Growing up in Mattapoisett, Martha’s Vineyard was always the island we saw off in the distance just outside of Buzzards Bay. But when it came to boating, it was always “so close, and yet so far.”

Those of us who boat on Buzzards Bay are quite fortunate to have such an exotic venue so close. People all over the world know about the Vineyard. It has been presidents Clinton and Obama’s summer vacation home, James Taylor and Carly Simon summer getaway, even Jimmy Buffett once kept his schooner in Menemsha.

Menemsha Christy Brinkley House
Christie Brinkley’s House in Menemsha

My first visit to Martha’s Vineyard came in the 1980’s aboard my father’s 35′ Pearson Sailboat – The Aquarius. Our most frequent overnight destination was Oak Bluffs, but we also stayed in Vineyard Haven a few times.

Oak Bluffs was great because we always got a slip right in the middle of town which made it very easy to just go to shore and walk around.

In 2001, Martha’s Vineyard was the first destination in my 26′ Boston Whaler and with that trip I learned just how furious Vineyard Sound could be when the wind and the tide went against you.

As we moved up to Mean Kitty, we started venturing to Edgartown and to this day, it’s probably our #1 Vineyard Destination.

Where To Go?

Martha’s Vineyard is a big island and accordingly, there are a lot of options for cruising. Which is best for you depends on the size of your boat, the size of your wallet, and what you’re looking for.

Here’s my breakdown on each option…

Vineyard Haven

Let’s start with Vineyard Haven since that’s the closest port to Woods Hole and Buzzards Bay. Although it doesn’t look much further than Oak Bluffs, it seems that no sooner do you clear Woods Hole that you’re banging a right and heading into Vineyard Haven. You completely avoid East Chop when you go to Vineyard Haven and severely mitigate the West Chop craziness.

The Black Dog a great breakfast Dock and Dine venue for someone with a small boat wanting to get home before the Southwester kicks in at 11:00. The Black Dog Tavern offers incredible breakfasts and has a very convenient old school wharf.

Black Dog Wharf 4
Vigilant on Black Dog Wharf

They do not take day reservations at The Black Dog Wharf, but if they have room they’ll squeeze you in. If not, you can always pick up a Town Mooring and use the launch service. The Harbormaster provides an excellent fact sheet – click here to access the latest version.

I haven’t stayed overnight in Vineyard Haven in years, but they do have several options on Dockwa – click here to access the latest availability. Beyond Black Dog Wharf, there is also Tisbury Wharf, Vineyard Haven Marina, and Prime Marina (moorings only).

All of the major ports on the Vineyard have different vibes, strengths, and weaknesses. Beyond it’s close proximity to Buzzards Bay, I also like shopping on Vineyard Haven.

They have all the usual MV shops like Black Dog and Vineyard Vines, plus a couple of serious stores like LeRoux, Brickman’s, and Island Music– the only music store on Martha’s Vineyard.

Brickman’sis a great place to buy island clothing, boat shows, and unique kid’s toys.

I could easily spend an hour shopping in LeRoux and I hate shopping!

LeRoux 2
Endless Kitchen Gadgets at LeRoux
Unique and Classy Home-goods at LeRoux

In terms of dining, I have tried The Black Dog Tavern and The Copper Wok multiple times. They are both excellent and totally different from one another.

The Black Dog is an authentic seaside tavern that offers all the classic dishes you’d expect to find. The Copper Wok offers Chinese and Japanese cuisine. Both are open year round.

By the way, last summer the Town Fathers lifted the centuries old ban on liquor sales in Vineyard Haven and you can now buy booze and order regular cocktails in Vineyard Haven.

Despite this change, which allows Vineyard Haven to compete with the other Vineyard Towns for diners, I’d say that it’s still a little light on first class dinner restaurants.

Here’s one more story I wrote about The Boys Day Out last fall that took us to Vineyard Haven and frightening passage through Woods Hole in pea soup fog.

Oak Bluffs

Moving east, the next port is Oak Bluffs. This is probably the most Beachy venue on MV. It’s got shops and restaurants that you might find on a Beach Boardwalk anywhere from Maine to New Jersey.

Very Neighborly Dock and Dine

It’s also a great day trip Dock and Dine venue with free town moorings for day trips and a decent launch service. The drawback to the free town moorings is rafting.

Rafting means strangers pull up to your boat on a mooring and tie up along side. There’s nothing wrong with this if everyone is a responsible boater, but that’s not always the case.

  • You better have at least 4 bumpers so you can leave two on each side in case someone rafts next to you in a stinkboat.
  • Be prepared for a jerk who ties to your boat instead securing his boat to the mooring. If everyone ties to the mooring, you simply untie your boat and back out. If they just tied to your boat, then you have to tie them up to the mooring before you can leave. This can involve a lot of awkward stretching and leaning maneuvers.
  • Always assume strangers will be walking through your boat – lock up all valuables and  hide your cooler.

I still think this is great Dock and Dine option for someone with a smaller boat who wants to know they won’t be turned away.

We also discovered during our visit last fall that Oak Bluffs is a great spot for grabbing a day slip in the off-season. We were there in late September and there were very few boats staying overnight. Virtually everyone was there for a few hours and paid a modest fee for a slip. Interestingly enough, there is no mention of hourly docking on the Oak Bluffs Marina website.

Just this past weekend we returned to check out Oak Bluffs on Cinco De Mayo and found the harbor even more desolate that September.


With no more than a half a dozen boats in the basin, we were able to grab slip #79 which is a beauty. It’s got a nice finger peir to port and very solid bumpers on the pilings.

Overnight Cruising

The Oak Bluffs Marina is the only show in town in this medium sized boat basin. You can book on Dockwa and see their reviews and cancellation policy there.

This is a unique marina in a number of ways. On the positive side, it’s pretty much in the center of town which makes it ideal for people looking to stay where the action is. Obviously, this is a negative for folks looking for peace and quiet.

Oak Bluffs Marina 2
Oak Bluffs is truly a Downtown Marina!

As you can see, your stern literally sits on the public walkway and the slips are tight enough to reach over and shake your neighbor’s hand.

Oak Bluffs is a great little party town and I think that’s who this marina caters to. I came across this very articulate negative review on TripAdvisor of all places.

1. No Customer Service. The Dock Master (DM) and his staff are very inattentive with a love it or leave it attitude. No dock hands to help tie up, simply a girl with a clipboard who checks you in so they can immediately charge your credit card. When I told the DM our slip with a beautiful view of the public restroom was disgusting, he offered a slip near the entrance of the harbor that was rocking and rolling…couldn’t stand up without holding on. When you offer two crappy choices and tell folks you provided options, that’s not okay! The DM reminded me that this was a public dock, not a private marina.. It’s run by the government, no surprise it had a DMV feel! I guess that makes looking at a public restroom for a week’s vacation okay.

2. I vacationed on an episode of COPS! When we told the DM about the vagrants, he gave me the Chief of Police’s phone number and told me he had already met with on the matter. He believed if I contacted the Chief, it might be helpful…I didn’t out of fear of retaliation from my new, high-class neighbors. We did end up calling the police the following day to remove a drugged-out guy who was sitting on the bench on the dock behind our boat screaming obscenities at 10 pm. 

3. A lovely view of the urinals! My sister has a larger boat and was placed in a slip directly behind the dodgy public restroom. She has two little girls who all enjoyed a view of the men’s urinals! Can you imagine waiting all year for a beautiful Martha’s Vineyard vacation only to end up watching drunks urinate? She spent two days there before the DM moved her to a different slip. At least it was an educational vacation for the girls who learned about the drug problem in Oak Bluffs!

4. Not a great marina for boats traveling together! The Marina’s layout is less than optimal when traveling with a group of boats. Each year we travel with a family flotilla made up of five-boats. Most of the time we can dock near one another. With the layout of this marina we had to walk a half mile to see each other. We made reservations months in advanced and requested to be closer to each other, it’s obvious that this wasn’t considered. Because we were so far apart, it really fragmented the families and didn’t allow for group fun. 

5. Dirty Boat! Because the slips are so close to the road, your boat is constantly filthy! If you don’t mind black, sticky road dirt, you’re okay!

6. No Privacy! The public sidewalk/ boardwalk is up against the bulkhead. People visiting Oak Bluffs in need of a restroom stop to peer inside you boat. You feel like you’re in a fishbowl!

7. No Amenities! Oh yeah, there was one, THE PUBLIC RESTROOM!

There are also plenty of very positive reviews on Dockwa, but based on physical proximity alone, I think it’s safe to say visit Oak Bluffs in the the Spring or Fall unless you’re looking to party.

Dining On Oak Bluffs

I think Oak Bluffs has better dining options than Vineyard Haven. For years we went there regularly and lunched at The Sand Bar which was attached to the Menemsha Blues Clothing store. It’s a very cool place in that you sit with your feet in the sand!

Sand Bar Oak Bluffs

The last time I was their was in the Mean Kitty days and we had Sushi, which was quite good.

We also had lunch many times at Fishbones, which is just a little further down the boardwalk. Also good food and exceptional Sweet Potato Fries!

More recently, we’ve eaten in a number of very good restaurants that I have also reviewed in detail on My Buzzards Bay…

The Offshore Ale House – Great beer, kind of a local joint, exceptional Parmesan Fries and the only place in Oak Bluffs that allows you to eat and drink with your dog! Click her for my full review.

The Red Cat Kitchen – This is not only very cool, but incredibly great food. We learned that this is Obama’s secret getaway for dinner on the island. If it’s good enough for Michelle’s discerning palette it’s worth checking out. Click her for my full review.

Linda Jeans – Take a trip back in time to your favorite hometown restaurant. Incredible breakfasts and good honest food all day. Click her for my full review.

The Lookout Restaurant – Without a doubt the most “islandy” spot on Oaks Bluff, comparable to The Seafood Shanty in Edgartown. There are over a dozen seats that look out at ocean. The food is great and it’s has a very funky atmosphere. By the way, the homemade potato chips and mango salsa are incredible. Click her for my full review.

The only other tip I have is to avoid Jimmy Seas Pan Pasta at all costs. The food is nearly inedible, the servers are disinterested, and the atmosphere sinks. Click her for the rest on my story.

Before I wrap up Oak Bluffs, I have to mention that it’s superb spot for beaching and golf. The beach begins near the Ferry Pier and runs almost to Edgartown. It is as good as island beaches get in New England and totally accessible to all.

Oak Bluffs Beach

Back to Obama for a moment. All the golf he played while vacationing on Martha’s Vineyard was at Farm Neck. It’s great links golf course and 100% open to the public.

Farm Neck Obama

As you may recall, I had a delightful time on mopeds on Block Island. That said, I would advise you to resist the urge to rent one for a few hours from all the rental spots in Oak Bluffs. It’s very dangerous! Mrs. Horne and my dear daughter Natalie rented there once and had an accident. The roads are narrow and the island is full of impatient city drivers who brought their cars over by ferry.

If you want to see the island – and I recommend that you do, I suggest you look over the tours on yelp and find one with a nice van and a guide who uses a microphone and PA. We did it years ago with fours guests from Texas.


Edgartown was almost always our ultimate destination when we took the Whaler to Oaks Bluff. We’d raft on a town mooring, take the launch to shore and then take the bus to Edgartown.

In 2008, we moved up to Mean Kitty — a 33′ Offshore Center Console and Gary McGrath talked me into trying to go all the way to Edgartown and tying up somewhere over there.

It turns out it was a breeze and never went back to Oaks Bluff!

4th of July Edgartown
Mean Kitty’s first trip to Edgartown

Without a doubt, Edgartown is The Ultimate M/V and Dine (click left to read report). The key requirement for any Dock and Dine is knowing that no matter what, you’ll end up with a place to tie up your boat.

In 2017 the town changed their mooring policy (see below) to make Edgartown the only Dock and Dine day trip venue you can book and confirm in advance!

We always went early so we could nab one of the 4 spots on the town docks. These docks are centrally located very close to shopping and the Seafood Shanty. The last time I was there it cost $15/hour. I always gave the dockmaster $40 and he’d tell me “come back anytime”.

These finger piers are limited to boats 30 feet long and 10 feet wide, but no one ever questioned me with Mean Kitty which was a big 33 footer with 10’6″ of beam.

In terms of town moorings, the free “blue town moorings” are gone. The town changed their policy in 2017 and I heartily endorse the new policy. I will admit that I didn’t fully understand it at first, so please pay attention!

1. The town now has all their moorings available for booking online (via Dockwa).

2. Whether your going to Dock and Dine for two hours or staying overnight, the price is the same – $40.

3. You can tie up anytime after 11:00 AM and you must leave by 10:00 AM or you’ll be charged for another day.

4. Besides the 4 first-come-first-served finger piers, the town also has space for two large boats at their docks on North Wharf. Today is May 4 and I just checked their availability for Memorial Day weekend and they are available. This is surprising as I have never found them to be available during the summer.

There are two other docking options in Edgartown. One is Mad Max pier which sits just north of the town finger piers.

Mad Max Pier.jpg

This is truly dockage for the rich and famous. It starts at $550/night and requires a minimum of 2 nights!

The other is the Harborside Inn which has become my new favorite day dockage in Edgartown (click here for my full report). It too seems very expensive for overnighing.

At this point in most reports I give you links to the 4-5 restaurants I’ve tried in the venue I’m writing about. In the case of Edgartown, I can’t! Although I’ve dined in Edgartown 30 or 40 times, I’ve never eaten anywhere other than The Seafood Shanty (click here for my report).

I love the vibe, the view, and the menu. The vibe is total island seaside eatery. I often compare it to the second floor Cheeseburgers in Paradise on Front Street in Lahaina on Maui.

The Shanty has wide opening doors out to a dining deck that overlooks Edgartown Harbor and Katama Bay.

Seafood Shanty View

The menu offers all the classic seafood eatery dishes you’d expect plus great sushi.

My daughter and son-in-law vacation in Edgartown every year and they have come to love Detente. This is a highly rated fine dining venue and one of Barack and Michelle’s go-to spots. Click here for a good review on Detente.

Obama Detente
The Obama’s entering Detente

Beyond eating and hanging out at the Seafood Shanty Bar reading the sports section, I also enjoy shopping in Edgartown.

Seafood Shanty Bar
My Happy Place!

It’s one of those places like Carmel By The Sea (California) with a few chains and a ton of one of a kind shops. I love the clothes at Vineyard Vines. I also love Backwater Trading Company which seems to stock things I didn’t need but want to buy!

While shopping, I like to grab an Iced Americano and watch the Jamaicans make fudge at Murdicks.

Murdicks Fudge Edgartown
The art of Fudge Making at Murdicks

One last shopping tip. If you’re not really into $45 tee-shirts with dogs and whales on them, stop into Captain Porky’s Bait and Tackle on Dock Street and check out their selection of tees.

Captain Porky's

They always have a good selection of well made tees with beautiful vibrant colored fish graphics on the back.

Captain Porky's Tee

They are all uniquely branded Porky’s Edgartown and they’re just $20!

Katama Bay

Once the crew are all back on the boat, we almost always take a little tour into Katama Bay and marvel at the Mansions on Chappaquiddick.

Here’s a few pics from recent trips…

Katama Cruise 5Katama Cruise 4Katama Cruise 3Katama Cruise 2Katama Cruise

My last tip on Edgartown has to do with leaving in the afternoon — when the winds and seas are generally the choppiest.

Once you clear the lighthouse and the south wind hits you in the face, your first instinct is to turn and head to Woods Hole as fast as possible. I’ve learned over the years that that’s seldom the best strategy. I’ve found that if you head straight out toward Hyannis a few miles before turning south, you’ll avoid the killer waves off of East and West Chop.


The fourth and most remote venue on Martha’s Vineyard is Menemsha. I have yet to stay or dine there, so this portion of the report will remain unfinished until I do.

There is one good restaurant – The Home Port, which has a 3 Star rating on yelp, but a lot of 5 Stars and 1-2’s. Many of the 1-2’s are based on price/value, which I dismiss given the remote geography. Also, Chilmark is dry, so this is a BYOB restaurant. This means you’ll pay a lot less for your wine and adult beverages.

We’re hoping to visit in July. In the meantime, I do have a report I did following a nice day anchoring offshore last season – click here to read my story.

So that’s everything I have to offer about setting Martha’s Vineyard as your cruising destination.