I worked hard and fast to get this MUCH REQUESTED Nantucket, MA travel guide up for you so you can take advantage if you’re heading there this summer! This was our second time back on Nantucket and we fell in love with it even more than we did the first time back in 2016. There really is something so special about heading to a secluded island that makes even a short weekend getaway feel like SUCH a vacation — especially in New England.
Nantucket, MA is a small island off the coast of Cape Cod, Massachusetts — the eastern most point in the United States and 50 square miles of beautiful landscape and beaches, about an hour ferry ride. It’s about half the size of neighboring island, Martha’s Vineyard (which I grew up going to during the summers), and one of the most charming places I’ve ever been to. For being such a “tiny island”, it sure is mighty and there’s so much to do and take in while you’re there — world class cuisine, beautiful beaches, walking and cycling paths throughout, art galleries, charming little shops, hydrangeas and rose covered cottages — it’s an actual New England dream.
Dune. A modern/chic little restaurant inside an old house right in the downtown with indoor and patio seating. Offers a smaller menu with creative dishes (the halibut was one of the most delicious bites of food I’ve ever had).
Lola 41. One of the restaurants of the famous hotel, White Elephant, this is our second time eating at Lola 41 for dinner (our first was in Palm Beach in the spring). It’s a very cozy vibe inside, they offer delicious craft cocktails and some of the best sushi on the island. We loved the Maruko roll and the Tsukiji roll + the kale salad was insanely amazing and so unique.
The Nautilus. One of the hot spots on the island and one of the hardest to reserve, this lived up to the hype. The decor is rustic/modern and the menu is small plates. We were totally lost when we sat down — literally, everything at other tables looked and smelled so good, so we ordered what our lovely waitress recommended: the runner beans (omg!), tempura oyster tacos, and the blue crab fried rice. She didn’t steer us wrong!
Oran Moore. A charming little location inside one of the historic homes right downtown, this is a very romantic little spot and perfect for date night. The overall vibe is very upscale and they have an extensive wine list menu!
The Pearl. Another charming little house downtown, they now offer patio seating right on the street under individual little tents. This had one of my favorite menus — the cuisine is so unique: Asian-inspired seafood, and IT IS DELICIOUS. They’re famous for their Wok Fried Lobster!
The Proprietors. Definitely one of our top spots, but it’s the most pricy! With a menu featuring farm-to-table small plates, we split a few to be able to try as much as possible. The hamachi crudo was actually insane (still dreaming about it), the red lentil falafel was a surprising favorite for my husband, but the tomato toast (with tomatoes from their famous Bartlett Farm) was SO delicious and fresh, we’ve already tried to recreate it at home. Can’t recommend this place enough!
Summer House Beach Side Bistro. We grabbed a bite here during both of our trips (along with a glass of rosé) mainly for the gorgeous view in Sconset. It’s definitely an expensive spot for lunch (and the portions are on the smaller side), but it’s more about the vibe. Summer House is a hotel of private cottages right on the beach with a pool. You can easily walk here from after the Sconset Bluff Walk and checking out the small downtown village.
Provisions. This place is FAMOUS, literally every person recommended and I get it. It’s a grab and go little sandwich and salad place right on the water with views of all the big yachts and ferries that come into port. Although they are known for their Thanksgiving Turkey Sandwich, I opted for the Italian sandwich (obv) and the veggie curry hummus wrap the next day.
Raw 167. A classic fish market with a food truck and picnic tables right on the route to Cisco Beach. We pulled off here for lunch and ordered the fresh fish tacos and ceviche! Beyond!
Black Eyed Susan’s. A Nantucket breakfast institution (that also serves dinner). Super casual, delicious omelettes and pancakes, cash only. Be prepared to wait in line! You can give your name at the front door and then go around the corner to grab a quick coffee while you wait.
Born & Bread. A delicious artisanal bakery in downtown Nantucket. They have great coffee, but I’d mainly go back for the pastries and bread. We lugged a sour dough bread loaf back with us on the ferry — it’s that good!
Lemon Press. This was my personal favorite spot to grab a coffee each morning. They also had a delicious healthy breakfast menu, salads to go (perfect to grab for the beach), and a juice bar!
Corner Table Nantucket. A relaxed little cafe with plenty of outdoor seating. They have amazing breakfast sandwiches, chai tea lattes, and also offer cooking classes!
CRU. This was the second time we couldn’t get into CRU for dinner, but it’s always recommended, so we found a way to get in without a reservation. We went to the bar after the lunch rush and were able to snag two seats in the back bar by the water and the docks. It’s absolutely beautiful inside and has such a fun location — being right on the water, it’s really a great scene! If you can’t get into CRU for dinner or lunch, definitely try this trick. Reservations typically book out WEEKS in advance, so it’s probably the toughest of the bunch to get into!
Lola 41. They have such great cocktails, small plates to share for apps, and it’s such a cozy and intimate scene inside the bar.
Sister Ship. This is a brand new restaurant and bar scene inside the Faraway Nantucket, a brand new hotel. This wasn’t fully open when we just went, but it opened July 20th, and we got a sneak peek of the inside bar (it’s absolutely gorgeous) and a sampling of their menu! Will definitely be on the list to hit when we go back!
The Summer House. A nice little spot to get a view and a drink if you’re in Sconset — about a 20 minute Uber from downtown (or a 40 minute bike ride). Grab a glass of rosé and head down to the beach!
Cisco Brewers. The most fun spot of the bunch. A huge outdoor venue with live music, food trucks from all the restaurants on the island, and lots of beer, wine and cocktails. It’s also dog and kid friendly!
*GLAM Travel Tip: A lot of these reservations can be found on either Open Table or Resy (if you book early enough) so make sure to JUMP on booking reservations as soon as you plan your trip! The earlier, the better!
Rent a bike from Young’s Bike Shop right downtown — they’re celebrating their 90th anniversary this year and we had a wonderful rental experience with them: plenty of bikes to choose from, Nantucket Bike Basket, helmet and bike lock included! The island is filled with bike paths (and bike racks) so it makes it super easy to get around! We chose to have the bikes for our entire stay!
Catch an Uber (or the Wave public transportation) and head over to ‘Sconset for the afternoon. Siasconset (known as ‘Sconset on the island) is located about 8 miles from downtown. I’d highly recommend the ‘Sconset Bluff Walk — about a 2-mile walk on a public path behind the most gorgeous private houses and gardens! You’ll be able to take in the gorgeous views, peep some of the prettiest properties on the island, and learn about the bluff erosion challenges (and efforts) the island is facing. When you’re done with the walk, head over to ‘Sconset market and get a famous muffin (the blueberry muffin is insane) or grab a sandwich at Claudette’s next door.
Spend an afternoon at Cisco Brewers. This is such a fun spot, we honestly could have spent all day here! There’s live music throughout the day, tons of unique beers on top, delicious cocktails, food trucks, plenty of picnic tables, and it’s just a really fun, relaxed island vibe.
Bike over to Cisco Beach. This is a pretty easy beach to get to from downtown — the bike path goes almost all the way there! It’s a very relaxed, dog-friendly beach with plenty of parking and a bike rack. On the way back, stop at Raw 167 (since it’s right on the way back) and grab lunch at the food truck outside. You can eat in the back on the picnic tables. Try their fresh fish tacos, they are delicious!
Take in the architecture and hydrangeas! If you’re not into biking, you can still get moving and go for plenty of walks — it’s a very pedestrian friendly island (since not many cars come over on the ferries). Just walking through downtown, you’ll see gorgeous little cottages with plenty of hydrangeas. If you want to walk out of downtown, I’d suggest Cliff Road! It has some of the prettiest homes on the island!
Check out the light houses! There are 3 total on the island but Brant Point Lighthouse is a short walk from downtown if you don’t want to venture out too far! You can grab an ice cream over at Juice Bar and walk over to check out the working light house, it was built in 1746 — would definitely be fun little activity with the kids, too!
On a rainy day, or cool misty morning (common in Nantucket), head over to the Whaling Museum right downtown! Nantucket was the whaling center of the world back in the 19th century so you can learn all about the history with a lot of ties to the island now. There’s also a rooftop with beautiful views of the harbor!
Get your shop on! Downtown Nantucket has some of the most gorgeous little shops to duck in and out of! I highly recommend spending a morning checking them out. Whether you’re looking for designer pieces (like Dior shoes or luxury denim) or looking for a classic Nantucket sweatshirt or hat, you can find what you need in the historic little shops! I personally love Skinny Dip by the harbor!
Grab a sandwich at Provisions and head to the beach. It’s really common to pack a lunch and head over the beach for the afternoon — Provisions is famous on the island for having some of the best sandwiches ever! Take your pick of beaches, there are over 12 to choose from and 82 miles of shoreline.
Check out the Boston Pops on Nantucket. This was such a fun night event we were able to attend last time we were in Nantucket. It’s an annual charity celebration that takes place each August on Jetties beach and features the Boston Pops Esplanade Orchestra — lots of seafood on the beach while watching live music is just the best! Unfortunately Covid has put on a damper on the plans both 2020/2021 seasons, but it’s scheduled to be back in action August 13, 2022! Mark your calendars!
We’ve only been to Nantucket twice and have stayed downtown both times (honestly just a few blocks away from each other). We first stayed at Veranda House which has 18 rooms overlooking a beautiful garden area that serves breakfast each morning. The location is great — it’s tucked behind the action so you’re close but not in the center of it all and we personally loved the free bike rentals, breakfast included each morning, and our personal porch off of our room that we used to sit and have a glass of wine at night. The second time we stayed, we stayed at Faraway Hotel — which used to be the Roberts Collection. This is a newer hotel that I’ll be honest, has some kinks to work out. Aesthetically, it’s stunning, the location couldn’t be better… we kept walking outside to go to dinner and would realize our reservation was under a block away. However, being a newer hotel — the service and amenities truthfully just aren’t there yet for how expensive it is and the rooms are very small! It’s tough to judge anything for the first time with COVID so I’m hopeful it’ll continue to grow and work out some issues for next season, but I like to be real with my readers and never want to send you somewhere without proper expectations! I’ve heard WONDERFUL things about White Elephant, so that’ll be on our list for next time!
Nantucket definitely has that island-vibe going for it. It’s casual but sophisticated if that makes sense! While you don’t need to worry about theme dressing in nautical attire, you DO need to worry about LAYERING UP. Nantucket is nicknamed, “The Grey Lady” for a reason — there’s a notorious cool mist over the island (especially in the mornings before the sun burns it off), and the nights tend to be on the cool side, so you’ll want to dress accordingly.
For daytime, casual beach attire, a sun dress, and COMFORTABLE walking shoes (or even athletic shoes if you’re planning on biking around). For evening, a long sleeve mini dress or a maxi dress should work, along with a blazer, cardigan or denim jacket because it’ll be chilly! Block heels or embellished sandals will work. Don’t bother bringing those stilettos — you’ll have a tough time walking around on all that cobblestone! I’d even recommend packing a light rain jacket if you can fit it — I wore mine just about every single morning to coffee!