Nantucket Travel Guide

I love Nantucket. It's truly one of the prettiest places in the country. Pre-pandemic, I made a point to go there each June, but we hadn't been since 2019. I 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 a lot more reliable. To do that, we fly into Boston and then either Uber or rent a car to the Hyannis Ferry. We have friends that live in Boston, too, 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. This past time, we stayed in the cutest cottage, and while I loved the house itself, I would never recommend it, as dealing with the landlord via VRBO was a nightmare. 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 relax, 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. 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. 

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 in a restaurant like Galley Beach; it is definitely not required. My husband wore 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 book up 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! 

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 it to the beach! 

Provisions

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. I don't think I have ever gotten anything else. It's so good and tastes like Thanksgiving. 

bACKyard BBQ

This past trip was my first time! I loved this place. 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've actually never eaten there; I only go to the Gazebo for drinks. They have a fun assortment of drinks. 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, but 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. The service this time was lackluster, but I love their sushi. This was my first time back since 2019. It 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 that is known for its donuts. I'm not a big donut person but the plain and the maple glazed are delicious. 

The Corner Table

Love this spot for coffee or tea. It's cozy and delicious! They also have a cute outdoor patio you can enjoy. 

Would also recommend... 

These are places we did not go to this past trip but places I have been to in the past!

Nautilus 

Millie's 

Town 

Claudette's 

Island Kitchen

Ventuno 

Or the Whale

Oath

Lemon Press

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. 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 are fine. 

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! They make a really great martini. 

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. 

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. 

Shopping 

There is SO much shopping. Seriously, you could spend an entire day 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! 

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 Brusters best. The JB waffle cone is better, but I think Brusters has the best ice cream ever. But, Nantucket does not have Brusters, 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 so 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. 

Other Activities

They have a Whaling Museum, Movie Theater, Indoor Ice Skating Rink; you can go on a sailboat ride, visit the many lighthouses, visit Bartlett's Farm, take a workout class, go golfing, etc.