48 hour Nantucket Travel Guide ~ Roses and Rain Boots .

Monday, November 4, 2019

48 hour Nantucket Travel Guide

It was Thursday night after what seemed like a long week when B&I decided we should take a trip to Nantucket. B had never been, and I had not been to the Island in nearly 15 years. 
We knew we wouldn't be able to make it work for Friday night. So we agreed to wake up early drive to Cape Cod and catch a semi-early ferry out to the Island. 

So truthfully, the post title is slightly misleading because we didn't have a full 48 hours, more like 34 hours, but that didn't seem as catchy.


Where to stay: The Greydon House

I found the Greydon House by doing some research online. Like most of us, I am reluctant to try new things without doing some research. Like many hotels on the Island, Greydon House came highly recommended. We chose this spot because of the quaint, boutique vibe.

I feel in love with the atmosphere just from pictures online, and we were SO lucky to find that they had an opening on such late notice. Upon arriving, I loved seeing our room that featured antique furniture that made you feel like you were staying in your home away from home. They also add unique details, like an old fashioned telephone and bookcase perfectly styled. 

The dining hall was adorable. I was majorly crushing on the rug and wall color. I also couldn't get enough of that natural light. I loved the whole aesthetic of the hotel. The hotel offers complimentary light breakfast, tea, and coffee to start your day. They also have a great hotel restaurant that offers both seating indoors and outdoors. 

The Greydon House is also in the perfection location, located just one block away from downtown Main Street. Local restaurants and that Nantucket charm surround it. Not to mention, it is also located on the same street as the only bike rental shop open during the offseason.  

What to do: 

Beach it.
Nantucket is famous for its beaches and not one, but three lighthouses. While an island, it is quite large, so I highly recommend you grab a bike and venture out to explore as many places as possible. B & I went the weekend just after Columbus Day, which is considered the Island's offseason. One of the lighthouses is quite far, 18 miles round trip, so you would need to pack snacks as the amenities near it are closed for the season. However, on the flip side, the most famous lighthouse (pictured above) is a 4-minute bike ride from the Greydon House. I think we visited this beach twice a day. 

Rent a bike. 
Be prepared to spend a pretty penny either bringing your bike on the ferry or renting one on the Island, but it is 100% worth it. We spent large portions of each day biking around as much of the Island as we could. Nantucket is just one of those lovely places, and you'll want to explore as much as possible. 

Visit the local Brewery.
Cisco Brewers, home to the Nantucket Brewing Company, is such a fun atmosphere. It seems like everybody on the Island makes their way there, and if you are not a fan of beer such as myself, there's wine from the local vineyard and spirits offered also. The brewhouse is an all-outdoor venue, so be sure to dress warmly. It is a bit of a hike from downtown, so I recommend either biking or calling for an uber. 

Downtown Nantucket is lined with delicious places to eat and lots of stores, ranging from local boutiques to post stores, such as Lilly Pulitzer and Ralph Lauren. B and I opted out of shopping and spent our time wandering the Island or biking from the beach to the beach. 

Explore. Get Lost.
Nantucket is an island, so it's hard to get lost. Take the opportunity to wander and explore the local streets. We woke up early to get a head start and just loved every street we walked down. Visiting Nantucket was one of our first trips that B & I planned last minute and had no agenda. Usually, I do tons of research beforehand, mapping out a daily schedule to ensure we get to do everything we both want too. We didn't have a plan, and it was lovely. 

Where to eat: 
I was worried that the restaurants would close since it was the offseason, but I was pleasantly surprised to see how many restaurants were open. Of course, we did some research online and saw that many of the hotel's brunches come up as options for brunch or dinner, but not the vibe or mood we were going for. Also, disclaimer, I tend to be a picky eater.  

Island Kitchen 
This delicious breakfast spot was B's favorite. I discovered it by doing some digging on places to eat that the locals go too. It was a bike ride outside of downtown and tucked into a mini town, right by a stop & shop. This place gets busy, so best to get there early. We opted to sit at the bar to take in the hustle & bustle of the town. Unfortunately, I did not get a picture of our food because it was too good to wait for the picture. 

The Whale
We ate free on the first day after arriving on the Island. I was obsessed. The food was delicious. I loved the European vibes and that they offered roasted tomatoes with your breakfast. I added one to my breakfast sandwich and could have eaten it all weekend long. For all my coffee snobs out there, this place is for you. I loved the vibe. The restaurant was packed with families, friends, etc. looking for a place to brunch. I was surprised to see how many locals were requesting tables outside. B & I snagged one of two tables that sit adjacent to the street to grab a view of the town. 

Rose and Crown
I'll be honest; I was struggling to find a dinner spot. I was craving a more relaxed vibe. I wanted to sample a bunch of appetizers. I love that casual vibe on the weekend away, so we stumbled upon this relaxed pub that offered a variety of American food. 

Charlie Noble
Following dinner, we stopped here for drinks and immediately loved the atmosphere. The Bartenders were obvious locals and regulars on the weekend shift. They knew many who entered and made everyone feel right at home. They are also known for their generous pours, you've been warned. 

B noticed this place while we were exiting the ferry and making our way into downtown. He is a huge fan of bbq, so we stopped at this place as our final destination for a snack before grabbing our ferry home. With more of a pub vibe, the restaurant was packed with football fans all crowding to watch the games. 

The Soda Fountain
While in Nantucket, you also want to make time for a stop at The Soda Fountain located in the Nantucket Pharmacy. This place is open 364 days a year, only closing on Christmas. The Soda Fountain is located directly inside the Pharmacy and offers all the New England charm. Chalkboards detail the various items available. No matter the weather, be sure to stop in for a float or frappe. 



  1. WOW, what a great travel guide, you really captured the beauty of Nantucket!

    xx, Elise