The kid-free Nantucket Itinerary Part 2
This is Part 2 of a Nantucket couples itinerary. Read Part 1: Getting There for the travel day, arrival, and dinner at Cru.
You made it home and slept in your own bed. If you’re lucky to be on Nantucket, you’re lucky enough. Today is the first real day of your trip and it deserves a plan.
First Full Day, Start With Coffee at the Hub
If you are staying in town, the Hub is my pick for morning coffee. It's on the corner of Main and Federal, the coffee is solid, and if you can get a bench seat outside, you have the best early morning people-watching spot on the island. Grab a blueberry muffin, my second favorite on Nantucket, and settle in. It’s also a great spot for some stylish souvenirs.
The space is small and the line moves fast, which brings me to a Nantucket lesson worth carrying with you everywhere on this trip: Nantucket is a small space. We are all trying to enjoy it, act accordingly. At the Hub, be prepared to order, be kind to the people taking your order, tip, and move out of the way.
If the Hub is not for you: Born and Bread on Centre Street does an insanely good breakfast sandwich (the line reflects this). Lemon Press is a popular sit-down option. I'm not a big breakfast person, but I love their smoothies. Order the Honeypot with a shot of cold brew. Pro tip, order online and pick it up. Skip the wait. Lemon Press became an instagram hotspot and can be pretty crowded at the most popular times.
Beach Day
Your beach pick depends on what kind of surf you want and how much effort you're willing to put in.
Jetties is closest to town. Calm water, rentable chairs, easy in-and-out if you only want an hour or two before lunch. It also happens to be home to the newly refinished public tennis courts, a worthwhile addition if you play. And it's also where you'll find the Sandbar, which is a great “on the beach” casual lunch or dinner spot or my favorite choice for late-afternoon happy hour.
Surfside is the big-wave option. The walk from the parking lot to the sand is genuinely punishing, but the beach is worth it. Lunch is at the food shack, great burgers - but watch the seagulls. They are not subtle.
Cisco is the most remote and the most beautiful. There is no food on the beach, so stop at Bartlett's Farm on the way and pick up sandwiches. And once you're out at Cisco, it is a quick, logical, morally acceptable stop at Cisco Brewery on your way back. Live music, lots of dogs, easy vibes. If you're not a beer person, order the Nantucket Red.
If you want to consider some other beaches, take a look at the Nantucket Beach guide. There is somewhere for everyone, just depends on what type of day you want and your transportation options to get there.
Not a Beach Day?
If the weather isn't cooperating or someone in your group needs a non-beach option, hit the Whaling Museum or the Life Saving Museum. Both museums are excellent and both are a good way to prove to yourself that you did something on this trip other than eat and drink.
Museums are the second best bad-weather move on the island. The first will always be shopping. The shopping in downtown is perfection. Visit all the stores. My loop usually starts at The Haul-Over, then Skinny Dip and Remy in the Old Wharf (and check to see if any new stores have opened, there’s always one to two…) then I’ll hit the stores at the Straight Wharf including Respoke and see what new creations they have rolled out. From there it’s just a wander up and down the streets. Some of my favorites are (in no particular order) Nantucket Looms, Murray’s, Erica Wilson, Dawn, Wheat, Gypsy, and a favorite of my pups, Pawsitivity. I know I forgot to mention some and I left off the chains like Ralph Lauren and Veronica Beard but there is no shortage of good shopping and window shopping on Nantucket.
Tonight: Lobster at the Rental
You had Cru last night. You are exhausted, a little sunburned, possibly a little buzzed from the brewery if you made it there. This is the perfect night to stay in. If you have decided to split a rental home that has some dining space, why don’t you spend a little time with your group and enjoy a clambake at home?
If you call Sayle's Seafood you can order lobster dinners to-go. The 1.5-pound dinners are the right size for lobster lovers. They come with lobster, corn on the cob, potatoes, clam chowder, the whole thing. Yes, you can get lobster cheaper at home. It will not taste as good. You will have to pick them up yourself but they’re located right in town, an easy uber drive if you don’t have a car.
If you are running low on wine, stop at Hatch's, Murray's, or Fresh on the way home. And make sure you sort out dessert before you're back on the porch and too comfortable to move.
The Juice Bar is the famous Instagram ice cream stop. It is fine. It is not as good as the line is long. If you want real fresh ice cream made fresh in-house, stop at Island Kitchen and pick up a few pints. And I highly recommend the chocolate coffee Oreo. If someone in your group is gluten-free, Bartlett's Farm makes a flourless chocolate cake that will make them forget they had dietary restrictions. Nantucket Meat and Fish also makes great pies.
Eat your lobster. Drink your wine. Enjoy your dessert and go to bed early. Tomorrow you are on a boat at sunrise.
Second Full Day starts on the water
You went to bed early for a reason. You are doing a fishing charter with Captain Bob and Albacore Charters, and doing this trip hungover is, speaking from experience, HIGHLY discouraged. I have been there. It is not good.
The website lists a 5-hour inshore trip, but we've done shorter options. Call ahead and ask what they're offering this year and book this before you arrive. This is not a walk-up situation.
A few things to expect. You will see the full shape of the island from the water. On a good day you'll see all three lighthouses. The crew is excellent. Pack a small cooler, snacks, drinks, seltzers or beers if you're of age. It’s easy to grab an empty cooler (rentals usually have them) or backpack and stop in Fresh downtown to get anything you’d want to drink and snack on. You will almost certainly catch more fish than you need. We always leave most of ours with the crew and they always seem genuinely glad to take it.
Lunch at Straight Wharf Fish
You're back on land, salty, a little windblown, and hungry. Lunch is at Straight Wharf Fish. Start with the onion rings with caviar and crème fraîche, I know how that sounds, I know what they cost, and I am telling you to order them anyway. Looking at the price will not bring you the same joy as tasting them will.
Follow that with a lobster roll or a fish sandwich. Sit on the water. Don't rush.
Tonight: Adulting
Go home. Shower off the salt. Put on something nice. Tonight is a dressed-up dinner and you have two directions to choose from.
Company of the Cauldron — if food matters more to you than the room. It's a prix fixe menu, a tiny space, and near one-on-one service. The chef is Joseph Keller. If that name rings a bell, it should; his brother's restaurants include French Laundry and Per Se. Good cooking runs deep in that family. If you're lucky enough to be there on fried chicken night, go. Don't overthink it. You will also probably end up talking to the table next to you, which is part of the charm.
Galley Beach — if the space and the view matter as much as the food. This is where I'd wear the one dress I splurged on. Request a covered patio seat and book as early as they'll let you. Reservations here go fast and the rules shift year to year, just be ready. You could also have a seat in the sand and a front row seat to one of the best spots on the island to watch the sunset if the weather is cooperating. But when that sun goes down, the sand gets chilly, pack layers.
Last Day, make it count . Coffee, then Move
Coffee first. Light breakfast if you need it. You're working off last night's dinner today.
If your rental or hotel doesn't have bikes to use, pick up rentals at Nantucket Bike Shop. Before we go further, a real safety note, and I'm not kidding about this. I am not advocating for helmet-less biking. But if you're using a rental helmet, insist that they spray it with whatever kills lice before you put it on your head. Ask me how I know. You can also pick up a cute basket here to send home to keep on your bike. It’s a fun souvenir idea other than a t-shirt.
The Ride to Sconset
Put ‘Sconset Market ('Sconset is the common name for Siasconset) into your map app of choice. It's about 8 miles from town on a dedicated bike trail. Rolling hills, not much scenery, but good sun and good air.
When you roll into 'Sconset, park your bikes and wander inside. Twenty years of eating blueberry muffins on this island and ‘Sconset Market sells the best one. There's a hint of lemon zest, or at least I think there is. Order one and see if you agree. If you aren’t a muffin person there are other freshly made pastry options. The cold brew is good too. The people-watching can be enjoyable too, especially if someone alerted the media they too were going to be on a bike ride, in full glam. Linger a little, you’re on vacation.
The Bluff Walk
When you're fueled up, leave your bikes where they are. It's 'Sconset, it's fine. Walk over to the 'Sconset Bluff Walk, a public path that runs behind some of the most beautiful oceanfront real estate on the East Coast. Take Front Street (it's a shell road) and you'll find the entrance marked with an ever-growing list of rules. Instagram put this walk on the map and the locals are actively trying to manage the traffic it brought. Read the link above for the Bluff Walk etiquette if you wish but the short of it, stay on the path. Don't stare into people's living rooms. Keep it moving. Enjoy the views, take your pictures, but be cool. This is a real neighborhood.
The walk is about a mile. You'll come out around 65 Baxter Road. From there, take a right and you're a short walk from Sankaty Head Lighthouse.
On your way, you'll pass 93 Baxter. Say hello for me. That was our vacation home from 2007 to 2021, and I loved every summer in that little house.
Spend some time at the lighthouse. It is, objectively, one of the prettiest spots on the island. Then walk back to your bikes along Baxter Road for a different view.
Lunch
Two options depending on your energy. Claudette's in 'Sconset does a hearty sandwich on fantastic bread — nothing fancy, but exactly what you want after a morning on a bike. Or ride the 6.5 miles back to town and grab lunch at Millie's rotary location. Either works. Save some room for tonight.
Tonight: Pick Your Weather
Your last dinner gets two options, and the weather will tell you which one. I’d book both and then decide within the proper window to cancel the one that doesn’t work.
If the weather is cooperating: Topper's at the Wauwinet. Take the water shuttle from the White Elephant for an early seating. Dressy, expensive, and genuinely worth every dollar. The sunset from the water on the ride over is the kind of Nantucket moment you will think about in February. Book this as far ahead as they'll let you.
If the weather isn't cooperating — or even if it is: Ventuno. Fresh, homemade pasta, warm atmosphere, and the restaurant itself feels like you're eating inside a stylish Nantucket historical home. The food is excellent. The vibe is the kind that makes you stay for one more glass of wine or another cocktail at the backbar. Honestly, Ventuno is great in good or bad weather.
Either way, this is your send-off dinner. Treat it like one.
Before You Leave
Try to pack your bags tonight. The ferry line in the morning is not where you want to be rushing if you’re leaving the island by boat. Take one more walk along Main Street before you go, even if it's early and even if you're tired. That's the part of the trip you'll miss most. Grab some last minute souvenirs for the loved ones at home and start planning your next trip in your head.
Nantucket will still be here. That's the whole point of it.