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We just can’t stay away. Nor, it seems, can we turn off our overwhelming desire to introduce everyone we know and love to our little island home. What can I say? My family just has this infectious obsession with Martha’s Vineyard, and we can’t help but feel that everyone’s life would be better with a little infusion of island time. Which is how we ended up with nine people in one Polly Pocket.

Martha's Vineyard Campmeeting Association

Yes, Fourth of July week was going to be a busy one. My mom started the week solo, slowly adding on a loved one or two per day until we’d reached our peak capacity of nine — kind of the max you can manage with one shower — by the big day itself. The more the merrier, just the way we like it.

This was my second year spending this particular week on the island, and I was thrilled to be one of the first to arrive, along with my cousin Kirsten, who flew into Albany to accompany me and Tucker on our drive out to Cape Cod. We had a lot to catch up on since we last saw each other in Belize!

Our first order of business upon arrival was, as always, marveling at the magic that is our town of Oak Bluffs. I always feel a wave of tranquility roll over me as the ferry rolls into the harbor.

Martha's Vineyard Campmeeting Association

Martha's Vineyard Campmeeting Association

Oak Bluffs Police Station

That first night, we celebrated our arrival with a dinner at , a Martha’s Vineyard institution I’ve long been longing to check off my list. I’ve got a post coming up this week about my favorite island restaurants, but suffice it to say — State Road made the cut. And I’m not alone. Even on a Monday night, we barely got on the books with a 9pm reservation, made two weeks prior!

With a hectic week ahead, it was great to catch some quiet girl time with two of my favorites.

State Road Martha's Vineyard

The next morning, my mom’s boyfriend Miller arrived and the two got down to their usual business — home improvement! Meanwhile, Kirsten and I snuck away to check out an aerial yoga class, a first for both of us. Also headed your way soon? A post about my favorite yoga studios on the Vineyard, a list was quickly added to after this fun hour in the air.

I loved having my yoga buddy on the island to check out a new studio with — and play around with my  with!

Aerial Yoga Martha's Vineyard

Yoga on the Vine Martha's Vineyard

That afternoon, a very special delivery arrived — BB, straight from Nicaragua! Except fun fact — BB recently told me that he doesn’t like being BB on this blog. So, henceforth he shall be known by his real name of Ian (I mean really his name is Robert, but like let’s not even go down that road). So anyway. I’d last seen IAN when I dropped him off at the Boston airport five weeks prior after our Memorial Day weekend in Martha’s Vineyard. In between, I’d bopped around the US while he bopped around Central America. So we were pretty smiley while he walked up that pier. And then my mom made him put together a grill. Welcome back!

The next day, we were all hard at work getting ready for the final influx of some of our favorite humans. That evening, the kids — the kids being the three youngest yet still fully functional adults, obviously — unwound with a movie at the newly renovated  followed by dinner and drinks at our newest obsession, . It was the perfect Vineyard evening, kicked off with sunset wine on the porch.

The photo below makes me smile, not because it’s particularly flattering, but because it reminds me of everything I love about life in Oak Bluffs — walking everywhere, wine in hand, zero flips given.

Summer in Oak Bluffs

Strand Theater Oak Bluffs

Strand Theater Oak Bluffs

Now, I can practically hear you begging through the screen —  where are the Tucker pictures?! Yes, Tucker was there too. He was having a grand ‘ol time, as usual. One of my favorite moments of the week came when we were in a cleaning and construction frenzy and my mom noticed a tourist lingering outside the house. When my mom answered her knock on the door, she pointed upward. “Um… there’s a dog on your roof.”

Tucker had slipped through one of the broken banisters and was overseeing his kingdom from a very regal perch. Because we basically live in a dollhouse, he wasn’t much higher than our heads. It still kind of cracks me up just to think about.

Dogs in Martha's Vineyard

Dogs in Martha's Vineyard

Dogs in Martha's VineyardTucker — fan favorite and frequent star of Aunt Olivia’s snapchats

The next morning, we made the grueling three minute commute to the Oak Bluffs pier, where we welcomed my two beloved aunts from Florida. I was so happy to see them! My Aunt Linda had visited the island once decades before (and she had the photo albums to prove it) but my Aunt Karen had never been, so we were excited to give them both a grand tour. As soon as they were settled we hopped in the car towards Vineyard Haven, another one of Martha’s Vineyard’s five official townships.

Vineyard Haven is probably the least charming of all the Martha’s Vineyard towns, which is really saying something about the competition — because really, it’s pretty darn cute.

Vineyard Haven Martha's Vineyard

Vineyard Haven Martha's Vineyard

We tried a new restaurant for all of us — . It was a hit, and I was excited to add a new spot to my mental rotation, especially now that The Strand’s sister theatre The Capawock has reopened. Gotta find that great spot for pre-movie dinner and drinks! (And Vineyard Haven is a dry town, so it must be dinner and drinks — there are no bars and you can’t order alcohol at a restaurant without the purchase of an entree.)

After working off our lunches with some window shopping, it was back to Oak Bluffs again.

Vineyard Haven Martha's Vineyard

Vineyard Haven Martha's Vineyard

That evening, our wolf pack grew again by one — Ian and I’s dear friend from Koh Tao, Janine, arrived to meet us on another island halfway across the world. We were so excited when we realized we were all going to be on the East Coast at the same time, we knew we had to make a meetup happen.

At this point we were getting a little cramped for cars, so luckily we had reserved the small private patio at the Oak Bluffs outpost of , one of our favorite island eateries. (Can you tell how excited I am about this upcoming Where To Eat on Martha’s Vineyard post?)

Sharky's Oak Bluffs

Sharky's Oak BluffsGang’s all (almost!) here!

We were just one blonde short of a full deck. And my baby sister arrived just as we finished up dinner, prompting a big ‘ol hug-fest back at the house, followed by the younger generation taking a spontaneous tour around some of the island’s lively bars.

The next morning, we found ourselves in a familiar formation…

Martha's Vineyard House Rental

Martha's Vineyard Breakfast

Ian, Janine and I concocted a beautiful meal — and by that I mean Ian and Janine cooked everything, and I stood in the corner wringing my hands and shouting various culinary vocabulary words while trying not to burn anything with my eyes.

They outdid themselves.

After such a delicious homemade brunch, we needed a few hours to roll around like beached whales in the sand. Thankfully, the sun was out in full force for the first time in days. And we were going to take full advantage.

State Beach Martha's Vineyard

State Beach Martha's Vineyard

State Beach Martha's Vineyard

After a morning filled with towel flopping and jumping off the famous Jaws Bridge, we resumed our town-hopping itinerary. Next stop, Edgartown, with Janine helpfully volunteering to ride in the trunk (aren’t we amazing hosts?). I think of Edgartown as Oak Bluff’s older, slightly uptight and extremely polished older cousin. You know, the one who went to boarding school and participated in equestrian sports.

While I wouldn’t want to live anywhere but Oak Bluffs, I do love Edgartown as a destination for bike riding, house-peeping, and general touristing. So, y’all know I’m obsessed with , right? Our mission was to take the in order to celebrate the iconic movie’s . Jaws and Martha’s Vineyard are forever fused together in history and film, and my passion for each feeds the other. I was bummed that Jawsfest didn’t come back for such a big moment, but this highly recommended tour helped me get my shark fix for the summer.

Edgartown Martha's Vineyard

Edgartown Martha's Vineyard

And it’s not a bad looking town for a wander, is it? No trip to the island is complete without one.

Edgartown Martha's Vineyard

Edgartown Martha's VineyardI swear I’m not giving Janine the finger. I swear!

Edgartown Martha's Vineyard

Edgartown Martha's Vineyard

On our way back to Oak Bluffs, we made one final stop at one of my new favorite finds on the island  — . The place was packed but we managed to find a table from which to enjoy live music, our gorgeous cheese plate and brews, Martha branded board games, and each other’s company.

Bad Martha's MV

Bad Martha's MV

Bad Martha's MVOlivia, not taking a backgammon loss quite so well

One of my favorite things about Bad Martha? Dogs are welcome, too!

Bad Martha's MV

Bad Martha's MV

Things may have gotten hectic at times, but being surrounded by a crew like this is the best kind of chaos. Before this trip a friend was asking who all was coming along, and I laughed a little as I realized how funny my answer might sound to some. My mom and her boyfriend, my mom’s niece, my dad’s two sisters (they and my mom still consider each other to all be sisters and travel to see each other, years after my parents have separated), my sister, the guy I’m dating and our friend from Thailand. You know, the usual.

And we managed to survive a week with just one bathroom.

Martha's Vineyard Travel Blog

Stay tuned for Part II, posts about where to eat and where to do yoga in Martha’s Vineyard! Do you ever take huge family-and-friend trips? Does your family have a more is merrier policy like mine? Can’t wait to hear all about it in the comments…

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24 Comments...
  • Olivia Snapchatceleb Baackes
    November 15 2015

    FINALLY my snaps are getting the celebration and credit they deserve.

    Your pics are okay too.

    • Meihoukai
      November 21 2015

      Anything with Tucker in it is a pretty guaranteed win…

  • Katie
    November 15 2015

    So many winning photos in this post! Your giving-no-flips wine pose, not giving the finger snap and that hat — not to mention Tucker! Love love love. Funny how traveling around the world makes the back-home family vacations even more magical 🙂
    Katie recently posted..

    • Meihoukai
      November 21 2015

      It really does. I always note that no matter where I am in the world, Martha’s Vineyard always feels special in comparison. That’s a big call! I’m just thrilled I always get to go back there.

  • Linda
    November 15 2015

    Loved the story and being part of it. Liked “boarding school and equestrian” part. stay safe. Hope your computer comes back fixed.

    • Meihoukai
      November 21 2015

      Thanks Aunt Linda! Loved spending this time with you so much. Let’s do it again next year!

  • Mary B
    November 15 2015

    I’ve never been to the Vineyard, but you make it sound like a magical place – I want to go right now! Although maybe it’s not quite so magical in mid-November. I’ll work on finding my own brunch-making bearded bartender to accompany me before next summer 😉
    Mary B recently posted..

    • Meihoukai
      November 21 2015

      I can highly recommend them as travel companions 😉

  • Emily
    November 15 2015

    This post is SO full of stunning photos – and patriotic ones! You have me missing good ol USA a little bit 🙂

    • Meihoukai
      November 21 2015

      I love going back every summer! It’s a pretty great country to explore… and to call home.

  • Tory
    November 16 2015

    Yes!! My husband and I are also huge Jaws fans and have done the Jaws tour, too. So much fun 🙂

    Lovely pictures!!

    • Meihoukai
      November 21 2015

      Wasn’t it a great one? Loved the guide’s enthusiasm!

  • Dominique
    November 16 2015

    Ahh, thanks for reminding me about Polly Pocket! It’s been ages since I’ve seen them or heard anything about that! This is a great post, and the pictures are beautiful as always!
    Dominique recently posted..

    • Meihoukai
      November 21 2015

      Ha, I LOVED my Polly Pocket collection. This post has inspired me to head to the basement at my mom’s house and dig around for it when I go home this summer 🙂

  • Laura
    November 17 2015

    These photos make me so happy! I just did a little fall visit to the island after not visiting for almost 5 years! It was a summer favorite growing up – we’d spend months at a time there! What a place <3
    Laura recently posted..

    • Meihoukai
      November 22 2015

      Ah, I love hearing from other Vineyard addicts 🙂 It is such an unbelievably special place and I feel like you have to see it to believe it. I’m already looking forward to returning again over the summer.

  • Izy Berry
    November 17 2015

    This is so cool your family is looks very united

    • Meihoukai
      November 22 2015

      They are some of my favorite people 🙂 This week was great.

  • Oh My Janey
    November 18 2015

    Your hometown is gorgeous!!!!! It really looks like an awesome week. I wish my family would be so willing to go out whenever I go back to my hometown, too. We just usually spend days at home, haha. But man, the 2nd and 3rd photo really make me want to visit your town. It’s lovely. You’re lucky to grew up in such a pretty area. 🙂
    Oh My Janey recently posted..

    • Meihoukai
      November 22 2015

      Actually, I was born and raised in Albany, New York. But Martha’s Vineyard was our summer getaway spot, and now we have a house there, so it is like a home away from home 🙂

  • Leigh
    November 19 2015

    Martha’s Vineyard looks like the best kind of summer camp for adults! I hope you do a list of all the dog friendly places for those of us owned by 4-legged friends!
    Leigh recently posted..

    • Meihoukai
      November 22 2015

      I have to admit it’s not the most do friendly island (or state, for that matter), but I have definitely learned a lot over the last few summers about bringing a dog there, so maybe I should compile it into a post… though it would sadly be a short one!

  • Marni
    November 20 2015

    Okay, you and Ian are just adorable in those pics. I am a HUGE fan of Jaws (recently they replayed it in theaters and I swear I was the first to buy a ticket), so that Amity Tour sounds beyond amazing.
    Marni recently posted..

    • Meihoukai
      November 22 2015

      The guide is awesome — he’s a total Jaws enthusiast! I was class pet answering all the questions about the movie before anyone else could get a word in edgewise 🙂 Martha’s Vineyard is a must visit for any obsessive fan of the movie. You’d have so much fun spotting all the filming locations!