Travel Guide: Martha’s Vineyard

We can all agree that Summer 2020 isn’t going as planned. Thank you COVID-19. Hell 2020 isn’t going as expected. But I’m making the most of it – enter my trips to the Hamptons and Martha’s Vineyard. Traveling is difficult right now and at times depressing – I was supposed to be in Spain right about now, possibly heading to Ibiza and maybe even back down to Africa alas that’s not happening.

Instead I’m embracing this forced slower pace of life, this life that is parking me at home – doesn’t hurt that It’s a new city with new people and areas to explore. But truthfully we’re being a gift that none of us expected. Many of us are being given an opportunity to explore our own country, one that I often gawked at when my cool European and Australian friends used to love to come and explore.

Exploring the states isn’t what it once was but possibly dare I say better? With fewer tourists, fewer festivals and even better? Less hustle and bustle. Fewer events. Fewer obligations. Covid has definitely slowed us down.

After my move out of New York, I headed for 10 days of R&R in Martha’s Vineyard with a few girlfriends. This idlyiic island that I think many of us consider a sleepy island where JFK Jr and Caroline Basset Kennedy never made it to in the 90s is seemingly remote. An island that I truthfully didn’t know much about before this trip but consider me charmed and looking forward to hopefully many more visits back.

My friend had been visiting Martha’s Vineyard for over 30 years, this is a second home to her but we gave her a reason to get out and explore.

Listen up: One disclaimer, and I cannot stress this enough, respect the rules on the island. Wear the mask (you should be anyways.) Only have one member of your family go to the grocery store or the wine shop. They have TWO yes only 2 ICU hospital beds on the entire island. They cannot afford your recklessness. We all had covid and anti-body tests prior to going. We also had a private home where we stayed with the exception of a few social-distancing activities such as beachside sunsets, two dinners out in Edgartown and a few days of exploring the island via car. Be smart. Respect the rules. Respect the elderly (trust me they’ll yell at you, just ask Meredith, Julie or Jocelyn, we all experienced it!) And more than anything act like this is your home wherever you’re from.

How to get there?

From New York City it’s a 6 hour drive or a quick 45 minute direct flight on Cape Air. Yes other airlines fly there but I don’t want to name names but some of those airlines I refuse to fly as they are flying and operating at 85- 100% capacity. No thank you. I’ve flown Cape Air a number of times and always feel great about my decision. I also don’t mind the smaller planes because it also means fewer people! Check their direct route schedules from NYC or Boston to Martha’s Vineyard HERE.

Where to stay?

Get a house. Trust me on this, there are hotel options but you’re going to want to go for a week – 10 days primarily because of how calming and relaxing the island is.

We stayed in Chilmark which I absolutely adored. This is the house we stayed in with the incredible views of the ocean (yes these views where we saw the seals at sunset and where I was doing morning workouts!) It’s right on the beach too and there is the Chilmark Market just up the road that serves up fresh made coffee, delicious banana bread and pizzas (along with a full market! And those YOMMI popsicles.)

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Being in Chilmark was great, we were a 25 minute drive to Edgartown as well as the airport. Oak Bluffs to be entirely honest was rather disappointing. It was PACKED with people, so much so that the three of us didn’t feel comfortable waiting for a table for lunch because there were too many people. The boats there were also packed, making it more like spring break in the Florida panhandle than the relaxing lovely island that it is.

There are a variety of house options in the area we were in that all can be rented. I’m interested to know if you would go to Martha’s Vineyard in the traditional off-season because I may just try to get back up there.

Don’t forget you can connect with me on inquiries to go to Martha’s Vineyard or any other trip no matter how big, small or even if it’s happening in 2022 as I would love to help you plan the most incredible trip and get special perks like upgrades, property credits and exclusive offers.


How long to stay?

A minimum of a week, if you can. Once you get to the island you will quickly realize that you can do as much or as little as you want to but there is a lot to do if you’re looking for daily adventures of any nature. While it is easy to get there I recommend a house for all of the above reasons but also with travel being so limited this year why not stay, relax and enjoy your time away.

What to do? (See my Instastory Highlights for ALL of this!)

First things first, dining options are incredibly limited and they all highly recommend reservations. This we learned the hard way is a must. Get the reservations because if you don’t you’ll be doing dinner at 9:30 PM on a Wednesday and your crew is real HANGRY. You cannot just go to a bar for a drink so don’t think that’s an option. While we waited for a table at a restaurant we grabbed those amazing Straightaway cocktails you saw me posting and hit the water to catch what was the most breathtaking cotton candy sunset I’ve ever seen.

Porter House was amazing, they have indoor and outdoor dining options, all socially distanced to comfort.  All of their food is locally sourced from area farmers and Highly recommend the buffalo brussels, the fried cheese curds, the summer salad and the farm chicken. The three of us split that and it was perfect.

Atria Martha’s Vineyard was wonderful. They are fully outdoors only seating and great if you have a slightly larger party. They have tables under open air tents in the event of in climate weather or as we experienced, very unusually hot days. Their portions are large so think about getting a few things for the table to share, we definitely over ordered by accident!

We got dinner at a local fish market one evening for a beachside picnic and I cannot recommend it enough! It was so fun and the food was incredibly fresh. Prepare for a lengthy wait but you can bring snacks and drinks to hold you over!

Rent a boat! We would have rented a boat for an entire day but waited a little too late to make that happen so we couldn’t get one with a captain and no one in our group could truly drive one. We opted for a two and a half hour evening sail out of Edgartown that was incredible. I could not recommend this more!


We did a tiny bit of shopping but not much. A few stand out shops that I highly recommend are June (they are appointment only right now), Slate had a great selection of brands that we all know and love plus some of the best straw bags I’ve seen stateside (sadly I think we can all agree after seeing my packing situation that I’m maxed out on the number of bags I’m allowed to own!). I was also smitten with Salte, the sister shop to Slate, that carried some of the best housewares I’ve seen in a while. Such a well curated home store.

Sunset at Aquinnah Cliffs, check out my IG post. This was beautiful but definitely one of the more tourist attractions. We went on a Monday evening and luckily it wasn’t packed but there were definitely groups there.

West Tisbury Farmer’s Market – Again another very social distancing activity – they’re only allowing in so many people but this was awesome. There are local farmers, bakers artisans, coffee shops and we even stumbled up the best find ever – YOMMI popsicles.

I could do a whole post on these guys but wow, they’re $7 nondairy popsicles made with all fresh real ingredients were incredible and didn’t make me feel bad afterwards.

Beach beach beach and just when you think you can’t do any more go to the beach. They’re on the NE so they’re rocky but I wore some of the ugliest water shoes and was just fine. Get the ugly water shoes, get in the water and enjoy every minute of it.

Surf! There is a lot of surfing on the island and there are even surf camps all summer long!


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