The Travel Trio Reunited in Martha’s Vineyard

We’ve partied in Miami, adventured all over Bonaire, and chilled out in Aruba — our blogging trio gets together whenever we can. But Kristin, Angie and I don’t get to see each other nearly as much as we’d like to, which would ideally be like, oh I don’t know, every day or so. (Which luckily is how often we touch base in our therapy-like group iMessage.)

Last year, I was thrilled to host our crew for a five-night adventure around the East Coast. After one brief but fun night in Boston, we were off to one of my favorite slices of this planet: Martha’s Vineyard.

My mom very generously allows me to host friends whenever we can make it work in the cottage’s hectic summer schedule: in the past, I’ve hosted a girlfriend getaway of my childhood friends from Albany, a couples weekend for two of my friends from Brooklyn, and now, my very own travel blogger bonanza.

Our first stop was my mom’s cottage — of which I’ll be doing a renovation update post soon! — and strolled around the ever-charming town of Oak Bluffs. The girls were ga-ga for all of it, but what really got my heart rate racing was the sight of the freshly renovated Summercamp, formerly known as the Wesley Hotel.

My family knew the Wesley fairly intimately — we used to shower and do laundry there when our only bathroom was being renovated! — and so it was wild to wander through this fresh and fun iteration. I swear, if my family didn’t have a cottage a stone’s throw away, I’d be tempted to move right into this playful and colorful new hotel.

Since I was showing two travel journalists who just love site inspections — industry sarcasm there, folks — I also couldn’t resist showing them Dockside Inn as well, another slightly more budget-friendly option in Oak Bluffs.

We punctuated our lazy day of wandering the town with two great meals at a few of my island favorites: a quick and easy lunch at Slice of Life, and later a fancy dinner at Red Cat Kitchen. Red Cat is one of the few Martha’s Vineyard restaurants that I just can’t go on living without visiting once a summer, but this particular meal was a bit of a letdown. I was miffed by our table placement out on the closed-in porch — turns out I hate three-tops facing a wall with a passion. Self discovery is so important, isn’t it? From now on, I’ll be specifically requesting a table in the main dining room when I make a reservation (and yes, you need a reservation.)

Early the next morning, Kristin and I hopped over to Mansion House in Vineyard Haven for a hilariously showtune-oriented zumba class. I’d been dying to try the fitness classes at Mansion House for ages and having a fellow group exercise addict in town was the perfect excuse. Fellow Vineyard folk, take note — despite being one of the fanciest gyms on the island, the class packages at Mansion House are an insanely good value, include access to the fitness center and pool, and they don’t expire for twenty-four months! I couldn’t wait to see where the rest of my twelve pack would take me.

After scooping Angie up back at the house, we were off. I actually had a very snazzy plan for the day, but it was quickly crumbling. We were running a little behind schedule, so I ditched the new (and slightly out of the way) brunch location in favor of reliable ‘ol Sharky’s Cantina in Edgartown, so that we would still make it to our Chappaquiddick Lighthouse Tour in time.

Except whoops, I kinda screwed that up too — the website had two different times listed for the tour on two different pages on their website, just thirty minutes apart. For some reason the later one stuck until I called to ask some detail about where to park or something and realized my mistake — and that we’d never make it on time at that point. Oops.

So we were on to Plan B, a different lighthouse. Bonus: Sharky’s is delicious, and a lighthouse is a lighthouse. And this one did not require a tour. (Though I’ll get you someday, Chappy Lighthouse! I’ll get you someday!)

Photo courtesy of Kristin Luna

Can you believe I’d never been to Edgartown Lighthouse? No surprise I missed in my childhood visits to the island, however, considering public access was only added in 2007.

After a scenic stroll down the short path from Edgartown’s Harbor View Hotel, Kristin and I happily scrambled up to the top of the lighthouse for a bargain $5 donation to the Martha’s Vineyard Museum, and a friendly chat with the ticket man, who works in the island’s public school during the year and its lighthouses in the summer.

Photo courtesy of Kristin Luna

After, we wandered around the boutiques, ice cream shops, and cafes of Edgartown and I took the girls for a house-peeping drive through my favorite residential streets. Edgartown is so different from Oak Bluffs, it’s really fun to compare and contrast and brainwash new Vineyard visitors on the superior choice between the two. (Just kidding! Sort of.)

Photo courtesy of Kristin Luna

Photo courtesy of Kristin Luna

Photo courtesy of Kristin Luna

And then I thought, oh, wouldn’t it be nice to show the girls South Beach? Growing up, South Beach was our go-to stretch of sand, as we always rented houses around Edgartown Great Pond (this was before my mom became an Oak Bluffs resident, of course.)

Of course, this being my major fail of hosting day, the beach was cold, windy, and completely abandoned — the second time I’ve hauled guests to the other side of the island to discover so. Lesson learned, from here on South Beach in a July and August only zone.

Photo courtesy of Kristin Luna

Photo courtesy of Kristin Luna

On our way out of town, we stopped for goodies at Black Sheep, an Edgartown favorite for home-cooked grab-and-go meals. I’d arrived on the island with a case of wine for the summer and we decided to tuck into it with dinner at our own dining room table. After, we were joined by my Hawaii friend Caitlin, who I realized via Facebook just so happened to be in town for a wedding, and we hit Circuit Avenue for a hilarious night of dancing at The Trampost, er, The Lampost. (Sorry guys, that joke gets me every. single. time.) I love any nightlife that involves a five minute walk to get to!

Sunday, we woke up relatively early to head to a class at the Yoga Barn. While the gentle fascia-focused yoga wasn’t my favorite class I’ve ever taken, the space is stunning and it was probably a nice transition for our bodies in recovery from the night before. Want more yoga? Check out my list of the island’s best studios!

And then, having ticked off the “health” portion of our Sunday, it was time to move onto the “treat yo’ self” segment! I’d been dying to check out brunch at island darling State Road for ages, and I absolutely loved it. Luckily, so did the girls.

Personally, I preferred it to dinner, though that’s probably for strangely particular only-to-me reasons like I find the lighting too dark at night (honestly, I have a problem) and State Road occupies such a rustically beautiful space I really enjoyed admiring it during the day. Want more food? Check out my list of the island’s best restaurants!

The rest of our day was delightfully low-key. I’d suggested a drive up-island to see the Aquinnah Cliffs and the Menemsha, but it was so overcast and foggy we weren’t sure if it would be worth the trip. Then Angie suggested (slash begged for) another idea — Jane Austen’s Love and Friendship at the Martha’s Vineyard Film Center, a limited release movie which she reckoned wouldn’t run in her hometown of Jacksonville.

I have to admit I went completely out of the desire to see my friend happy and be a good host; I personally had no interest in the movie whatsoever. But WOW am I glad we went — I can’t remember the last time I laughed out loud so often in a movie theater, and I have a newfound interest in Austen’s works as a result.

Photo courtesy of Kristin Luna

Our next and final morning, I was determined to take the girls to one last impressive meal. And so we headed to Art Cliff, my favorite choice for weekday brunch — it’s a fools errand, unfortunately, to try to go anytime in the summer on a weekend — with a driving tour through East Chop en route.

As usual, it was a treat! The girls and I split several dishes, including blueberry and brown sugar pancakes. I love Artcliff’s twists on traditional breakfast food, as well as their kitschy cute decor.

Photo courtesy of Kristin Luna

Photo courtesy of Kristin Luna

And then, in what felt like the blink of an eye, we were headed off the island! Thankfully, it wasn’t goodbye just yet, as we still had one last night together in my hometown of Albany coming up.

This trip, like any time I spend with these girls, was glorious. Granted, I had a bit of hosting guilt over all the things we didn’t do or see. I had planned a gorgeous itinerary, a lot of which fell apart due to weather (it was unseasonably cold and overcast all weekend), planning snafus (I made some oopsies) and all of us craving a bit more down time than expected (understandable). I can only hope I can convince them to come back soon for round two!

Want to see more photos and hear more stories from our trip? Check out Angie’s blog post and Kristin’s blog post for a different take!

What’s your favorite girlfriend getaway destination?

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!

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