Travel Guide: Weekend on Nantucket


36 hours on Nantucket…what a whirlwind! There is so much to see, lots to do, and even more to eat! A mid-September trip to the island was just what I needed to get one last dose of summer in. My college roommate and I jetted off to the Cape after work on a Friday and hopped on the Ferry. I had a pretty filled itinerary in mind for the weekend, and we had such a blast! It was great to spend some quality time with my bestie, who I no longer get to see everyday, but it was even better to explore the island with her. To me, Nantucket really just screams “quintessential New England summer” in all the best ways possible!

I have to say, that although the temperatures weren’t exactly conducive to beach weather, I think September just might be the most ideal time to visit the island. It wasn’t so crazy busy as it would be in July and August, but there was still plenty of hustle and bustle in the downtown. September is wedding season on Nantucket, and I heard there were 42 weddings on the island the weekend we were there. That right there says it all – September is one of the best times to visit!

Without further ado, I wanted to share all my favorite spots, since there are so many! Some of these were planned stops on the itinerary I made for us, and some were impromptu!




1 // Cru Oyster Bar Nantucket

This was one of my favorites! We stopped in at Cru for lunch on Saturday, and I mean, it just doesn’t get better than fresh New England seafood with gorgeous views of the harbor. Having grown up in the heart of New England, I love a good oyster and fish sandwich! Cru has a variety of oysters for all palettes, so we opted for a few of the smaller guys. We scarfed these down with a shrimp cocktail and some signature drinks. The Life Aquatic cocktail was my fave – if you like rosemary, you absolutely must try it!

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Beet hummus! Is it weird that one of my favorite things on menu was the beet hummus? It must be the veggie lover in me, and I was expecting to eat primarily seafood, but this beet hummus was just so fresh and delicious (especially with that feta cheese), that I couldn’t leave it out.


I opted for the crispy cod sandwich, first because I love cod, and second because it came with pickled red onion and cilantro aioli…yum! I didn’t think I could finish it all (my eyes are always bigger than my stomach when ordering), but oh I came so close! Maybe I would have if I didn’t eat so many of the fries, but I just couldn’t stop! Anyone else have that problem?


Dessert? Um…yes, please! Cru was nice enough to surprise us with this at the end of our meal, and I’m glad because I definitely didn’t have enough room to justify ordering it. However…We. Ate. It. All.

2 // Oath Craft Pizza

An Oath recently opened up in Chestnut Hill, MA right next to the Sweetgreen I frequent, so I’ve had my eye on it for a while. And so, I’ve been eager to get out to the Nantucket location where it all started. Oath is located right by the ferry and right across from Cru, so we had been smelling delicious aromas wafting out of the Oath kitchen all weekend.


^^We started out with these delicious Stubborn sodas made without GMOs, corn syrup or artificial sweeteners. My favorite was the lemon berry açai.


One of the best aspects of Oath pizza is that the crusts are made ahead of time, so your pizza can be ready to eat in just 90 seconds. Plus, since the crusts are ready to go, you can order two different flavors without having the toppings get all mixed up. We opted for half Walley and half Spicy Mother Clucker. As a longtime fan of mozzarella and pesto and with a newfound love for spicy foods, these did not disappoint!

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3 // The Bean

Delicious iced coffee! We rented bikes for a few hours (keep scrolling for more on that), but The Bean was our first stop to bring coffee with us to enjoy on the beach. (Don’t ask me how we pedaled with coffee in our baskets…I’m still not sure how we managed).

4 // The Juice Bar

Homemade Ice Cream! This really hit the spot after dinner on Saturday. We wanted something sweet (despite our massive lunch at Cru), so we hit up The Juice Bar on the way back to our hotel. The homemade waffle cones, cake batter ice cream and (lots of) rainbow sprinkles. If you were following along on Snapchat, you just may have seen that we were truly in rainbow sprinkle heaven (i.e., they gave us TONS of extra).

5 // Nativ Made

On Sunday morning, after all the ice cream and seafood, we were just craving some fresh green juice! We actually just stumbled across this place and were so thankful for it! It had everything we needed, such as some B12 shots and plenty of green juice. I love my green juice in the morning, so my body was quite thankful for its regular dose of kale.



1 // The Skinny Dip

I had been following Skinny Dip on Instagram leading up to the trip, and I could hardly contain my excitement when we got there. The shop is the cutest! So many fun brands! Founders Taylor Ivey, Millicent Armstrong and Sara Rossi have curated a wonderful assortment of goods from each of their own brands and many others. We got a full tour and explanation of the backgrounds behind all of the brands, and I have to say that each one truly has a unique story, and many have great causes behind them. Take a peek at the full list here! If you like what you see and want to learn a little more about how this style collective came about, be sure to check out this Boston Common article.

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^^Loving these one-of-a-kind loafers from Artemis!


^^ This sweatshirt (c/o) is the cutest  and the coziest. My bestie and I got matching ones and we’ve both been wearing them pretty much every day since.nantucket-weekend-guide-22

^^ Rothy’s makes the most amazing shoes…because get this – they are made by a waste-free process from 100% recyclable water bottles. Plus, they are machine washable, moisture wicking, and were even featured in Vogue. While perusing around Skinny Dip, I got stuck on this pair and just had to take them home with me.


2 // Summer Shades

I can’t resist a good pair of sunglasses, and with light blue eyes, I truly need them for protection from the sun. Whenever I walk into a sunglass store, I immediately feel the need to try them ALL on. The owner of Summer Shades was super helpful in directing me to find the new perfect pair for me. Even though Nantucket was a bit cool the weekend I was visiting, the sun was out in full force. Ergo, a new pair of sunglasses was absolutely necessary. I ended up with these Chanel babies that I just couldn’t resist.

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3 // Shift 

As soon as I walked into Shift (which I’ve been following on social media), I knew I’d be an immediate sucker for EVERYTHING inside. With the summer basically over, there were so many great deals. After much consideration, I ended up with this loose cotton Sail to Sable dress (so comfy) and a Harding Lane cap (that I’ve been wanting for a while).


4 // Haul Over

Such a great spot for gifts! If you want to get something that is very Nantucket, but also very nice, Haul Over is a great one-stop-shop. You’ll find Patagonia, Harding Lane, North Face, Toms and so many other options to bring home for friends & family. I picked up a few gifts here for some upcoming birthdays!

5 // In the Pink

Always a classic. I love to pop into the In the Pink on Newbury Street in Boston from time to time. Lilly’s palette of vibrant colors always brighten my day. You’ll definitely find lots of outfits, perfect for island wear. I left with these unique tortoise earrings to wear into the fall.

6 // Sara Campbell

One of my all-time favorite tote bags (seen in this post) is from the Concord, MA location, so I knew I had to pop into the Nantucket location. It is a bit of a further walk from the downtown, but definitely worth it! The prices are more affordable than many of the other shops, but the clothes and accessories are just as cute.


1 // Young’s Bicycle Shop

You definitely do not need to take a car on the island. Instead, rent a bike for a few hours or a whole day. The guys at Young’s were so nice and helped us get set up and on our way. We got bikes with baskets to put all of our stuff in, and then pedaled off to the beach!


2 // Steps Beach

All of the Nantucket beaches are amazing, but Steps Beach might be the most beautiful one I’ve ever seen. Okay, I’ve been to quite a few beaches in my time, so I know that is a bold statement. But you have to descend about three flights of stairs to get down to the beach, and the views are totally breathtaking. Since parking is limited, this is a great beach to bike to, plus you’ll definitely get some good exercise in climbing up and down those stairs. Don’t let that deter you though, the views are worth it!  You can see a few more of my photos of Steps Beach in this post.

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3 // Whaling Museum

This is the only thing on my itinerary that we didn’t get to, and I regret it! Nantucket is so rich with history, I mean you can just see it in much of the architecture of the island. Nantucket’s community got its start in the whaling industry, and it is that history that lends so much to Nantucket’s charm and culture. I’ve heard great things, so the Whaling Museum will be my first on my itinerary next time!

4 // Explore

The entire island is so quaint and full of charm. You’ll definitely want to allot some time to just walk around the downtown. As you leisurely stroll around, you’ll no doubt be stopping for photos. There is so much beauty and inspiration around every corner!


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After a long day of eating, shopping, and exploring, be sure to get a good night’s sleep so you can do it all again the next day! We absolutely loved 21 Broad (a Lark Hotel). Read more about our experience HERE!

Anyone planning a trip to Nantucket? If you are a frequent Nantucketer, did I miss any of your favorite spots? Let me know in the comments below so I can check them out next time!
xo -L

*Thank you to Cru, Oath, Skinny Dip, and Summer Shades for hosting and providing some of these goodies!

The Lilac Press


  1. September 30, 2016 / 2:06 pm

    Woohoo thanks for visiting our stores lady, so glad you enjoyed Shifty + ITP! LOVE that STS dress on you–too cute! And I cannnnnot leave that island with at least one acai bowl from Nativ Made.

    xx, e