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Nantucket is such a special place! I photographed my Pink Lily collection there back in 2022 and my best friend got married there in 2019… and every time I visit, I discover something new about the island that I didn’t know before, and fall deeper in love. I am actually going back again in August (I told you guys I was already planning my return!!) so I will probably have to update this Travel Guide then. But for now… here are my recommendations!

Abercrombie Eyelet Maxi Dress // TKEES Foundations Matte Flip Flops

Ralph Lauren American Flag Sweater // Good American High Waist Raw Hem Straight Leg Jeans // Amazon sunglasses

Abercrombie Drama Ruffle Tiered Maxi Dress // Polo Ralph Lauren Sweater // Show Me Your Mumu Seashell Rattan Bag // TKEES Foundations Matte Flip Flops

Hill House Home The Ellie Nap Dress // Polo Ralph Lauren Sweater // TKEES Foundations Matte Flip Flops

Walmart Eyelet Button Front Dress // Walmart Crochet Trim Cardigan // TKEES Foundations Matte Flip Flops // J. Crew Heart Small Heart Straw Bag

Ralph Lauren American Flag Sweater // Good American High Waist Raw Hem Straight Leg Jeans // J. Crew Heart Small Heart Straw Bag

Free People Ruffle It Up Midi Dress // TKEES Foundations Matte Flip Flops

Hill House Home The Ellie Nap Dress in “Wisteria” // TKEES Foundations Matte Flip Flops

Abercrombie Harper Tailored Linen-Blend Pants // Abercrombie Short-Sleeve Graphic Skimming Tee // Ralph Lauren American Flag Sweater // TKEES Foundations Matte Flip Flops

Abercrombie Linen-Blends Squareneck Set Top // J. Crew A-line denim shorts // similar floral cardigan // Show Me Your Mumu Seashell Rattan Bag // Steve Madden Bigmona Raffia Slingback Platform Sandals

Lake Hamptons Shorts Set in Carolina Blue Batik

How to Get There

If you’re visiting Nantucket for the first time, there’s a few things worth noting. First, since it is an island, you can either arrive via plane or ferry. We caught a flight out of Charlotte and had a layover in Boston… but Charlotte now offers direct flights to Nantucket! (Wish I had known that at the time of booking, haha!) Nantucket has its own airport (ACK) and it is small but very quaint. If you choose to take the ferry, you can catch it out of Hyannis, Massachusetts. I would opt for the passenger-only high-speed ferry which gets you there in under an hour (there’s no need to bring a car, the island is very walkable!).

Nantucket’s historic downtown district, also referred to as Town or Brant Point, is where the ferry docks. It’s also where all the cute shops, restaurants and intimate hotels can be found! Ubers and taxis are readily available, as well as shuttles, but I definitely recommend the island’s preferred mode of transportation: bicycles! Nantucket’s high season is definitely July and August (when the temperature is highest!), but we visited in May and had a wonderful time. Although it was still a bit chilly, the island wasn’t too crowded and the weather was very stable – sunny and 50/60 degrees.

Where to Stay

We stayed at the Cottages at Nantucket Boat Basin and absolutely loved it!! The cottages have recently undergone a renovation, so everything is brand new and beautiful. The cottages are located right on the harbor and are as close to the water as you can get (without staying in a boat, that is!). Our gorgeous cottage offered beautiful sea views and tons of natural light, as well as two bedrooms and a full kitchen. The location is also fabulous, it’s right downtown and within walking or biking distance of everything we wanted to do! And on that note, they do offer complimentary bikes when you stay there!

Where to Eat

Obviously, there are tons of amazing restaurants on Nantucket… I’m just sharing about the places that we actually went!

BRANT POINT GRILL: Brant Point Grill is the restaurant within White Elephant Hotel. We dined here several times on our trip, both for breakfast and dinner, and it was amazing every time! I also love the view overlooking the harbor and the unique cocktail creations.

LEMON PRESS: This is a perfect little breakfast or brunch spot with tons of fresh, healthy options! Their lattes and smoothies are good and they have a wide assortment of food offerings from waffles to açaí bowls.

PROVISIONS: This little grab-and-go sandwich place is the perfect spot to grab lunch and either pack it for the beach or enjoy it on a bench near the harbor. Both Chris and I agreed that the sandwiches were phenomenal!! I had the caprese and it was truly delicious.

BORN & BREAD: Another sandwich place, this one is located downtown and the perfect option if you are out and about shopping. I didn’t think it was possible, but this sandwich was even better than the one I had at Provisions!!! I had the Cream Cheese Veggie panini on sourdough… everything was perfectly melted and the sourdough bread was lighter than air.

TOPPER’S: Topper’s is the restaurant inside Wauwinet, it is a little bit of a treck to get there but well worth it!! We hopped on the free shuttle from downtown for a quick 30-minute car ride to the Wauwinet. The restaurant has a beautiful view of the sunset and the food is seasonally-inspired New England cuisine with an emphasis on local produce and seafood – I had the steak frites and French fries. I am still dreaming about the French fries!

LOLA 41: I made a same-day reservation at this restaurant one night for dinner at the recommendation of my friend Krista. Apparently it’s a bit of a hot spot on the island and reservations are hard to come by – I think I got lucky and there had been a cancellation! Lola 41 offers a global menu featuring sushi, delicious cocktails and gourmet burgers. Everything we had here was great!

AUNT LEAH’S FUDGE: Although this isn’t a “restaurant” per say, it is a fudge shop… and I HIGHLY recommend stopping here for some fudge during your stay! I personally loved the chocolate peanut butter and could have eaten an entire pound myself. We did buy enough to bring back home and boy was it gone quick!

JUICE BAR: The little ice cream shop is a must-do on your trip to Nantucket. With more than 40 homemade flavors, you can’t miss this little place, as people line up down the block every evening!

What to Do

GO TO THE BEACH: There are tons of beaches to choose from on Nantucket, and you can’t go wrong with any of them! Our favorite was probably Steps Beach. It has a gorgeous view from the top of the many steps down to the beach, and we found all kinds of cool shells and signs of marine life washed up on the beach.

CISCO BREWERS: We biked out to Cisco Brewers one afternoon. It was a bit of a bike ride (it took us around 30 minutes and some of it was uphill), BUT it was completely worth it! The brewery is awesome. It’s an outdoor venue with plenty of seating, live music, and a wide variety of drinks available (including beer, wine and cocktails). There’s even a few food trucks so you can nibble on some appetizers, too!

BRANT POINT LIGHT: If you’re wanting to visit an iconic Nantucket spot, look no further than Brant Point Lighthouse. Only a quick bike ride away from downtown, it’s such a cute little spot to park your bike and relax. You can walk right up to the lighthouse or bring a blanket and book to relax on the little sandy beach. It’s a beautiful sight! Fun fact, it’s actually America’s second oldest lighthouse!!

‘SCONSET BLUFF WALK: This scenic walking path is not to be missed! It begins in the adorable fishing village of Siasconset and ends at the Sankaty Head Lighthouse. As you make your way to the beach either by foot or bike, you’ll pass some of the most stunning homes on the island (and during the summer, I heard they are covered with roses!).

SHOP: No other island rivals Nantucket when it comes to shopping! You’ll find the best, preppiest stores on the island from Hill House Home to Murray’s Toggery Shop. I personally love Peachtree Kids for its wide assortment of kids’ clothing and Nantucket sweaters. We also stumbled across Bon Ton, a cute little antique shop with the prettiest vintage items, from tea pots to paintings.

VISIT THE WAUWINET: Even if you don’t stay at The Wauwinet, it’s worth visiting (make a reservation for Topper’s while you’re there!). This historic hotel has been around since 1875 and boasts classic New England charm and seaside tranquility. This side of the island has a wonderful view of the sun setting over the ocean, grab a glass of wine and enjoy it from The Wauwinet’s oceanfront lawn.

What to Pack

You’ll definitely want to bring a sweater (or multiple) to Nantucket, since it’s so far north and an island, it is quite chilly for most months of the year. Even in May, we were pretty cold and always had a sweater or jacket nearby (or tied around our shoulders!). This cable knit sweater came in handy sooo many times on our trip – the ivory color ensured that it matched with every outfit, and it looked equally as cute on as it did around my shoulders. Another Nantucket favorite is this Ralph Lauren flag sweater – I myself brought one and also saw several ladies rocking them as well! The style on Nantucket is pretty sophisticated, most people dress up for dinner and even for shopping around during the day. I most certainly did not see anyone in a T-shirt or sweatpants! As for footwear, I also highly recommend comfortable shoes, as we did a TON of walking. I mainly wore my TKEES sandals or my Golden Goose sneakers since they offered a little more warmth than my sandals.

Let me know if you have any questions! 🙂