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!
I woke up on the third day of my inaugural Wander Women Retreat with a huge smile — both because the sun was out, and because I had some surprises up my sleeve. If you missed part one of my retreat recap, catch up here!
The first order of the day was making up our rained-out yoga class on Inkwell Beach from the morning before. In the quiet early morning hours in front of the sea, it was the most at peace I’d ever felt teaching yoga.
How could I not, with a backdrop like this?
I can’t tell you how much this picture tickles me — dogs and downward dogs!
One of the things I love the most about our house in Oak Bluffs is that we can walk almost anywhere! After a quick stroll back to the house for a lush and healthy breakfast by Ian, we were off for another active adventure — stand up paddle boarding.
Now, this was originally intended to be a stand up paddle yoga class. I love mixing in working with local outside vendors for our retreats, but sometimes I do cede a bit of control, and I was surprised when I called to confirm the private SUP class I’d booked months prior and was told that actually the SUP teacher was off-island, so it was going to be more of a paddle tour instead.
I was bummed at first, though it actually worked out quite well in the end as almost none of the girls had been on a paddleboard before — so it ended up being a pretty great introduction!
For half the tour, I stayed on shore and sent up my DJI Spark to capture some aerial snaps before frantically paddling out and using my CanonG7X and underwater housing to snap some paddle portraits. I wore a lot of hats on this retreat, but photographer might just have been my favorite!
Once we were back on dry land, it was time for lunch. I was super excited to take the girls to one of my more recent Martha’s Vineyard discoveries, The Right Fork Diner. Sat smack dab in the middle of Katama Airfield, I thought the small planes that are constantly taking off and landing from right off the deck would make the perfect photography subjects.
However, a few of the girls had another idea! When four of them expressed interest in actually going on a biplane ride, I couldn’t have been more psyched for them! Our girl Tiffany went right in on negotiations and arranged a great group rate.
And then, when one of the girls decided to hold off last minute, I pretty much had no choice but to push my quasi-fear of flying aside and offer to take her place, right? I’ll be writing a full post on my very first and very spontaneous bi-plane ride, but suffice it to say I was thrilled that even I managed to have a new Martha’s Vineyard experience that week.
Next up, wandering around Edgartown! I always tell our visitors to the Vineyard that there is this huge Oak Bluffs and Edgartown rivalry, but there’s a very good chance that it is very much just me loving Oak Bluffs a little too hard and enthusiastically for my own good.
Still, while there’s nowhere else on Martha’s Vineyard I’d rather live than where we do, I can see the charms of Edgartown, which very much retains its historic whaling town feel. And its lighthouse is truly something straight out of a postcard.
It’s my goal to make it inside all the lighthouses on Martha’s Vineyard that are open to the public someday, which I plan to recount with a victorious blog post! For now, this one is my go-to.
Lighthouses are kind of a cover story, though — my true motivation for heading East on the island revolves around my favorite ice cream shop, a hotly debated topic among Vineyard residents and visitors.
I’m making it official and putting it in writing: Scoop Shack is my jam. With creative flavors like lavender lemon and green tea with mint, it really stands out even on an island known for its ice cream cones.
Our day had gotten a tad off track what with the impulsive airplane rides and all, so we rushed back to Oak Bluffs for a sunset yoga class in Ocean Park.
It ended up being perfect — we were all silly and exhilarated from the hustle, which was the perfect mood with which to embrace a partner yoga practice. Just look at these smiles!
I love partner yoga both for the deeper stretches it allows you to access, and how it can push you just slightly out of your comfort zone. I think I’ll always try to have one in my retreats from here forward.
And we ended just in time to nab the most stunning sunset silhouette photo of each of the girls in front of the iconic Ocean Park bandstand. One of them even generously grabbed one of me that I’m obsessed with!
Ian had an amazing dinner waiting for us back at the house — I really came to cherish our time around this dining room table.
As it was our final night on the Vineyard (that crept up quickly — three nights go so fast!), we were ready to hit the town! I’d been absolutely itching to get to The Barn, Martha’s Vineyard’s hip little bowling alley, and this was the perfect occasion. With regular events, raved-about food, and five sets of lanes each dedicated to one of the island’s five towns, it’s quite the year-round island hot spot.
I absolutely loved the place — and not just because I crushed the competition, sorry ladies! After, we hit Circuit Avenue for some dance floor action, which I still smile at the memory of.
The next morning, we treated ourselves to smoothie bowls for our final breakfast at the house. Ian did such a truly fantastic job as our chef for this retreat, we were lucky to have him!
After breakfast it was time for my big surprise of the retreat — alpaca yoga! Originally, I’d been obsessed with making my beloved goat yoga a part of the itinerary, but had to let that dream go when the instructor was unavailable for the weekend. Then, months later, once the retreat was already planned, set, and sold out, I saw a freakin’ alpaca yoga class being offered on the island.
I knew I would stop at nothing to include it.
And believe me when I say I had to pretty much make good on that, ha. It took some serious logistic backflips to make it happen, but the pure joy we all experienced that morning at alpaca yoga was worth it — and deserves a blog post all its own.
And finally, our biggest gamble of the trip — trying to get a group table at ArtCliff Diner, arguably the most sought-after brunch spot on the island. Even being shoulder season, since it was a Sunday morning in the shoulder season, it was still a somewhat risky move — one that would be completely impossible in the summer.
Still, the short wait allowed us time for a stroll around Vineyard Haven, and once we made it to a table, it was the perfect setting to muse on the highlights of the trip — and make plans for future meet ups.
I’ve gotten a lot of questions about if I plan to hold future retreats in Martha’s Vineyard and the answer is I would love to. I have a dream of holding a sustainability-focused retreat here, where we visit the island’s farms, discuss conservation and do workshops on things like composting, making your own toiletries and household products, and of course, practice lots of yoga.
I’m not sure when this will come to fruition, but it’s on my mind — let me know if it’s something you might be interested in, too!
I was so touched to share this very special place and make these precious new memories in my lifetime island home away from home, and I’m so grateful to the girls who joined me for making it the positive experience it was.
This island is magic, and I felt privileged to share that.
Here’s to another wonderful Wander Women Retreat!
Bookings are currently open for Dominican Republic and Thailand. Find out more about our latest retreats and be on the mailing list for future Martha’s Vineyard retreats here!
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!