We started our summer trip this year at the wonderful island of Martha’s Vineyard. In this episode we talk about our favorite family activities, tips for getting to the island, restaurant recommendations, and more. If you’re on the fence about visiting this calm, yet beautiful place, then listen in!
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Transcript
Jess: Welcome to the Jetsetting Family Travel Podcast. I’m Jess, and I’m Rod, and today we are diving deep into Martha’s Vineyard.
Rod: Martha’s Vineyard was a place that we were looking forward to visiting for a long time, I would say, and it was the first stop on our summer trip. And the way that we got there, I don’t think it was that difficult, but it takes some time to get to, so plan accordingly.
We flew into Boston, Massachusetts. It was 11 p. m. at the time, so there were, I don’t think there were ferries running to get to the island anyway that late, and I don’t think we would recommend that, so what we did is we ended up staying in Plymouth, Massachusetts, which was about 45 minutes from Boston.
And once we got there, we had the morning, we had booked a afternoon ferry. So one word about the ferries there. It’s a little bit of unique because if you want to drive your vehicle onto the ferry, one of the things that we would recommend is to definitely book in advance. A lot of the vehicle lanes or spots on the ferry themselves book weeks in advance.
So if you want to make sure that you have a car there, and I would say. Recommend highly recommend getting a car so you can drive around the Island. You don’t have to spend a bunch of money trying to get taxis from one place to another, but you know, what do you think?
Jess: Definitely. I loved having a car on Martha’s Vineyard.
I highly recommend that. What you decide to do, if possible, I thought we would have definitely not explored as much of the island. If we had not had our car there. But it was hard in the sense that when you book, you have to book the ferry for the car way in advance and we like to have flexible travel and be able to move things around.
And that made it very difficult to adjust our schedule. We had a last-minute change come up because. It was sold out the entire rest of the week. Apparently, there’s a standby line that you can risk going to, but I don’t want to spend my vacation sitting in a parking lot praying I get on a ferry.
Rod: Yeah. So that, that ferry itself is called the Steamship Authority.
So you can go on their website, you can book your own spot there. You’d have to buy individual tickets for each of the passengers too, or if you don’t want to drive around on the island, say you’re staying at a resort there, then you just buy tickets for yourself. That ferry is huge, and you take it typically from Falmouth down to either the ports of Oak Bluffs or to Vineyard Haven, which are the two kind of main pick up and drop off areas when you get to Martha’s Vineyard and that ferry ride is 45 minutes. The ferry ships do have a lot of indoor space, outdoor space. There’s a cafeteria there where you can relax bathrooms. If you’re driving your car, and then you kind of drive directly into the lower level where all the vehicles are held.
Then you can get out of your car and then walk around and admire kind of that short trip. They’ll eventually tell you when you need to get back, on your car and it’s super smooth. You just drive right on out and you’re right there on the island.
Jess: So if you fly in and want to go directly from Boston Logan to Woods Hole, which is where the ferry takes off, it’s about an hour and a half total.
I’d say Plymouth was closer to an hour from the airport, but. For us, it was nice. The kids got to see Plymouth rock and a little bit of that area, which I will say Plymouth rock for me, at least was very underwhelming. I think it’s cool to be like the kids saw it. It’s a part of history that they learn here in America.
Rod: But the rock itself, I mean, yeah, it’s just a large rock. It’s not as big as you’d expect it to be. There’s a little plaque and a lot of information that tells you the history of the rock itself, how. I think it’s got split into three parts and the one part that’s in actual Plymouth there is where you can see and the others are stored in museum somewhere, I think.
So I don’t, I don’t think you need to, I would say must stop on your way.
Jess: Unless you’re flying into Boston late. It’s a good, it was cheaper for us to get a hotel there than like, near the airport and it’ll cut the morning drive. I think it’s about 30 minutes from the ferry instead of having to drive an hour and a half.
Rod: Yeah, that’s true. And it’s a lot more affordable than staying in Boston. That’s for sure.
Jess: But once you get to Martha’s Vineyard guys, oh, there’s so much to do. I will say something I loved about our trip. I realized it’s not possible for everyone, but if you’re in one of the states who gets out for summer break before the Northern states, so like we get out around Memorial Day.
Yeah. And we left directly that next week. And so what was nice is, is the, the Northern states, I believe, get out more towards like June 10th, maybe?
Rod: No, it’s like later in mid-June. So June 18th through the 20th, something like that.
Jess: So since they get out later, if you have a school that gets out earlier, if you could go at the beginning of June, we found that we had a lot of the island without crowds.
I mean, there was still enough of a vibe to like feel what Martha’s Vineyard’s like, but there were no waits at restaurants. There were no crowds. We didn’t have traffic. It was beautiful It wasn’t till our very last day on the island, which was the Saturday, like right after the Northern schools got out, that the island changed quickly, like the number of crowds that were there in the traffic.
So if you can plan to go, I would suggest highly trying to go like before, or like the weeks before or after the peak season there.
Rod: Yeah. The one downside to that I would say is the weather itself. I wouldn’t call it summer weather, when you’re visiting that first week of June, the temperature, especially for an island, right?
We’re coming from Florida where we were getting used to the heat and we show up to Martha’s Vineyard and sometimes when it’s cloudy, the, the weather and temperature is like lower sixties and you’ve got that sea breeze coming in. Then it’s going to feel a little bit chilly. So just be prepared for that.
You’re, you know, hopefully the resort or wherever you’re going to has a heated pool. I wouldn’t say that the ocean water is going to be a high enough temperature for it to be like enjoyable to spend the whole day in the water on the beach. But, you know, just, yeah, just take that into consideration when you’re planning a trip that early, but I would still recommend going early because having Martha’s Vineyard, it felt like we had it to ourselves. And that was an awesome feeling not to have to wait in traffic and at lines to get food in restaurants.
Jess: So for things to do there, we spent our whole week. It was pretty jam packed. There was a lot to do a lot more than I anticipated on the island.
So we’ll start with things to do and then go into some restaurants we recommend. So there is an amazing fishing boat. It’s pretty, it’s smaller than I anticipated and it’s not fancy, but it was incredible because it’s well known at Martha’s Vineyard. I guess they get a lot of famous people that go on it.
But besides that, they’re great at helping the kids fish. And we’ve gone fishing a lot as a family. We’re not great fishermen. And I just think of spending hours waiting for that one fish. But we were on this boat for what? Three hours? Yep. And I think we took five kids with us on this trip. I think they caught, I don’t know, 30 to 40 fish.
It was just nonstop.
Rod: So yeah, the captain has had 30 plus years of experience. So he knew where all the good spots were, depending on how rocky the water was, what the temperature was, and he’d go to a specific spot. He would put the anchor down and all of a sudden there’s, I think there were what, maybe.
25 people on the boat. So everyone had their own fishing rod and we had a guy next to us that came with his cooler, had a couple of drinks and he kept all his, his fish. So pretty much as soon as you put the anchor down and you put that fishing rod in the water, somebody caught a fish like 10 seconds later.
It was pretty crazy.
Jess: The kids absolutely loved it because they were catching fish left and right. You can choose to either catch and release. They had to be a certain size to keep them if you chose to keep them. But the cool thing is, is if you did choose to keep them at the very end, they’d actually fillet them and have them prepped for you to cook on a grill.
So they did all the work for you. And then you get to take like a little, if you bring a cooler, you can put it in your cooler, get off the boat, and then you can grill some fish. But the party boat skipper was one of the kids. favorite activities because they did catch so many fish and they each they were, they had people on board to help the kids take the fish off or get stuff on the line.
So it was super easy, super laid back, and it was a great experience. Another thing we did with the kids is we went over to an area called Menemsha. And Menemsha had it’s, well, there’s a little Menemsha market where you can actually see where the fishermen bring in the fish and the lobster and you can actually buy fresh lobster bisque or fresh lobster rolls and you can eat right there as you see the boats coming in and as well as Menemsha is really famous for sunsets.
So you, a lot of people take dinners. They pack little picnics and they go and they watch the sunset at Menemsha beach for us. It was too cold when we went to swim, but the kids still had so much fun skipping rocks and like playing around. It was super calm in that area. So they could skip rocks and seeing a sunset or sunset was still beautiful.
It was just different. Cause we were there in the middle of like. The Northeastern fire, so it was so hazy and smoky.
Rod: Yeah, the Canadian wildfires had come through, so the air quality wasn’t great. There was haze, and that kind of blocked the sunset view. But it was still fun. It’s still a thing to do, and if you go, you definitely should see the sunset there.
It’s like at the northwestern end of the island there, so you’d have a pretty good view of the sunset during the summer.
Jess: Yeah, another area that was absolutely gorgeous. I honestly felt like since we were on an island, I picture in my head like Florida Island, like islands for some reason that are just flat, but we drove around Martha’s Vineyard and people told us to go to the Aquinnah Cliffs.
Rod: Yeah, Aquinnah Cliffs are on the west end of the island. I’d say if you’re staying in Edgartown, which I’d say is the main kind of hub town in Martha’s Vineyard, it’s probably about 30 to 40 minutes from there driving. So that’s why we recommend having a rental car. A lot of the way there, you’re going to lose reception.
There’s not a lot of stuff to do or to stop at and see, when you get to Aquinnah. But the Aquinnah Cliffs are really… Surprising, I’d say. I think that we love seeing the view from there. It’s the striking cliff views kind of reminded me of Ireland or the cliff beaches in Iceland for a little bit.
So it was nice. They have a viewpoint there. There’s also the Gay Head lighthouse. It’s there and right next to the Aquinnah cliff, so you can park your car and then walk to the little area where the view point of the cliffs is. And then you walk on over to the lighthouse. I think sometimes the lighthouse is open during certain times in the summer.
So you can even go and inside the lighthouse and see the view from there too. It wasn’t open when we were there. But that’s something that you can check and, and see if you can do as well.
Jess: Another highlight to do is, I mean, there’s so much to do.
Rod: Oh yeah. And before we talk about other ones, there’s a little beach.
So we were trying to stop at a little beach on our way to Aquinnah. And we, we went to a beach that ended up being for locals only. And we got turned around, there was a security guard there. What we ended up going to, I think it was called Squibnocket beach. And that one was a public beach. Had a good level of parking there.
It had cool little, I’d say like mini cliffs that you can walk along the beach at there’s also a path that takes you to this little grass and wooded clearing. That’s really nice. And then you can see some of the, like, massive homes that are very close to the coast there. And some have their own paths to the beach.
And it was really cool just to have the kids there play and make sand castles, walk along the beach and enjoy the time there. That wasn’t very populated when we were going there too.
Jess: Yeah, it was beautiful. Of course, spend time in the different towns. We spent a day with the kids in Edgartown and they just have little shops to like the toy stores and souvenir shops and ice cream.
It’s a great place for date night. So the towns are really cute and definitely worth a visit. When you go in between the two main towns, which is Edgartown and Oak Bluffs. Oak Bluffs. Slipping my mind here. Mm hmm. You will see a famous bridge. Now, you have to pay attention because, to be honest, when I always heard about this Jaws Bridge, it’s because it’s in the movie Jaws, so it’s called the Jaws Bridge.
I thought I would definitely, like, recognize it. I mean, you can literally drive past this bridge when no one’s on it. And you wouldn’t even know it, but once busy season hit, you will not miss it because there will be a ton of lines of people at Jaws bridge, because despite all the signs saying not to jump, it is a place where it’s like tradition that when you go to Martha’s Vineyard, that you jump off Jaws bridge into the water.
And then you just kind of swim out. And. Everyone told us, like, when you come, you have to jump off Jaws Bridge, so Rod and the kids did jump off Jaws Bridge. It was so cold.
Rod: The water was freezing, I’ll be honest, but I think you’ve got so much adrenaline going, even though it doesn’t look like you’re jumping very far down.
Once you’re standing, I mean, you’re crossing over this iron rail and you’re looking down at the water and you’re like, oh, that’s, it was probably, I’d say maybe 15 feet tall but it felt like you were diving off a massive cliff. And when you go in the, in, the water is just freezing cold. Immediately just like gets you so alert and pumped up to get out of the water.
So, it was great. Yeah. I think when we first got there, there was nobody there and we were like, Ooh, are people really doing this? Is this going to be safe? And then this group of like three teenagers just like shows up in their bathing suits and they just climb over the rail, really quick, jump off. And we’re like, Oh, okay.
I guess if the teenagers can do it, then so can we.
Jess: Yeah, it was pretty cool. It’s funny cause. I was kind of like, everyone talks about this, but it’s not, it doesn’t seem that popular. And then on our last day out, once the crowds came, it’s like, there was a huge line of people waiting to jump off the bridge.
Oh yeah. Santi was super excited. He did it. And Nora didn’t want to miss out when she saw everyone else doing it. So something else on Martha’s Vineyard, we were really lucky with this stay at Martha’s Vineyard in that we booked it through a travel club Rod and I joined called Third Home. We’re actually going to do a separate podcast specifically dedicated to Third Home and how that works.
But the Third Home we booked was on a hotel property that’s open to everyone, whether you’re a Third Home member or not. And that is called the Winnetu. And the Winnetu, guys, to me, that was part of the highlight of our stay. And I’m going to tell you why for several reasons and why. You should consider it.
It’s extremely pricey. We were very fortunate that the travel club made it affordable for us. I’m just going to put that out there. It is pricey. But they had an incredible kids club daily that the kids really, really enjoyed. They take them on scavenger hunts to the beach. They do little mini-Olympics. I mean, they kept them busy.
Rod: Oh, yeah, they have a little mini tennis court where they can play tennis or pickleball, playground. They go to, yeah, they go to the main resort area where there’s big chess, there’s Ping pong, they have little fire truck rides that they do.
Jess: It’s amazing. They do s’mores at night. They have daily cookie time.
I mean, the resort itself was just perfection for a family. We had a heated pool that was wonderful. It had like a bar next to it for when the kids were at the kids club. Sometimes we just hung out and had a drink. It was steps from the beach. So overall to me, the Winnetu is what made our stay. It was like, we were busy and we went out and did something on the island every day, but the resort allowed us to also have a lot of relaxation because in the morning we dropped the kids off at the kids’ club and they’d stay there till around noon or one.
And then we would take them and go out and do something on the island, but it made it for the perfect mix of like family relaxation with exploration. And I just thought the Winnetu, when you think of Martha’s Vineyard and this like family friendly, beautiful summer vacation, it’s like, I think of that resort.
It was like everything I pictured in my mind. I felt like I was nervous going to Martha’s Vineyard because I had such high expectations because I always heard about it that I was going to be disappointed, but that hotel really. Made it a beautiful experience. And while we were there, they even had a car show on the weekend, which was cool to see, too, in their field.
So if you can, it’s not in everyone’s budget, but if you can, I would definitely check out the Winnetu Hotel. Because that was a place that we spent a lot of time in their pool and doing all their fun activities.
Rod: Yeah, yeah. And Winnetu was south of Edgartown, kind of on the southern southeastern end of the island, about 20 minutes.
I think it’s a 20-minute drive from Oak Bluffs where the ferry terminal is over to get to the window to and highly recommended. In Katama itself. There’s also this cool little airport. I don’t know if we’re transitioning over to like places to eat.
Jess: Oh, yeah, we can do restaurants now, guys. Because it’s pretty cool.
Rod: Yeah, we’ll start off with that one. This one was called the Katama Kitchen. And I think they have breakfast and lunch there. They don’t do dinner, but it’s at this grass airport at the southern end of the island where You eat in this nice little patio, the food there was very good, but also, you’re overlooking these really small, like acrobatic planes that are taking off and landing.
There are these by, like the bi wing planes and you can book a trip to go on that. We didn’t do that this time, but they’re the ones that can do flips and stuff. So they’re pretty small and there’s only like three or four of them. So when we went, it was in the morning when they’re first starting to do their tours and taking people up.
So we were able to see some take off, see some land while the kids also have this like little play structure that’s shaped like an airplane that they can play at too. So overall, I think that’s a great place to do a, I’d say maybe a weekend breakfast brunch type of thing.
Jess: Yeah, definitely. And when we got off the ferry in Oak Bluffs right away. We went straight to a restaurant called Lookout Tavern, which I have to say, out of all the places we tried lobster rolls on the island, that one was the most impressive. So if you’re just looking for a lobster roll when you get off that ferry, head to that Lookout Tavern. It was really, really good.
Rod: Yeah, I mean, I had this expectation of a lobster roll in Massachusetts to be You know, you have the little hoagie roll with a little bit of lobster, some coleslaw, and some sauce on it. That is what I expected to have in a lobster roll, but when we showed up to the Lookout Tavern, that’s actually the very first place that we ate when we first got out of the ferry.
And we ordered, it’s like, hey, we’re in Martha’s Vineyard, we hear that the lobster rolls are a thing to do here, so that’s what we ordered. They’re like 30 dollars. But once they come out, it’s this like, it’s a hoagie roll, but it is just filled to the brim, overflowing with pure, just like lobster meat, nothing else on it.
There’s some butter and then they’ll give you some like condiments if you want to put ketchup on it or whatever, but it was an overwhelming amount of lobster rolls. So I think you are getting your money’s worth if you’re paying the 30 for it, I do highly recommend to have a lobster roll at one at some point during your stay there because it’s so fresh.
Yeah, lobster bisque is good too. So between there and the Menemsha fish market where we watched the sunset. That’s where we had lobster rolls. So we had them twice. I think maybe we had it a third time, but I can’t remember the other place where we had it. So those are the ones that we would recommend.
Jess: And then my absolute favorite place on the Island for family time was a place called Nomans. Nomans guys. If I was a local, I would go to Nomans every night at just, I could probably be. I don’t know a local favorite there. So Nomans is a restaurant on the Island that is super, super casual. And it is perfect for families because it is this like mix of indoor outdoors.
They have tons of games for the kids. So when you get there, they’re going to have Jenga and corn hole, and they might’ve even had horseshoe. There’s a field right next to it where kids were throwing footballs and soccer balls and running around. And it also has, when we went, they had live music. So Nora and I got to dance and it just was like the perfect place for our family.
It’s kind of closed off, so like the kids can’t run off into a road or run away. It’s like fenced in. So it’s just a great place to go and have a drink. You can have, you know, they had a whole full bar. So you can have cocktails, beers, listen to music, watch the kids run around and play. It was perfect. It isn’t, fancy in the sense that like there are tables inside outsides. It’s mostly like picnic tables or they have bonfire pits. So it’s like seating around bonfire pits and I believe you placed your order and then they deliver it to your table. So it’s not service ready. Yeah. But I thought the food was great and the kids.
And us as well had so much fun. Like they met little friends to play with and I don’t know. I just loved it. I love the live music. I just love the vibe, the whole place. We kind of went towards the end of our trip, even though people were like, you should go to Nomans. And I kind of wish we’d gone multiple times.
Cause that was probably one of my favorite evenings.
Rod: Yeah. I think Nomans really embodied the vibe. I think that you get on the island. What I expected when we first got to Martha’s Vineyard, you get a lot of comparisons between Martha’s Vineyard and some place like the Hamptons, where people are always dressed up, super proper looking.
What we ended up finding is Martha’s Vineyard was pretty casual in terms of the vibe and the way that people dressed and stuff. I think in the evenings when people are out doing date nights and bars and stuff, then you get a little bit dressed up, but just in general throughout the day. And at Nomans, there are people there that were getting ready and celebrating a wedding. There was us with families and we had friends that were visiting and we went together as well. So we had our own table. There were groups of, maybe it was a bachelor party or something, but they’re like groups of 10 guys that had their own table doing their own thing.
So everyone, there at Nomans was. All from like different backgrounds, celebrating different things with the different reasons for being in Martha’s Vineyard, but just being there altogether in this very casual setting with the live music was super memorable. So if you go, definitely go early. One of the things that does have a smaller parking lot.
So if it does fill up, then they’ll ask you to like drive down to. Closer to where the jaws bridge is. So Nomans is close to Oak Bluffs between Oak Bluffs and Edgartown. So they’ll ask you to go park near the beach and then they’ll take a shuttle to go pick you up and take you to the restaurant itself, and then they’ll shuttle you back to that parking lot.
So. There is overflow space if you need it, but yeah, do show up early. And I think they only close, they close at like 11. So it’s not like it’s a late night place that becomes a party spot. It’s really just a nice dinner place with a big open area for people to enjoy. Yeah.
Jess: Overall, that was probably, I mean, as far as restaurants, that was definitely my favorite.
We also went on a date night with our friends. We went with a couple and their family on this trip. And for that one, we went to a restaurant in Edgartown that was called.
Rod: Chesca’s. We looked up fine dining. We had gotten a lot of recommendations to go to Chesca’s. It was really cool. The, the thing I remember there was one of the cocktails that Jess ordered was based on Jaws.
So it’s like they, they bring you the drink. And then I think it was based off of the name of the first like Jaws victim from the movie. So they’re pouring this grenadine syrup onto the drink to make it simulate like it’s blood in the water or whatever. So it was a nice little touch. A lot of pride there for the Jaws movie for everything that that’s been kind of filmed in and around Martha’s Vineyard, the food there at Chesca’s was really good.
So highly recommend that place. I don’t know about going there with kids. I think we did see kids there when we were there for date night. So I think it’s family friendly. Other family friendly places there in Edgartown, there’s a place called The Seafood Shanty, and this is close to the dock. So you can get a seat and their little patio that overlooks where a lot of the boats that leave that Harbor are, but that place was super family friendly.
They had a kid’s menu. They had really good food there as well. I think they had lobster rolls and lobster bisque there too. We tried the lobster bisque there, which, was pretty good. And a lobster dip, I think is what we had. So that was another good place that was super family friendly. There’s a bunch of ice cream shops, little toy shops, souvenir shops, all over Edgartown.
So if you want a place to kind of spend the day, then that’s, that’s the place to
Jess: go. Something to note is finding parking in Edgar Town proved to be difficult. So if you stay at the Winnetu, they do offer a shuttle service.
Rod: Yeah, like every half hour or every hour that will take you there and return you.
So that’s that was a benefit. We, even though we had a rental car, we did take the shuttle into Edgartown because the parking situation there was, unless you wanted to park far away, like a half mile away and walk into the town, which you could totally do if you had more time. Then you can do that, but otherwise you’re going to be circling, especially during the lunch and dinner hours where people are driving into the town there.
So yeah.
Jess: But overall, I absolutely love Martha’s Vineyard. It’s definitely 1 of the places I’d be happy to return, especially while the kids are little. I found the island to be. Super safe, super family friendly, and just a beautiful time. Yes, the beaches weren’t Florida warm, but I feel like there were so many other things to do on the island.
You could still enjoy building sandcastles and hanging out on the beach, just swimming. I mean, people did it, but maybe because we’re from the South, it just didn’t seem as comfortable. But definitely a place that I would add to your travel list, especially for the summer…
Rod: Yeah. Yeah. So next week we’ll be covering some more of these kind of Northeastern cities, either Boston or New York City.
We’ll talk about next. We can talk about the Catskills as well. That’s another place that we visited, but you know, if you enjoy the podcast, make sure that you’re subscribing so that you can get a little ping notification every time we have episodes coming, which is every Tuesday. So as always, thank you so much for your support.
We appreciate you being part of this little community that we have. And until next time, Happy Jetsetting!
