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Martha's Vineyard Travel Guide: 3-Night Itinerary in September | Plus Nantucket vs. Martha's Vineyard

Recently, Josh and I spent a week exploring Nantucket and Martha's Vineyard, and you can read about our 4-night stay on Nantucket here.

After four pretty perfect days on Nantucket, we hopped on a ferry to Martha's Vineyard. It had been about three years since we last visited, and we've previously done a day trip and another 3-night stay, and have loved it each time. So, needless to say, we were excited to get back.

We get asked a lot if we prefer one island over the other, and we actually do. Nantucket wins by a small margin, and I think it has everything to do with the fact that you feel as though you've stumbled back in time. Like I said in my last post, it's managed to maintain an old-world fishing village feel even though it's now deeply rooted in wealth and old money, and also considered a bit trendy. I really don't know how it pulls that off, but it does. It's also easier to explore without a car because most accommodations are right in the main downtown area, where the ferries drop you off. The towns on MV are more spread out, and depending on where you stay, it can be tough to get around and see more of the island (I'll go more into this later). 

For the longest time, I could also never quite put my finger on how to exactly describe MV, either, but on this trip, it finally came to me. It's a mix of coastal New England, rural countryside and Southern charm. You can kind of get Savannah or Charleston vibes while walking around, especially in Edgartown. That's one of the many reasons I really love the island, but for convenience purposes, and that magical feeling I get when stepping onto Nantucket land, I ever-so-slightly prefer Nantucket. 

But, that said, MV is absolutely gorgeous, and I love visiting. There are some really wonderful things to do and sites to take in while on the island, and I'm excited to share how we spent our three days here.


We chose to stay at the Winnetu Hotel. We actually stayed here during our previous overnight visit, and we loved it so much that we desperately wanted to come back. It's owned by the same people that own The Nantucket Hotel, where we stayed during that portion of the trip, so the same level of attention to detail, friendliness and gorgeous rooms applied. We were somehow lucky enough to get another complimentary upgrade during our stay, and got to spend our nights in a beautiful suite that had an amazing view of the sunset each night. My favorite thing about the Winnetu is its proximity to South Beach, which is one of the most beautiful beaches on MV. It's a very easy, 3-5 min walk via a little path to the ocean, and then from there, you have a very long stretch of beach to enjoy. They also provide complimentary breakfast each morning, have a heated pool and a lot of little touches like a giant chess set (which Josh loves), corn hole games on the lawn, a little miniature Edgartown Lighthouse overlooking their pond, and Adirondack chairs to enjoy outside. 

The Winnetu provides these cute little slippers. 

The Winnetu has a little mini Edgartown Lighthouse replica on their grounds. 

Yes, we played a whole game. Yes, Josh won. Yes, I beat him in a game of bags later. 

The only potential downside to this hotel is that it's about 3 miles outside of the main town of Edgartown. For us, this wasn't an issue during either stay. Last time, we brought our car to the island, and this time, we relied on the hotel's complimentary shuttles to bring us to and from town. They ran every half hour or every hour, depending on the time of day, and we never had any issues, or felt inconvenienced by having to rely on them. And we also both kind of enjoy that the hotel is secluded from town. It's very quiet and peaceful, and it's one of our favorite hotels we've ever stayed at.


Because of the size of the island, and how far things are spread out, I would recommend you either bring your car over with you, or rent a car for a day or two during your stay, especially if it's your first time visiting. The island does have a public transportation system, which we used during our day trip, but it just takes a while because the towns are spread out, and there are a lot of stops along the way. It can be done, even for a day trip, but I feel like with how much time you spend on the buses, it makes more sense to budget for a car. And, visiting Aquinnah, which is one of the best things to do, is really hard to see if relying on public transportation. It would likely take you at least an hour one-way to get out there if staying in Oak Bluffs, Edgartown or Vineyard Haven. 

For this trip, since we didn't have our car, and definitely wanted to visit Aquinnah again, we rented a car for a day just to get out there, and also, explore the other towns with more flexibility. We splurged since it was Josh's birthday and rented a Mini Cooper convertible. We've wanted to rent a convertible for the longest time, and had always planned on doing it for a California coastal road trip. Once we realized that the daily cost to rent it for a 10-day or more trip would be insanely expensive, we ruled it out, though. So renting it for the day on MV was really quite perfect, and, it was as fun as we thought it would be. The down side is, now I really want to own this little car to bring with us while we explore New England destinations. It's absolutely adorable, easy to drive and I fell in love with this bright blue color. We rented through MV Auto Rentals, which was extra convenient because not only were their prices competitive, they also have a partnership with the Winnetu, so we were able to have the car dropped off and picked up right at the hotel. It was a great experience. 


MV has three main towns, which are the biggest ones on the island: Oak Bluffs, Edgartown and Vineyard Haven (also called Tisbury). Our personal favorite is Edgartown. It has that Southern charm I mentioned before, while still being very traditional New England, and has really great restaurants, shops and a nice little "downtown" area for walking around. Vineyard Haven is really beautiful, and has more of a quiet fishing village feel. But, I will say, even in just three years, I feel like VH has developed more since our last visit. During this trip, we found more restaurants and shops than we did last time, but it still maintained that sleepy village feel. The downtown area is smaller than Edgartown, but still has shops and restaurants. Oak Bluffs, of the three, is my least favorite. It's definitely worth visiting, and I absolutely love the Gingerbread Cottages, but I personally feel like it has the most touristy feel of them all. It does have a lot of really great restaurant options, but most of the shops are geared toward tourists (which is great if you're looking for a MV sweatshirt as a souvenir). But overall, we don't usually spend more than an hour or two in Oak Bluffs, and wouldn't likely want to stay here. Just a personal preference.

The rest of the island is comprised of smaller, more rural towns. From what I understand, most people choose to stay in one of the three towns mentioned above because the further out you go to, say, Aquinnah, Menemsha or Chilmark, the fewer options you have for restaurants and definitely no "downtown" feel. But maybe that's what you want, in which case, these would be good options to look into. 

My favorite house in Vineyard Haven, right across from Waterside Market.


Chances are, if you've Googled Martha's Vineyard, you've seen pictures of the completely adorable and storybook Gingerbread Cottages, which are part of the Martha's Vineyard Campground Association. Yes, you can rent these little guys out during your stay if you want to, and each of them is uniquely painted and designed. I really, really love walking around looking at these cottages. It's hard to be sad while meandering through the streets with these in the background. They're pretty centrally located right off the main streets of town, so if your ferry docks in Oak Bluffs, you can easily walk to them. 

This is probably my favorite thing to do on MV, but like I said, it's hard to get to unless you gave a car. Some companies also offer Aquinnah tours that will take you out here. It's about a 40-min drive from Edgartown, but it's so very worth it. You'll start by visiting Gay Head Light, which sits atop the cliffs. You can get right up to the lighthouse, and also meander a bit further down the road (where a small cluster of eateries and shops are - walkable from the lighthouse) and take a marked path to see even better views of the cliffs and lighthouse together. Then, drive your car to the beach parking lot down the hill, and find the path that will take you to the beach. Even the walk down in the field is gorgeous. Once on the beach, walk toward the lighthouse to get close to the red-clay cliffs. It's just so stunning there, and you can't not go during your trip.

Fun fact: Part of the stretch of beach from where you enter to the red-clay cliffs is a designated nude beach. It was a bit chilly this most recent trip for any sunbathers to be out, but the last time we were there, it was definitely in use. Something to think about if you have kids with you so you can prep them ahead of time.

Close to Aquinnah is a little town called Menemsha, and it's a great spot to catch a sunset. There's a little beach there to watch the sun go down, and the rest of it is a very quaint fishing village. There are a few small restaurants/fish markets for fresh seafood, and there's also a Jetty you can walk out onto. It's a really lovely little pit stop if you've made your way out to this part of the island. 

It's not exactly the most gorgeous thing you'll ever see, but it is kind of cool to visit something that was featured in such an iconic movie. And, it's surrounded by some very calming water views. It's located outside Edgartown, and you'll need a car to get here, but the scenery and atmosphere is rather nice. While there are signs all over that say "No Jumping," one of the shuttle drivers at our hotel told us that no one will stop you, and everyone always expects people to jump off the bridge. The sign is just there for liability reasons. Josh was actually all ready to jump off it to start his birthday with a bang, but when we arrived, a police officer was parked right at the bridge, and we thought we'd get in trouble if he did it, so he passed. We found out the next day that no one would have said anything to us. Next time! But that's why he's in his swimsuit in the photos. 

With so much focus on beautiful coastline, a lot of people forget that MV is actually very rural. And guys, you can visit an alpaca farm while on the island. We've never done it, but it seems to be a popular thing to do, especially for families with children. One house in Edgartown even had alpacas in their front yard. Not sure if they had their own personal farm, or not, but it was really cute. 

If you come to MV, even if just for the day, I don't think the town of Edgartown should be missed. Of all the towns, I think it has the most to do, even though it's still rather small. You can walk to the lighthouse (see below), browse quite a few really nice shops, have your pick of lots of restaurants, wander the marina and walk the brick sidewalks, lined with white fences, to admire the beautiful homes. It's really such a beautiful town and spending time here is always one of my favorite things to do. 

One of my favorite little houses in Edgartown.

The bookstore in Edgartown is beyond charming.

We almost made it to Chappy this trip, but we ran out of time. Chappy, an extension of Edgartown, is mostly residential and also a wildlife sanctuary area, so no shops or restaurants, which is why I was really curious to explore. It's also home to Cape Poge lighthouse. From what we've read, you really need a car to explore the island, or take a tour so someone can cart you around and take you to all the best places. In the summer months, they have a Cape Poge Wildlife Jeep Safari tour that sounds really great, and you'll be taken in a Jeep over the sand out to the lighthouse (much like Great Point on Nantucket). Next time, we plan to do this. 

There's obviously no shortage of beaches on an island, but we are rather partial to South Beach, which is often named as the best one on MV. This is one of the main reasons we love staying at the Winnetu, being that it's a very short walk to get to South Beach. Every time we've been, except once, it's had really big waves and the water, even in September, has been warm. The sun will set over the water here, as well, which is just the icing on the cake. 

I know I say this about every lighthouse, but I really love this one. Within walking distance from the main downtown area of Edgartown, it sits on a nice little beach where you can watch sailboats float by on the water, and get really close to the lighthouse. It's so beautiful out there, and I always drag Josh to it whenever we're on the island because I love it so much. 


Much like Nantucket, we're limited on places we can eat because of Josh's diet, but we've found some really fun restaurants during our time on the island. Almost all of these will be based in Edgartown because that's where we stay. My favorite lunch spot is Among The Flowers Cafe because of the great food, and the cute atmosphere. They have fresh flowers at the tables, and it's one of my all-time favorite lobster rolls. 

Seafood Shanty has an amazing upper deck overlooking the marina, and you can watch the Chappy ferries from here while you enjoy your meal. It doesn't have the best reviews online, but I actually really enjoy the food. And they have vegetarian sushi for Josh, so he's always really excited to come here. It gets pretty popular at peak times, so plan accordingly. 

The lobster roll at Seafood Shanty in Edgartown, overlooking the Chappy ferry. 

Newes From America Pub has some of the best fish 'n chips I've ever had. Inside is a really cute tavern, and they also have patio seating outside on the sidewalk (at least, during COVID they did). Rockfish had a delicious rosemary crusted swordfish that I was thinking about the next day (and the day after that). 

We had lunch in Vineyard Haven one afternoon, and loved Waterside Market. They have a nice little breakfast and lunch menu, and a cooler full of canned and bottled cocktails to make your lunch that much more fun. They also had delicious baked goods, and we really loved our caprese sandwich. 

For something sweet, Back Door Donuts in Oak Bluffs is something you have to do. They have apple fritters the size of your head (literally) and they're absolutely amazing. They also have donuts and other pastries and treats. For ice cream, Mad Martha's is the best. Josh and I both agreed that their M&M's 'n Cream was our favorite flavor. 

You haven't had apple fritters until you've had them at Back Door Donuts in Oak Bluffs.

That's a wrap on our Cape island-hopping adventure. Despite COVID making 2020 a year that we'll all be happy to see end, this trip was one of the silver linings. Every day, we both felt so grateful that we were even there, and honestly, it was a great opportunity to splurge on some things we've always wanted to do. A lot of fun things this year were cancelled, but we got to cross off some bucket list things thanks to this trip. 

To Josh: You're my favorite travel buddy, and this trip was such a dream. Thank you for helping to make it happen, for letting me chase ocean waves every day, for creating some of my favorite memories, and for just being everything that you are. I hope it was a birthday for the books. 


Striped Skirt: Gap
Open Cardigan: LL Bean in Oatmeal
*Everything else is older or unavailable

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  1. As always, your trips always seem so dreamy and nostalgic. Thank you for taking the time to share the details. I long for the day when we will be living on the east coast again and can more easily do some of these vacations. Burlington, Vermont; Kennebunkport, Maine; The Cape; Martha's Vinyard; Nantucket; Block Island...I have quite the list, thanks to you :)

  2. Oh, thank you! Where do you live now? You have the perfect list for adventures when you're back.