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Nantucket is a charming island located around 30 miles south of the Cape Cod peninsula, and it packs a surprising amount into fourteen miles of moors, beaches, and cobblestone streets.
Bordered by the Atlantic Ocean, the island’s whaling-era history is still visible downtown, while the outer beaches and cranberry bogs give it a quieter, wilder side once you get away from Main Street.
You can reach all activities on Nantucket with a bike ride or a short drive, making it a relaxed place to vacation. Browse Nantucket vacation rentals to find a hotel or vacation home for your trip, then use this list to fill in the days once you’ve settled in.
These are the best things to do in Nantucket, whether you’re visiting for a long weekend or settling in for the whole summer.
1. Climb Brant Point Lighthouse
Photo Credit: Faina Gurevich
- Location: Easton Street, Nantucket
- Best for: A quick walk from town, photo ops
- Cost: Free
- Best time: Late afternoon or early evening
One of the most photographed lighthouses in New England, Brant Point marks the entrance to Nantucket Harbor and sits just a short walk from the ferry terminal.
This popular attraction is actually the site’s tenth lighthouse, since the previous eight were lost to fire, storms, or simply torn down and rebuilt closer to the water. This iteration was built in 1901, but the very first was built in 1746.
You can’t climb inside, but the short walk out along the jetty gives you a clear view of ferries and sailboats passing directly beside it.
2. Bike the Path to Siasconset
- Location: Old South Rd Bike Path
- Best for: Cyclists of all levels
- Cost: Free; bike rental extra
- Best time: Morning, before the afternoon heat
A paved, mostly flat bike path runs roughly 8 miles from Nantucket town out to Siasconset, the historic fishing village on the island’s eastern shore. It’s one of several paved paths that crisscross Nantucket Island, so you can rent a bike in town and ride out without ever needing a car.
The ‘Sconset Bike Path cuts through moors and past cranberry bog land, so it’s worth pacing yourself rather than rushing straight to the other end. Along the way, you’ll pass quiet stretches of open landscape, wildflowers, and sandy trails branching into the surrounding countryside.
Bring water and allow time for stops, especially once you reach Siasconset, where you can explore the village’s narrow lanes and weathered cottages.
3. Wander the Historic Cobblestones of Main Street
- Location: Main Street
- Best for: Shopping and architecture
- Cost: Free to browse
- Best time: Morning, before shops get crowded
Nantucket’s Main Street is still paved with the original cobblestones, laid in the 1830s to keep wagon wheels from sinking into the sand and mud. The surrounding blocks are lined with well-preserved 19th-century whaling-era mansions, now home to boutiques, galleries, and restaurants.
Wear comfortable shoes, since the cobblestones are uneven underfoot. Plan to spend a few hours wandering the historic downtown streets and browsing the shops.
4. Explore the Nantucket Whaling Museum
Photo Credit: EQRoy
- Location: 13 Broad Street
- Best for: History buffs and rainy days
- Cost: Paid admission
- Best time: Midday
Run by the Nantucket Historical Association, the Nantucket Whaling Museum is housed in a former spermaceti candle factory and holds a full sperm whale skeleton suspended overhead.
Exhibits walk through the island’s whaling history, once the center of its economy, alongside scrimshaw and ship models. It’s a good anchor point for a walking tour of the rest of the historic district.
5. Relax at Surfside Beach
- Location: Surfside Road
- Best for: Swimmers and families
- Cost: Free
- Best time: Morning, before the lot fills
This south-shore beach is one of the most popular on the island, with a wide stretch of sand and reliably rougher surf than the harbor-side beaches.
A paved three-mile bike path connects it directly to town, so you can skip the parking lot altogether if you’d rather ride than drive. A concessions stand near the lot serves burgers, tacos, and drinks for lunch if you’re staying all day.
6. Watch the Sunset at Madaket Beach
Photo Credit: Charles Lupardo
- Location: Pennsylvania Ave
- Best for: Sunset watchers and surfers
- Cost: Free
- Best time: Evening, shortly before sunset
On Nantucket’s western end, Madaket Beach faces the open ocean in a direction that makes it the go-to spot for watching the sun drop into the water. It also picks up more consistent surf than the calmer south-shore beaches, so it draws a handful of local surfers on the right day.
The Madaket Bike Path runs the whole way to the beach from town, making it a manageable ride if you’d rather not deal with parking. Pack a picnic or drinks, and allow extra time to settle into the sand before sunset, when the beach takes on its most atmospheric light.
7. Tour the Old Mill
- Location: 50 Prospect Street
- Best for: History buffs and families
- Cost: Paid admission
- Best time: During the summer season between May and September
Built in 1746, the Old Mill is the oldest functioning windmill in the United States and still grinds corn using its original wooden gears on breezy days.
This Nantucket Historical Association property sits just a short walk from downtown on a small hill, giving it a clear line to the wind. Kids tend to get a kick out of watching the gears turn if the sails happen to be running that day.
8. Walk the Milestone Cranberry Bog Trails
- Location: Just off Milestone Road
- Best for: Nature lovers and quiet walks
- Cost: Free
- Best time: Fall, during the cranberry harvest
The Nantucket Conservation Foundation manages this working cranberry bog, which is one of the largest of its kind still in operation.
With public trails that loop around the flooded fields, it offers a genuinely different side of the island from the beach towns; it’s quiet and often nearly empty even in summer.
Visit during the October harvest, when the bogs turn a vibrant shade of red and harvesting is in full swing.
9. Sip Local Drinks at Cisco Brewers
- Location: 5 Bartlett Farm Road
- Best for: Groups and casual evenings
- Cost: Food and drink costs vary
- Best time: Late afternoon into evening
Cisco Brewers houses a brewery, a distillery, and a winery side by side, with a big open-air patio and regular live music in peak season.
It’s grown into one of the island’s most reliable hangouts, especially for groups who want something more casual than a sit-down dinner. A rotating lineup of food trucks usually parks on site if you want to make a night of it.
10. Take a Seal-Watching Cruise to Great Point
- Location: Straight Wharf
- Best for: Wildlife lovers and photographers
- Cost: Charter rates vary
- Best time: Morning, for calmer water
A colony of gray and harbor seals hauls out on the sandbars near Great Point, at the island’s northern tip, and several local charter boats run trips out to see them.
You’ll find many reputable companies running tours out of Straight Wharf. Some operators combine the seal-watching with a stop at Great Point Lighthouse itself, seen from the water. Bring a zoom lens for your camera if you want good photos, since boats keep a respectful distance from the animals.
Plan Your Nantucket Adventure
From the cobblestones of Main Street to the seal colony off Great Point, Nantucket rewards visitors who mix the historic core with the island’s quieter, wilder edges. If you want more ideas once you’ve covered the highlights, read our guide to Nantucket’s hidden gems.
Ready to plan your trip? Explore the best areas to stay, book a vacation rental in Nantucket, and start planning your visit to this incredible island.
