My Martha’s Vineyard Guide

I hope everyone has been having an amazing summer. We had one of our best ones yet! Although, it’s been a whirlwind of travel and we didn’t have much time to enjoy our own home and back yard, it was super quality and lots of memories were made. Also, it’s been one of the nicest summers weather-wise. The weather has been amazing everywhere we have been. So that is always a bonus.

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My Dress: Lilly Pulitzer | Elle’s Matching Romper: Lilly Pulitzer (on sale!)

One of the places we holidayed over the summer was Martha’s Vineyard. Last time I was there, I was pregnant with Elle Rose on our baby moon (we went to MVY & Nantucket!). This time, I was pregnant, again, with baby girl number 2! So I didn’t get to enjoy any wines or cocktails, again, haha.  However, I was definitely able to let the foodie in me explore, which is fun, as we love to gain inspiration for our own restaurant.

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I admittedly loved the Vineyard more the first time I went. That isn’t to take away from the amazing time we had there, but just something I noticed and was trying to understand. I think it’s possibly because I had been there already, so the initial excitement that accompanies exploring a new place wasn’t fully in high gear. The biggest difference also could have been our accommodations. This time, we rented a home, as oppose to staying at a hotel, since there was a larger group of us traveling together. Don’t get me wrong, it was a lovely home and right in the heart of Edgartown, but definitely different vibes.

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Last time we stayed at the beautiful Harbourview Hotel, which was so amazing (and dog friendly). The concierge at the hotel was one of the best (ask for Darlene!). She even helped us with some of our arrangements during this vacation! Just a lovely lady and so good at what she does! The hotel is in Edgartown, right across form the Harbour Light (a beautiful lighthouse). I loved my morning walks along the beach with Sadie, and Elle Belle in my belly. Also, the neighbourhood was so quaint and charming. I swear MVY has some of the prettiest gardens & landscaping I’ve ever seen – total Hydrangea heaven!

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(pregnant with Elle on this sailboat)

The home we rented during this stay, was very nice and antique, like most of the historical homes here. It was well appointed, but pricey, however location was great (right in the heart of Edgartown). We could walk to restaurants and shops. Honestly, most of the homes we looked at here were pretty pricey compared to other places we have visited. Maybe it was because we started so late with our search, so I recommend planning in advance (we tend to be last minute people!). Either way, I personally recommend staying at a nice hotel if possible, especially the Harbourview. Perks like, having someone clean your room (daily) and all the other amenities hotels offer, directly at your fingertips, are especially appreciated on vacation.

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(gingerbread houses)

If you decide to visit (and you should!), I’ve complied a list of things to do & places to see. For instance, you really should go for a sail! We did a private sail both times we visited and it’s just so beautiful and totally part of the MVY lifestyle! Also, you need to check out the oldest carousel in America – especially if you have children. It’s called Flying Horses and located in heart of Oak Bluffs!

If you’re a fan of the movie Jaws, you can check out several sites where the movie was filmed, including the Jaws Bridge (people love jumping off this!). The gingerbread cottages are SO cute -definitely worth seeing. I have never seen so many cute little dollhouse like homes in one place!

The Gay Head lighthouse has amazing views, although it was raining when we visited it! Oh, and cant’t forget some homemade ice cream, which is a staple here. Our daughter Elle actually had her very first ice cream EVER, here, at a local ice cream parlour called Vineyard Scoops and it was such a beautiful memory captured!

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Aside from this, below are a list of my fave restaurants and shops:

L’toile – Upscale & romantic. They have indoor & outdoor dining. We opted for the outdoor under an enchantingly decorated white tent. Food is French style & lovely.

Chesca’s – This was a comfortable, casual and lively spot. Italian style.

The Terrace: Upscale & romantic. Food was amazing. First time we went was excellent. Second time our server was really not friendly or on the ball (he served me an alcoholic mojito! when I asked for a faux-jito (visibly pregnant – haha). Still recommend tho, him aside, the place is so full of character and loved it.

Back door Donuts: this is in oak bluffs. It literally started as a back door donut shop, but recently has been taken over by new owners and expanded. They had great iced lattes and the apple fritters were to die for.

Alchemy: This place was lively and food was good. They are especially known to have the best cocktails, which I was only able to enjoy in virgin form.

Behind the Bookstore: this was a sweet little coffee shop by day (dog friendly!), serving lunch and dinner (by reservation only) at night. It’s also licensed and the the people are so nice and helpful.

Shops:

Salte: Home decor & lifestyle

Slate: Women’s fashion

Orchard Mile: Women’s fashion (amazing designs)

Nell: Women’s fashion (lots of great pieces)

Vineyard Vines: Men’s, women’s and children’s fashion (where the brand began)

Portobello Road: Such an amazing little store for books, especially coffee table books.

Rosebud Kids – the cutest store – I wanted to buy everything!

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Other helpful recommendations: bring your car if you want to drive around and see things. We didn’t do this the first time and it was fine, because it was just Andrew, I and Sadie. We were within walking distance from everything in Edgartown, so just rented a driver to give us  a day-long tour to see important things on the island, which was great.

Second time visiting,  we had more cargo with Elle and just wanted to have her carseat etc, so we took our vehicle on the ferry. You need to do this in advance though, so make sure you give yourself a week or two at minimum to book it if you want to be sure you can drive on.

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Whether you’re staying in Edgartown, Oak Bluffs or another little town, is totally dependent on your style and what you want to be close to. Both Edgartown and Oak Bluffs are the larger of the towns and about 10-15 min drive from each other. Accommodations seem to be a bit more economic in Oak bluffs and they have lots to see there, but Edgartown has better restaurants in my opinion. Also, I prefer the shops in Edgartown. I feel like Oak Bluffs has a bit more of a touristy vibe, which isn’t really my style. So, really, just depends on personal preference as both are beautiful in their own way.

That said, as you will notice, my recommendations are heavy on the Edgartown side, since that’s where we stayed, both times. If you have been to MVY, please feel free to comment below and share other tips, restaurants and shops you would recommend! I would love to hear more! Also, if you plan on travelling there, don’t hesitate to reach out and ask me any questions – I’ll gladly help where I can. Although summer is high season, I’ve heard it’s beautiful in autumn and even during the Christmas season (also will be much better deals around that time too!)

Thanks for reading and have a wonderful weekend!

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