Cape Cod, Martha's Vineyard, Nantucket: Charming Massachusetts Getaways

From the Cape Cod peninsula to the nearby islands of  Martha's Vineyard and Nantucket, Massachusetts offers some of the most charming towns and activities in the U.S. And Leon Bolivar, a true Cape Codder, leads us along the way.

We start on the Cape, discussing places to go and things to do in and around Falmouth, Sandwich, Hyannis, Yarmouth, Dennis, Chatham and Provincetown. Then talk about Cape Cod pastimes including baseball, golf, croquet and whale watching. 

Food and drink faves include  clams, oysters and lobsters -- including lobster ice cream! (With local potato chips, and maybe a cranberry Cape Codder.) 

We  go on to Martha's Vineyard -- what to see and do, in and around the cliffs and beaches from  Oak Bluffs to Edgartown. And then, Nantucket -- what to see and do on this extremely charming little island filled with whaling history and cobblestone streets.

Lea offers a limerick she adapted about Nantucket. And Leon ends with his special memory.
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Leon Bolivar is director of marketing for Ocean Edge Resort in Brewster, Cape Cod. He has loved the Cape region since he arrived from South America as a young man.
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Podcast host Lea Lane blogs at forbes.com, has traveled to over 100 countries, written nine books, including Places I Remember, and contributed to many guidebooks.

Contact Lea  @lealane on Twitter; PlacesIRememberLeaLane on Insta; on  Facebook, it's Places I Remember with Lea Lane. Website: placesirememberlealane.com. 

New episodes drop every other week, on Tuesdays. Please tell your friends, family and colleagues about us, and follow, rate and review this award-winning travel podcast!

Transcript

Lea Lane  0:00  
Cape Cod, the beachy Massachusetts Peninsula an hour or so from Boston is a favorite for relaxing by the water with some 560 miles of shoreline, and the nearby resort islands of Martha's Vineyard and Nantucket and you have one of the most well known summertime travel destinations in the world. The Cape juts into the Atlantic and looks to me like a strong flexing arm. Some people say it looks like a hook. It offers so many charms quaint villages, seafood, shacks, lighthouses, gardens, filling with hydrangeas, ponds and days, Sandy atlantic ocean beaches and lots of fun things to do. We'll be talking about the Cape with Leon Bolivar, director of marketing for the stunning Ocean Edge Resort and Golf Club in Brewster Cape Cod. Welcome Leon to places I remember.

Leon Bolivar  0:50  
Thank you Lea happy to be here.

Lea Lane  0:51  
So Leon, a major road goes right through the Cape if you drove it without stopping How long would it take to go from end to end?

Leon Bolivar  0:59  
So from the Sagamore Bridge to Provincetown will most likely take you about hour, hour 20,

Lea Lane  1:06  
Wow, that's a lot of stuff to pack in a very, very short road. Wow. So there's so many things to see and do. Let's start with a few towns with a stop. Let's start with Falmouth, the quaint seaside village closest to the mainland and the Cape's primary gateway to the island of Martha's Vineyard seven miles off shore. What are some of the highlights around Falmouth?

Leon Bolivar  1:27  
Well, that was a beautiful, a beautiful place. So right as you cross the Sagamore Bridge, you bang a right and you go straight down to Falmouth down there. There's one of my favorite places, Lea, the place called the Nobska lighthouse. This lighthouse dates back to 1829. And if you know, when you think of quintessential New England,  Cape Cod lighthouses always kind of come to mind. So this one is very historic right there on the water. Beautiful, overlooks the sea. So that's definitely worth checking out. If you are into biking, we have the Shining Sea bikeway as well, cutting through Falmouth. It's about 11 miles or so right by the water. So again, very dramatic ocean views. Definitely worth seeing, Main Street in Falmouth has all the restaurants and cute little shopping boutiques for you to go in and kind of buy some souvenirs. And so that's very nice. And if wine is more your thing, you know, Cape Cod, wineries, if you will be able to indulge in some locally grown wine as well. 

Lea Lane  2:18  
Also, there's Woods Hole. Tell us a little bit about that. 

Leon Bolivar  2:21  
Yeah Woods Hole's a very iconic oceanic institution. So a lot of great things happen out there in terms of studying the ocean and really all that it provides the world, really and so it's a great institutional hub down there with for you to walk down, go down to the harbor, take some pictures, maybe even see a seal or two. It's a great day, a great place for you to enjoy just a nice sunny day.

Lea Lane  2:43  
Yeah, what I like about Falmouth, very historic village green; there's  a white picket fence around it. Very New England and very sweet. Now Sandwich is the oldest town on Cape Cod, settled in 1637. The name is not about sandwich; that word came later. It's like peanut butter and jelly. But it was named for the seaport of Sandwich in Kent, England, and the town motto translates to: quote, After so many shipwrecks, a haven," which tells us something about the Atlantic, especially in the winter. It's famous for its glassware, which was produced here in the 1800s. Tell us a little bit about Sandwich glass and how it was made.

Leon Bolivar  3:21  
It's actually one of my favorite museums on all Cape Cod. So when it comes to Sandwich, they're known for two museums: one of them being the Sandwich obviously, Glass Museum, and the other one being the Heritage Museum and Gardens. So back in 1825, that's when the Boston Sandwich Glass Company actually relocated to Cape Cod because of the sand was so kind of lends itself nicely to the glass blowing. The great thing about that museum is it kind of takes you through a walking history of the evolution of glassblowing every hour on the hour. They also have live glassblowing sessions, so you can actually see a glassblower kind of give a demonstration on how they pretty much create these beautiful ornate pieces. I was there recently and he did a whale's tail, you know, beautiful. You see that sand and how it all goes into the big fiery hole how it comes down to how he molded and melts it and it's a great educational component. They also have a great little gift shop for you to be able to go in there and buy some of the wares that are created directly on site.

Lea Lane  4:18  
There's also the Cape Cod canal which just goes through Bourne, Sandwich ... tell us a little about that canal.

Leon Bolivar  4:25  
Yeah, so that was so basically Cape Cod was originally part of the mainland. However, in 1914, they decided to build this canal to have a cut through from Cape Cod Bay to Buzzards Bay. So it's 11 miles long. And there's a bikeway that goes past that you can go down there and just picnic and take a look at the boats. There's restaurants down there as well, and Sandwich, my favorite, is a fisherman's view. So you have a beautiful view of the canal and to the boats going in and out and it's a great place to also go fishing.

Lea Lane  4:54  
How about the large town of Hyannis and the center of the Cape?

Leon Bolivar  4:57  
Yeah, so Hyannis would be the economic hub of Cape Cod. That's really the heart of it all, if you will know made famous, obviously by the Kennedys who have a compound, there still till this day. They've got some Main street some very long Main Street, as you can imagine, has a lot of restaurants cafes, bars; the JFK Museum is also there. And one of my favorites, I highly recommend for anybody who's going to be on the Cape to go see that museum. It's also the place where you get most of the ferries to actually go out into Martha's Vineyard and into Nantucket. So, beautiful place, great place to go do some people watching, walk along the water by yourself, some souvenirs, and it's a lot of fun.

Lea Lane  5:35  
Well, I have a memory of Hyannis that goes way back to the very early 70s. It was a spotting of a very famous person. It was near Hyannis. It was not in Hyannis because it was at a place where Peggy Lee, the singer, was performing so I'm not sure where that would be but it was close enough. 

Leon Bolivar  5:52  
Do you remember maybe the Cape Cod Melody Tent? 

Lea Lane  5:54  
Yes, probably was it. But who should be there, but Jackie Kennedy Onassis; at that time she was accompanied, I remember that, by the astronaut John Glenn. And her children were there and she was having a wonderful time. Afterwards, there was dancing on the stage. At the end it was raining and I went outside to get a car and I was standing right next to her. It was wonderful. I was thrilled. That's probably one of the best spottings of my life. That's Hyannis to me. Anyway how about Yarmouth?

Leon Bolivar  6:25  
Yarmouth is right next door to Hyannis, you know kind of its neighbor there. I think for me what comes to mind when I think of Hyannis is now they have the Pirate Museum, which houses the largest collection of pirate artifacts recovered from a single shipwreck anywhere in the world. That shipwreck happened in 1717. And so they have pirate festivals, kind of a unique experience considering that ship that shipwrecked outside of Wellfleet, which is up north on the Cape, but the museum is there now and so they really embrace that whole pirate theme. You know, putt-putt for us is very popular at mini golf. And so we've got Skull Island and Pirates Cove where you actually get to learn more about some of these famous pirates;  they navigate to the Caribbean and eventually will make their way up to up to New England. So a lot of fun.

Lea Lane  7:08  
Very interesting. I know you can go through a life size replica as you walk through the museum of the ship. So it's very, very special. How about Dennis; tell me about what's going on there.

Leon Bolivar  7:18  
Dennis right by the water on the bay there. My favorite restaurant to go to when the summer is actually there. The Harbor hotel, the harbor cafe, actually sits outside of a marina. And so basically you see the boats going in and out. all of the sailing, if you'd like some fresh oysters, best place to get them, lobster rolls as well. So a great place for you to be able to go out there and do that. One of the best beaches actually on Cape Cod in my opinion, Lea is also in Dennis: it's called Mayflower beach. We know there's parking, there's concession stands for you to be able to get some ice cream and whatnot. And so it's kind of beautiful. Sometimes when the tide goes out, you can go out as far as two miles, which is wild. Yeah, to be able to see in person but Mayflower Beach, to me comes to mind. Cecil at Harbor Cafe comes to mind. And it's also home to the Cape Cod Museum of Art, which is beautiful. They have you know, they have a lot of rotating exhibits that pay homage to, for example, the Wampanoag tribe who are the original inhabitants of this peninsula alongside just contemporary artists and a lot of sculpture. So if you're wanting to get into the arts, enjoy some arts while you're down here. I highly, highly recommend the Cape Cod Museum of Art in Dennis.

Lea Lane  8:24  
There's also theater there there's the Cape Playhouse, which started in the 1920s. And it's a very famous summer theater so that you get all the arts there. It's a wonderful place to do that. How about Chatham tell us about the Jaws screenings. Those are my favorites.

Leon Bolivar  8:40  
Yeah. So Chatham is a is a great little town. You know, they're very well known for the Chatham House strolls over the holidays. They're known for their main street. One of the major restaurants that you are encouraged to visit is the Chatham Squire, you know, the kind of place that has the license plates on the board on all over the walls and it's just live music and so it's a lot of fun. They do Jaws tapings, showings, excuse me, on the water, which are also a lot of fun. And so it's a great place for you to be able to kind of walk around, take a look at the Chatham Lighthouse as well as Rome Main Street, and then take boat tours as well, you know, over to Monomoy Island and you know, get a natural excursion and go visit some of the other places around that part of the ocean side of the peninsula.

Lea Lane  9:21  
Well, the Cape Cod National Seashore starts in Chatham and stretches all the way to Provincetown, where you have six swimming beaches, 40 miles of coastline, lots of dunes; I remember taking a dune buggy around there, there were lots of beach plums and beach grass and we visited little shacks on the dunes. It was a wonderful way to see the beach. I love that. I love the memory. Now, the Cape's Northern end is Provincetown. It has a really distinctive vibe. How would you describe Provincetown?

Leon Bolivar  9:51  
It's a party town, if you will. It's a party town. You know, you go up there you know they've got Commercial Street which is the equivalent of Main Street which is lined with people restaurants cafes bars. It's a very gay friendly place. So I'm assuming is bustling with live right now during pride month. And there's a lot of art galleries there as well. And so it's a great place to be on the peninsula. It's actually where the Pilgrims originally landed on Cape Cod, they landed in Provincetown. You know, they really couldn't sell the land, it was a bit too harsh for them. So they ended up getting back into boats and crossing the bay over to Plymouth. There's also Pilgrim Monumen;  go all the way up to the top and you can see all of Cape Cod and the ocean and the surrounding bay. So it's a very beautiful. Certainly worth the trek out there. Again, you just mentioned the dune tours. Those are a lot of fun. And you know, the gallery and the food and the great ambiance, you're never going to be bored if you go to Provincetown.

Lea Lane  10:41  
Oh, never. You'll never forget Provincetown. It's really great. Tell us about summer baseball on the Cape.

Leon Bolivar  10:47  
Oh, the Cape Cod summer league is very iconic down here. I actually work for a resort in Brewster and the Brewster Whitecaps actually won the championship last year. So we're all 

Lea Lane  10:58  
Congratuations. 

Leon Bolivar  10:59  
Absolutely, yeah, we are very happy for the guys. You know, they come into the property once a week during the summer and do drills with the kids and the guests. So that's a lot of fun. A lot of folks come down here and kind of cut their teeth before heading out to the majors and to the minors within the MLB. And so basically, they're all the other games are free, you know, grab a grab a lunch or a blanket, a picnic basket and just go out and support the team. All of the towns have so you know, Wellfleet Chatham or liens, Brewster Cotuit, any of those towns that you may be staying in is gonna have their own little baseball team so highly, highly encouraged. It's part of the it's like ice cream and pot pot and lobster. It's part of a Cape Cod summer.

Lea Lane  11:39  
Absolutely. It's awesome biking, kayaking, world class golf. I know there are many courses that are really excellent.

Leon Bolivar  11:47  
Many courses. Yeah, some private, some public but definitely a great place for you to get out there and just swing the club away. And you know, when

Lea Lane  11:53  
I played croquet speaking of clubs. I remember I was on a press trip a few years ago. It's very old fashioned, but lots of fun. It's a lawn game. I do remember one of the people on the press trip was the great French chef Jacques Pepin. He wasn't very good at croquet. But he's a great chef. But we won't tell anybody. 

Leon Bolivar  12:18  
On our resort, actually, we have a regulation-size croquet court, and so we invite folks to do tournaments out there and just kind of have fun. Put your whites on -- you're supposed to wear all white when you play the game. Yes, it's kind of it's very reminiscent of the Gilded Age, if you will.

Lea Lane  12:33  
Very, very nostalgic and very fun. Now, of course, Cape Cod's major industry used to be whale hunting, and now it's whale watching. We talked about this pasttime in Episode 40. Tell us what you can expect in the waters around the Cape.

Leon Bolivar  12:47  
Yeah, so the Cape has two sides really. It's got the ocean side and it's got the bay side. The bay side is where you will see most of the whale watching -- so humpback whales with the little babies kind of following them around. Typically, you will hop on these Whale Watch tours in Hyannis in the Barnstable area. And you know, you're out there for about 2,3,4 hours, you know, there's concessions on the boat, but you get out there enjoy the sun and really see these massive beautiful majestic animals swimming along the bay. And then if you go to the other side of the peninsula, on the ocean side, that's really where you would see things like seals and things of that nature. And that's kind of what separates the land. The wildlife, I guess,  has all the seals and the other one has more of the whales.

Lea Lane  13:29  
I do know when you go out to the beach, and when you're looking for the whales, I guess you can sometimes see them from the shore. One of the things that you want to think about is some of the seafood. So I think of fried clams, and I'm thinking of Wellfleet oysters, and lobster, of course in all forms. I remember one form -- I have to say I've talked about other ice creams before but I had lobster ice cream. Have you had that one? Chocolate Emporium. Very sweet, sweet and savory ice cream. It's sort of butter flavor with bits of lobster in it and it was really different.

Leon Bolivar  14:07  
That's something; so unique. You know, I haven't even spent so much time down here. Obviously I haven't come across that one yet, but I'm gonna have to give it a go. 

Lea Lane  14:13  
Absolutely. And I would also have some Cape Cod potato chips. I know they're made on the Cape and actually you can go over to the lighthouse and it's Nauest light in Eastham and that's what's featured on the bag, and you can have potato chips and look at the lighthouse

Leon Bolivar  14:29  
When you're in a certain part of Hyannis where the factory actually is you can actually smell the potato chips in the air. Yum. Delicious. It's absolutely delightful. And it's you know I love those kettle chips and right nearby is also Cape Cod Brewing so you know you want to make an effort and then go.

Lea Lane  14:47  
A brewery and how about a lobster roll too

Leon Bolivar  14:51  
That's Cape Cod for you.

Lea Lane  14:53  
There's also the Cape Codder cocktail. Have you familiar with that one?

Leon Bolivar  14:58  
That kind of cocktail. We do have a variation of that, we call it a Cape Cod Mojito. So Cape Cod, as you know, is very well known in the fall for the cranberry bogs. We use fresh cranberries and it's delicious and delightful, very refreshing in the summer.

Lea Lane  15:11  
Well, the Cape is glorious, but so are the two resort islands connected by ferry and seaplane to the mainland Martha's Vineyard and Nantucket, both less developed in nearby Cape Cod, and each has its own vibe. Let's start with the closer Island and the larger island Martha's Vineyard just south of Cape Cod and covering about 100 square miles. Now about that name. I read that the Wampanoag Indians call the island "land amid the streams." It's thought to be named for either the mother-in-law or daughter of English explorer Bartholomew Gosnold, who discovered it when he discovered Cape Cod. Both of these women were named Martha. In 1641, the island was purchased by colonial businessman Thomas Bayhew. It was settled in 1642 and considered part of New York until 1692. But now it's very much a part of Massachusetts How would you describe Martha's Vineyard?

Leon Bolivar  16:05  
Well, Martha's Vineyard is beautiful -- very laid back it's got these to you know, quote unquote larger towns and a good town and Oak Bluff is just very serene. It's got these amazing cliffs for you to be able to kind of enjoy and soak in that view. The acquiring of cliffs these cliffs that were carved out by glaciers millions of years ago and so absolutely stunning you should rent a moped and just go around the island. That's a lot of fun. There's also the Edgartown lighthouse, which is one of the last five remaining on the island. Definitely worth seeing one of our my fun kind of quirky stops Lea whenever I go, there's the alpaca farm.

Lea Lane  16:39  
They're so cute. It looks like llamas, but they're cuter. 

Leon Bolivar  16:43  
They really are and it's definitely one of those things that make a trip out to Martha's Vineyard that much more unique and then you know, the movie Jaws in the 80s was actually mainly shot in Martha's Vineyard, and so there's there's a bridge there that near where things were shot that people nowadays go and jump off of and so yeah, so it's actually a lot of fun and actually get a ferry from Woods Hole circling back to Woods Hole, get a ferry there it's a quick ride over.

Lea Lane  17:06  
Well Oak Bluffs is one of the towns I love there. It's very charming. It has a lots of Gothic Revival, Gingerbread cottages with little accents and brightly colored paint. It's so pretty I think that that's a great place and there's a carousel there.

Leon Bolivar  17:22  
You'll see, you get off the ferry, you're in Oak bluff and you see the carousel right there old, and carousels go so great with a with an ocean backdrop. You know, it's such a seaside type of thing. So it's actually one of the musts as well, great for photo ops.

Lea Lane  17:36  
Absolutely. Now, Edgartown, you mentioned it has lots of galleries and cafes and that's where you come and go from the ferry. Right. That's the best place to maybe have dinner before you go on the ferry and sightsee downtown. There's some very nice shops and lovely places to stay. And there's some great restaurants around there as well. The Menemsha beach show me about that.

Leon Bolivar  17:58  
Beautiful, beautiful just kind of sprawling Beach, get there early, get a seats, you know, get comfortable and just kind of soak in the rays. It's beautiful place.

Lea Lane  18:07  
An interesting fact it used to be big whaling industry town. I know that and one of the earliest known deaf communities in the United States is there. So there's something called the Martha's Vineyard sign language which is which is a predecessor of the modern American Sign Language, which is something I never knew. Great place to relax. How about Nantucket, the other famed island off Cape Cod 30 miles south of the Cape? Once considered the whaling capital of the world, it's just 100 miles in area and has a population of about 10,000. Without the tourists. The beaches are typically quiet and the coastline is known for cliffs and lighthouses and charming cobblestone streets and more than 80 miles of beaches. Now National Geographic once described Nantucket as the best island in the world; that can be heavily debated. But it is charming. Tell us some of the highlights.

Leon Bolivar  18:58  
Yeah, it's extremely charming. You know, one of the first things you see as you pull up on the ferry is the Brandt Point Lighthouse. It's a big massive lighthouse. You can't miss it. And for those folks who live on island whenever they see that it's a welcome home sign for them over the summer. You know, they drape it in an American flag and it's just a beautiful set as you pull into the harbor there. Once you do you know you're on a street with a lot of shops, restaurants, cafes, the Whaling Museum is right there. Lea. So circling back to what you just said, an amazing place for you to go and it's been a few hours in there, you walk in, they've got this big, massive whale bones, the skeleton,  kind of hanging so you can kind of learn from it and take tours with docents, and learn about you know what it was that made whaling such a prevalent industry on the island, Wisconsit bluff walk is also one of my favorites. Again, this is one of those islands where I recommend you either get a moped or you rent bicycles and just kind of really tour all the sights and sounds of bluff walk as it sounds. It's a beautiful destination for you to be able to see the big bluffs, the dunes go down to the ocean. Take the stairs all the way down. and just kind of enjoying the afternoon down there. Cisco brewing, very popular there as well. They've got a big old compound: live music, great food, great place for you to enjoy some of the local beer; and then, you know, the architecture for me like for you in Martha's Vineyard. I think the architecture in Nantucket is really worth some photos.

Lea Lane  20:17  
Absolutely. I know in terms of whaling, Herman Melville, who wrote Moby Dick, never visited the island, but he set it in Nantucket. So that's kind of an interesting fact. Also, there's a wildlife refuge where if you want to see some deer, horseshoe crabs, all kinds of local wildlife, that's a nice place to get away. That's a little different from going down the main street, if you want to check that one out, too, with a lobster ice cream. Lots to do. Actually, there's a famous Limerick about Nantucket, so I adapted it a bit. Want to hear it? Okay: There was a gal from Nantucket With a travel list called a bucket. But no place compared to her islands, So fair. So she tore up the list and said ... suck it. That's my Ode to Nantucket. 

Leon Bolivar  21:08  
I love it. I love it. 

Lea Lane  21:10  
Okay, well, Leon, the name of the podcast is Places I Remember. Will you please share one special memory of the Cape Cod region with us?

Leon Bolivar  21:19  
Absolutely. And thank you again for the invitation. So Cape Cod, you know, I've been coming down to this peninsula for pretty much my entire life. My father grew up in South America and migrated to the US in the 80s, --JFK's Alliance for Progress, to strengthen relations with Latin America. And he remembers as a kid receiving these humanitarian packages from the Kennedy administration. And so that for him, you know, really built this admiration for President John F. Kennedy. Even so when my dad was dying, we would always come down fishing every single week and over the summer, off a jetty behind the Kennedy compound, and we will be all the way out in the jetty the Kennedy compound back there. And that was my my dad's way of really kind of showing our mutual respect to to the Kennedy family. And so we always came down to Hyannis and Barnstable. And so for me coming down as a kid going fishing off those jetties and then going into the Kennedy Museum and kind of sharing that with my father, to me is very reminiscent of why I love Cape Cod. You know, never mind also the lighthouses the fried seafood, the beautiful beaches, the oysters, the dramatic sunsets, the bogs, the putt-putt, the drive-in that we have. And then the Cape Cod National Seashore, which is one of my favorite places on the on the planet. Make this place very special for me.

Lea Lane  22:31  
Wow. Thank you so much for that memory. I'm glad you're back. I think it's a great place to live and a great place to visit. So thank you Leon Bolivar, director of marketing for the stunning Ocean Edge Resort and Golf Club in Brewster, Cape Cod. You really help bring this glorious region to life for our listeners.

Leon Bolivar  22:52  
Thank you, Lea. I appreciate the time. Thank you.

Lea Lane  22:54  
And can I just ask are you related to see Simon Bolivar?

Leon Bolivar  22:57  
I like to say yes. But I don't know. So he was a Venezuelan. Yeah, I'm Colombian. So maybe, maybe.

Lea Lane  23:07  
Maybe. Kudos, he got around.