From two girls who have spent some time there.
Congrats, if you’re reading this you are either on the vineyard or considering going there. It’s a great place to be and full of so many wonderful memories from time spent there with my family and of course, my best friend Sam. Sam has a beautiful home on the island and her family split their time between there and Boston as she grew up. This means she knows all the best spots and I was lucky enough to learn about most of them from her. Check out our suggestions below for the perfect vineyard weekend.
Saturday
- Grab a coffee at Toccopuro in Oak Bluffs and walk through the camp ground. It’s a hidden gem on the Main Street downtown that opens early and welcomes you with smiling faces behind the counter. The coffee machines there are top notch and so are the people, this is one local business we loved supporting during quarantine. We would pop in as soon as they opened, grab our coffees and take a walk through the camp ground (right behind the shop) to look at the gingerbread houses. The gingerbread houses are historic and iconic pieces of New England history and you have not been to the vineyard if you have not seen them.
2. After your walk, hop in the car to head to Edgartown for breakfast. You’ll want to head towards the harbor but stop before you get too close to the water. Hidden around the corner you’ll find my favorite restaurant on the island, Among the Flowers. Sit outside and order coffee (yes, another one) and the waffles. You won’t be sorry.
3. Prepare for a casual beach day – at least that’s how we liked it. Jump back in your car and head for Tony’s Market in Oak Bluffs. This small but mighty store has everything you need to camp out at the beach – alcohol, sandwiches and snacks.
4. Head for State Beach in Oak Bluffs and park along the street. Pick literally any spot and just relax for most of the day.
5. If you’re about ready to pack it up, head to Noman’s down the street for a quick afternoon snack and maybe a drink or two. Don’t be alarmed when you walk in and the interior seems huge, just order what you want at the counter and head to the left for the patio space. There is tons of outdoor seating in an adorable backyard area, it’s one of my favorite little places to hang out and there’s no way you won’t feel happy just being there.
6. This part is crucial – live like a European and make your dinner reservations for later in the night, like around 8pm or so. As you get ready for dinner you MUST put out a cheese platter, drink at least two cocktails and listen to Carly Simon songs on repeat. This is the most important step, it’s practically a rule.
7. Dinner at Jimmy Sea’s in Oak Bluffs. This restaurant is like going to your Italian grandmother’s house and bringing all your friends. The staff? So nice. The food? Amazing. The rooftop? Even better. The drinks? Just order a bottle of wine for the table. This is family style, Italian food to feed your family two times over. Whatever pasta you order it comes to you at the table in the pan it was cooked in and you just share (or you don’t). Don’t forget to talk to the other tables around you like you’re old friends and sing along to the music they play – that really makes the night.
8. Before you go home, head across the street to get a Backdoor Donuts – yes that is the actual name. It’s literally right across the street from Jimmy Sea’s. You won’t miss it because you will see a line of people in a parking lot, paying cash at the backdoor of this bakery specifically for late night doughnuts. Waiting in line is half the experience, talk to the other strangers also waiting, dance around, enjoy it.
Sunday
- Sleep in, there’s no rush to take on the day. You’re on vacation after all. But don’t sleep too late, you’ve gotta get up and hit the town. Edgartown, that is. I love Edgartown, it’s my happy place, truly. Jump in the car and head for Downton Edgartown and grab a coffee at Behind the Bookstore. It’s literally a cafe on the main street of downtown that is (you guessed it) behind a bookstore. You’ll see it.
2. Shop around, pop in and out of stores and see if anything catches your eye. We always peruse like this but rarely buy anything, it’s honestly an expensive area but it makes for the best window shopping.
3. Back to the car, you’re driving to the airport. Well, sort of. You’re driving to Right Fork Diner for brunch to sit outside at the picnic tables and watch vintage planes take off and land. You can pay about $300 for one ride. Although the planes are adorable, I haven’t worked up the courage to get in one yet, but they’re a nice view to eat next to.
4. Conveniently, Right Fork is just down the road from South Beach, which we sometimes go to if we’re in the mood for a good swim. The waves are pretty strong there so it can be fun, but if you’re looking for a good tan – Aquinnah is where you want to be. Gay Head beach (or the Aquinnah cliffs) is our beach our choice because the natural cliffs along the shore are os beautiful but also- it’s a nude beach. No tanlines, no one bothers you, you can just totally let go and enjoy nature.
5. Head to Menemsha closer to dinner time, this is where you will have a casual but amazing dinner. Find a parking spot and order take out from the Menemsha Fish Market and take it over to the beach right next to it. Settle in on the sand and face the water to eat dinner while watching the sunset. Don’t be surprised if you’re not the only ones there either. Last time we did this we brought a bottle of wine too and a sweet little girl was walking around selling rocks to everyone. There’s nothing better than moments like that.
There you have it, the perfect vineyard weekend, our way.
