Wander Women Martha’s Vineyard Recap Part I: Welcome to My Island Home

Where we’re at: I’m recapping the fall of 2018, including my Wander Women Retreat in Martha’s Vineyard. Bookings are currently open for Dominican Republic and Thailand. Find out more about our latest retreats here!

After successfully launching my first ever Wander Women Retreat on Koh Tao, it wasn’t long before my mind wandered to other places on this planet that are so special and precious to me, I was just bursting to share them with all of you. Places I knew I had a unique perspective on, and where I felt I could create an experience that no one else could. 

First on the list? My family home in Martha’s Vineyard.

Staying in the Oak Bluffs Gingerbread Houses is such a unique travel opportunity, and one that’s more or less closed off to solo travelers due to cost and availability (the historic community only allows a certain number of weeks of rentals per year, and are designed for families, making them somewhat price prohibitive for solo travelers or small groups.)

So how much fun would it be, I mused, to open up our house to a small group of women for an intimate yoga retreat showing off the best of the island, from a lifelong explorer of it? And since the place is so dang photogenic and y’all are always asking me for photography advice, I added that in too. Soon, Wander Women Martha’s Vineyard: A Yoga + Photography Retreat was born.

With just eight spots available, the retreat sold out almost immediately — and I quickly got giddy at the thought of welcoming a very fun group of women to one of my favorite places in the world. Due to the size and the personal nature of our accommodation, I knew this would be completely different from any other retreat I’d ever run.

As usual, putting together the retreat’s welcome bags was one of my favorite things. Ian — who cooked for the retreat — and I arrived a few days ahead of time to get settled, and putting those welcome bags out on the beds really made it all feel real!

What was inside? A map of the island, a welcome packet with our itinerary and other important info, a steel straw and straw cleaner, eco-friendly Bite Toothpaste Bits, a yoga strap from sustainable brand Prana, a Wander Women journal and pen, a local chocolate bar from Not Your Sugar Mamas, and most proudly, custom Martha’s Vineyard charms from my dear friend and fellow entrepreneur Amy of Amy Jennifer Jewellery. 

It just worked out that almost all the girls arrived on the same ferry into Oak Bluffs, where I welcomed them with open arms and walked them the short stroll to our home for the next four days. I swelled with pride while they oohed and ahhhed over every detail, though we eventually tore ourselves away to head to Ocean Park, the waterfront heart of Oak Bluffs. 

There, we rolled out our travel-friendly Prana yoga mats and saluted the sun as it set over the water and painted the sky with color.

We ended the evening, as we did every night, back at the cottage around the dining room table, enjoying Ian’s beautiful home cooked meals and getting to know each other. I say this every retreat, but once again I was truly blown away by what a great group the universe brought together for this trip. I felt exactly like I dreamed I would when I started fantasizing about these retreats — surrounded by friends.

The next morning we woke up to an epic downpour, which put a damper on our plan for a yoga class on the beach and a photo walk around Oak Bluffs. Instead, we got cozy in the cottage with tea, and had a photo editing lecture and workshop. Being largely self taught, I was fairly intimidated to dive into these topics, but doing so was a nice reminder of how much experience I’ve gained in the last ten years (and I constantly have to remind myself that I do have a BFA from a prestigious art school, and took several photography and editing classes there). 

It was still moody and wet outside when our driver for the day arrived and whisked us to Not Your Sugar Mamas in Vineyard Haven, where we’d pre-ordered yummy organic vegan food for a body-fueling lunch. Getting to meal plan and take everyone to my favorite restaurants is one of my favorite aspects of retreats!

While none of our retreats are fully vegan or vegetarian, we always have those options available and incorporate a vegan meal or two for the whole group in order to lessen our environmental impact.

When I’m hosting friends on Martha’s Vineyard, I generally try to make sure that, at the very least, we hit up the charming towns and beaches of Oak Bluffs and Edgartown, and make at least one journey “up island” to enjoy the rural area’s farms, galleries, and iconic sights.

Without a super rigid schedule, we pulled over anywhere I suggested that got a thumbs up from the group, including Chilmark Chocolates (soon to be a memory from the past!), Martha’s Vineyard Glassworks, The Field Gallery, and of course, Alley’s General Store.

Alleys in particular is such a staple from my childhood, I can’t not stop here when I’m up island. It’s a true relic from the past — a general store with snacks, summer toys, household hardware, and mail pickup for nearby rural residents. They’ve also added a farm stand, and 7a Foods, a great cafe in a building around the back.

Next stop, the Aquinnah cliffs and lighthouse. Originally, we’d planned to go up in the lighthouse, but it was closed due to the rain. So, we wandered around, cameras in hand, and had fun playing around with how to photograph outdoor scenes in less-than-ideal conditions.

I might be a tad biased, but I find the island beautiful, even in the rain. Lucky for me, so did the girls.

Thankfully, our next stop wasn’t weather dependent. From the moment I decided to hold a yoga retreat on this island, I knew that The Yoga Barn had to be a part of it. Of all my many favorite places to do yoga on Martha’s Vineyard, this is, in my opinion, one of the most beautiful and peaceful.

And when I saw the island’s aerial yoga teacher, who I’d practiced with before, had started teaching there, I immediately set up a private class.

How stunning is this space! Jen’s classes are gentle and welcoming, and at the end of the retreat, many girls named this reflective hour as one of their highlights.

Our last stop for the day was a treasured one, for me. I think Menemsha is hands down the most photogenic town on Martha’s Vineyard, and so there’s no way I was bringing a photography group to the island without a wander there.

It’s also the island’s most iconic place to watch sunset, so I’d packed my classic setup of beach chairs, beach blankets, wine, cheese, and other local snacks, which the girls supplemented with seafood from the fresh markets along the harbor.

Fun fact: Menemsha is where much of Jaws was filmed! It’s just an absolutely iconic little New England fishing hamlet, and the girls had so much fun running around taking photos here.

The photography portion of this retreat was very casual and unstructured and honestly I’m not sure if I’d do it again, since I tend to be prefer being over-the-top and perfectionist instead. But I admit I had a great time, giving impromptu little lessons on framing and taking portraits and remote shooting. Some of the girls came with dSLRs and some of them came with iPhones, and we all had fun and learned something — myself included!

Now, by the time sunset was rolling around it was more than obvious that we weren’t going to be actually seeing any sun setting. Nope. So I asked the girls if they still wanted to stick around, and they said, heck yes! And I loved them for it. 

We scooped up some seafood — it was well into the shoulder season, and the staff at Larsen’s were friendly and playful in a way you just won’t find them in the midst of a chaotic summer — and made our way down to the beach.

In the middle of summer, you have to arrive an hour early to find a place to stretch out a beach blanket to watch the sunset on this beach. On this late September evening, we literally had the entire beach to ourselves, aside from a few bemused fisherman who gave us waves and smiling head shakes as they pulled in their catch.

We sipped our wine and noshed on seafood and talked about life and travel and imaginary sunsets and laughed so hard I knew I’d remember the moment forever. In fact, this too was brought up several times as one of the highlights of the trip. What’s better than a group of girls who can turn a flop of a chilly sunset into a highlight of a trip? 

Back at the house, we enjoyed the light dinner Ian had prepared for us — since we’d already had our scenic first course on the beach — and snuggled into the living room for yet another can’t-miss-Martha’s-Vineyard-moment. I’m referring, of course, to eating dessert — in our case, local pie from Pie Chicks — and watching Jaws.

(I may or may not have recited most of the lines from memory. Sorry ladies.)

Lucky for us, the weather was about to turn — and the company was going to stay divine.

To be continued!

Bookings are currently open for Dominican Republic and Thailand. Find out more about our latest retreats here — and get on the mailing list for future Martha’s Vineyard retreats!

If you’d like to see Martha’s Vineyard through my eyes, my family’s historic Oak Bluffs gingerbread cottage is available for weekly rentals. We renovated each room by hand and I’d love to share its magic with you!