To The Cape! Our Anniversary in Martha’s Vineyard

Things can get weird when you’re both a prescriptive planner and a perpetual procrastinator. When we decided to spend our 1-year wedding anniversary in Boston & Cape Cod, I immediately set off on planning mode…and then got incredibly distracted / frustrated by Mike’s lack of opinion on the matter / overwhelmed by the sheer number of options for a “Cape Cod vacation” and put it off. For a long while. Then, without warning, Mike booked our Boston hotel and tasked me with booking the Cape Cod leg of the trip.

Martha's Vineyard Ferry View

Martha's Vineyard views

Cue stress and anxiety. You see, when he suggested these destinations for our trip, I thought he for sure had recommendations. It turns out Cape Cod isn’t just a place, it’s a whole area with thousands of recommendations, none of which sounded like just what I had in mind. It seems like one of those places that you have to visit a few times before you find your spot. And then, fortuitously, Holt Renfrew’s Lisa Tant took a long weekend jaunt to Martha’s Vineyard and it was like the heavens opened up via Instagram. I booked her B&B (more on that later) and then set to making an itinerary for the week.

First look Martha's Vineyard Ferry to MV review

If you’re thinking of heading to Cape Cod and Martha’s Vineyard, the short answer is: do it. But if you’d like a bit more detail…

Our Martha’s Vineyard To-Do List:

Ice Cream at Mad Martha’s / A BLT or Cuban at Skinny’s Fat Sandwiches / Relax on the Porch at Oak Bluff’s Inn / Luxuriate on the beach / Play in the Arcade on the Strip / Sunset Dinner at Fishbones / Admire the Gingerbread Houses / Explore Edgartown

Our B & B

First view of MV port Oak Bluffs

I knew from the second I spotted this beautiful pink bed & breakfast in Oak Bluffs that I’d love it (for obvious reasons). We weren’t sure what to expect, but I can tell you now that our expectations are far exceeded. The Oak Bluffs Inn was cozy, homey and entirely the perfect place to stay on Martha’s Vineyard. Erik, the innkeeper, should write a book on hospitality. We felt immediately comfortable with him and were constantly impressed by his knowledge of MV and the surrounding areas. No recommendation from him went unloved.

Oak Bluffs Inn Martha's Vineyard review anniversary couple

Oak Bluffs Inn review Martha's Vineyard

We spent every night and many an afternoon on this relaxing porch, reading books, enjoying a few drinks and mingling with the other guests. The whole bed & breakfast has a cottage feel, like you’ve gone to visit a good friend for a weekend. Our bedroom was beautiful, clean and comfortable and had its own washroom with a shower. I loved the little writing desk, too, and made sure to leave a note in the guestbook.

Bedroom Oak Bluffs Inn Review B&B Martha's Vineyard Best B&B Oak Bluffs Martha's Vineyard MV reviews

Review Oak Bluffs Inn bed and breakfast Martha's Vineyard

If you’re thinking of visiting Martha’s Vineyard, definitely stay in Oak Bluffs and definitely visit Erik at The Oak Bluffs Inn. And make sure to eat the chocolate chip cookies he bakes fresh every afternoon. I’m *so* glad I spotted this adorable accommodation on Lisa’s Instagram!

What to Do in Martha’s Vineyard / Oak Bluffs

Skinny's Fat Sandwiches BLT Oak Bluffs best sandwich

First thing’s first: we were starving by the time we made our way over on the ferry and dropped our bags off at the Inn. Luckily, we spotted Skinny’s Fat Sandwiches along the main strip and ordered up two BLT sandwiches – arguably the best BLTs we’ve ever had. Mike would coo at the windows of the restaurant as we walked past each day as if there were tiny puppies inside. But alas, it was just the BLTs and his One True Love sandwich, the Skinny’s Fat Cuban, giving him *all the feelings*.


We spent the first afternoon walking the main drag and popping into all of the tiny shops, most of which sell any variety of beachwear and souvenirs. The beach has my heart in a big way: we lay out, took a dip in the ocean and enjoyed a good book apiece. It was incredibly relaxing and felt like we’d flown thousands of miles away. Of course, we followed up with delicious ice cream from Mad Martha’s – this is the best chocolate chip cookie dough I’ve had in my life.

Gingerbread Houses MV Oak Bluffs

I knew from my Googling that Oak Bluffs is home to hundreds of Gingerbread Houses, these beautiful, brightly-coloured homes with all the ornamental trim and kitschy decor. We spent over an hour wandering the streets and admiring them. I’d say I have a favourite, but I really don’t. They’re all just lovely. But if I was forced to pick…these would be my favourites.

Gingerbread houses Martha's Vineyard photos Gingerbread Houses martha's vineyard must see what to do

Stephanie Fusco and Michael D'Amico annivesary trip

Houses in Oak Bluffs MV Hot pink gingerbread house Oak Bluffs MV

Say hello to Barbie’s dream house! Isn’t she a beaut?

Back at the Inn, I had purposely saved my Martha Stewart Living to read in Martha’s Vineyard. No connection, I know, but it felt like the thing to do. It’s like Martha knew my motivations: there was a recipe for the perfect lobster roll inside!

Martha Stewart in Martha's Vineyard Kate Spade pineapple sandals

For our anniversary dinner, Erik suggested we head over to Fishbones to watch the sunset and enjoy some fried seafood. When he said fried, I didn’t realize absolutely everything on the menu was of the crispy, crunchy, golden-brown variety. But oh, those curly fries and fried sea scallops… We didn’t regret it for a second. But we also couldn’t empty our baskets if our lives depended on it.

Michael D'Amico Oak Bluffs Anniversary trip

best fried seafood oak bluffs fishbones

Stephanie Fusco Fishbones Restaurant Martha's Vineyard review
Stephanie Fusco D'Amico Anniversary wedding

Definitely stop by Fishbones if you’re in Oak Bluffs and be sure to get the fried scallops…and fried clams…and say yes to the curly fries. We ended off our anniversary evening with a little bottle of Patron and the rocking chairs on the Oak Bluffs Inn porch – perfect!


A Visit to Edgartown

For our next visit to Martha’s Vineyard, we’re planning to spend at least a week exploring the island. Each area is full of must-dos and must-sees and I only wish we had enough time to visit more of them. One spot we made sure to visit was Edgartown – a posh little area with the sweetest shopping strip and harbour views.

Edgartown harbour views Edgartown strip martha's vineyard

We arrived just in time to walk the strip and find someplace delicious for lunch. We ended up ducking into Among The Flowers, a quirky little cafe with the perfect lunchtime menu. Mike got (yet another) delicious lobster roll while I went for the salad with grilled shrimp. Are you getting the feeling that we ate mostly seafood on this trip? Because we did.

Among The Flowers Lobster Roll Edgartown MV Among the Flowers Cafe review Edgartown

Edgartown Vineyard Vines bike

Edgartown Lighthouse Martha's Vineyard romantic weekend

We had the best time exploring Martha’s Vineyard for our anniversary. We’re already talking about renting a place there for a week with a few other couples next summer…and maybe every summer after that. The Island feels exactly like cottage country, only with a slightly beachier twist. After our visit, it was no surprise that so many celebrities and Americans choose to spend their time there.

Martha's Vineyard Ferry Stephanie Fusco D'Amico Michael

Freckly, relaxed and happy on the ferry back to Falmouth. ‘Til the next time!

Do you have any must-sees along the Cape? I’d love to hear about them for our next visit! xo