getting him back on the dock.

Lobster Dinner on Vigilant

Despite our years of overnight cruising, the closest we’ve ever come to having dinner on board was take-out pizza. I love Sopranos Pizza and that would have been my choice, but Mrs. Horne insisted on steamed Cuttyhunk lobster and that was that.

We ordered them from the Cuttyhunk Cafe. They offer a Lobster Boil that includes corn, potatoes, and Chorizo, but we opted for just lobster and melted butter.

My mother always served lobster with a salad, chips, and hot bread, and so do I. I made a broccoli slaw and heated up ciabatta rolls in Vigilant‘s oven. A bag of Miss Vickie’s Sea Salt chips round out the dish.

By the way, the lounge on the Back Cove 41 easily converts to a booth style table for four. It was quite comfortable for our big spread.

Disco Inferno Erupts!

Cleaning up was a breeze and after dinner we were sitting out back enjoying the beautiful Cuttyhunk sunset…

There’s really no where else like Cuttyhunk. There’s no restaurant, a general store, and not much more. Yet it was packed last weekend.

There seems to be two types of people who visit this tiny island; people who want getaway for a quiet weekend and just a book.

Then there are groups who travel in a Flotilla with an eye toward having a party. There were at least two Flotillas like this on Pier One.

At approximately 7:30 PM, Kay said “Do you have any Aretha Franklin?”

Of course I do and knew just where it was. Last year Mrs. Horne and I sat on an anchor near Bassett’s and created a two hour “disco mix” that includes a couple of hits from The Queen of Soul. After switching to Respect, I noticed Kay and Mrs. Horne were on their feet dancing, so I cranked the volume up a few ticks.

The next song was Real Thing by Audra Mae and I may have turned the volume all the way to half. Suddenly, a couple from a Flotilla two boats down came running down the dock and started dancing.

Within 3-4 songs we had 20-30 people from ever Flotilla joining in.

At this point I turned it up to 10 and all 3,000 watts were screaming out Staying Alive (I heard the next day that people thought there was a concert going on.)

Needless to say, Security showed up and in a friendly voice told Mrs. Horne the quiet period started at 10:00. This was not a problem. Our pop-up Disco closed at 9:00.

We were still “beating the heat” when we woke up Sunday morning.

Although we’d seen a few low 80’s, we were mostly in the high 70’s and always with a sea breeze.

The plan was to hike over to The Cuttyhunk Fishing Club for breakfast and depart for Martha’s Vineyard around 10:30.

We arrived at The Fishing Club around 8:30 and there was only a short wait.

If you’re not familiar with the Cuttyhunk Fishing Club, you can read my full report here.

As always, the breakfast was wonderful…

But even more so was the view out to Vineyard Sound…

Before we left, Ellie Garfield (our server in 2018 and niece of Captain Garfield who owns the Cuttyhunk Shellfish Company) approached and said “You’re Dave of My Buzzards Bay aren’t you? Can you take another photo of me? I don’t like the one on your website.”

Of course I can…

Ellie Garfield

Day Three – Oak Bluffs

I followed the Autoroute course through Quick’s Hole and due north to Oak Bluffs. Although the breeze was the stiffest yet, we were running downwind. This meant doing 25 mph and getting more than one mile per gallon – sweet!

After three days on nearly deserted islands, we were ready for a little action. In case you don’t know, Oak Bluffs is the Coney Island of Martha’s Vineyard complete with the old Merry Go Round in America and arcade games.

After tying up, we headed out for ice coffee and lunch at The Lookout.

Unlike the outer islands, Oak Bluffs was closer to 90 than 80. It was also a zoo with the harbor packed with boats rafting and swimming.

Much to our surprise, we were seated immediately at The Lookout despite the crowd. My main mission was to sample their award winning Lobster Bisque…

We had met a fellow named Josh from Block Island when we were in Cuttyhunk and he was totally addicted to this stuff. He told me he buys gallons of it in the fall and freezes it to serve watching football in the winter.

It did not disappoint. Unlike most Bisques, which are heavy and creamy, this was more like a slightly thick Cioppino. It also had about a half a lobster in it and only cost $10.95.

By the time we got back to Vigilant, it was 88 degrees and the wind was still. We opted to go inside Vigilant’s air conditioned salon and watch Shane Lowery win the British Open.

We’ll sort-of. Kay and Mrs. Horne adjourned to their cabins and after about 20 minutes, Steve and I caught “cat naps” watching JB Holmes try to beak 90!

The Oyster Bar 02557

We’re big fans of Ben Deforest’s restaurants in Oak Bluffs – The Red Cat Kitchen and The Cardboard Box. When were on the island in May, we noticed a “coming soon” sign above The Cardboard Box announcing Ben’s newest restaurant- The Oyster Bar 02557.

As reported in my recent review, this is now my favorite of Ben’s three restaurants on the island.

I’m a big oyster fan and this place represents a totally authentic tribute to these tasty little shellfish.

Indian Cove Oysters from Onset
The Fried Oyster Appetizer

Not only was all the food great, but it also offers a very clean, very chic, New England restaurant vibe.

The Holy Rock and Roll Revival

One of driving forces behind my decision to make Oak Bluffs our Day 3 destination was the fact that The Holy Rock and Roll Revival plays at The Ritz every Sunday night.

Despite arriving 30 minutes early, it was already “standing room only”. We claimed the spot near the stairs and the band and enjoyed the entire first set…

Sean McMahon

Bye Bye Oak Bluffs

Steve has a board meeting in London and Kay was flying back to the Bay Area on Monday, so we had to leave around 9:00 AM.

Both the Sound and Buzzards Bay were flat so we arrived back in Mattapoisett in 45 minutes.

If you ever see a heat wave coming and want to getaway, head to the outer islands. It’s such a special treat.

By the way, if you haven’t seen it already, I also did an MBB Video of the trip set to Santana’s hit Smooth.

Vigilant 2019 Island Tour Video

Hope you enjoyed this…