As a pedestrian, you have a few more options to get across, including short flights from Boston on Cape Air and Jet Blue. Rental cars on the island will be expensive, and most likely of the Jeep Wrangler variety. You can easily rent a scooter, but get ready to constantly be the cause of traffic on the narrow streets (and downtown, the stone streets will lose their quaintness pretty quickly). Bicycles are a great option as well to extend your range but also provide the freedom to come and go when you please. The bus system on the island, the Wave, is a great and very inexpensive option to get around to the main attractions. Uber is also active on the island, the drivers are great, and ultimately this may be the best way to balance your trip (keeps you mobile without the hassle or expense of getting a car on the island).

MY FAVORITE THINGS ON NANTUCKET

CISCO BREWERY, 7 Bartlett Farm Road
is heaven on earth. Combining a brewery, distillery, and vineyard in an incredibly casual setting with picnic benches and other open seating is a great idea. Adding live music daily makes it better. Making it kid and dog friendly – wonderful. Having a shuttle that can get you there and back to town – ingenious. But then you add in some food trucks!!! Outstanding! They have a bar making cocktails, three different spaces for tasting the different offerings, some retail to get souvenirs, and an atmosphere that is incredible! Did I mention that I love this place? I’d suggest ordering a Madaket Mule.

 

167 RAW, 167 Hummock Pond Road
is a seafood market close to Cisco Brewery. This is a great option to pick up something to grill later on the beach or to make for dinner. They’ve also got some meats, cheeses, etc to help you throw together some snacks before the meal.

 

NANTUCKET CYCLING & FITNESS, 25 Youngs Way
(just past the Nantucket Health Club – which you should avoid) offers a number of classes to make you feel like slightly less of a lazy you-know-what while you’re on the island. They have spin, yoga, CrossFit, and probably a few others. They are really welcoming and will adjust to all fitness levels.

 

NATIV MADE, 10 Broad Street
is a new little food place right in between Stubby’s and the Juice Bar. It has healthy and delicious items and fresh fruit smoothies.

 

HENRY JR, 129 Orange Street
is a sandwich place East of downtown. Great place to stock up for a day at the beach or just to pop in for lunch.

 

FOR KIDS (OR THE KID IN YOU!)

You can spend countless hours roaming the shops downtown and finding the cutest outfits for the future Nantucketers. Let’s face it, little girls look adorable in Lily Pulitzer and what four year old boy isn’t a stud with a little popped collar on his Polo polo?

THE JUICE BAR, 12 Broad Street
is the aptly named corner location that is known far and wide for its ice cream. At night in the summer, plan on standing on line for a while. A long while. But at other times it is a relatively quick experience. Just grab some napkins for drips!

 

CHILDREN’S BEACH, Harbor View Way
is walking distance from downtown, and has everything you need for younger kids. The beach itself is safe and the water is shallow. They’ve got a snack bar for when kids or parents start getting hangry, and a wisely positioned playground in between. There’s also a field to play on and around, have a picnic, or just let your kids chase birds on. At night, they often set up family friendly events on the stage located there.

 

WHALING MUSEUM, 13 Broad Street
also located downtown, might be better for older kids (7 +). It is about whaling, not whales, so going in hoping to see all sorts of fun pictures of whales is the wrong expectation. They do have a huge Sperm Whale skeleton and also an interactive kids’ room there, but otherwise a lot of the artifacts and information is geared to an older audience with slightly longer attention spans.

 

MADAKET HARBOR, Western Nantucket
was also a quiet, shallow, and overall wonderful place to bring kids. You could walk out for a hundred yards at times without being deeper than your waist, and kids can run and collect shells, see crabs, and try to catch tiny fish in nets. It also puts you close to Millie’s which is home of one of my best meals on the island.

 

THE NANTUCKET INN, 1 Miller Lane
is a newer property that offers a lot of kids’ activities. They make it easy for parents to have some adult time while their kids are having a blast and meeting other kids of the same age. The property itself is new and pretty, but don’t expect the level of service you’d get at the White Elephant.

 

DINING

MILLIE’S, 326 Madaket Road
is fantastic. It has a Mexican influence and extraordinary flavors. Dining is inside (upstairs or at the bar) or outside on picnic tables. The staff is great, and it certainly feels like they want you there. Additionally, they’ve got a food truck that travels to Cisco Brewery every day offering a variation of their menu. You can observe a great sunset from here, but I’d actually say either finish dinner before and head to the nearby beaches or wait until after the sun goes down and then go eat.

 

GALLEY BEACH BAR & GRILL, 54 Jefferson Avenue
is famous for having the best view during dinner. As a result, they book up quickly and also have a less than welcoming approach to their diners. Actually, just expect to pay rent. You know you’re going there to see the beautiful colors over the water, they know you’re coming to do it – it’s a tacit agreement. Unfortunately their service philosophy is based on what they want (to get you in and out and seat another couple) instead of what you want (a nice meal, a couple of drinks, and a pleasant server). Drinks are overpriced and the food is ok. The nice thing is that it is a short walk from downtown (about 15 minutes), so once the sun goes down you have a short stroll to somewhere where you will feel appreciated.

 

BRANT POINT GRILL, White Elephant, Easton Street
if you want great service, a great location, and great food and drinks, then visit here. On Fridays they often do ‘buck a shuck’ oysters outside. When the weather is nice, outside is where you want to be, but the White Elephant definitely ‘gets it’ when it comes to quality and service.

 

LOLA 41, 15 South Beach Street
is right near the White Elephant, and is known to be one of the best places to eat. Cool bar scene, great great food, and a tricky reservation system. You need to be at the restaurant at 4 pm to make a reservation for that night (calling is tough). But the struggle is well worth it. They are good all around!

 

CRU, 1 Straight Wharf
is a restaurant and bar at the end of the wharf where all the yachts are parked. It is a great place to people and yacht watch for sure, very popular, and has a back room that opens right onto the water as well. Two bars, outdoor seating, and I seem to remember that it has food.

 

PARTING THOUGHTS

In the Oscar Award Winning (not at all) film Road Trip, Rubin is trying to calm his friends down before they have to jump a car over a river. “It’s supposed to be a challenge, that’s why they call it a shortcut. If it was easy, it would just be the way.” The exclusivity and the challenge of getting to Nantucket is part of what makes it special. As busy as it is, if it were easy to get there it would be overrun. But as I mentioned in the beginning, it is well worth it.
If you get the chance while there, go to the south side of the island and sit out on the beach at night. There are no lights in that direction, and the view of the stars is unbelievable. You can see the Milky Way as clear as day, and the rest of the sky seems to twinkle like Christmas lights with all the stars. There’s no place I feel more on vacation than Nantucket – no better place to wear a linen shirt, drink a Whale’s Tale, and climb a tree!