My husband and I just returned from a trip to Martha’s Vineyard as a family. We booked it shortly after Audrey was born, and I’d be lying if I said we did so thinking it would be a relaxing trip, traveling with an almost three-year-old and five month old.

We were excited, but we definitely knew it could get ugly really quick. One week, in a cottage on an ISLAND with no help if we needed (or wanted) it!

But can I just tell you – this trip was so sweet, fun, refreshing and surprisingly relaxing.

It worked to our benefit because we were in a secluded area on an island, we were forced to have limits! Everything we could possibly do was within a 20-minute drive. We never felt pressure to drive a bit farther to visit another destination. Another bonus? Our plans were simple – beach, eat, nap, eat ice cream, repeat. A true vacation (and toddler’s dream, if we are being honest).

I was nervous about taking two littles on an airplane ride, 2-hour car drive and then an hour long ferry ride. I was nervous about eating multiple meals out a day. I was nervous about tantrums, explosions… you name it, I was probably nervous about it. But can I just encourage you to travel with your kids?! DO IT NERVOUS. Keep your expectations low (ha!), and I am willing to bet you will be pleasantly surprised.

I am no expert, but I have come to believe that as parents we hold a lot of weight in helping our children feel comfortable and act in a well-behaved manner in certain environments. If we never bring them to a nice restaurant, how will they ever learn what is acceptable behavior in a nicer restaurant? And if we bring them to that restaurant, and just stick an iPad in front of them to entertain them, how will they learn to be present and control their wiggly bodies and easily distracted minds?

I mentioned this on my Instagram, but I think it warrants being repeated. BOOK A FAMILY TRIP TO THE BEACH. I know it’s a little overwhelming, but friends, seeing your toddler’s toes touch sand for the first time, and seeing their eyes light up at the mention of ice cream after an afternoon at the ocean are the true treasures of life. Do whatever you need to do – cancel cable for a year, don’t buy silly things for a few months that hold no real value, or if you just have money sitting in your account book a trip now. You will not regret it!

Yes, there will be tantrums, and likely a few outfit changes due to spit up or explosions. But those are not the things you remember. I promise. It brings tears to my eyes just thinking of all the treasured memories we made that week on the Island. So sweet.

Now that I have sold you on booking a trip to the ocean I wanted to provide you with some of our favorite spots on Martha’s Vineyard during our time there!


We booked our flights into Boston and then rented a car (I highly recommend getting a car, especially if you are traveling with kids). You then have about an hour and a half to two hour drive to the ferry port in Woods Hole.

If you are planning on going during a busier season (ie. Summer) I highly recommend booking your ferry tickets when you book your flights. The reservations to bring a car on the ferry book up quickly for busy weeks! The ferry will bring you to Vineyard Haven or Oak Bluffs. They recommend getting to the ferry thirty minutes before your scheduled departure. You can park your car and then go up to the top deck and order coffee, beer or wine and enjoy the ride!


Traveling with kids is no joke! We rented a few larger items from, and had a great experience. They dropped everything off at our front door the day we arrived, and picked it up the day we left. We rented a Pack N’ Play, beach toys (highly recommend doing this so that you don’t have to pack them), a beach chair and would have also rented a beach umbrella if the house we stayed at didn’t already have one. For more detailed tips check out my blog post on traveling with a baby.

We brought along a blow-up toddler bed for Hadley that worked great for her! That way we didn’t have to be concerned about her rolling off a bed, and she was really excited about it and slept great. We also packed our Hatch night light/wake-up clock (Hadley knows that she has to stay in bed until it turns yellow – meaning “wake up time”) and our own monitor for Audrey. Per usual, we also packed sheets from home for both girls’ bed/Pack N’Play.


Type Destination Details
Brewery Bad Martha Farmer’s Brewery We didn’t end up making it here but looked really fun! The beer is served all over the island and my husband loved it.
Sights Aquinnah Cliffs The most stunning views! A great place to go, grab a coffee and do some hiking and enjoy the views of the Cliffs and lighthouse.
Beach South Beach A beautiful beach, big waves and strong current (not young kids to play in alone).
Activity Flying Horses Carousel Oldest carousel in the country – a classic stop on Martha’s Vineyard.
Activity Ocean Park Large green space with ocean view, a perfect picnic spot!
Beach Joseph Sylvia State Beach Small waves, beautiful water (perfect for little kids to play in).
Sights Edgartown Lighthouse A nice walk to the lighthouse, beautiful to take family photos.
Sights Martha’s Vineyard Camp meeting Association (MVCMA) Quaint eclectic houses, great to walk around with coffee and look at!
Activities Island Alpaca Company of Martha’s Vineyard Good for kids – not anything special, but a cool thing to check out for the littles.
Activity Morning Glory Farm We didn’t make it here, but it looked like a sweet little spot to check out.


Type Destination Details
Breakfast Among The Flowers Café Beautiful spot to eat outside in Edgartown.
Breakfast Linda Jean’s Restaurant Delicious food and great service – top rated on Trip Advisor, in Oak Bluffs.
Casual dinner Lookout Tavern Where the locals eat, ocean views (not fancy at all! Burgers and seafood).
Casual dinner Nancy’s Restaurant Double-decker outdoor seating, casual dinner with beautiful views at sunset.
Lunch spot (quick) Waterside Market Cute spot for a healthy lunch, perfect place to stop after some shopping in downtown Vineyard Haven.
Breakfast Black Dog Tavern Famous restaurant – we ate there for breakfast and dinner! Great food and fun gift shops.


Type Destination Details
Coffee Espresso Love 17 Church St, Edgartown, Martha’s Vineyard, MA
Coffee Mocha Motts 10 Circuit Avenue, Oak Bluffs, Martha’s Vineyard
Coffee Dock Street Coffee Shop 2 Dock St, Edgartown, Martha’s Vineyard, MA
Ice Cream The Sweet Spot 12 Circuit Ave. Ext, Oak Bluffs, Martha’s Vineyard, MA
Ice cream Mad Martha’s 7 N Water St, Edgartown, MA 02539

Happy traveling!


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