📆 Itinerary: One Perfect Day in Oak Bluffs for a First Timer

A Martha's Vineyard bucket list: featuring where we would bring our friends + family when they visit for the first time

Jun 21, 2022

Quaint homes along Ocean Park in Oak Bluffs

I get so many requests for itineraries or “What to do ____” for various amount of time and from varying types of Vineyarders - first timers, repeat visitors, residents…it’s a difficult ask! First, it depends on the weather, the time of year, the preferences of the person, the group size…there is simply no one-size-fits-all MV experience! But, I’ll do my best 😊

For now, this post is about spending ONE day on island, in-season, with 2 adults, for someone who’s never been here before and wants a good gist of what we have to offer.

First off, for Day Trippers in season - we always recommend passengers taking the Island Queen Ferry into Oak Bluffs. ⛴️ If you want more info, check out this post about how to get from Cape Cod to Martha’s Vineyard.

Lastly, this list is not exhaustive, and instead just features where we PERSONALLY would take a friend or family member who is visiting the island for the first time.

MV in One Day Bucket List

⛲ Walk Around Downtown Oak Bluffs

Here are some of the more scenic walk suggestions of places you can route to in your phone while you walk around town

MV Camp Meeting Association - see the “Gingerbread Houses”
Ocean Park - large open area with a gazebo that overlooks the water
East Chop Lighthouse (45 min walk)
Inkwell Beach towards Joseph Sylvia State Beach (30 min walk)
Circuit Avenue is a main street - common shops/attractions here are Vineyard Vines and The Black Dog (now successful national chains, both established on Martha’s Vineyard)

🦞 Eat some Seafood with a View

Some personal favorites:

The Lookout Tavern - our favorite lobster roll on island, and if you want to do it like a local, get it hot! We also love the popcorn shrimp.
Nancy’s - we love the lobster mac + cheese here!
Giordano’s - Take Out Window - Get some fish + chips or fried scallops to go, and eat them on the picnic tables in Ocean Park!

🌊 Beach!

If you’re into laying on a beach, you can go to the beach to Oak Bluffs town beach the left of the ferry, or Inkwell to the right. It is walkable within minutes of getting off the ferry, and close to town.

📍Do something tourist-y

Whether or not you’re into history, there’s a few quick spots of note you can check out

Trinity Park Tabernacle - walk over to the largest covered outdoor performance space on the Island, has been a center for cultural, religious, and social activities on the Island for more than a 100 years
Flying Horses Carousel - take a ride on the oldest operating platform carousel in America. It’s tradition to try to catch the brass ring to win a free ride!
African American Heritage Trail - explore on your own some of the 30 sites dedicated to the formerly unrecognized contributions made by people of African descent to the history of the island. Info here

🍦🍹 Get a treat or drink

Cocktail - we love a Dirty Banana from Donovan’s Reef at Nancy’s
Ice Cream - we love Ben+Bills for ice cream

Itinerary:

Now that you know the main players - here’s how this could realistically look for under $150 per person, leaving travel time on either side of the trip.

10:00 - Arrive, Park + Purchase round-trip ticket at Island Queen $25 (Parking +$20)
10:30 - Depart Falmouth
11:05 - Arrive in Oak Bluffs, walk along harbor and explore the MV Camp Meeting Association + Tabernacle
12:15 - Eat Lunch at Nancy’s, order a lobster roll + a dirty banana $55
1:30 - Go for a ride on the Flying Horses Carousel $10
2:00 - Walk up and down Circuit Avenue shops
3:00 - Grab an ice cream at Ben + Bills and walk over to Ocean Park. If you’re good on time, go sit on Inkwell Beach in the sand. $10
4:15 - Walk back and board the 4:30pm Island Queen Ferry home

I hope that helps! Eventually, I hope to post weekend-long and week-long bucket lists across various towns. More soon, MVactioners!

Before we go, I’d love to mention that none of the content on my blog is sponsored in any way. These opinions are based on our own personal experiences (as a mixed race couple) dealing with high-quality service consistently and paying our own money. We hope you come to trust our recommendations over time. Know that subscribing and sharing our content is the kindest way to support us ❤️