Inside Martha’s Vineyard: Daytripping for Beginners

Hey Dolls! If you’re headed to Martha’s Vineyard for the first time, you might be overwhelmed. I suggest day-tripping to Martha’s Vineyard– Here’s how:

Ditch the idea of renting a big house… trust me, booking it and filling it with friends and family it can be a hassle. Instead, I suggest day-tripping to Martha’s Vineyard and booking your lodging in Woods Hole. Let’s dive into why this is the perfect beginner’s guide to experiencing Martha’s Vineyard!

Why Stay in Woods Hole?

Woods Hole is a charming village on Cape Cod and the gateway to Martha’s Vineyard. The ferry from Woods Hole to Martha’s Vineyard is only a short ride away, making it super convenient to hop on and off the island. Plus, staying in Woods Hole means you get to enjoy the laid-back, picturesque charm of Cape Cod while still having easy access to the Vineyard. Click Here for where to stay in Woods Hole!

Your Oak Bluffs Morning Itinerary

8am: Catch the early morning ferry from Woods Hole to Oak Bluffs. Enjoy the fresh sea breeze and stunning views as you glide over the water. Once you arrive, you have some fabulous breakfast options. You could hit up Linda Jean’s or Biscuits for a hearty breakfast. But, let me share an insider tip with you, Dolls: the move is to grab a coffee and a donut from Backdoor Donuts. It’s a local favorite for a reason!

Take your goodies and head over to the Inkwell Beach. There’s nothing like sitting on the grass or right on the beach, enjoying the beautiful scenery and your delicious breakfast. Plus, you never know what you might stumble upon – we came across a wedding proposal! How magical is that?

10am (kid friendly!): If you have kids with you, or if you’re just a kid at heart, make sure to stop by the Flying Horses Carousel. It’s the oldest operating platform carousel in America, and it’s such a whimsical experience. Between breakfast, the carousel, and some beach time, you’ll have a lovely morning soaking in all the charm that Oak Bluffs has to offer. Click Here for your full Oak Bluffs Morning Itinerary

Where to Stay in Woods Hole

I highly recommend staying at the charming Woods Hole Inn. It’s the cutest bed and breakfast with the most beautiful vibes in the Northeast. You can easily walk over to the ferry from there, making your trip stress-free.

Related: My Stay at The Woods Hole Inn Bed & Breakfast

For a more modest option, check out the Sands of Time Inn. This lovely hotel is just a five-minute walk from the ferry terminal and boasts an epic 9-foot pool.

Your Oak Bluffs Afternoon Itinerary…

After your charming morning, it’s time for a delightful afternoon:

12pm: Long Sunny Lunch– Head to Nancy’s for a delicious Caesar salad with shrimp and don’t forget to try their famous Dirty Banana drink from Donovan’s bar. It’s a must!

3pm: Treat yourself to an ice cream cone from Big Dipper Ice Cream. It’s the perfect way to cool down and enjoy the vibrant atmosphere of Oak Bluffs.

What to Wear on Martha’s Vineyard

Dress comfortably and chic for a day of exploring. Think flowy dresses, comfy sandals, and a wide-brimmed hat. Layers are key as the weather can change quickly.

Lunch in Woods Hole: Lee Side

Before you head back, grab a bite at Lee Swim in Woods Hole, right in the same parking lot as the ferry terminal. Their lobster bisque pizza is a game-changer! And if you’re curious about local delicacies, try a quahog. It’s a type of hard-shell clam that’s a Cape Cod favorite.

Final Thoughts on Daytripping to Martha’s Vineyard…

Exploring Martha’s Vineyard doesn’t have to be overwhelming. By staying in Woods Hole and day-tripping to the island, you get the best of both worlds. Plus, you’ll have a stress-free, enjoyable experience without the hassle of renting a big house. I hope this guide helps you plan the perfect first trip to Martha’s Vineyard. Enjoy, Dolls!

And don’t forget, all of the outfits I wore on the Vineyard are listed in my Nordstrom Anniversary Sale blog post on If you’re ready to add them to your cart, you can find them here with ease.

Stay fabulous, dolls!

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top