One day, while drinking a Nantucket Nectar from Potbelly’s, I found myself wondering where Nantucket actually was. That night I researched it on the internet. The remote island off the coast of Massachusetts seemed like an interesting place. Colleen and I were planning to go on vacation somewhere this summer, but were unsure of where. Nantucket seemed like the answer. I pitched it to Colleen and she agreed. We booked the trip and a few months later we were on a plane to Nantucket.

There were no direct flights there from Chicago, so we had a connecting flight in Newark, NJ. The flight from Newark to Nantucket was a little scary at first. Probably the worst turbulence I’ve ever experienced. I can handle a little erratic shaking, but when the plane makes little dips, that’s when it gets scary. It was the same sensation that you have when you go down a big hill on a roller coaster, when you lift up in your seat, except it was just for a split second at random times. We only experienced this during the first 15 minutes or so, and then the ride got much smoother.

The Nantucket airport was very small and so different from what we are used to at O’Hare. There are no connecting hallways at the terminals. You exit the plane via staircase onto the runway. The baggage claim area was about the size of your average convenience store with 3 windowed garage doors on one wall. Your luggage is removed from the plane and put onto a handcart. The employee rolls the cart over to one of the garage doors, opens it up and throws the luggage through the door. You then walk 20 feet and you are outside in front of the airport to claim a taxi.  Definitely the smallest airport I’ve ever seen.

We hopped in a taxi to get into town. Paula was our driver and she was fantastic. She was very social and friendly, unlike most Chicago cab drivers. She took us on a little back alley tour of town, telling us lots of things about the town and the island. A very nice start to the trip!

Paula dropped us off at our bed & breakfast, The Brass Lantern Inn. It’s a 3 story house that was built in the late 1800’s very close to downtown. Upon our arrival, we walked in and had to search around a bit for an employee. We finally came across someone, a guy in his late teens / early 20’s. He gave us our key and showed us to our room. We were on the 2^nd floor, facing the street. Our room had several windows and was decorated very traditionally with floral wallpaper and one of those beds with the tall corner posts and the fabric draping over the top. It was quaint and charming.

After settling into our room, we decided to hit the town, which was a 2 minute walk down the street. Downtown Nantucket has tons of shops, bars and restaurants. One thing I found interesting is that there are no chain stores or restaurants on the entire island. Everything is independently owned. I think it’s the only place on earth that you’ll never pass a McDonalds or a Starbucks. Also, Nantucket is very strict about historic preservation. There are no big bright neon signs on the shops. All businesses have the old style painted wood signs that hang above the door. And pretty much every building is either old, or very very old. Additionally, several of the streets downtown are still made of cobblestones, which is great for aesthetics, not so great for biking, which I’ll cover later in this blog post.

We hit up some of the shops, the first one was called The Emporium of Nantucket. It had a lot of neat seafaring items like telescopes, sextants, compasses, etc. There were all made to look old, and were reasonably priced, which was very surprising. I ended up buying a seafarers telescope for $40. Collapsed, it was about 6 inches, but telescoped out to about 2 feet long.  I liked the “old school” focus, which you actually have to adjust the length to a perfect spot to put it in focus.

Since we both like antiques, we decided to check out an antique shop. However, this shop was like none we’ve ever experienced. This shop included a lot of glassware, silver and porcelain items. After seeing an ornate set of serving bowls for $4000, we concluded that this shop was way out of our price range and decided to leave. There were a lot of high end shops downtown. We walked through a couple of art galleries with really beautiful, but really expensive artwork.

There are also a lot of restaurants downtown, many of them quite pricey. The fact that all the restaurants had their menus posted outside their doors made choosing one a lot easier. Even with all the options, it was still a little bit of a challenge picking places to eat with Colleen being a vegetarian. The vegetarian options were a little bit limited.

The first night we decided on a place called “The Tavern” and got a table outside. I ate a stuffed flounder that was to die for! Colleen enjoyed her specialty salad and we both enjoyed several rum based drinks.

The next day we rented a two person moped.  I have never driven a 2 wheeled vehicle other than a bicycle before, so this was a new and challenging experience for me. The three minute overview of the moped with a staff member, and a quick ride around the block was hardly enough to make me comfortable riding it. But we went for it anyway. Having Colleen riding on the back made it additionally challenging. It was quite stressful leaving the rental place, since it was mid-day and there was lots of traffic in that section of downtown.

I got very discouraged at first. It felt like the first time I drove a car with stick. It was nerve racking enough to know that I’d have to keep myself from crashing and hurting myself. But to also be responsible for Colleen’s safety, that made it even more so.

After a bit of practice on some less congested streets, I started to feel a little more comfortable riding it. I eventually was able to balance better and got a better feel for accelerating and braking. The worst part was riding it on the cobblestone streets. It felt like the bike was going to fall apart into a million pieces. I did my best to avoid them, but we couldn’t avoid them entirely since our b&b was on a cobblestone street.

Our first adventure on the moped was to Surfside Beach, on the south side of the island. This was by far my favorite beach. The waves were really big! Not so big that you fear drowning, but just big enough to throw you around a little. So much fun, I could have stayed there for hours just jumping in the waves. It was pretty sunny out that day, and the path from the beach to the parking lot was all sand…very hot sand. As we walked down it in bare feet it got hotter and hotter until it was almost unbearable. It felt like walking across hot coals. I ended up sprinting down the path just so I could get off of it. I did not have sandals, just shoes, and I didn’t want to put them on with wet and sandy feet.

Getting back to the parking lot, we found that some jackass in an SUV parked in our moped. I was still able to get it out, but had to squeeze my body along one side of the car and walk the moped and maneuver it though a small opening between cars. I decided to write a profane message on the SUV’s dirty back window.

We headed back north, and explored the outer perimeter of the town. We came across a really old cemetery and decided to stop and take a look. I took tons of pictures. Within the cemetery, there were several smaller areas that were sectioned off by low fences and very ornate gates. It looked as if each family had their own section. It was very interesting.

We also checked out Jetties Beach, on the north side of the island, very close to town. We didn’t swim here, but just walked around and explored. The water was MUCH calmer here. Hardly any waves at all. One thing that was really interesting about this beach was the amount of shells on the shoreline. Thousands of tiny little shell fragments everywhere! This beach also had a nice looking restaurant / bar area overlooking the water. The food smelled great and the drink menu looked tasty, so we made it a point to go back there on another day.

After our daytime moped exploration, we hit the town later that night. We ate dinner at Cy’s Lobster Pot, where there was a really good female singer and acoustic guitarist performing. I ended up talking to her for a couple minutes during one of her breaks. She was from Ireland, and said that the economy is pretty bad in Ireland and there aren’t a lot of jobs. So a lot of young people come to places like Nantucket for the summer to work. She have us one of her demo CD’s with some original songs on it. We listened to it later that night back at our room. Pretty good!

I think by this time, Colleen realized that heels were not the best shoe choice for Nantucket. It was quite difficult for her to walk the cobblestone streets and sidewalks wearing 5 inch stilettos. Oh well. You live, you learn.

We had the moped for one more day, so we decided to take advantage the best we could. We cruised over to Sconset, on the east coast of the island. The road there was basically the expressway of the island. It was a very straight road, one lane in each direction, with a speed limit of 45 mph. I did get the moped up to 45 mph, even though technically we weren’t supposed to drive it faster than 25. But even driving 45mph, people in cars still passed us.  

Sconset is a quaint little village. All the houses are much smaller, and very old, a lot dating back to the 1700’s, some from even the 1600’s. A trend in this village is to grow roses on the walls and the roofs of your home. This made the whole village very picturesque.

Just north of the village is the Sankaty Head Lighthouse, which we went and explored. It was very foggy out that day, so you couldn’t even see the ocean. But it did give the whole place a very cool effect. We met some fellow tourists who were nice enough to take our picture by the lighthouse. One of them actually knew a little about photography, posed us and framed up the shots very well. That was probably the best “asking a stranger to take our picture” experience that I’ve ever had.

Apparently there was a steep cliff on the coastline which we could have seen by the lighthouse on a normal day, but since it was so foggy, we couldn’t see shit. One of the guys in the other group of tourists told us that we should go explore this abandoned lot back off the main road to go see the cliff. We left the lighthouse and started going back down the main road when we came across an overgrown lot with a No Trespassing sign. We figured that this had to be what the guy was taking about. We parked the bike and walked 2 steps onto the property when we heard the voice of some old lady from the house on the other side of the street. “Don’t even think about going over there!” she said in her crabby ass voice. Not wanting to piss off the locals, we aborted that mission, got back on the bike and got out of there.

It was kinda sad when we had to return the moped later that afternoon. I had gotten really comfortable riding it. I asked Colleen if she wanted to give it a try, but she declined. I think she saw my frustration trying to learn it the first day, and figured she would get equally as frustrated. She enjoyed riding on the back while I drove. And she did an excellent job of recording some video while she was back there too.

That night we went on a haunted tour of Nantucket. It was a walking tour that took you to 5 different locations around town. Our tour guide was quite the character, and he told a story at each stop. Interesting and entertaining.

Later that night, we decided to walk down to Jetties Beach to look for hermit crabs, or other signs of life. It was probably around midnight or so. It was really dark and no one was around. What started out kinda creepy turned out to be quite romantic. Just me and Colleen with the entire beach to ourselves, looking at the stars.

The following day we rented 2 bicycles. We toyed with the idea of renting a tandem bike, but I think it would just be too hard to control. Our destination this day was the west side of the island. There is a nice bike path all along Madaket Road, which leads all the way to the west coast. About halfway there, we ventured off the path to check out Dionis Beach, another beach on the north coast. It was kinda off the beaten path, so there weren’t nearly as many people there. We went for a quick swim. The water was pretty calm, similar to Jetties Beach.

Back on the bikes, I was planning our route back to the bike path. We could have gone back the way we came, but looking at the map, it seemed to backtrack a bit. With the help of Google Maps on my phone, I planned an alternate route back to the path. Well, this didn’t turn out so well. Eel Point Road went from pavement to dirt pretty quickly. I kept checking Google for alternate routes, but roads that appeared to be on the map didn’t seem to be there in real life.

We eventually turned off onto Landing Road. Why this was even labeled a road is still a mystery to me. It was nothing more than a 2 foot wide dirt path though a prairie of tall grasses and little trees. You would not be able to drive a car down it, even if you did have 4 wheel drive. It also was not marked by any kind of sign. The only reason I had any idea of where we were headed was the GPS on my phone. Thanks Sprint!

At this point, Colleen was irritated and said that she would be temporarily divorcing me. But when the shitty dirt path finally lead back to the main paved bike path, she decided to re-marry me.

We were back on track, but kinda tired and thirsty. That was when we came across some kids selling cups of Tang on the bike path. Score! It was a nice little break after the rugged and bug infested detour. We were actually their first customers. We chatted with their parents for a bit and got a picture with the kids before we left.

We finally made it to Madaket Beach on the west side of the island. Before we went swimming, we stopped for lunch at Nellie’s, which overlooked the coastline. A little over priced for lunch food, but it was tasty. I got several comments on my Goonies shirt, which seems to happen a lot when I wear it on vacation.

Down at the beach, the waves were very intense. There were a lot of people on the sand, but very few people out in the water. Most people didn’t go more than a few feet in. You could stand in an area that had no water, a wave would come, and then in an instant there was water up to your waist. It felt a little too dangerous to go much further out.

Time kinda flew by. We had to leave because we need to return our bikes by 6. I was actually worried that we wouldn’t make it back to town in time. We high tailed it back with no ridiculous detours this time and made it back to the bike shop before they closed. I was very impressed by Colleen’s biking skills. She was a trooper. She said that her rental bike was actually much easier to ride that her one at home.

That night we went to a place called The Chicken Box. It was a little bit of a grungier place on the outskirts of town. It had a college bar type atmosphere. We got there a little earlier, so there was hardly a crowd at all. This was nice, because we avoided a cover charge, and we got dibs on the shuffle board and pool tables. That night there was a classic hip hop cover band playing, who were actually really good and a lot of fun. The place got very crowded when the band went on. We took a cab home that night, but I completely forgot to close out my tab at the end of the night. This was apparently a common occurrence, because when I went to pick up my credit card a couple days later, the bartender had to find my card in a stack of 20 or 30 cards.

The next day was our “history day”. We spent a couple hours at the Whaling Museum. Very interesting and informative. We strolled around town taking lots of picture of buildings and such. It is very easy to get lost in town. The streets are laid out in no order whatsoever. Some are very narrow and not well marked. A map is your best friend when exploring Nantucket.

We made it over to a tour of the oldest operating windmill in the U.S., built in 1746. We also went for a tour of the oldest house on Nantucket, built in 1686. There was a garden in the back of the house which replicated a garden that they would have had back in those days. The tour guide was talking about all the plants and we actually got to taste a lot of the veggies and herbs right off the stems. It was an unexpected end to a great tour. We also checked out the old jail, which did not have a formal tour, but you could walk into and check out.

We also found ourselves exploring more cemeteries, including the “Colored Cemetery”. We were really intrigued by the cemeteries on Nantucket, probably because of how old they were.

One of the nights we ate dinner at a place called The Brotherhood of Thieves. I liked the décor of this place a lot. It had a very medieval feel to it. It reminded me of Lord of the Rings: when the hobbits first get to Bree and go into the pub where they first meet Aragorn. Our food was great. I also got a beer sampler of local microbrews.

The last night on Nantucket, we attempted to go out to Jetties Beach for dinner and drinks. We spent 10 bucks for a short cab ride there, only to find out that the place was closing soon and the grill was closed. Apparently, once the sun goes down, the place clears out and they close. We took too long to get ready and got out there way too late. We didn’t want to make it an entirely wasted trip there, so we ordered some drinks from the bar. They were overpriced and not that good. The trip to Jetties was a total bust. Refusing to waste money on another cab ride, we walked back to town in attempt to redeem our night.

We made it over to the Rose & Crown, and we were lucky enough to put in a food order right before the kitchen closed. Soon after getting our food, karaoke night started at the bar. I actually ended up singing a couple songs:  “Call and Answer” by Barenaked Ladies, and “Longview” by Green Day. The atmosphere was just right for karaoke. It wasn’t too crowded, and there wasn’t a whole lot of people signing up to sing. So there really wasn’t much of a wait from the time you sign up, til the time you get to sing.

The next day was a Monday, and our final day on Nantucket. Our flight wasn’t til the afternoon, so we decided we had time for one last adventure. We packed up our luggage and checked out of our room. We then headed down to the pier for a ride on a sailboat, which took you up and down the coastline. It was a very nice ending to the trip. And it gave me a chance to use my nautical telescope that I bought the first day.

Our last meal before heading to the airport was at the Even Keel Café. They had a nice little outdoor patio. I got to enjoy one last bowl of clam chowder. We actually ran into Laura Cunningham, the Irish girl who was performing in the bar several days before. Apparently her day job is a server at the Even Keel. How crazy!

We made it back to our b&b to get our luggage and call for a cab. We called the same cab company that picked us up from the airport when we arrived. We were hoping to get Paula, because it would have been a fun ending to the trip to talk to her and tell her about all of our adventures. But instead we got Chunky (at least that’s what the business cards said), a large hairy man wearing overalls who was not the least bit social. Oh well.

At the airport, it took all of about 10 minutes from the time we got out of the cab, checked in, through security, and at our gate. Freakin’ amazing!

The flight home was fine, but we were returning home to an absolute disaster. There was a huge storm in the Chicago area that morning, knocking out power to something like 800,000 homes, including ours. The power was out for the next 5 days. Anyways, that’s another story.

I have little regrets about our Nantucket trip, but I wish we would have had a better bed & breakfast experience. Don’t get me wrong, the Brass Lantern Inn was nice. I liked our room and the old style architecture. The patio was also nice….I sat out there several mornings to drink my coffee and read a magazine. The location was great (very close to downtown) and the chocolate chip cookies they put out in the afternoon were amazing!

 It’s kinda hard to compare this place with anywhere we’ve stayed in the past, since it was our first time staying in a bed and breakfast. But we didn’t feel like we really got that personal touch that we were expecting. We had little to no interaction with the staff, except when they were clearing our plates at breakfast or when we happened to say hi when passing them in the hallway. Also, their orange juice at breakfast was not good. It was usually not very cold and very pulpy. Bleh! Staying there was fine, but if we went back I would almost definitely try out another b&b.

To sum up Nantucket…it is a gorgeous place. It’s so much fun to just wander around, because everything is just so visually interesting. The architecture is really cool. There are flowers everywhere! It’s like a storybook village. I really like the historical aspect to the island. It can be relaxing, romantic and adventurous. The food options were endless. The weather was nice. I felt safe everywhere we went.  We got to know the island so well by the end that it kinda felt like home. The only downside was that it was kinda pricey.  But the whole vacation just blew us away. It was even more fun than both of us anticipated.