Ah, Nantucket. Quite possibly my favorite place on Earth, with its fabled cobblestone streets, idyllic cottages, sweeping beaches, and more trendy restaurants per square foot than most small cities. The moment you step foot onto the wharf, it feels as if you’ve left all worries back on the mainland, and a fairytale awaits. As I lounge on a hydrangea-spotted patio enjoying my fourth summer trip to the island, I can’t believe it’s taken me this long to jot down all the joys there are to experience in my favorite place. So without further ado, I share with you all of the Nantucket need-to-knows in order to have the New England Summer vacation of your dreams!
What to Know
Nantucket is many things, but accessible it is not. Even once you’ve secured a place to stay, the challenges in getting to your dream vacation don’t stop there. For a place in relatively close proximity to my home city, traveling to Nantucket is no small feat and requires a significant amount of planning in advance. To get to the island, you have your choice of flying or ferrying – and flying is the more expensive but arguably easier option. Having always opted for the latter option myself, I can provide a bit of color to the logistics. You first have to make your way down to the Cape or New Bedford to meet the ferry – where you will have your choice of the fast ferry or the car ferry. If you want to bring a car on island, it will cost you no less than $500 per vehicle and some serious dedication to grabbing a reservation for the ferry of your choosing early in the year. Car tickets open in January, and you’d better be ready to refresh the page faster than you did for Taylor Swift in order to snag one. If you’re able to obtain a golden ticket, I do recommend having a car in order to explore to your heart’s desire, particularly since Ubers and taxis can be a bit hard to come by. That said, you can certainly make it work without one, particularly depending on where you are staying – you can rent a car, walk, rent bikes, or even hop on the friendly island shuttle the Wave to get where you need to go if all else fails!
Once travel plans are sorted, you might think that you’re ready for a carefree vacation. Think again! We must not forget to consider where to eat while on said vacation, and this is another area where you will benefit from some forward thinking. Many of Nantucket’s best restaurants are, naturally, very popular – which makes them extremely hard to secure a table for. Each releases reservations on its own timeline, so I recommend noting when reservations will become available for the spots you’re dying to try that season, and once again being ready to hustle to grab one the second they open. I highly encourage making a few backup reservations in case you aren’t able to secure your first choice options. And luckily, there are plenty of amazing options, so you really can’t go wrong!
Where to Stay
Now onto the fun part – where you should find your home. This depends on many factors, including how long you’re staying and what your goals of the trip are. If you’re there for a weekend, or are looking to prioritize convenience, I would recommend a hotel in town – you can walk most places and truly enjoy all that Nantucket has to offer. A few favorite options include:
- White Elephant. Arguably Nantucket’s most iconic hotel, and for good reason. Situated right on the harbor and in the heart of town, everything about this hotel is complete perfection. If you can swing it, you might as well stop reading here – you’re about to have the trip of your dreams.
- The Nantucket Hotel. It’s based on Elin Hildebrand’s The Hotel Nantucket – enough said.
- Faraway. Also located in town, this hotel is the perfect mix of modern and swanky while simultaneously feeling historic and quaint. Home to Sister Ship, a trendy cocktail lounge, Faraway is worth a visit or an extended stay.
- The Wauwinet. This one isn’t located in town, but the journey is worth it. Nestled in Sconset and home to Topper’s Restaurant, it doesn’t get more picturesque than this.
- Periwinkle Inn is our more budget-friendly alternative in a quaint Bed and Breakfast setting that allows you to stay within walking distance of all that town has to offer.
If you’re staying for longer than a weekend, or traveling with a large group, I personally am a fan of renting a house on Airbnb or Vrbo. This can be a more affordable option (operative word being can) and allows for more space to enjoy spending time at home – because how can you not enjoy taking up residence in a beautiful, multi-million dollar, potentially oceanfront home? Some of my favorite memories from these trips have been lounging at home, soaking up the Nantucket sun with my best friends! If you’re lucky, you can also secure a house within walking distance to the beach or town, or even better, with a pool. Pro tip – I’ll also add that as a general rule of thumb, you’ll want to avoid mid-island areas near the airport and Tom Nevers if possible. Just trust me. My suggested areas to stay would include:
- Town. Just as convenient as a hotel but with a bit more space, renting a house in town might just be the best option there is. We stayed within walking distance to all the best spots this year and it has been my favorite year yet!
- Steps Beach. A beautiful area filled with stunning homes, Steps is convenient to town and arguably Nantucket’s most iconic beach.
- Madaket. I’m partial to Madaket, which is farther away from town but absolutely stunning, filled with sweeping views, spacious houses and is home to Madaket’ Milllie’s. You truly feel like you’re off the beaten path, in the best way.
- Sconset. Formally known as Siasconset, this little village is known for its quaint cottages and rose arbors, complete with a charming little market. It’s a bit farther away from other beaches and town, but it’s truly a standalone destination.
What to Do
- Obviously, my number one suggestion is to go to the beach – and there’s plenty to go around (82 miles of it, to be exact). My personal favorite is Steps Beach – featuring beautiful views on the way down but yes, many steps to climb on your way out. Other notable options include Surfside, Cisco to watch the surfers, and Nobadeer if you have a car that you’d like to drive on.
- Stroll around town and shop. You can spend days doing this alone, with everything from vintage antiques to Vineyard Vines scattered around the cobblestone streets. Skinny Dip, Salt Boutique, and Erin Hielle are my personal favorites for fashion finds.
- Get ice cream from the Juice Bar. There will be a line, and it will be worth it. I don’t know what is in the Nantucket water, but it’s truly the best ice cream I’ve had.
- Bike the bike trails – all of a sudden you’ll feel as though you’re in the middle of the African Sahara.
- Stroll along the Sconset bluff walk and prepare to have your breath taken away.
- Bring charcuterie to Steps Beach for sunset. We’ve done this every year, and it’s always my favorite part of the trip. Sunsets on Nantucket simply cannot be beat.
Where to Drink
- Get a Blueberry Lemonade from Cisco Brewery
- Have a Gazebo mudslide (or three)
- Get a Crucumber from the back bar at Cru
- Sing karaoke at Gaslight
- Listen to the live band at the Chicken Box
- Sing the piano bar at The Club Car
- Go to buck a shuck at Sandbar
- Grab a beer from Slip 14
- Have an espresso martini at Sister Ship
Where to Eat
- For Breakfast + Coffee
- Island Kitchen for a gourmet sit-down brunch worth the inevitable hour-long wait.
- Lemon Press for breakfast sandwiches, pastries, and iced lattes that people line up for miles for. The Grey Lady iced latte is the coffee of my dreams.
- Handlebar for a a slightly quieter cafe with a particularly delicious iced vanilla latte.
- The Hub for a quick bite and some great coffee located in a quaint market setting.
- Jack and Charlie’s for breakfast sandwiches and bagels – and don’t forget to come back later for ice cream!
- 45 Surfside for a mid-island sit down breakfast sandwich destination.
- Born & Bread for gourmet breakfast sandwiches and toasts on – you guessed – some really great bread.
- Downyflake Donuts for – you guessed it – the best donuts on island.
- For Lunch
- Provisions for a Turkey Terrific. There is simply no other order I can suggest.
- Sandbar at Jetties for buck a shuck oysters – preferably with a side of fries, and best enjoyed with a mudslide.
- Bartlett’s Farm for truly anything your heart desires. From sandwiches to fresh bread to mac and cheese, they have it all and they do it well.
- Fresh for yet another fantastic sandwich – because it’s vacation. Their Smokey Yardbird might top even the Turkey Terrific for me.
- Something Natural for yet another sandwich option that tops the charts.
- Nantucket Tavern for a casual but delicious meal with plenty of options for everyone – from salads to chicken fingers to burgers to lobster tostadas.
- Millie’s at the Rotary for a fast-casual version of one of an island favorite.
- Claudette’s for more sandwiches – this time enjoyed in scenic Sconset.
- For Dinner
- Galley Beach for a five-star meal with a stunning sunset view reminiscent of a beach club in the South of France.
- Millie’s for a casual Mexican-inspired meal with a perfect margarita to go with it. Get the lobster quesadilla and it won’t disappoint.
- Bar Yoshi for Asian fusion small plates and plenty of sushi. Their lobster fried rice is one of my all-time favorite dishes on island.
- Cru for any and all seafood and an unbeatable harbor view. Everything from their lobster roll to their shrimp are top-knotch, and the cocktails are to die for. I will again remind you of the Crucumber – it’s not to be missed!
- Brant Point Grill for an outdoor meal overlooking the harbor at the best hotel in town – but somehow always with reservations to spare.
- Pizzeria Gemelle for takeout pizza. When all else fails, this is a fool-proof option to satisfy the masses.
- Topper’s for an elegant dining experience at the Wauwinet.
- or, The Whale for a trendy bistro vibe with something on the menu for everyone.
- The Nautilus for upscale Asian small plates.
- Lola 41 for a chic destination for both sushi and burgers – and most notably, the king crab rangoons.
- The Club Car for an incredible all-American meal and some of the best halibut on the island, best followed by a trip to the piano bar.
Whew! That’s all my Nantucket need-to-knows. Keep in mind, no matter where you stay or what you do, a trip to Nantucket will never disappoint. It is truly a magical place guaranteed to provide once-in-a-lifetime memories. Enjoy! ☼
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