Marthas Vineyard: 3 Day Itinerary

Jul 6

This past weekend we visited Marthas Vineyard. This was our first real getaway as a family since our babymoon. We wanted a quick weekend trip that was drivable from Boston but still beautiful and a place that we haven’t adventured to before. We booked the trip a month in advance, the tricky part was getting our car over on the ferry. Apparently they book up months in advance, but we were put on a wait list and ended up getting it on. We departed from Woods Hole Ferry terminal on the cape at 6:15pm. I always love taking the ferry in the evening, the light hits everything it touches with beauty. When we got to the hotel and unpacked and got Maximus into his pack and play and relaxed on the deck with the night view of the harbor.

Okay, so first impressions! It’s hard not to love this place, its so picturesque. The houses and landscaping are straight out of a magazine. Driving around the island there is a large agricultural scene, that I love. Little farms, lots of land and space. Lots of little art galleries and boutique shops that adds to the magic of the island. I imagine this would be a beautiful place to retire, I mean it was just a slice of heaven, in my opinion. The best of both worlds, farm land and oceanside access. Also all the food was really yummy and fresh, so that made the overall experience extra enjoyable. I hope we can make this a yearly trips to this island for memories for our kids to grow up with. So without further adue, here is our 3 day itinerary of Marthas Vineyard.

Travel Day

Thursday June 29

We booked our ferry tickets directly through the Steamship Authority (ferry service) from Woods Hole to Vineyard Haven terminal. Booking with a vehicle apparently books up months in advance. Luckily we were put on a waitlist and was able to get a spot with our vehicle on. We departed at 6:30pm, I love this time because the sun is softer and sometimes a sunset on the water is so beautiful on a ferry. The ferry ride was quick, about 45 minutes total. The drive from the ferry terminal to Edgartown was about 20 minutes. We checked into the Harborside Inn & unpacked and relaxed for the evening enjoying the evening view of the harbor.

DAY 1

Friday June 30 - Edgartown

We woke up around 5am for a sunrise photoshoot with Sam Brooks. It was beautiful waking up this early because the fog was sitting in the harbor. We did our photo session at South Beach it was such a fun morning of frolicking on the beach and in the dunes. After our session we relaxed a bit longer on the beach before we headed back to town. On the way back we grabbed breakfast at Rosewater Market and took it back to our hotel to eat while Max napped. Once he woke up we headed to beach on the other side of the island called Menemsha Beach, this was a public beach. Leading up to the beach there was a few cute art galleries and little food shops, or as my husband called them “shanties”. After we hung out at the beach for a bit we came back and Paul got his lobster, he is obsessed with his lobster in the summer. Then we headed back to catch our 5pm reservation at The Covington Restaurant, it was absolutely divine. I would highly recommend this as a nice dinner out. It was conveniently a 1 minute walk from our hotel, we sat on the patio and people watched while we ate and they were very kid friendly which was nice. All the food was delish. After dinner we strolled around the town a bit before we went back to the hotel to put Max to bed. We enjoyed the last moment of sunlight on our deck and visited the moon. That was day 1!

DAY 2

Saturday July 1 - Edgartown

While the gang was still sleeping I slipped out early to grab coffee and croissant breakfast sandwiches downstairs at this cute coffee whop Toccopuro. The breakfast sandwiches were so delish and they were very accommodating for my requests for Max. Once we rounded ourselves up for the day we decided to explore the far side of the island and ventured to Aquinnah Cliffs Overlook. Leading up to the lookout there were artsy little shops. I found a few treasures to take home. The lookout was simply, stunning. Picturesque out of a magazine. There was a few lookout points including a nice big platform, a great spot to take pictures. In this area there was also the Gay Head Lighthouse that was another attraction but we decided not to walk there with Max, it was quite hot. We grabbed some food at one of the little shops and then back in the car again. After driving for a bit we found ourselves at Long Point Beach. This was a bit tricky to drive to, but it was well worth it. This beach is part of a conservation land, so tickets are required. My impression is that they book up quickly. We were able to purchase as we drove up as non-members, it was $25 for the day. There was a bit of a walk up to the beach, so I would suggest to pack light with your beach gear. It was a bit foggy the day we went, but it was a beautiful beach. The sand was very soft. One thing to note about Marthas Vineyard is that wood-ticks are very prevalent, and they have high levels of Lyme disease. On the beach where we were sitting there were a bunch of them. I’m not sure if we were sitting on a nest area, but i was so surprised to see them on the beach. I thought they only lived in the woods (hence their name, haha) just something to be aware of! After we were all beached out, we went back to the hotel, showered up quick and made our way through Edgartown to find dinner. We found ourselves at Alchemy Bistro & Bar. We sat on the patio again, with a little one this was way more comfortable and relaxed. I had the CAMPANELLE PASTA, it was simply the best pesto pasta i’ve ever had. It had this goat cheese on top that melted into the pasta and made it extra creamy, pasta dreams right there. After we finished up here we strolled back to the Harborside Inn, less than a 5 minute walk and got Maximus to bed. We enjoyed some wine on the deck to close up the evening.

DAY 3

Sunday July 2 - Oak Bluffs

Today I woke up a bit early before the gang and had a nice little stroll to myself through the lovely neighborhood. Edgartown is such a pretty town to stroll around, everything about it is picturesque. After we packed up and checked out we drove over to Oak Bluffs. This was a much more lively town, it had a younger sense to it. The house styles were surprisingly a lot different, gingerbread houses as i called them lined the streets. Parking was tricky here, only street parking so we drove around a bit looking for parking, but enjoyed seeing the different areas of the town. We ate lunch at the Lookout Tavern, they had a comfortable outdoor seating area that was nice to be outside. After paul enjoyed another lobster there, we took Maximus on a horse carousel ride, that was a fun little family moment. There is a strip of little shops and food spot that is nice to explore, also a strip of restaurants along the dock that was very energetic. It was a great vibe, but i’m happy that we stayed in the Edgartown area. We took one last car ride over to the North Tisbury area, so that Max could have his afternoon nap. I love driving and looking at the different houses in the area. Our ferry departed at 6:30pm, another nice evening ferry ride home. Next time I would do 1 more day to explore some more beaches, but overall I think it was a great amount of time to experience the island.

The Covington had the best espresso martinis.

RE: The Covington: Bolognese

Re: Lucky Hank’s: Florentine Benedict

3 Day Itinerary Marthas Vineyard - Alchemy Resturant

Dinner at Alchemy Bistro & Bar. This was the CAMPANELLE PASTA on the menu, the best pesto pasta i’ve EVER had. So many different flavors, yet you could taste them all. The cheese made it extra creamy, this is pasta you have dreams about.