My Island from Above: A Spontaneous Martha’s Vineyard Biplane Adventure

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!

Recently, I was lamenting to a friend that I felt a little guilty about heading back to a certain destination for a fourth time. There are so many places on my bucket list, it feels like the only way I’ll ever start making a serious dent is to press pause on all the repeats. “But isn’t that kinda like, your thing?,” she asked.

And it’s true. I go back to the same places over and over, until they feels like homes away from home. And I adore getting to know them deeply, go off the beaten track, and find new ways to be surprised on every trip. One of those places is Martha’s Vineyard. I’ve been visiting since childhood, and practically grew up here. I know it intimately. So, imagine my joy at a truly spontaneous, totally brand new adventure there. 

I went on a biplane ride. 

I woke up that morning having no idea I’d do so. I did know I’d be bringing my Wander Women Retreat guests to the Right Fork Diner, where we’d dine outside in the fall sun, watching planes take off from the adjacent airfield. (Did you catch my retreat coverage? It’s been a while, so make sure you’re all caught up on the full retreat recaps before you dive in — you can find part one here, and part two here.)

While we were enjoying lunch, a few of the girls started chatting about how they wouldn’t mind heading up in one of those cute little biplanes as a passenger, as a matter of fact. I was impressed — I knew my retreat guests were badass chicks, but this was next level! Since four of them were onboard, our master arbiter Tiffany headed over to the Classic Aviators outpost to negotiate. 

Typically, flights — which can take two passengers — cost $250-650 and last from 15-60 minutes. However, since it was the end of the season and near the end of the day and we had a group, they kindly agreed to the rate of just $100 per person for their fifteen minute tour of Chappaquiddick and downtown Edgartown.

I had a pang of FOMO as the girls giddily set a return time, but my occasional fear of flying kept me from being too overwhelmingly jealous. I was quite content to watch my girls have a good time. 

Or so I thought. As the flight time approached, one of them did a double take and realized she wasn’t as enthused as she’d originally expected. Now, Tiffany was in danger of having to fly solo. Well, as retreat leader, I simply couldn’t let that happen, could I?!

Throw me a headset, pilot! 

Tiffany and I were the last passengers of the day, and as we watched Shelby and Alex take off ahead of us, the butterflies in my gut started fluttering. The girl manning the ground operations gave us a briefing while we waited and asked if we wanted to tack on an upgrade to our tour. The “add a thrill” option basically means they add a trick or stunt to the flight — like a barrel roll or flip. I was pretty squeamish at the idea, and the $129 price tag made it easy to shrug it off. “Well, this pilot kind of loves doing them, so you might luck out anyway!,” she chirped as my smile froze in place.

Oh does he?

Soon it was our turn to step up into the plane, and get strapped in and suited up with headset radios that we’d communicate via during the flight. This is all happening so fast, I remember thinking — probably a strategic move to avoid last minute ditching from jumpy passengers like myself.

Girl, you’ve been hang gliding over Rio, helicoptering over Malibu, hot air ballooning over Laos, and paragliding over Hawaii. Hell, you even went skydiving! That was my little pep talk to myself. Pep talks are important.

And they work.

But pretty soon, I felt the tension ease right out of my body as we reached a comfortable cruising height. The only thing on my mind? These views. Wow.

In fact, I felt so at ease that when our chatty pilot asked if we wouldn’t mind a barrel turn, I found myself getting swept up in the moment, looking at Tiffany, and shrugging out an unsure… “okay?”

WOW. What a wild ride! It happens so fast you barely know what’s happening, other than the adrenaline that lingered as we whooped and cheered. It felt completely unlike the terrifying sensation of turbulence or the sometimes nauseating motion of roller coasters — it was truly, all thrill. 

Our pilot must have been so impressed by our reaction that he asked if he could wow us one more time. I was basically in a daze at this point but almost passed out from disbelief when our plane rolled forward tail over tip. This trick, which I literally did not even know was a thing, is apparently called a loop. What! How does this madness even exist?! I couldn’t stop laughing like a crazy person. 

Short of jumping out of a plane, it might have been my biggest sky high adrenaline jolt to date.

As you can see from our faces, we were giddy. I was so happy to share this moment with this girl!

As our heart rates made valiant attempts to return to normal, we took in the enormous hidden houses of Chappaquiddick and Edgartown. This part of the island is super private and I loved spying on all the houses you rarely see since they are hidden back from the road. These are the crazy compounds Martha’s Vineyard is kind of famous for, though they feel a million miles away from our cute, colorful little cottage.

I also hung on our pilots every word as he shared facts and stories about the island that I was suddenly seeing from a whole new perspective.

Martha’s Vineyard, you continue to amaze me.

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!