I love Nantucket. It's truly one of the prettiest places in the country. You know how social media can show something and make it look incredible, but in reality, when you experience it, it's fun but not that great? In my opinion, Nantucket is truly that great. I was just there last week, as I was invited on a press trip, so I wanted to update my travel guide from over the years. I already can't wait until we return again! If you are considering planning a trip to Nantucket, I hope this travel guide helps you plan! This is a photo and word-heavy post, so keep on scrolling!
Getting There
I've gotten to Nantucket by flying and by ferry. Flying is quickest and easiest from Pittsburgh if all goes smoothly, BUT, the caveat is that you are then beholden to the airlines, and there are only so many flights on and off the island per day. If there is bad weather or something else that interrupts flights, you can get stuck or have tons of delays/travel issues, so it is a bit of a gamble.
The ferry is more reliable. To do that, we fly into Boston and then either Uber or rent a car to the Hyannis Ferry. We also have friends who live in Boston, so when we go with them, they drive us! There are also buses available that service between Boston Airport and Hyannis. It's about a 2/2.5 hour ride, give or take a bit, depending on traffic. Hyannis is where you snag the ferry. I recommend the fast ferry that takes about an hour. The ferry is easy and seamless, and when you get to Nantucket, you get off right in town and can walk/uber/taxi/wave to where you are staying.
Where We Stayed
I have stayed in both hotels and rental homes via Airbnb and VRBO. I just stayed in a home rental on the press trip on the Miacomet golf course which was lovely. I love both hotels and rentals, but it all depends on who you are traveling with and the type of trip you would like. If it's a quicker trip for a long weekend with just a couple, I'd personally prefer a hotel near or in town because it's easy to get to things. If you are staying longer and want to have beach days and space to lounge and cook meals, I'd go the rental route. I always prefer being somewhat near town. I'm not a big beach person, and the island is so small that getting to any beach is easy, regardless of where you stay. It's nice to be able to walk into town, browse the stores, grab some coffee, walk to bars and restaurants, and all of that.
I recommend booking your rental at least a year out if you want a good selection of options, especially if you want to visit during the prime season, which is July and August.
When To Go
Prime season is summertime: June-August, though July and August are the busiest. This is because it's cold otherwise. Not only the air, but even in June, the water can be far too cold to swim in. I'm not a beach gal, nor am I a 'get in the water' girl, so the ocean temperatures aren't something I care about, but in July and August, the water warms up a bit. I prefer early June because it's still far away enough from the business of July, and you can get a bit of quiet on the weekdays. The weekends in June are still pretty crowded, though. Plus, in early June, some reservations are easier to snag. I don't like all of the people and the crowds and SO many cars. I've never been in the shoulder season, which is like April/May/September, but I'd love to visit then. One year, I'd love to go during Stroll in early December, too! Nantucket is quaint and charming, and I think sometimes too many people can take away from that. I think it's become more crowded in recent years!
Who Should Visit
Everyone! It can be difficult to get to depending on where you live in the country, and it's pretty pricey both for accommodations and food/drink, but if you can get there and afford it, it's worth it. I really believe there is something for everyone. There are lots of playgrounds and cute activities for children, beach time fun for young tweens/teens, nightlife for college-aged/early post-grad, so many romantic spots for couples, and lots of family-friendly places for generational vacations. It's safe, clean, and easy to get around on the small island.
What Should I Pack
In case you missed it, here is my
blog post where I shared all of my outfits from my Nantucket trip in case you are looking for packing inspo! I would suggest comfortable shoes to bike/walk and remember there are many cobblestone and uneven streets/sidewalks. I would bring wedges over heels. I would bring lots of sweaters, wraps, jackets, and maybe a light raincoat. If you go end of May into early June, check the weather first, but I'd even suggest a lightweight, packable puffer of some sort because it can get really cold at night and in the early mornings. There are some dressier restaurants and bars, but for the most part, the island is casual. I can't think of a restaurant off the top of my head that I know of that requires a jacket for men (which is usually how I gauge fanciness), though a jacket would be appropriate if dining at a restaurant like Galley Beach; it is definitely not required. My husband wears mostly chino pants, a button-down, a sweater, and loafers to our dinners because it gets chilly in the evening.
Getting Around
You can Uber or taxi around. You can also rent a car, bring your car over on the ferry, or rent a bike or scooter. If you are staying in or near town, it's nice and walkable. It's pretty easy to bike around the island, too. If you are staying in Sconset, it's also a great walkable area, but it's a bit of a further trek to town. Same with other areas like Madaket. If you are bringing your car over on the ferry, I recommend making reservations as far in advance as possible, as they sell out quickly.
Where We Ate + Drank
Half of the reason I visit Nantucket is to eat. The food is SO darn good. Living in Pittsburgh, we just don't have any incredible seafood, so it is such a treat every time we visit. I would recommend making as many reservations (for dinner) as you can.
Not the best photo, but this is such a good cold lobster roll! Brotherhood of Thieves
This is my favorite restaurant on the island. I like the basement the best. It's like a dark wood pub vibe, and their lobster roll (cold) is SO good. They recently added the other levels, and they're nice, too. The bar has a classic, old-school vibe to it. It's so cozy and no frills. You could wear jeans or a beautiful dress, and both would be fine!
Cru
This is the best lobster roll on the island. You have to get the hot roll! It's tough to snag an evening res, but you can also go for lunch. At night, it has swanky nightclub energy. It's almost like a nautical clubby version of the polo bar (LOL). Sceney, if you know what I mean. I usually dress up when going here.
Jetties Sandbar
Love this place. It's unpretentious, right on Jetties Beach, and serves casual food and fun drinks. Go with a swimsuit coverup on and relax on the picnic tables with a rum runner. The food is good, too! I love the lobster salad on a caesar!
Something Natural
I feel like everyone compares Provisions and Something Natural, which are both sandwich shops. Something Natural is my personal favorite, but you can't go wrong with either. I like the Italian sandwich, but I switch it up every time I go. You have to get their Portuguese bread! They have picnic tables outside, but it's also nice to take them to the beach!
This one is near the ferry, so I always get it on our last day. They have a 'Turkey Terrific' sandwich with turkey, stuffing, cranberry, and mayo on Portuguese bread. It's so good and tastes like Thanksgiving.
bACKyard BBQ
Super casual and an easy, quick spot for lunch. I was questioning how good BBQ would be on an island in New England, but it was excellent! It's right by the ferry, so you could grab lunch before you head home.
Bar Yoshi
This is on South Wharf, and it was my first time this past trip! The food was excellent. It has sushi, rice, noodles, etc. I loved everything, but the Japanese Udon noodles (pictured) were my favorite! It's a small place, so definitely make a reservation if you can!
Sister Ship
Sister Ship was in the hotel we stayed in on our last night (Faraway) because we had issues with the VRBO. LOVED this place. It has a Mediterranean flair to the menu, and everything we ate was out of this world. It's smaller plates, so it's nice to go with a group so you can share everything and taste a lot! A cute date night spot- it's cozy and, overall, well done. There is an outdoor patio where you can have drinks, snacks, food, etc.! The service was some of the best of our trip!
167 Raw
Like Cru, this is another one of those 'can't miss' things for me. This is the OG 167 for those of you who love the one in Charleston. It's a little seafood market down the road from Cisco Brewery, but they operate a food truck with a little garden where you can eat. The tuna poke is amazing, as is the lobster roll, which is the same as the Charleston restaurant. Literally, EVERYTHING is amazing; you can't go wrong. I think this and the Charleston restaurant might be my favorite food in the country. Also, the people who work in both locations are just so wonderful- nice, pleasant, attentive, and you can tell they are all into food and proud of their product.
Tavern and Gazebo
This is a casual, chill spot in town. I only go to the Gazebo for drinks. They have a fun assortment of drinks but are known for their mudslide. I'm not a big mudslide gal, but it's pretty good. The later it gets, the livelier the atmosphere. No frills.
Galley Beach
Probably my favorite spot on the island. In my opinion, it's worth the hype. The food is excellent, as is the service, and it's beautiful. However, I think there are better meals to be had, so I prefer to go here for sunset cocktails and oysters and then go elsewhere for dinner! They make a perfect dirty Hendricks martini. The sunset is why you are there. It's the best spot and just such a relaxing and wonderful experience. The staff is so attentive. I like to dress up when I go here, but remember, you may get a little sandy on your feet!
Lola 41
Love Lola! I've been to the one in Boston, Palm Beach, and Nantucket, which should prove it's delicious! During the summer, they don't take reservations. At 4pm, you have to call and try to snag a reservation for that evening. I set an alarm on my phone, and a few of us called, and we got a reservation for 5 people for 8:15, which was pretty ideal. TIt had a more nightclub vibe to it than I remember, which I don't know that I loved. I feel like maybe they are trying to compete with Cru? Not sure; maybe it's always been this way, and I just never noticed!
Downyflake
A quaint, no-frills diner known for its donuts. I'm not a big donut person, but the plain and maple-glazed are delicious.
The Corner Table
I love this spot for coffee or tea. It's cozy and delicious! They also have a cute outdoor patio.
Lemonpress
The best breakfast! It's always so packed but I love it there. Your spot for smoothies, juices, oganic dishes, coffee, and more. I love love love the avocado toast. It's next level and I don't often order avocado toast. Just trust. Hot tip is that you can order online!
Bartlett's Farm
This is a true farm that has been in one family for many generations. It's beautiful and fun to visit. It has a large barn-style shop with lots of premade foods. Their lobster salad is amazing as are their baked goods- the scones!!! They are known for their beefsteak tomatoes.
Would also recommend...
Other places I have been to in the past!
Nautilus
Millie's (the quesadilla is so good!)
Town
Claudette's
Island Kitchen
Ventuno
Or the Whale
Oath
Lobster Trap
Slip14
Blackeyed Susans
Rose and Crown
Gardiner's Corner, a popular photo spot on the corner of Main and Washington in town
Things To Do
Cisco Brewery
Even if you don't drink, this is a must. I don't think you can go to Nantucket and not go to Cisco. It's a brewery/distillery/winery. It's all outdoors, and it's so much fun. They have live music and food trucks. It's casual, and the vibe is lively but unpretentious. You could show up in a swimsuit coverup and flip-flops or a pretty dress, and either is fine. Sometimes it gets packed and it is a *vibe*. My favorite time to go to Cisco is around 3/4pm ish after beach/bike ride, etc. and then popping to Cisco for a few pre-shower drinks before a dinner res.
Club Car
There are a lot of fun and nice bars on the island, but the Club Car has something special... it turns into a piano bar at night! It's tiny- it is literally in a club car, but if you can get in, it's a blast! This past time, we couldn't get in becasue it was at capacity but you can hear everyone singing their hearts out and it's just a really fun time. They make a really great martini.
Gaslight
This is a true bar with live music and kareoke. It gets packed with a line around the block sometimes. The live music is so much fun. You have to be in the mood for this, though- it's loud and packed and gets sweaty and hot. I fangirled this past time because I saw Elin Hildebrand from across the bar!
Chicken Box
This is an iconic divey/live music bar! So fun, no frills, tends to skew younger like college/young 20somethings, but it's fun for anyone. This is one of those iconic spots that has been there forever that you have to experience at least once. My uncle (dad's brother) lived on Nantucket when he was just out of college and he still talks about the Chicken Box. They get some well-known artists, too. For example, I see The Revivalists and Mat Kearney on the calendar.
Go on a sailboat
The
Endeavor is a must. It's tough if you get a trip with bad weather, but if you have gorgeous weather, DO IT! Captain Jim is an icon. He built the 50s style sailboat himself about 40 years ago. You can do a private charter or pay per person. You can bring your own drinks onboard and he sails out onto the Nantucket Sound.
Sconset Bluff Walk
This is where SO many photos are taken and posted to social media because it's so picturesque. The flowers are incredible, the homes are beautiful, and the ocean is right beside you. The entrance can be hard to miss (off Front St). Once you are walking on it, it almost feels like you are trespassing into people's yards, but no worries—it's a public walking path!
Sconset Market
Picture a cozy, adorable, neighborhood market, and this is exactly what that is. The blueberry muffins are what they are known for. Similar to Bartlett's just without the actual farm.
Shopping
There is SO much shopping. Seriously, you could spend an entire day or even two going in and out of the shops on Nantucket. I usually like to spread it out over a few mornings or afternoons. Pretty much every shop is adorable and worth a pop-in, but I do have my favorites. Most shops are concentrated in town, so you can just wander in and out of most of them. I love Murray's; that's probably my #1. Beau and Ro, Alice Walk, Centre Pointe, Cold Noses, Erin Hielle, Blue Beetle, Skinny Dip, For Now- the list could go on and on and on! When you are packing, leave room in your suitcase for all of your goodies.
Force Five Water Sports
If you are a candy person, you'll want to stop into Force Five, which is like a surfshop but in the back, there is a hidden candy shop!! Filled with so many goodies- lots of gummy options for my fellow gummy lovers!
Juice Bar
It's an icon. The line is worth the wait. Ice cream, for those that don't know, and the homemade waffle cones are amazing. Literally, everyone is going to hate me for saying this, but I still like Bruster's best. The JB waffle cone is better, but I think Bruster's has the best ice cream ever. But, Nantucket does not have Bruster's, and the Juice Bar is the best on the island. I prefer getting it during the day when there is usually little to no line. If you wait until after dinner time, that's when it gets soooooo busy!
The Beach
There are so many beaches on Nantucket, and you can't really go wrong. I like Steps for convenience, and because it's close to the Sandbar. The stretch of Cisco, Ladies, Miacomet, and Surfside is nice because it usually isn't too crowded and the beaches are wide, and Sconset is always nice, too.
Play Tennis/Pickleball
This is right next to Sandbar at Jetties and has 5 tennis courts and two pickleball courts. They are public courts! You can book one
here, and even take lessons. We took a pickleball lesson on my latest PR trip and it was SO much fun!
Go on a bike ride
You can rent bikes in town and they will deliver them to your rental! Many hotels have house bikes you can use, too. The island is bike-friendly with lots of paths. It's nice to bike to Cisco or 167 if you are staying in that general area or bike to town!
Other Activities
They have a Whaling Museum, Movie Theater, Indoor Ice Skating Rink; visit the many lighthouses, take a workout class, go golfing, etc.
