I feel like I’ve been to Nantucket enough times where I can offer some advice on how to plan a great trip. That said, I’m not an expert on the island. Despite its relatively small size (less than 48 square miles!), there are always new pockets to explore. I certainly haven’t covered it all, but isn’t that the fun of traveling to the same place over and over again? I never feel in a rush to try to do everything, and instead pick a few new places to explore every time I go, in addition to my already favorites.
Having mostly grown up in Florida, I didn’t even know about Nantucket until I went to college. I had been to the Cape as a kid when we lived outside of Boston, but never Nantucket. After my first trip there with friends when I was working in NYC, I was hooked. I try my best to get there as often as I can now. It’s without a doubt, my favorite place on Earth. It can be a nightmare to get there, but stress and worry just melt away the second my feet hit the island.
Carter filmed this video during our trip last week and, guys, it makes me so happy. I cried when I watched it for the first time!
This is an extremely long post. I thought about breaking it up for easier reading, but I wanted everything to be in one place. I did my best to be as thorough as I could, although I’m sure I forgot things. Leave a comment if you have a question, and I’ll try my best to answer!
WHEN TO GO:
I’ve visited Nantucket in June, July, August, and September. It’s still pretty cool in June and, therefore quieter, but lovely nonetheless. Everything is green, although not in full bloom. July and August are definitely the busiest times, which makes lodging more difficult and more expensive. Additionally, July is the “prettiest” of the months with all the flowers in full bloom. I enjoyed my two weeks in July and would highly recommend it if you can swing it. And if you go in August, try to align your trip with the annual Boston Pops concert. It is THE best.
My FAVORITE time of year to go however is mid to late September. You have a slightly elevated risk of hurricanes, but it’s quiet as most people are back to school and work. (This also makes things a little more affordable.) It’s warm during the day with the slightest hint of crisp fall air. Everything is still green and the days are a tad shorter. It’s nice to be able to go outside and enjoy nearly perfect weather during the day and then get cozy at night with sweaters and blankets.
HOW TO GET THERE:
Getting to Nantucket is the worst part. There are a few options though, so take your pick. I would say that the “easiest” way to get there is to fly, but that’s only IF you don’t run into any problems flying. The first time I went to Nantucket, we flew, and it ended up being a 24 hour ordeal. Many things can go wrong with flying so I just never recommend it if you can avoid it. (Missed connections, the unpredictable fog that the “Grey Lady” is infamously known for, delayed flights, canceled flights, missing luggage, etc.) If you do want/need to fly, go in with the expectation that things might go awry. A few delays may be okay if you’re staying for a week, but if you’re only going for a couple of days, those delays may significantly cut into your trip. If you have to fly, I recommend flying into Logan airport and adding a day trip to explore Boston and then taking a car service to Hyannis the next morning for a ferry.
(Also, if you’ve heard people refer to the island as “ACK,” that’s the code for the tiny airport!)
Taking a ferry seems a little more inconvenient, but you’ll run into significantly fewer issues– and I actually love the ferry experience. There are a few options you have for the ferry, and the best depends on where you’re coming from. Just be sure to double check which one you end up choosing so you don’t end up at the wrong terminal location! Hy-Line and Steamship Authority from Hyannis are both popular, and each has a “fast ferry” option. I LOVE the Seastreak ferry from New Bedford, MA. It’s a two-hour “slow ferry,” but the convenience of not having to drive down the Cape (or more importantly leaving the Cape on the return trip) makes a world of difference. The parking is a BREEZE, and I find the small terminal super easy to navigate. Note: if you want to bring a car, you’ll have to take a slow ferry from Hyannis and book way in advance to reserve a spot.
There is also a Seastreak ferry from NYC. It doesn’t run as often and from what I’ve heard the five+ hour ferry can be a little rowdy with people starting their vacation a little early.
Bottom Line: If you can drive and do the ferry, do that. If you have to fly, know that it might be a longer journey than expected.
WHERE TO STAY:
You have three options for where to stay on Nantucket: a hotel, a rental house, or a friend’s spare room. I’ve done all three and, honestly, all are great. If you have a friend who has a house on island (or more likely, their family does) and you get invited to stay, go for it! There’s nothing like staying with someone who knows the ins and outs of the island.
Hotels are a great option if you’re traveling by yourself or with one friend or your significant other. There are plenty to choose from so I’d recommend finding one based on your budget, travel dates, and “style” of hotel. I’ve stayed in the White Elephant‘s apartment-style loft with Nantucket Island Resorts. And I’m personally dying to stay at Greydon House.
My favorite thing, though, is renting a house. If you’re going with multiple friends, this ends up being the most economical route. (Although, take “economical” with a grain of salt because Nantucket is just downright expensive no matter which way you slice it.) The more friends you can round up, the better the house you can get and the more the price is divided. I found my rental this July through HomeAway (also VRBO). Airbnb is, of course, another option. And there are plenty of websites that group specific home rentals. I recommend dedicating an afternoon to scouring various rental websites to find the perfect house for you. One tip about booking: the earlier you book, the better. People are already considering homes for next season! Even when I booked last December for July, I think 30% of homes had been rented.
I don’t think there’s a bad neighborhood to stay in. They’re all a little different, but again, the island is so small that you can explore a bunch over your stay. If you’re only there for a few days and/or it’s your first trip, you might consider staying somewhere near Town as it’s centrally located. ‘Sconset is quieter, although a little more secluded. Madaket is a bit more remote and rustic. While you’re looking for rentals, don’t forget to see where it is located on the island and do a little research on the particular neighborhood to make sure it aligns with what your vision for the trip. You can’t go wrong though, so don’t worry too much!
DO I NEED A CAR?
The short answer is that having a car isn’t entirely necessary. If you’re staying in Town, you can mostly walk to restaurants and shops with no problem. (Parking can be annoying!) There are also plenty of bike paths around the island if you plan on renting (or bringing) a bike. Cabs and Ubers are also generally pretty accessible and affordable. If you’re staying for a couple of days, I would skip the car and plan on using Ubers or bikes to get around.
That said, I think having a car makes everything so much more convenient. If you’re renting a house, I would say that a car is more necessary than not, as you’ll likely be there for a week or longer and have (at the very least) grocery store runs. If you don’t bring your car over on the ferry (which is around $400), renting a car is your next best option. Be prepared for insane prices. Even the “affordable” route won’t feel that affordable. But hey, you’re on an island with limited options plus a lot of tourists, so it’s to be expected. This is also where it helps to have other people chipping in to help divide the costs. Renting a Jeep with a beach permit is an excellent idea and a LOT of fun.
While they look cool, I would suggest avoiding renting a scooter. Not only are they dangerous, but they’re also kind of looked down upon by locals.
WHAT TO PACK:
This is where you probably shouldn’t follow the route of bloggers or what you see on Instagram, to be honest. Nantucket is pretty casual. If I were packing for a true vacation and not for work (which is outfit posts that require a lot of extra packing), I’d stick to the basics: linen dresses, cover-ups, a few swim suits, denim shorts, sandals, white jeans, etc. Pack sweaters, regardless of when you go as it gets chilly every night and I always bring my Patagonia Nanopuff, even in July. I’d also bring a rain jacket.
Maybe bring one cute outfit for a nice dinner, but otherwise, you can wear your favorite and well-loved summer clothes. One thing to definitely not bring? Heels of any kind. Stick to flats and sandals and if you think you need some kind of height, go for a low wedge. Comfortable and casual will go a long way!
Oh, and one thing you need to pack without question? CASH. Make a trip to your bank before you get on island unless you’re okay with racking up some ATM fees. A lot of places are cash only.
As I mentioned earlier, July and August are the warmest months. Even on the hottest day in July though, it still cools off at night. I always throw a sweatshirt into my beach bag in case the sun goes behind the clouds, and I always bring a sweater, if not a jacket, if I’m going out to dinner. The weather is predictably unpredictable. This is the one case where watching the weather won’t really do you any good. If you look a week out, you’re pretty much guaranteed that it won’t be the forecast. Even on an hourly basis things can change, and things can change fast. The best thing to do is to expect a range of weather and temperature, every day, and to plan accordingly. Watch the sky! Clouds and fog can appear out of seemingly nowhere (half the fun of Nantucket in my opinion!), and they can disappear just as quick. In one day, you might have a humid/foggy morning; a scorchingly hot, cloudless day; and a super cold and rainy evening.
While I love a summery day spent at the beach, I also love watching the fog roll in while sitting by a fire just as much. (And, again, that can happen in the same day!)
WHAT TO DO:
Still with me?!
So what to do when you’re on the island? I’m going to assume you’re planning a trip in the summer for this part.
BEACHES: Nantucket has some of the best beaches in the world, and that’s a major thing to do. I would go every day where it’s warm enough if I were you. There are various beaches to explore around the whole island, and each has its own vibe. There’s something for everyone, whether you want something remote, something a bit more natural, something for the family, something for swimming, etc.
Everyone has their particular favorite beach… so I’d recommend going to a few different ones during your stay to see which one speaks to you the most. I love Jetties, Great Point, Surfside, and Tom Nevers.
SHOPPING: There are a ton of shops in Town to pick up souvenirs. Unless it’s something you can’t live without, I would honestly skip purchasing a lot of things. I’ve found that the markups on the island are out of control. (Some stores sell things that I’ve seen at HomeGoods for a FRACTION of the cost.) If you need something to wear try The Shift, In the Pink, or CJ Laing.
One store to not miss is Murray’s, which is the home of the famous “Nantucket Reds.” It doesn’t look the fanciest when you go inside, but they carry a ton of brands for men, women, and kids. Also, you don’t want to miss Peter Beaton Hat Studio.
Every summer there are a bunch of pop ups that open too. This summer, my faves are Margaux, Beauty Counter, and Skinny Dip.
I think the best “t-shirt” shops are Annie and the Tees and 3 Girls and a Dog. They’re right next door to each other and have a good selection of shirts, sweatshirts, and hats.
There is a lot to do beyond just shopping and beaches, of course!
– Rent a bike (highly recommend Cook’s) and follow a bike trail or two
– Charter a sailboat (highly recommend Endeavour Sailing) for a tour around the sound
– Go paddle boarding, golfing, or fishing
– Visit the Whaling Museum in town
– Spend an afternoon outside at the popular Cisco Brewery
– Explore the ‘Sconset Bluff Walk
– Not technically an activity, but just driving or biking around and looking at houses is always fun for me. Highly recommend doing that, especially if it’s your first visit so that you can get a lay of the land.
WHAT TO EAT:
There are MANY restaurants to choose from on Nantucket. I haven’t even tried a fraction of them. I’ll share the ones I’ve gone to and enjoyed, but know that this is not an exhaustive list. I have had a pretty good experience with Yelp for Nantucket restaurants, and you can also just go where the wind takes you. Some restaurants require reservations, but you’ll probably only find that to be an issue on Friday/Saturday nights during peak weeks in the summer. (But if you call a day or two in advance, they should be able to squeeze you in.)
– Cook at home! This is not a restaurant, but I have to start this off as a top recommendation. If you’re renting a house, I highly recommend cooking at home. There are two on island Stop & Shops to pick up the necessary goods for dinner at home. It’s going to be the most affordable meal you have, and it’s really fun if you’re with your friends. No need to worry about what you’re wearing or valet parking or Ubering. When I was there last week, we spent $130 at the grocery store (including the purchase of a pot we needed) for breakfast, lunch, and dinner for three people. You can easily spend $100 at lunch for three if you go out; don’t say I didn’t warn you.
– Downyflake is a MUST VISIT spot. You can sit down or (my preference) pick up doughnuts to go. If you’re lucky, they’ll be fresh out of the oven. They do sell out, so try to get there early! They have chocolate, sugar, plain, and (omg) coconut. Get more than you think you’ll eat because you’ll want more for sure.
– Provisions is one of my favorite places to get food on Nantucket. I always make it a priority to go here and often find myself going a handful of times every trip. It’s a little sandwich shop and cafe right next to the Wharf. Sandwiches taste so much better on Nantucket for some reason, and I can never get enough. Pick up a few to bring to the beach or stick around town for a casual bite. My favorite is the BLT (super light on the mayo), but they’re probably best known for the Turkey Terrific (on Portuguese bread, a Nantucket staple). You can also grab breakfast sandwiches here.
– Handlebar Cafe is the best coffee shop in my opinion! I could swing by every afternoon for a cup of coffee or iced latte. Addicting.
– The Hub is a little corner store right on Main Street where you can pick up small bites, bagels, breakfast sandwiches, smoothies, etc. alongside your morning coffee and the paper. They also have a lot of great trinkets for souvenirs.
– Cru is a happening restaurant down the Wharf. Personally, the scene can be a little much for me… BUT, I swear they have the best lobster roll ever. I dream about it. I prefer to swing by for lunch and sit outside, but you may want to try it for dinner and drinks.
– Brant Point Grille is connected to the White Elephant. I had a great lunch here, but I’ve heard they’re known for their epic Sunday brunches.
– Galley Beach has the BEST food. Seriously delicious, it’s worth every penny. This is also a great spot for sunset drinks.
– Millie’s (with Georgetown roots, woo woo) is also a favorite of mine. It’s pretty expensive for what it is, so be prepared for that, but honestly, the food is so good that I don’t even care. It’s more relaxed and casual than other restaurants. The Wauwinet salad is amazing as are all of the tacos.
– The Proprietors is the most recent restaurant I tried. Everything is small plates and meant to be shared. Best to go with a medium sized, adventurous group. The atmosphere is also really cool.
– Oath Pizza is a gem. We picked up a couple of pizzas one night to eat at home, and we all wished we had bought at least another pie… not because we were that hungry, but because it tasted so good. Sometimes you just need a little pizza in your life, you know?
– Claudette’s is located in the heart of ‘Sconset. It’s another favorite sandwich shop. Seriously, I don’t know why sandwiches taste so much better here, but they do. The turkey is the best! We stopped by for sandwiches a couple of times, even bringing them to the beach for a picnic lunch one day.
– Island Kitchen is a great spot for breakfast or lunch. Everyone loved what they got, and it was pleasant to sit outside!
– Something Natural is a local favorite and (yay!) just opened up in Greenwich as well. Cookies and sandwiches… how can you go wrong?
– Brotherhood of Thieves is a crowd-pleasing bar, but you can also grab food here as well.
– Black Eyed Susan’s is one of the most recommended places every time I go. I haven’t had a chance to dine there though, mostly because I’ve heard there’s always a wait! I felt like I had to include it here because I know so many people love it.
– The Juice Bar is one place you could easily go every day of your trip. The ice cream is delicious, but it’s the waffle cones that really steal the show. You can’t walk by without being drawn in by the scent of freshly made waffle cones! There is often a long line, but I promise, it’s worth it! (While you can’t go wrong with flavors, I have grown quite fond of the coffee one!)
All in all, this post makes it seem like you have to cram everything into one trip. Trust me, you’ll be back. (Be sure to throw two pennies off the ferry when you go past Brant Point to ensure your return trip!) The real magic of Nantucket though is to just take things slowly. Sleep in, wander around, enjoy your coffee, relax at the beach, eat the buttery lobster roll and creamy ice cream cones, and stay up late chatting with friends.