Summer Vacation on Martha’s Vineyard with Kids

A decade ago, we went to Martha’s Vineyard for our honeymoon. Read more about that trip here. When we left, we made a pledge to go back…in the summer! Ten years later, we planned our trip, traveled by car, and took the kids. This is a recap of our summer vacation on Martha’s Vineyard with kids.

I hope we can go back sooner than a decade from now! By the time we went on the trip, all the hydrangeas were done blooming. There were a few here and there hanging on to those beautiful petals, but we missed peak. While that was a bummer, our trip overall was fantastic!

As a parent, you may know August can be chaos. Summer camps are over and for two, three, or four weeks before school starts, you need alternative childcare. And you wonder why so many families vacation in August! Our camp schedules left us with three weeks to figure out plans for the kids. We planned a week at my parents and a week on Martha’s Vineyard.

With our ten year wedding anniversary this year, Fatima and I decided this should be the year to revisit Martha’s Vineyard and take the kids on a summer vacation!

How to visit Martha’s Vineyard?

For our honeymoon, we flew in on JetBlue. This time, we took the car ON the ferry! The hotel and ferry were booked by mid-February. By this point in time, we were having to figure out summer plans due to summer camp registrations. By February, the majority of our summer is booked. Even when we planned Disney, we booked the trip in February. I know Martha’s Vineyard is a popular vacation destination, so this trip would need to be booked early.

Booking a trip on a Martha’s Vineyard ferry

When my parents visited the Vineyard, they hopped right on a ferry (no car). However, I wanted to make sure we had a ticket for the car on the ferry. One of the only car ferry services is operated by Steam Ship Authority out of Woods Hole, MA. Every January-February they begin to open bookings for the summer. These are released in priority order from residents, to frequent riders, to the regular tourists like myself. With this in mind, I waited until it opened for my group, and booked away! Once we had our hotel and ferry squared away, I didn’t think about my trip until much closer to our vacation.

What to do on Martha’s Vineyard with kids?

There’s so much to do on Martha’s Vineyard with kids! My kids love to walk around, go to the beach, run through parks, and eat ice cream! When planning our trip, I kept in mind all the fun things we did on our honeymoon. I looked at all the places where we’d likely eat and took note of their menus–whether kid-friendly options were available or not. And if they weren’t, making sure there would be options for the kids.

I made a list of all the things I wanted to do. From shopping, to exploring, to beach days. Then I bucketed those things into themed days: Beach, Explore, and Nature. We were arriving on a Monday and leaving on Friday, so Monday and Friday were loosely planned with meals in mind. And for peace of mind, I planned a few rainy day activities to have in my back pocket.

We stayed at the Harbor View Hotel in Edgartown. While no celebrity sightings, we had an amazing time. It was conveniently located in Edgartown and with a small beach located across the street (Lighthouse Beach). We were among a bunch of other families and the whole atmosphere oozed rest and relaxation.

Here’s a snapshot of our itinerary with a whole Google Map down at the end!

Monday – Travel Day

The was packed and we left New York around 8am. Our ferry out of Woods Hole was at 2:30pm. However, I did not want to cut it close. We left earlier than planned just in case we hit traffic. Interstate 95 was not terrible until Rhode Island. That’s when we hit a bunch of traffic due to construction–so our total travel time came in at four hours and thirty minutes. Car-wise, it was an easy ride. We packed lunches for the kids and snacked the whole ride.

Stop for gas! If you’re traveling to Martha’s Vineyard and taking your car, stop for gas before you get on the ferry. We got to the ferry early and they had room for us to get on early, it was a treat! I’m so glad we did, because once we left Woods Hole, a terrible thunderstorm was following us…

Once we reached the island, my plan was to stop at The Net Result, and eat outside at one of their picnic tables. We stopped, but we ended up eating in the car. The moment we parked, the skies opened the flood gates and it let out torrential rain, lighting, and HAIL! In the thirty seconds walking to the door, we all got soaked. We ordered, ran back to the car, and enjoyed our first lobster rolls.

We made our way to the hotel, checked in, went to dinner, and walked on the beach at sunset — a great way to end a wild weather day!

• The Net Result (Vineyard Haven) – great lobster rolls! The rolls were hot and buttered. The chilled lobster salad was piled on top. It was wrapped perfectly to go.
• Rockfish (Edgartown) – my kids voted this place as the #1 destination for fried calamari. The breading was so light and they mixed in fried banana peppers and it was all so delicious. We went here TWICE because they were that good. My wife had the lavender lemonade cocktail and I had the paloma, both are delicious!

Beach Day at South Beach

You guessed it! We spent the day at South Beach! Tuesday was looking like it was going to be the sunniest and warmest of the week, so we up moved ‘beach day’. To start our day, we went to breakfast at Edgartown Diner. Our kids love pancakes and waffles and these were delicious.

We went back to the hotel, packed for the beach, jumped in the car, and drove to South Beach/Katama. I read of bunch of Reddit threads that said South Beach would be crowded and to get there early. Maybe it was a Tuesday and during a slightly lower-crowd week, but there was plenty of parking.

My plan for beach day was to take a family photo. We were dressed for the photo with our swim suits on underneath. I set up the camera, took a few snaps, and we were good to go! For the next few hours we build sand castles, waded in the water, and enjoyed the sun. South Beach is phenomenal. The sand is like brown sugar. We had a ton of fun.

After the beach, we headed back to the hotel to get ready for a late lunch at The Seafood Shanty. This place has a great spicy margarita. And the lobster rolls? Really good, too! We ate outside on the lower porch. The family really enjoyed this place. We walked around Edgartown for the remainder of the day, and stopped by Ice Cream and Candy Bazaar for a pre-dinner ice cream treat. Fatima got a scoop of coffee cookies and cream–HIGHLY RECOMMEND. I got a cookie sandwich to share with everyone…OMG this is HUGE. Delicious and definitely for sharing!

• Edgartown Diner (Edgartown)
• The Seafood Shanty (Edgartown)
• Ice cream and Candy Bazaar (Edgartown)

Exploring Oak Bluffs via the bus

Wednesday was all about exploring another part of the island. We got up early and hopped on the bus for a 15 minute ride up to Oak Bluffs. I planned for us to have breakfast at Linda Jean’s. Once we sat down, our honeymoon came rushing back to Fatima. She realized she had a few pictures from this place on her phone from our trip ten years ago. Here’s a 2014 to 2024 shot! Oh how I’ve grown up…

After breakfast, we planned on walking around, do some souvenir shopping, and visit the camp association and the gingerbread houses. Bur first, coffee at Mocha Motts! When we walked by Ryan Family Amusements, the kids said we needed to stop. So we stopped and played a ton of games.

Before leaving Oak Bluffs, we stopped by Lookout Tavern for lunch. This place was voted the best lobster roll for at least the last 12 years. And I agree! What makes this lobster roll the best? The bread–it was soft, not too bread-y, and it complemented the heaping pile of lobster meat on top.

We walked around and before we went back on the bus, Liam asked us, “What about ice cream?” Luckily, I had a spot in mind. Ben and Bill’s was our destination for some great treats. Fatima made everyone walk swiftly to the park and sat in the shade with our ice cream before it all melted. The cool mint oreo was really good.

We hopped on the bus and made our way back to Edgartown. Everyone needed a minute to chill, so we spent an hour doing just that. We hung out on the balcony and played some games. Eventually, we got dressed and made our way back to Rockfish for dinner. Fatima got their blackberry smash whiskey cocktail–it was really good. Something we want to try to recreate…

• Linda Jean’s (Oak Bluffs)
• Mocha Motts (Oak Bluffs)
• Lookout Tavern (Oak Bluffs)
• Ben and Bill’s for ice cream (Oak Bluffs)
• Rockfish (again!)

Nature Walk

Our last full day on the island was a total change from our plans. We were all exhausted. I looked at what we wanted to do and decided to visit Aquinnah and the cliffs overlook.

First, we stopped by Behind the Bookstore for breakfast. While it was a nice setting outside, this was my least favorite place to eat. I didn’t like the food as much as our other breakfast places and our kids were not thrilled with it either. I read dinner may be better, but I don’t think we’ll go back as this was the least kid-friendly menu.

We hopped in the car and drove down to the Aquinnah Cliff Overlook and Gay Head Lighthouse. It took about 40 minutes to get there–I was not expecting that long of a drive! When we got there, parking was really limited. Luckily a spot had just opened up as we were pulling into the parking lot. We walked up to the overlook to see the cliffs and the ocean. It was beautiful–just as I remembered it. Then we walked over to the lighthouse and climbed up to the top!

Before we left for the day, I packed lunches for the kids. Fatima and I bought lunch from a takeout window at a place onsite the cliff overlook called Cliff Hangers.

After lunch, we followed the nature trail down to the beach. It was a longer hike than we thought, and Fatima and I looked at each other like “Is this too much?” The goal was to tire the kids out, and we accomplished that. However, I regret not being beach ready. We could have easily stayed at the beach. We spent a few minutes walking on the beach and headed back up to the car.

When we got back to the hotel, the kids asked to go back to the beach. So we changed and headed across the street to Lighthouse Beach for some fun in the sun. It was a little windy and a lot cooler than it had been all week…we didn’t stay long. We saw a horseshoe crabs and an adventurous crab while we hunted for shells!

After some freshening up, we headed towards Oak Bluffs for some dinner at Nomans. This place is really cool and I’m glad we went. If you know Pig Beach in Brooklyn, then this is exactly that vibe: it’s an open air, takeout counter-style restaurant. Order at the counter, find a table, and grab your food when it’s ready. There are table games on most of the tables, and open grass areas for your kids to run around. There was live music and it was just a total vibe. Parking sucks, but we lucked out because we went for dinner at 4:30pm. By the time we left, the parking was out of control and a line of cars were waiting to get in–so plan accordingly or take the bus (a little bit of a walk) to get there!

We made our way back to Edgartown for one last ice cream. The begged to go back to Ice Cream and Candy Bazaar and enjoyed our ice cream by the docks under the most beautiful sunset–it’s one of my favorite pictures.

We walked around town and headed back to the hotel for our last sleep.

• Behind the Bookstore (Edgartown)
• Nomans (Oak Bluffs)
• Ice Cream and Candy Bazaar (Edgartown)

Friday – Travel Day

My plan for the day was to pack up the car and eat somewhere in Oak Bluffs. That’s where our ferry was leaving from and I thought it would be best to stay close. We had breakfast at Biscuits and it was delicious. By the time we left, there was a line of people waiting to sit.

Before getting back in the car, we stopped by Back Door Donuts for a road snack. The buttermilk glazed donuts are amazing and their iced coffee is really good, too. We got back in the car and eventually boarded the ferry.

• Biscuits (Oak Bluffs)
• Back Door Donuts (Oak Bluffs)

Travel tips for Martha’s Vineyard with kids

Our trip was the best. We lucked out with the weather with the exception of our afternoon on the day we arrived (but it gave us the most beautiful sunset). However, I’m going to make a pledge to go back when the hydrangeas are at their peak!

• We loved our last week in August vacay. It wasn’t as crowded as I was expecting. Maybe it was due to our trip falling Monday-Friday or it’s possible the Labor Day week crowds are lower than peak summer. However, I wish we were there for the hydrangeas (peak season is mid-July). We saw a few bushes that were still colorful, otherwise, they were all brown 🙁
• All the restaurants we went to (except for Behind the Bookstore) had kid-friendly menus for our picky 6 and 2.5 year olds. I recommend all of them. Their atmospheres were also very kid friendly! None of the restaurants took reservations, so I planned for early morning breakfasts, 11:30am lunches, and 4:30pm dinners. We never had to wait to be seated.
• Plan your days for flexibility–for the crowds, the weather, your family’s battery levels!
  • My rainy day activities included: arcades, movies, and trips to the local bookstores.
• If you can plan a sunset dinner in Menemsha! I scrapped those plans after seeing how exhausted my kids were, but here’s what I would have done:
  • Order some to-go food from Quarterdeck (Edgartown). Bring a bottle of rosé or your favorite wine.
  • Take the bus to Menemsha OR drive to the shuttle lot and take the free sunset shuttle to Menemsha Beach. I read parking at the beach is a beach.
  • When getting off the shuttle, stop at Larsen’s to pick up lobster rolls and any more seafood before heading to the beach.
  • Setup on the beach and enjoy dinner with the sunset.