A First Timer’s Travel Guide // Martha’s Vineyard, MA


Slushy snowstorms and bitter cold weather has me digging through vacation photos and thinking about packing a suitcase and taking another trip back to Martha’s Vineyard this year. Since we have been restricted to staying within our state, this is a great alternative that feels like a vacation without needing to talk to a travel agency.

The mister and I spent our anniversary in this beautiful New England destination to celebrate. We have been trying to travel more for anniversaries and birthdays as part of our gift to one another and it have been a delightful change. I honestly, don’t know what took me so long to get to Martha’s Vineyard since I grew up in New England, but I am glad we made the decision. I get the allure now.


To get there, there are really only a few options since driving is not one of them. One is via a boat. You can get a ferry from Hyannis Port or through another port we found in Bedford for the Seastreak Ferry. We prefer this port because it’s smaller and more intimate. Sometimes traveling can give me anxiety when you are fighting for seats!

The other option is via flight, I believe that JetBlue has options to go, but they are limited times and days. So however you choose to get there – here is a first timer’s guide to having an amazing weekend from our first time too!




Summer Camp Hotel – Loved it here! If you are looking for a Martha’s Vineyard hotel, this is a great option. It is located in Oak Bluffs, the main area of the island that we visited during our stay. It was the perfect mix of fun and casual and even though its more of a family hotel, the rooms are clean and perfect for the week. Tip – when checking in – ask for a room in the second house that is not attached to the main building. It helps with the noise of people entering in and out and less flights of stairs to carry your luggage up and down.


Martha's Vineyard_1

Bad Martha Brewery – we always try to find a brewery and this one was intimate, great beer flight options and a cute seating area outdoors. We made a few friends there and had some great convos before parting ways. You do need a car to get here since it is not in the center of town.

Art Cliff Diner – This is a non-negotiable. If you can get here go – and go early. Thankfully we are typically early birds anyways – but this place packs up real quick! The food is amazing and the menu is expansive!

Mad Martha’s Homemade Ice Cream – I don’t know about you, but I usually lean towards a cookies and cream or mint chocolate chip flavor. The only one that can beat those options are black raspberry chocolate chip – much harder to come by. I got cookies and cream here one night after dinner and it was a total treat. 

The Red Cat Kitchen – My favorite meal of the entire trip. This was our anniversary dinner night and boy was I blown away. I had an heirloom tomato gazpacho and I couldn’t stop talking about it. Roast Duck as an entree and saved room for dessert! Make yourself a reservation because it is 100% worth every bite.


ToccoPuro Coffee Shop – Stopped in for an iced chai tea latte one morning and it was a delight!

Nancy’s Restaurant – Get off the boat and immediately stop here! Get yourself a dirty banana and sit on the top deck for the view. You’ll thank me later for it.

Seaweed’s – A cute little bar/restaurant that has live music on certain nights. We stopped in for a charcuterie board and a glass of wine one day and loved the vibe.

Other’s – Offshore Ale Company for good pub food, Mocha Motts for Coffee and Giordano’s Pizza.




Rent a Car – Its ok if you don’t plan for this, there are several local shops on the center of town where you can rent day of! Just get there early to have your pick. Most of the Jeep Wranglers are gone by then, but we got a sweet convertible Mini Cooper and it was perfect to cruising the island.

Gay Head Cliff – Go there. It’s beautiful and the perfect drive with the rental car. There are so many lighthouses and beaches, find them all and go! The journey is just as great as the destination.



Flying Horse Carousel and Arcade – this downtown staple is one of the first buildings you see when you get off the ferry. It is right in the center of the road – you cant miss it. They have n old school Zoltar machine – so you know we had a blast! We are all just kids on the inside.

Jump from Jaws Bridge –  You know – like the location where they filmed the Jaws movie! Ok this was not a ‘we did’ moment more so than ‘he did’ moment. I was too chicken to make the jump and the water was freezing. It didn’t stop my mister from taking his turn. We signed out the bikes and two helmuts from the front desk of the hotel and took a ride out to the bridge – great day trip. (tip: pack a towel in a backpack for the ride, the water can be chilly!)

Edgartown – A part of the island that is just as cute as the rest. We really loved the center of town full of restaurants and shops. I wish that we got to spend more time here – but there is always a next time!



Wesleyan Grove – If you are looking for those infamous cottages that you see when you google Martha’s Vineyard, this is it! Since we stayed at Summercamp Hotel , there is a road behind there that cuts right through to main street. It is charming, colorful, and everything you imagine it to be. Be weary that people do live there, so be respectful – but say hi!!



Johnny Cupcakes – a local new england shop with an imaginative shopping experience. Per their name, you think that they sell baked goods – but they sell apparel. The entire shop is set up like a bakery for you to select tee shirts, pins, stickers, sweatshirts, hats and more. We left with matching tees!

Vineyard Vines – For all the new englanders out there – this is a must stop. You see the Vineyard Vines logo and apparel everywhere – but where else to get it then on the vineyard?

Black Dog – Another Cape Cod brand that is local to the area! I have a few items from them and it is classic! Get yourself something comfy for the chilly nights on the water.


With so many more things to do – these were the most notable things that we still remember! If you plan a trip and have questions – feel free to reach out!! Martha’s Vineyard is beautiful and definitely a place to put on your bucket list if its not there already. We may have to visit again this year.

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Author: Jackie

A marketing professional and lover of all things fashion and style, blogging on nights and weekends.

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