A Day Trip To Martha's Vineyard With Our Dog Ivy

A Day Trip To Martha's Vineyard With Our Dog Ivy

Last summer (which feels like a lifetime ago) AMH and I travelled to Cape Cod and decided to take our pup, Ivy to Martha's Vineyard for the day.

Here's a link to the post I wrote about the dog friendly Airbnb rental we stayed at in Cape Cod.

By the time I sat down to write this blog post, summer had already ended. In my mind, I thought I would save that post for March/April of this year so it would be helpful to travellers that are planning their summer vacations. And then COVID-19 took over the world.

I've gone back and forth about how to navigate the blogging/social media worlds right now. Firstly, and quite personally, my heart hasn't been in it. I've run the range of emotions from hyper to bed ridden with stress. I'm struggling to keep motivated. My focus really has been on work and my family without much thought for anything else.

Secondly, seeing influencers and companies going ahead with their planned spring content has been so tone deaf, like they just can't see or understand how much people are suffering. I didn't want to be a part of that, especially seeing how angry it made me and my friends. So I scrapped all my planned content and said a firm no to any and all sponsorships.

Finally, I've landed in a place where we've had some time to mourn (highly recommend this HBR article That Discomfort You’re Feeling Is Grief) and now we need a little something pretty to look at. While this blog post might not be helpful to you this year, since I know so many travel plans for 2020 have been cancelled, it might be helpful in the future. And if nothing else, you get to see some cute photos of a beautiful dog. That will surely lift any spirit!

So that's where my head and heart are at. I had so many plans for this year, just like many of you, and everything is back to square one. I'm going to try and spread some happiness in amongst all this uncertainty but please know that I'm not perfect and I'm struggling to get through the days too. And while we can't go anywhere right now, I do find myself daydreaming about the day when we can get back to exploring this great big amazing world.

With that all out of the way, let's dive in and I'll share all the details on how we visited Martha's Vineyard for the day with our dog. There are so many things I wished I had known before visiting and a few things I really wish I had considered before the trip. Nevertheless, we had a fantastic day trip and I know I sure fielded a lot of questions the day I posted our photos to Instagram, so I've compiled all this information into one (hopefully) helpful post!

We were in Cape Cod for a week with one night out at a Grateful Dead concert at Gillette Stadium in Foxborough. We brought Ivy along with us because she and I have separation anxiety and can't go more than a few hours away from each other (Kidding. Sort of.) and both of my kids had plans that week and couldn't watch her. Plus, she loves rides in the truck and has always been a good sport about road tripping.

Our plan was to take a morning ferry, board a city bus in Oak Bluffs to take us to Edgartown and spend a few hours walking and picnicking. Then take the bus back in the late afternoon and sail back to Cape Cod. Our costs were only going to be our ferry pass, bus fare and some lunch.

But not every plan works out the way you planned...

A Day Trip To Martha's Vineyard With Our Dog Ivy

Travelling with a dog is a bit like travelling with a toddler. You can plan for almost everything, and they will still surprise you.

It was a warm June day and we made sure to stuff our backpacks with Ivy's food and water dishes with a big bag of treats and bottle after bottle of water along with ice packs to keep them cool. We also brought a big towel for her to rest on. We ordered our ferry tickets a few weeks before on the Hy-Line Cruises website, $120 for two adults, Ivy rode for free. Once we got there in the morning we had to line up and show ID to get our boarding passes. Once on the ferry, we found a quiet place outside to sit.

A Day Trip To Martha's Vineyard With Our Dog Ivy

Ivy has been around water, boats and canoes since she was born. We didn't think the ferry would be any different than our friend's boat that she had ridden in before. She started out the trip sitting perfectly fine. Even when the ferry started to more away from the harbour, she was fine. And the second the ferry picked up speed....

dog friendly vacations

She got scared and jumped right into my lap! You never can tell how your pup will react to the speed and sounds of the ferry. We ended up going inside the ferry and found an empty row for us. The workers reminded us that dogs are not allowed on seats, just as Ivy was putting her paw up to jump on one 😬 So she spent the ferry ride sitting right by our feet. If you plan on taking your dog to Martha's Vineyard or even Nantucket, probably a good idea to start them off inside. 

A Day Trip To Martha's Vineyard With Our Dog Ivy

Every website I read said the best way to get around Martha's Vineyard is to use their public buses. The cost is $10 each for a day pass and dogs are allowed on the buses and ride for free. What those websites fail to mention is the insane lines to get on these buses! We took one look at over 200 people waiting for a bus and quickly decided we needed a better option. Just off the ferry dock was a Jeep rental company and even though the cost was high ($200 dollars US) it turned out to be the best option. 

Renting a car gave us freedom to explore the entire island, not just Edgartown and Oak Bluffs. We ventured out to the small fishing village of Menemsha, stopped at the Aquinnah Cliffs Overlook and drove down some rustic roads to explore the wildside of Martha's Vineyard. And of course we spent time gazing at all the architectural eye candy! We stopped at an artist fair, a strawberry social at a church, a festival at Morning Glory Farm and marvelled at all the farm animals we passed.

The best part for Ivy was a safe place to rest after all that exploring. The car had air conditioning and we made sure she was comfortable. I have to admit that my biggest worry about taking her for the day was not finding a cool enough spot for her to rest. But I had heard that the island usually has a nice cool breeze coming off the ocean and I can attest to that. Even though it was late June, I wore pants and a sweater and was comfortable the entire time. 

One destination we had in mind was the Joseph Sylvia State Beach, better known as the beach and bridge in the movie Jaws. It also happens to be the only dog friendly beach on the island. What we didn't know until we got there was dogs are only allowed on the beach at certain times, before 9 am and after 5 pm which was not when we were visiting. Lesson learned. I had googled it before hand but didn't find anything about specific times. After we got home I found the website Bring Fido. They have the inside scoop on almost every travel location. Visitors can update information and leave reviews. This website is now my first stop before travelling with Ivy. 

Our main destination was the town of Edgartown. When you think of picturesque Martha's Vineyard, this is what you are thinking of. We found Oak Bluffs, where the ferries are, to be a busy and bustling tourist destination filled with families looking for a beach to plunk themselves on. Not my cup of tea. 


We wanted a slower pace, quiter, somewhere we could stroll with Ivy and admire the homes and do a little shopping and sightseeing. Edgartown was all that and more! 

dog friendly vacations

 We found this Beware of Sharks sign and bench on the side of a shop we stopped in at. Ivy's such a good little picture taker because she knows it means a treat is on its way! A few people stopped us to say this would make a good photo and they were right! 

dog friendly trips

And no visit to Martha's Vineyard would be complete without a shopping trip to Vineyard Vines! Ivy was wearing one of the dog bandanas from the Vineyard Vines x Target collection. The staff just loved that! 

Vineyard Vines

After picking up a few items for ourselves, Ivy included, we headed out but not without a last sip of water. The town and shops are all very dog friendly and welcome these little four legged shoppers. There were fresh water bowls everywhere which made those heavy water bottles in our backpacks unnecessary. 

The only shops dogs are not allowed in are ones that serve food, totally understandable. If the restaurant has an outdoor patio, then dogs are welcomed there. We had our lunch at the The Menemsha Deli which is a great sandwich shop with plenty of picnic tables and umbrellas outside. 


The day went by quickly and we headed back to Oak Bluffs to return our Jeep rental. While waiting for our ferry we grabbed some ice cream and stopped at The Black Dog outlet store to buy a few t-shirts and bandanas for Ivy. 

Ivy had a long, adventurous day and slept like a baby on the ferry back to Hyannis. We too were looking forward to a quiet hour long cruise with some snacks and drinks. We finished our trip with a local beer and some Cape Cod Chips (seriously grab a pack if you can find them, so good!) at the on-ferry bar. 

All in all we are glad we visited Martha's Vineyard and brought Ivy along for the ride. She sure was popular, so many people asking to pet her and a few even asked to take her photo! Next time we have a reason to be in that area, we'll take her for the day to Nantucket but this time we will opt to bring our car on the ferry. Our 1970 Mercury Montego that is! But first, there's some work and a paint job that has to be done.