Nantucket is the most preserved historic island in America — an 1800s whaling town that never modernized, with cobblestone streets, grey-shingled cottages, and moors covered in heather and cranberries. The beaches are spectacular in every direction: calm harbor swimming at Children's Beach, dramatic surf at Surfside, and the most beautiful dunes in New England at Great Point. Nantucket moves slowly by design.
✓ Nantucket has almost no development beyond the historic district and scattered beach areas — it feels like 1890 in many parts
✓ Children's Beach and the Brant Point Lighthouse are both five minutes from the ferry dock — the first afternoon is immediately perfect
✓ The food quality on Nantucket is exceptional — the island has a remarkable concentration of excellent restaurants per square mile
→Nantucket Town: a perfectly preserved 19th-century Main Street with cobblestones, antique shops, and excellent restaurants
→Great Point Lighthouse: a 9-mile drive on the beach to a lighthouse at the island's northern tip (4WD required)
→Children's Beach: calm harbor water, a playground, and a snack bar — the perfect grandkid headquarters
→The Whaling Museum: one of the best maritime museums in New England, with a 46-foot sperm whale skeleton
🌟 Start Here
Children's Beach & Brant Point Lighthouse
Five-minute walk from the ferry dock. Children's Beach has calm harbor water, a small playground, a snack bar, and lifeguards. From the beach, walk out the harbor jetty to Brant Point Lighthouse — the second oldest lighthouse site in America (1746) — for the view of boats entering Nantucket Harbor.
Free·All ages
Nantucket Whaling Museum
A comprehensive maritime museum in a restored 1847 spermaceti candle factory. The centerpiece is a 46-foot sperm whale skeleton. The scrimshaw collection, the whaling captain's logbooks, and the exhibits on the Nantucket Sleigh Ride are extraordinary. One of the best museums in New England for ages 7+.
$25/adult · $10 ages 6–17 · Under 6 free⏱ 2–3 hoursAges 6+
Grandparent note: The cupola on the roof (extra stairs) has the best view of Nantucket Town and the harbor. The museum's lightship basket shop sells the finest Nantucket souvenirs.
Surfside Beach
Nantucket's south-facing ocean beach with open Atlantic surf — more dramatic than the harbor beaches, with waves for older grandkids and a long flat beach for walking. The bike path from town (3 miles) is flat and beautiful. Lifeguards, snack bar, and restrooms.
Free · Parking $20/day or bike (free)⏱ 2–3 hoursAges 5+ for swimming · All ages for beach
Grandparent note: The Atlantic surf here is real — 2–4 foot waves most summer days. Perfect for older grandkids who want actual ocean swimming. The snack bar's clam chowder is excellent.
Great Point 4WD Tour
A permit-only 9-mile beach drive on the sand to Great Point Lighthouse at the island's northern tip. Exposed sandbars, seal colonies, and incredible bird life along the way. The lighthouse sits at the meeting of two tidal currents — a dramatic natural spectacle. Requires a 4WD vehicle with beach permit.
NRTA Trolley to wayside tour OR $25 Great Point AWD permit from Trustees of Reservations⏱ 3–4 hoursAll ages
Grandparent note: Self-drive requires an AWD/4WD with proper deflation (to ~18 psi). Eco-tour operators offer guided trips in their vehicles if you don't want to drive it. The seals at the tip's sandbar are extraordinary.
Cranberry Bog Walk (Windswept Bog)
Nantucket has the largest wild cranberry bogs on the East Coast. The Windswept Bog off Polpis Road has a free walking trail through working bogs — extraordinary in late September and October when the berries turn red. In summer, the heath and moorland is covered in wildflowers.
Free⏱ 1 hourAll ages
Grandparent note: The bog walk is flat and easy. The harvest in October turns the whole bog a brilliant red — if your timing allows, it is one of the most beautiful seasonal spectacles in New England.
White Elephant Hotel
Luxury Hotel · $600–1,200/night
On the harbor with private docks and a marina — the best location and the best service on Nantucket
Jared Coffin House
Historic Inn · $300–550/night
An 1845 brick mansion in the heart of Main Street — authentic Nantucket character, walking distance to everything
Vacation Rental (VRBO)
Cottage · $400–900/night
Nantucket rentals are expensive but essential for multi-night stays — the only way to experience the residential island
Cru (Nantucket Harbor)
Seafood/Raw Bar · $$$$
Raw bar on the harbor dock — the oysters and lobster roll are Nantucket at its finest
Lola 41
American · $$$
Best lunch in town — the tuna tacos and lobster guacamole are the go-to Nantucket lunch order
The Downyflake
Breakfast · $
The Nantucket breakfast institution since 1945 — the doughnuts are famous, the lines are worth it
1
Take the fast ferry from Hyannis (1 hour) — the standard ferry (2.25 hrs) saves $10 per person but costs 2.5 hours round-trip
2
Nantucket is the most expensive island in New England — budget $400–600/day above accommodation for food and activities
3
Book fast ferry tickets 4–6 weeks ahead for July and August — the Hy-Line fast ferry sells out regularly
4
Rent bikes or scooters (adults only) at the ferry dock — the Nantucket NRTA trolley also covers the main beaches
5
Nantucket's grey-shingled aesthetic is enforced by strict design codes — there are no billboards, no chain restaurants, no neon signs
6
The shoulder season (late May, September) is the best value — restaurants are less frantic and the weather is still excellent
•Drive to Hyannis, fast ferry to Nantucket (1 hr)
•Check in, walk to Children's Beach and Brant Point
•Afternoon: Main Street and the whaling town walk
•Evening: Dinner at Cru on the harbor
•Morning: Nantucket Whaling Museum
•Midday: Bike to Surfside Beach (3 miles, flat)
•Afternoon: Ocean swim and beach time
•Evening: Lola 41 for dinner
•Morning: Great Point guided AWD tour (book ahead)
•Midday: Downyflake for doughnuts
•Afternoon: Windswept Cranberry Bog walk
•Evening: Ferry home
More guides at GrandkidsGuide
14 more destination guides for grandparents in the Northeast — plus a full local directory for Fairfield County CT, Westchester, Nassau, and Suffolk County NY.
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