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It only seems fitting as we’re about to bid summer adieu, that I share our day trip to Martha’s Vineyard (“MV”). P and I had always envisioned MV to be the vacation destination for the ultra preppy à la The Great Gatsby, which honestly didn’t really appeal to us all that much. I guess you could say that we’re hippies at heart and aren’t really interested in the “bourgey” lifestyle that MV seemed to portray. Boy, were we wrong! Sure, there was a little bit of prep. But the people were friendly and laid back, the food was fantastic, and the best part of MV was the seemingly untouched coastlines that stretched as far as the eye can see and the magnificent beaches. Why didn’t we come sooner?!

First things first. Island geography. Towns in MV: Oak Bluffs, Edgartown, Vineyard Haven, West Tisbury, Aquinnah, and Chilmark.

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From Boston, you can access MV from different ports (for more information, click here). P and I caught the early afternoon ferry from Woodshole (about an hour and 20 minute drive from Boston) to Vineyard Haven. The ferry ride was about 45 minutes and had a great deck with plenty of seating and fantastic views. There’s also wifi and food on board as well.

Everything was easily accessible by bike, so when we docked at Vineyard Haven, we immediately rented bikes from Martha’s Vineyard Bike Rentals for the full day. There’s not much to do in Vineyard Haven, except a little downtown area and the famous Black Dog campus. After a delicious meal at Black Dog Tavern, we headed straight for Oak Bluffs, about a 15 minute bike ride away.

Oak Bluffs is the heart of the action at MV with a small boardwalk of seafood restaurants, boutiques, and ice cream parlors, quaint Gingerbread cottages, and fantastic beaching. The bike path leads straight into the hustle and bustle of the town with the beginning of the colorful Victorian influenced style cottage neighbor to your right and the blue blue ocean on your left. We parked our bikes in the many bike racks in the town and went exploring.

Adorable Gingerbread cottages in Oak Bluffs…

We then continued along the bike route along the ocean. The views were just amazing with Sengekontacket Pond on the right and the ocean on our left. Kids were jumping off the famous Jaws bridge, and locals were kite surfing. I only wished we had more time!

Our plan was to bike to downtown Edgartown, but we got lost along the way due to a construction detour, ending up in Katama, which is a more residential area of Edgartown. After checking our bike map, we realized we were only a few blocks away from South Beach. So, we shrugged our shoulders and headed to the beach! Born and raised in California, I’m a certified beach bum. The feeling of the sand between my toes and the smell of the ocean breeze always brings me back to my childhood. South Beach was beautiful and perfect for lounging and swimming.

After our approximately 30 mile bike ride (a quarter of the ride being uphill from Katama to Vineyard Haven), I was spent. As a reward, we got pizza slices from Porto Pizza before we caught the evening ferry back to Woodshole.

What we learned from our first trip to Martha’s Vineyard? Go for more than just a day. Seriously. We only barely covered a slice of the east side of the island. The island may be small but there’s just so much to do. We plan on coming back with our beach towels and swim suits in tow! There’s still a few more weeks of warm weather so get on it and visit Martha’s Vineyard!

A little video of our day here.