Last week we finally took the 3 day cruise I’ve been talking about for years. It turned out to be a bit of a trip back to simpler times as we visited Cuttyhunk and Menemsha for a little Island Tour.

Cuttyhunk will always be a special place for me since it was the scene of our Honeymoon a few years back.

The funny thing is that there was more going on in Cuttyhunk back in the 80’s than there is today. But if there was anything to do we found it!

The options are far more limited in 2018 than they were in the 80’s. Back then both the Allen House and the Bosworth House served high-end fare.

A Very Friendly Marina

Because there aren’t a lot of tourist attractions on Cuttyhunk, people tend to be friendlier and that was the case last weekend.

I made a minor tactical error requesting Slip 22 at the end of the far southern dock. The access and views were great, but there was only one cruising neighbor with the rest of the dock full of commercial fishing boats.

We could see a lot of action over at the other docks (where we’ll venture next time).

Our neighbors were Richard and Judy aboard the Knucklehead – a 58′ Hatteras LRC.

Richard and Judy

They’d been in Cuttyhunk since May. They also owned a 1969 25′ Bertram that had been restored to brand new showroom condition.

Sampling All The Cuttyhunk Dining Options

Despite the limited selections, we were determined to try them all. For lunch, there are three options; The Cuttyhunk Cafe for a lobster sandwich, The Cuttyhunk Shellfish Farm store for Chowder or Shellfish, or the Deli at the General Store for a hand crafted sandwich which was our choice.

If you’re on a boat with a decent dining table I think this is the best bet for lunch.

Mrs. Horne and I shared a “special” sandwich which was grilled pastrami, cheese, and pickles. Gail and Rudy split an Italian Sub. Both were excellent.

We pretty much hung out at the boat all afternoon and watched the day drift by. Around 4:00 (at four we pour), I called the Cuttyhunk Raw Bar and ordered 18 Oysters and 6 Cherrystones.

Cuttyhunk Oysters
Cuttyhunk Cherrystones

There is something very special about freshly shucked seafood that just came from the sea. Not only is it extra sweet, but it’s much closer to room temperature than what you get in a Restaurant. The higher temperature really allows the flavors to come through.

When we were out walking about, we noticed that it was Trivia Night at The Scuttlebutt Grille at 6:00. This sounded like fun plus there were a lot of fun foods on the menu.

The Picnic tables were fine…

…and our server Christina was excellent.

Wes all had Chowder which was very authentic; not too thick and lotsa clams. Rudy went for grilled oysters and the rest of us shared plates of Grilled Satay and Lemon Grass Chicken. These are small portions and I think I could have eaten two orders.

Cuttyhunk Trivia

This was the first time I’d participated in Pub Style Trivia. It costs $1 to enter and for that you get a form for your answers. The Caller is a woman named Cassie. She has a sassy attitude and good loud voice.

She also possesses the kind of evil mind one needs to keep tipsy trivia players on their toes.

Here are a few of the questions:

1. Name all 5 varieties of native Alaska Salmon.
2. How did James Dean die?
3. What NBA team does Green Bay Packers quarterback Aaron Rogers own?
4. Name the two current judges on The Voice besides Adam and Blake
5. Who played Rose in The Titanic
6. Who wrote Uncle Toms Cabin
7. What is the Indian word Cuttyhunk mean?
8. What does the word Laser stand for?
9. What country has the world’s most lithium reserves?
10. Name the top 10 selling cars in the US.
This is only about half the questions. Not only did we not win, but the we also gave away the answers to the few questions Rudy knew as he shouted out the answers!


This is the closest thing to a restaurant for dining on Cuttyhunk. The menu is pretty much pizza with a couple of seafood options. The kitchen is in someone’s garage and the “dining room” is a few picnic tables in the driveway.
Since we were still a little hungry after trivia, we ordered a couple of pizzas to enjoy back at the boat. Rudy wanted a “Red” pizza, but Mrs. Horne can’t eat tomatoes, so we had to order a “White” pizza as well (Alfredo sauce instead of Marinara). Both were topped with Lingucia, Kalamata Olives, Red Onions, and Pepperoni.
They are excellent! The crust was fairly thick, but airy. The toppings were plentiful and each unique flavor shouted out on the palette.
Two pizzas were way too much food and I quickly froze the leftovers which Mrs. Horne and I enjoyed last night.

Visitors at Last!

As we finished up our pizza, Mrs. Horne’s wish was granted and some folks from the middle dock walked close enough for her to greet them and welcome them aboard.

Art, Jeanne, Joan, and Bill

As you see, they were enjoying ice cream from the island stand. They were on a sailboat, but Art wanted a tour of Vigilant. I think I see a Back Cove in Art’s future!

The Fishing Club Breakfast

Since we were going to be staying in rather remote venues, I had stocked up to prepare breakfast on board both days. I had heard that the Cuttyhunk Fishing Club served a nice breakfast so We decided to check it out instead.

I’ll give you a full review later, but I will tell you that’s it’s a good walk from the Marina – well over 15 minutes.

This place is a definite “must do” if you’re in Cuttyhunk for breakfast. The views are spectacular and the property reeks of old seaside eatery. It only serves breakfast and it is the only venue on the island that resembles a regular restaurant.

We arrived at the worst possible time – 9:30 on Sunday morning and accordingly, we had to wait about 40 minutes to be seated. That said, we helped ourselves to coffee and enjoyed the view south to Gay Head and Martha’s Vineyard.

Mrs. Horne and her sister Gail looking toward Gay Head

We were served by Ellie Garfield, a wonderful young lady who is a Cuttyhunk native, but currently studying at Clark in Worcester.

Ellie Garfield

Illustrating how small the island is, Ellie’s uncle owns and operated the Shellfish Farm!

The menu and the details about our meal will wait until I do my full review, but I can tell you that I ordered the most unique sounding dish on the menu and it was very good.

It’s called The “Seagull’s Nest” and it’s Corned Beef Hash, Poached Eggs, and Hollandaise Sauce. By the way, I ordered the “Bolla” toast which is similar to an English Muffin, but softer and sweeter.

One word of warning – and this was true for pretty much all of Cuttyhunk and some of Menemsha, these are Cash Only Islands. Some will take a card, but many do not!

Destination Cuttyhunk Update

Last year I did a report on Cuttyhunk as destination. In it I mentioned the guy on the dock who sold grilled and fried food (AKA The Lucky Dog Grill). He is no more…

Dog Gone!

Menemsha Ho!

By the time we finished breakfast, we were due to depart (11:00 AM) so we skipped the hike to the top of the Island and got out of the Marina before we wore out our welcome.

The sea was calm, but about 3 miles out of Menemsha we hit a complete pea soup fog. I fired up the radar and I know we passed a few boats within 100 feet, but we never saw them.

I had visited Menemsha a few times, but this was my first overnight. Word of warning, the entrance between the jetties has a very strong current – I mean super strong.

I followed a boat in tow and had to go slow. As soon as I entered the channel, the current through me toward the rocks. It took full thrusters to avoid disaster.

Once inside the Boat Basin, all was fine. This is such a rare and beautiful spot. It really looks like it came out of the 1950’s or earlier – so quaint!

We were assigned slip 14, which was very tight. The Dockmaster asked me my beam and I told him 14′ (as stated in the Back Cove Specifications). We had less than 6 inches on either side. Next time I’m going to tell anyone who asks 15′!

Village Life

Menemsha is more of a village than Cuttyhunk. There are a couple of fish markets next to the dock store/gas station (AKA Squid Row). The fish markets offer fresh seafood and a wide variety of take out dishes.

Like Cuttyhunk, Menemsha is a BYOB Dry Town. I was lugging a cooler and we wanted to sit down to eat so we kept moving up the road.

The first stop was Bite. It was closed and upon further inspection, it looked like some serious repair or construction was going on inside.

We ended up at The Menemsha Deli for great handcrafted sandwiches. Mrs. Horne and I split the New York Reuben. It was a grill panini and very tasty.

The Best Dock and Beach Spot

After lunch we heard the beach calling and had to comply. I stowed 4 beach chairs and two umbrellas on Vigilant along with a Bose Micro portable speaker. The beach was literally 50 feet from the end of the dock.

There was a crowded area that was protected by a life guard. With 64 degree water, I knew we were not going in so we set up to the left just outside the beach that was marked for safe swimming.

New Friends in Menemsha!

When we returned to Vigilant we discovered a lovely couple had tied up next to us. We introduced ourselves and discovered they were from Central Massachusetts and the owners of The Wachusett Brewery.

Their names were Ned and Kim…

Ned gave me a few samples of their brews. It turned out that they were good friends with Mrs. Horne and Gail’s niece Jody who owns Lucca’s Restaurant in Leominster.

Since we pretty much play constant music on Vigilant I asked them what kind of music they liked. Ned said country and anything live. I told them we were musicians and Kim asked me if I knew any Johnny Cash. That was all I needed to hear and 5 minutes later I was doing Folsom Prison Blues!

Live Music at Squid Row

As we headed off to dinner, we passed a little all acoustic concert on the back dock near the Squid Row Store.

I wish we had more time to hang out an listen. The groove was captivating, effortless, and very tight. This is the kind of music I could sit and listen to for hours even if they never did a song a knew.

The Home Port Restaurant

This is the only serious restaurant in Menemsha. It has been around quite a while and the reviews on Yelp are either 4-5 stars or 1. Most of the 1-star reviews are about the long wait for a table, the prices, or the food from the take out window.

Most of the great reviews are from people who made reservations and sat inside.

Our experience was a solid 4-stars. I’ll do a full review later, but for now I leave you with photos of the two best dishes we ordered.

We had a great server too. He was from Cape Town South Africa. His name was Xolini, but he went by Spencer on the Island…

We had a great server too. He was from Cape Town South Africa. His name was Xolini, but he went by Spencer on the Island…

Great food, service, seaside ambiance, and sunset views -what more could you ask?

The Impossible Dream Project

After a breakfast of my famous English Muffin sandwiches, we headed into town on Monday morning. As we passed Squid Row we spotted a very nice Catamaran tied up.

It turns out that the boat is part of an organization called Impossible Dream (

Their mission is to get kids with disabilities out on the water. The boat was custom made from the ground up for sailors in wheelchairs like Deborah the captain.

Deborah of Impossible Dream

The chance encounter was truly serendipitous as Gail and Rudy have a disabled grandson (Cameron). They chatted with Deborah and made plans to bring him to Boston when they visit in August.

I would encourage everyone to donate to this special mission!

Beating The Crazy Current

As I mentioned above, the current at the entrance to the harbor can be insane. There is no outlet to the south end so it must just be the water entering and exiting with the turn of the tides.

When it came time to leave, it was even worse than it had been when we came in.

Remembering that we almost got tossed into the rocks coming in, I had a plan for a safe exit.

I idled in the Boat Basin until there were no other boats coming in or going out. I quickly moved to the center of the channel pointed out between the jetty’s. I warned the crew to hang on, threw the throttle all the way down, and escaped the current 747 take-off style.

Even with 715 HP behind us, I could still feel the current trying to shove us off course.

Falmouth for Mexican

It was too nice a day to just head home. After a brief crew meeting we decided to head up Vineyard Sound and go to Woods Hole or The Chartroom for lunch.

Mrs. Horne took the helm and I sat in the cockpit and enjoyed the ride. I got a sudden urge for Mexican and texted Joyce Richards at Boston Yacht Sales in Falmouth to see if she was around. She was and we changed course for Falmouth where Joyce picked us up and took us to Anejo.

Joyce Richards and Mrs. Horne

It was a great trip and a perfect little sampler of both islands. It looks like we’ll be heading back to Cuttyhunk this Saturday on our return from Block Island. Next time we’ll do two nights in one port or the other.

The Island Tour MBB Video

Last, but far from least, is my memorial video for this trip. This video compilation is accompanied by Christopher Crosses Ride Like The Wind.