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I first visited Nantucket as a kid, back when my family stayed in a little bed and breakfast—something that felt oddly fancy to me at the time (not to date myself, but that wasn’t the norm back then!). The island had a quiet charm: dusty bike paths, cedar-shingled cottages, and a harbor that always smelled like salt and sunscreen.
Fast forward to today and Nantucket still holds that same magic, though it’s undeniably evolved. The streets are a bit busier, the homes a bit shinier, and the Jeeps have multiplied. But even with its polished edges and summer crowds, Nantucket remains a beautiful and special place that feels like a true escape.
Now I get to bring my own kids here—who are finally at that perfect bike-riding age. That means our trip is car-free and fully two-wheeled. With backpacks, beach towels, and a little bit of nostalgia, we set out to explore Nantucket in the slow, scenic way it deserves.
Where to Stay
Warning, there aren’t any real economical places to stay. For this trip, we stayed at The Cottages at Nantucket Boat Basin, and I can’t recommend them enough—especially for families. The location is ideal: just a short walk from the ferry, right on the harbor, and close to bike rentals and town. We had a deck looking out over the docks, and the kids were constantly peeking over the edge spotting crabs and jellyfish. It also had a kitchenette, which made breakfasts and picnic packing super easy. You can request beach gear in advance, and there’s even a beach shuttle if you want to give the bikes a break.
If you’re looking for something a little quieter, The Wauwinet is on the opposite end of the island and offers a more secluded luxury experience—better suited for older kids or a parent getaway. It’s right near the Coskata-Coatue Wildlife Refuge and comes with complimentary bikes, beach chairs, and amazing views.
Another great family option is White Elephant Hotel, just outside of town. It has a pool, larger suites, and extra kid-friendly perks like complimentary continental breakfast and beach setups. Plus, it’s close enough to walk into town but far enough away to be peaceful at night.
Getting There
We took the ferry from Hyannis Port, and it’s a smooth and scenic ride that adds a fun sense of arrival to the trip. You’ve got two main ferry options: the Steamship Authority, which allows cars and takes about 2 hours, or the Hy-Line Cruises High-Speed Ferry, which is passenger-only and gets you there in about an hour. We went with Hy-Line and parked in one of their designated lots (there are several with shuttle service). Pro tip: make ferry reservations early, especially if you’re traveling on a weekend or planning to bring a car.
If ferry logistics sound like a lot, you can also fly. Nantucket Memorial Airport (ACK) has seasonal service from several cities including Boston, New York, D.C., and Philadelphia. You land just a few miles from town, and most hotels will arrange a pickup or you can taxi in. Flying is a great option if you’re tight on time—or just want to feel extra fancy.
When to Go
Nantucket is most definitely a summer island, especially if you’re visiting with kids. June through August is peak season, with the warmest beach weather, open restaurants, and tons of families around. That also means it’s the most expensive and crowded, so book early—hotels, bike rentals, even dinner reservations.
That said, May and September are underrated gems. In May, flowers are blooming, the island feels peaceful, and shops are just opening for the season. September might be my favorite time—the water’s still warm, the beaches are quieter, and most places are still open, just without the crush of summer crowds. If you’ve got flexible school schedules or are looking for a fall escape, it’s a great time to come.
Day 1: Ferry Ride, Harbor Views & Ice Cream Firsts
We kicked off the trip with the 9:00 AM high-speed ferry from Hyannis Port, which is just early enough to feel like you’re making the most of the day, but not so early that the kids are cranky. We arrived at the dock by 8:15 to park and check in—parking lots are spread out but well-marked, and a shuttle zipped us straight to the terminal. If you’re bringing more than just backpacks, you can check larger bags right at the dock (tagged and waiting for you in Nantucket). Easy.
The ferry ride itself is part of the fun. We found seats inside near a window, grabbed snacks from the onboard café, and let the kids wander the outer deck once we got moving. It’s about a 1-hour ride on the high-speed ferry, which is just enough time for coffee, photos, and soaking in that salty air.
Pulling into Nantucket Harbor still feels magical—even if you’ve been before. The ferry docks right in town, and within minutes of arrival we had picked up our luggage, snapped the “we’re here!” photo, and started walking toward our accommodations.
We stayed at The Cottages at Nantucket Boat Basin, just a few blocks from the ferry terminal. That walkable arrival is everything after a travel morning. The kids were instantly entertained by the harbor activity—boats coming in and out, crabs along the dock, and the salty breeze that makes it feel like you’re finally on vacation.
After settling into our cottage and dropping off our bags, we headed just a few steps away to Young’s Bicycle Shop to get geared up for the week. They made the process quick and painless—our oldest got a cruiser with a basket, our youngest had a tagalong bike, and they fitted everyone with helmets and locks before sending us off with a map of suggested routes.
With a few hours to explore before dinner, we did a relaxed roll through town. The cobblestone streets are a little bumpy for bikes, so we mostly walked them through the core and stopped into a few shops to browse books, souvenirs, and toys. Then we made our first mandatory Juice Bar stop—the line is worth it, especially for their made-daily waffle cones.
Dinner was just around the corner at Brotherhood of Thieves, which checked all the boxes: easy seating, solid kid’s menu, and something satisfying for the grown-ups too (plus a cocktail to celebrate arrival). We lingered a bit, talked about tomorrow’s beach plan, and strolled slowly back to our place—past the boats, under the soft glow of dock lights, and completely in Nantucket mode.
Day 2: Surfside Beach by Bike
We woke up to that crisp Nantucket morning air and the soft sounds of gulls outside our window. After a quick breakfast in our cottage—cereal for the kids, coffee for the grown-ups—we packed up our beach gear, loaded the backpacks, and hopped on our bikes. Today’s destination: Surfside Beach.
The ride to Surfside is one of those experiences that feels like part of the vacation, not just transportation. It’s about 3 miles from town and mostly flat, with a designated bike path nearly the whole way. The kids loved zipping along while we pointed out wildflowers and old shingled homes tucked into the dunes. We stopped once for water and a photo, but otherwise made good time.
We arrived around mid-morning and were glad we did—Surfside fills up fast on sunny days. It’s one of the most family-friendly beaches on the island, with wide stretches of sand, a snack bar, restrooms, showers, and—key detail—lifeguards. The surf here is fun but manageable; our kids stayed in the shallows while we took turns boogie boarding and playing frisbee.
We staked out a spot, laid down towels, and dug out the snacks. If you’re traveling light, you can rent beach chairs and umbrellas from vendors on-site, but we had ours strapped to the back of a bike with one of those bungee cord hero rigs. Worked perfectly.
For lunch, we kept it simple: sandwiches we brought from town, plus a snack bar run for fries and frozen lemonade. Surfside’s food stand has all the classics, and there’s something about eating sandy French fries with the ocean in view that just hits differently.
After hours of digging, swimming, shell-hunting, and sandcastle contests, we packed up mid-afternoon and pedaled slowly back to town. Everyone was a little sun-dazed and salty in the best way.
On the way back, we made a detour to Cisco Brewers, which is actually three places in one: a brewery, winery, and distillery with outdoor seating and live music most afternoons. It’s family-friendly in the most Nantucket way—kids chasing each other on the lawn while parents sip craft beer or rosé and graze from food trucks. We grabbed a bite and let the kids run off the last of their energy.
Back at the cottage, we rinsed off the sand, threw on sweatshirts (it cools off quickly here), and wrapped up the night with takeout and a movie. It was the kind of day that makes everyone sleep hard—and dream about doing it all over again tomorrow.
Day 3: Bluff Walk, Sconset Charm & Lighthouse Views
After a full beach day yesterday, we were ready for a change of pace—and maybe a little adventure that didn’t involve rinsing sand out of everything. Today’s plan: bike out to Siasconset (locals just say Sconset) and walk the famous Sconset Bluff Walk, one of the most scenic and surprisingly kid-friendly hikes on the island.
We left mid-morning after a hearty breakfast in town. (Born & Bread makes a great grab-and-go if you want to start pedaling early.) The ride to Sconset is about 7 miles from town along the Polpis Road bike path, and while it’s longer than our Surfside route, it’s a quiet, scenic ride through open moors and clusters of cedar trees. We took our time, stopped for photos, and kept everyone fueled with snacks and water.
When we rolled into Sconset, it felt like arriving in a different world—quieter, more residential, and impossibly charming. Think rose-covered cottages, shell-lined pathways, and a post office that looks like it belongs in a children’s book.
We locked up the bikes near the Sconset Market, grabbed lemonade and cookies (they’re famous for both), and walked over to the Sconset Bluff Walk. This public footpath winds behind private homes along the cliffs, with jaw-dropping views of the Atlantic and classic Nantucket shingle-style homes just inches from the trail. It’s about a mile one way, mostly flat, and completely doable with kids. Just keep a close eye—there are no fences between the trail and the drop-off in some spots.
The path ends near Sankaty Head Lighthouse, a red-and-white-striped beauty perched on the edge of the coast. We took a long break there—pictures, water break, snacks—and just let the kids run around the field while we soaked in the view.
For lunch, we headed back into the heart of Sconset and grabbed sandwiches at Claudette’s, which we ate at a picnic table in the shade. Simple and perfect.
The ride home was quieter. The kids were worn out in that content, beachy way, and we made just one stop to check out the Nantucket Shipwreck & Lifesaving Museum, which is along the return path and worth a quick detour if your crew has any maritime history buffs—or just needs an excuse to get off the bike for a few.
We arrived back in town in time for a low-key dinner. Tonight we kept it easy with pizza from Oath Pizza and sat out on the dock behind our cottage as the sun went down. No one even asked for screen time—which, on a trip with kids, is the surest sign of a good day.
Day 4: Island History, Shopping & a Little Fishing
By Day 4, we were deep into vacation mode. The kind where no one asks what time it is and cinnamon rolls count as a legitimate breakfast. We started slow—pajamas, puzzles, and more pastries from Born & Bread, then wandered into town for a dose of history.
The Whaling Museum, just a few blocks from our cottage, ended up being a bigger hit than expected. The kids were genuinely interested—especially by the enormous whale skeleton hanging overhead—and the interactive exhibits kept their attention longer than any of us predicted. The rooftop deck was my favorite part, with its sweeping views of the harbor and sea breeze in every direction.
Afterward, we strolled through town again and grabbed a quick lunch. The day felt wide open, and with everyone in good spirits, we decided to split up for the afternoon—sometimes the best way to make sure everyone gets their own version of a perfect day.
Our youngest daughter and I headed back into town, just the two of us, for a relaxed afternoon of shopping and wandering. We browsed boutiques, picked out small souvenirs, and spent an almost ridiculous amount of time flipping through books and gifts at Nantucket Bookworks. She chose a shark-themed book and a bracelet for a friend back home; I picked up a beachy candle I absolutely didn’t need but couldn’t resist. We grabbed iced lemonade and people-watched from a bench on Main Street. Slow, simple, and honestly, a highlight for me.
Meanwhile, my husband and our older child set off for a little fishing at Brant Point. They rented gear from Nantucket Tackle Center and headed to the jetty, where they spent a couple of hours casting lines and watching boats come in and out of the harbor. No major fish stories came home with them—just a couple nibbles and a crab—but they came back flushed from the sun and full of stories anyway.
We all met back up in the early evening and kept things easy for dinner with takeout from Provisions, eaten out on the dock behind our cottage. The light was golden, the air was cool, and we lingered long after the food was gone.
It was the kind of day where nothing huge happened—and yet it felt full in all the best ways.
Portable Beach Comfort!
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Day 5: One Last Stroll + Saying Goodbye
Departure day is always a little tug-of-war—you want to hold onto every last minute, but checkout clocks and ferry times wait for no one. Our checkout was at 10:00 AM, so we spent the early morning in a flurry of zipping bags, checking under beds, and rounding up the scattered socks and stuffed animals that had somehow migrated into every corner of the cottage.
Luckily, The Cottages at the Boat Basin made things easy—they held our bags at the front office after checkout so we could head into town one last time without hauling everything around. That gave us space for the perfect final morning: coffee and breakfast at Black-Eyed Susan’s, where the pancakes hit just as hard on Day 5 as they did on Day 1. The kids split chocolate chip pancakes, and I stuck with something classic—eggs, toast, and one last cup of strong coffee.
After breakfast, we took a slow walk along Main Street. The kids used up the last of their souvenir money (more saltwater taffy and a shark keychain), and we stopped into Something Natural one final time to grab sandwiches and cookies for the ferry ride.
We picked up our bags, made the short walk to the ferry terminal, and joined the crowd of sun-kissed families heading home—tired in the best way, a little windblown, and already talking about next time. As the ferry pulled away, we all leaned over the railing, waving goodbye to the island until it blurred into the horizon.
Nantucket gave us exactly what we needed: beach time, biking adventures, slow mornings, and some unexpected memory-making moments in between. We didn’t do it all—but we did plenty. And that’s the beauty of a place like this. There’s always a reason to come back.
Adventures We Missed (But Maybe You Won’t)
As much as we packed in, there were a few Nantucket adventures we didn’t get to—next time, for sure. Children’s Beach, right near town, is perfect for little ones with calmer water, a playground, and even summer events like puppet shows and music. We also had a sailing trip on our radar, but the wind and our schedule didn’t quite align—there are family-friendly options for harbor sails that look unforgettable. And while we biked most of the island, we didn’t make it all the way to Great Point Lighthouse, which requires a permit and 4WD vehicle to access (or a long, sandy walk if you’re feeling bold). Even after five full days, Nantucket still had more to offer—and that’s part of what makes leaving a little easier. You know you’ll be back.
