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Aspen, the Hamptons, Palm Beach, and Martha’s Vineyard: America’s luxury destinations. Growing up, I never imagined spending my time in any of these places, but I’m so thankful that I can now say I’ve enjoyed three of the four (Aspen, I’m coming for you).

When my mother-in-law approached me about spending Labor Day weekend in Martha’s Vineyard, I was immediately excited. Wealthy, preppy people with sailboats, right? Wrong. Well, right, but there’s so much more to this little island than meets the eye.

harborside-logoDue to some travel delays, we wound up arriving on the island a little later than planned. After the bus to the ferry, the ferry itself, and the bus from the ferry to our town, we checked into our hotel – the lovely Harborside Inn right around dinnertime. Luckily, check-in went smoothly and we were able to  relax. And with the view we had, relax we did.

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The next morning, we were unfortunately met with quite a bit of rain. In the words of Pete the Cat, “Did we cry? Goodness no!” We got out our rain jackets and umbrellas, and made our way over to the Edgartown Diner for breakfast. I had the Vermont Omelet, which tasted like the love child of a cheddar omelet and a McDonald’s apple pie. In other words, it was delicious.

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The rain subsided, so we took a walk over to the Edgartown Lighthouse. Well, surprise, the wind did not subside. That made our visit feel like much more of an adventure – hair everywhere, jumping over puddles, and getting sand all up in my shoes. My Tory Burch flats are still mad at me. But even with the crazy weather, it was beautiful.

After a break at our hotel (mainly to change shoes and brush my hair), we hopped on a bus to Oak Bluffs, home of Flying Horses, the nation’s oldest platform carousel, built in 1876.

There’s a Carousel in Oak Bluffs town,
The horses don’t go up or down,
The horses just go ‘round and ‘round,
On the Carousel in Oak Bluffs town.

All that to say it’s not exactly a thrill ride. There is an arcade attached, though. We actually even won something out of one of those claw machines. Winning!

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We enjoyed lunch at Giordano’s and a leisurely stroll through some shops on Kennebec and Circuit Avenues before stumbling upon the famous Gingerbread Cottages of the Martha’s Vineyard Camp Meeting Association. I had heard of these adorable houses, but hadn’t planned on checking them out originally. I’m so glad we did though!

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That night, we treated our in-laws to dinner at The Seafood Shanty… which turned out to be much fancier than we expected from the name. It was delicious though, and it’s always nice to sit down for a great meal.

Monday morning, we opted for a lighter breakfast of muffins and donuts from Martha’s Vineyard Gourmet Café & Bakery. Rumor has it, this place also serves donuts to the late night crowd out of their back door, which is fun.

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After a little mid-morning silliness, we took off for what was easily the highlight of our trip: Pirate Adventures.

As soon as we decided to go to Martha’s Vineyard, we knew the hardest person to please would be my son, Miles. He’s pretty easygoing and he’s used to traveling with us, but we wanted to do at least one activity specifically for him. So, I took to the internet and found Pirate Adventures.

To put it simply…

WORTH. EVERY. PENNY.

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Upon arrival, Miles was given a name tag with his official pirate name, “Mad Dog Miles,” and outfitted with a bandana, eye patch, and foam sword. We walked out to the dock where some other crew members were waiting to add a vest and sash to his ensemble, as well as provide his first “tattoo.”

The captain and crew went over all the rules, and we boarded the Sea Gypsy on a hunt for treasure. It was about an hour at sea, finding a map, following clues, and fighting off pirates. And Miles came away from it with a bag of “treasure” and a cup of “grog” (pineapple soda).

Since the weather was so lovely, we opted to enjoy a casual lunch on the deck of Nancy’s Restaurant before heading back down to our hotel and enjoying a little time at the pool. It was still too cold for me, but my son is such a water baby! He will go in any pool no matter how cold it is. Luckily, my husband was willing to join him. Picture them swimming and me in a sweater with a towel wrapped around me.

Part of our hotel is timeshare units, so we had access to grills and a kitchen. After a pit stop at the supermarket, we cooked ourselves steaks and baked potatoes for dinner that evening. Naturally, Miles made friends in the rec room, and he played while we chatted for a bit before bedtime.

And just like that, our trip was over. The next morning, we made our way back across the Vineyard Sound on the ferry and made the drive back home to New Jersey (with a pit stop for lunch, obvi).

Will we ever go back to Martha’s Vineyard? I’m not sure. It was lovely, but definitely a little expensive. And hello, not a Starbucks on the whole island?!

Have you ever been to Martha’s Vineyard? What did you think? Anything we didn’t get to worth a return trip? Let me know!

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