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Martha’s Vineyard – Like a Local

marthas vineyard
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Thinking about visiting Martha’s Vineyard? Or “The Vineyard” as it’s known? I have not been yet, but I’ve always wondered where to stay, what to do and how to do it. Kate Gillan is the newest member of the momtourage and she spends summers at the Vineyard with her adorable family and gives us the inside scoop.


Martha’s Vineyard Like a Local


Hey Luxury Travel Mom Readers, thanks for letting me into your exclusive circle of readership love! We’ve been hopping on the ole’ ferry to the Vineyard for the past nine summers, and below I’m going to give you the skinny on exactly how to vacation there with small children stress-free (Boston accent optional.)


How to Get There:


We book our ferry with Steamship Authority in January for a June trip. However, there have been years where someone was napping and we missed our boat. While it’s always good to book ahead, a sneaky secret is that if you line up your car and give your name, they always reserve one or two spots per ferry for extra cars. There is also a second ferry the Steamship Authority runs which is more of a commercial-type vessel with no snack bar or comfortable seating, but it will get you across the water just the same.


It’s a good idea to load up your car with non-perishables, because the island’s main Stop n’ Shop is expensive.  If you have a small car, or just need a lot of room for your golf clubs, a few years ago I discovered a great local delivery service, MV Baby Rent who deliver strollers, pack n’ plays, and other baby items and pick them up at the end of your trip.

Another space-saving company is Take My Linen Rental, which came in handy this year when we realized the house we rented had king sized beds, and we only brought queen sheet sets (whoops!) They also pick up and deliver.


Where to Stay:



The first time I ever stayed overnight with my husband (he was only my boyfriend at the time, shhh) we stayed at the Pequot Hotel. You can walk here from the ferry at Oak Bluffs if you don’t have heavy bags. With rooms under $180 a night even in the high season (and free chocolate chip cookies baked fresh daily in the lobby in a cute glass case) you can’t beat the price. It’s also walkable to the town of Oak Bluffs, plus the town beach.




When we had kids we started renting a house, found on We Need a Vacation. If your kids are young I really suggest getting a house that’s close to one of the town centers, so you don’t have to keep loading up the car.


To Do with Kids:


Beach: Martha’s Vineyard has many beaches, and each has a different vibe. South Beach’s waves are a little too crazy for children under five. The beach closest to town (between the Steamship Authority wharf and Farm Pond) has a great walkway running alongside it and we ride scooters here every morning. A great beach for kids is Joseph Sylvia Beach, or “State Road” beach. The sand is white and soft, and there are miles and miles of places to park. There are no public bathrooms here, so encourage little ones to try the potty before you leave the house, or bring a portable one with you in your car. A special, hidden beach on the island is Long Point Wildlife Refuge. My husband and I call it the “Dinosaur-era” beach, because on the day we went we were the only humans around, and as nothing is built up there you feel like you’ve traveled back in time! It does cost $10 a car plus $5 a person, but the scenery is so beautiful it’s worth it.





Kayak: The boys and I had an adventure kayacking. Island Spirit Kayak has a great location between Edgartown and Oak Bluffs, near the Jaws bridge. We were able to fit all three of us in one boat and the water is so shallow on the bay side that they spent most of the ride in the water, floating happily next to me in their life jackets. I didn’t bring water shoes but highly recommend doing so because there are crabs scuttling around and our friend’s son did get a pinch.


Golf: The fact that Farm Neck Golf Course is one of Obama’s favorite spots should give you a clue how nice this course is. My hubby played this year after 4pm to get the  twilight rate of $100 instead of $170. The ocean views are gorgeous.


Bike: There are bike rental places all over the island, but we rent from Anderson’s because they deliver. They also were very patient fitting my kids with the right size helmets, whereas the other local bike rental places can be a little pushy. When you come off the ferry there’s an information booth in the town square and they give out coupons for Anderson’s.


Eat: Edgartown has many wonderful restaurants, but with the sidewalks being a little narrow to accommodate a stroller we usually end up walking down to the water in Oak Bluffs and eating at the Sand Bar and Grill. The food is standard American fare, nothing fancy, but the whole eatery is outside on sand, so your kids can sit and make sand castles and dig while you enjoy a mojito and watch the yachts dock! Next to the Sand Bar is Nancy’s, which has a great picnic table area that’s fun for kids during the day, and for adults doing the bar crawl at night. My husband likes their lobster roll. For breakfast a mainstay of the island is Linda Jean’s. If it’s high season make sure you send someone down to put your name on the list before bringing all the kids, as it gets super busy. My favorite place to go when we get the grandparents to watch our brood is Jimmy Seas, on Kennebec Ave in Oak Bluffs. The space is small, but they bring you your pasta right in the pan. The dishes are huge and you can share for a fee but I usually (ahem, no judging) finish the course myself. Their linguini and clam sauce is my favorite, because they use clams found on the island.




Camp: We enrolled the boys in The Farm Institute camp from 9-12 each day and despite a lot of grumbling about going, they loved it! (And we loved the silence!) They learned how to quietly take eggs from a hen, catch a chicken, milk a cow, pick kale and feed it to the mama pig, weigh a baby pig… they were in heaven. The kids had both an “animal duty” and a “garden duty” each day, and the counselors were perky and friendly college girls that my sons fell madly in love with.





Water: We had two very different, yet equally awesome boat rides during our two weeks. The first was aboard the Skipper, which runs fishing charters most of the time (sometimes for Jimmy Buffet, check out the website.) Captain John is cool though, and also lends his boat for Ocean Discovery, run by Felix Neck Nature Preserve. On this ride, the kids hauled up lobster traps, checked out osprey nests with binoculars, and even got to drive the boat! The boat ride is run by two Science teachers on their summer break, and they can be a little talkative (I really don’t give a crap about plankton, sorry!) but my sons loved Captain John and loved the lobster traps. Our second experience was with MV Pirate Adventure. I recommend making a reservation, especially between June-August. Docked right in the harbor of Oak Bluffs, we took the 2pm sail and arrived early to get our “pirate names” and tattoos, which the crew hand-painted. (They also let you bring your stroller on board if it folds.) I thought it was sweet they even gave my 1 year-old a pirate name, “Sea Star Sophie.” The boys also got their pirate gear, most of which you’re allowed to keep minus the vests and belts. The boat ride is right around the town, and the crew of the captain plus three college kids did a great job of performing a little play which involves the kids and includes hunting for a map in a bottle, hauling a treasure chest over the deck, and best of all… hoisting the battle flag and shooting water cannons at a “bad” pirate! All of the crew’s constant requests to mention them on social media needs to be cut from the act, but if you want a wonderful way to spend an afternoon I highly recommend it!




This is Kate’s first contribution to Luxury Travel Mom but will not be her last. This post was not part of a comped review and is in no way sponsored. No chickens were harmed in the creation of this post.



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