Nantucket is a small, sandy island about 30 miles south of Cape Cod - far enough out to sea that the Wampanoag name is often translated as "faraway land," and remote enough that the entire island is a National Historic Landmark District. At its heart is Nantucket Town, a cobblestoned former whaling capital whose gray-shingled and white-clapboard houses, brick Main Street, and harbor full of sailboats look much as they did in the 1840s, when Nantucket was the whaling center of the world. The Whaling Museum, set in an old spermaceti candle factory, anchors that history with a full sperm-whale skeleton and a rooftop harbor view. Beyond town the island opens into miles of public beaches - calm, kid-friendly Children's and Jetties beaches near town; the big Atlantic surf at Cisco and Surfside; and the quiet east-end village of Siasconset ("Sconset"), with its rose-covered cottages, the Sankaty Head Light, and a bluff walk above the sea. Brant Point Light, the squat white tower every ferry passes on the way in, is the island's signature image and the traditional first and last sight of any Nantucket trip.
Getting here means a ferry from Hyannis on Cape Cod - either the slower car-carrying Steamship Authority boat (about 2 hours 15 minutes) or a fast passenger-only ferry (about an hour); Hy-Line also runs fast ferries. Bringing a car is expensive and must be booked far ahead, so most reunions arrive on foot and rely on bikes, the island's NRTA shuttle buses, and taxis - the island is only about 14 miles long and laced with flat bike paths. Hyannis (HYA), Boston Logan (BOS), and Providence (PVD) are the practical mainland airports, and Nantucket Memorial Airport (ACK) takes seasonal direct flights. Lodging runs from historic in-town inns (the White Elephant on the harbor, the Jared Coffin House, the Nantucket Hotel) to the heart of the group market - gray-shingled vacation rentals from cottages in town to 5-8 BR houses out toward Sconset and Cisco. Peak season is late June through Labor Day, with July and August the most competitive and expensive; June and September are the value windows - warm water, thinner crowds, and noticeably lower rates. Book the ferry and the houses early and the island gives back a slow, lantern-lit, salt-air week.
Where it is
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Things to do (with the family)
Hand-curated. Every entry links to its official source so you can plan without guessing.
Nantucket Whaling Museum
The island's landmark museum in an 1847 spermaceti candle factory - a full 46-foot sperm-whale skeleton, a working Fresnel lens, scrimshaw, and a rooftop observation deck over the harbor. The history anchor of any Nantucket reunion. Admission ~$25/adult; kids discounted.
Official source ↗Nantucket Town & cobblestone Main Street
The cobblestoned former whaling capital - brick Main Street, the Pacific National Bank, gray-shingled shops, and the harbor. Self-guided strolling through a National Historic Landmark District. The flat, walkable heart of the island. Free.
Official source ↗Brant Point Light
The short white lighthouse at the harbor entrance that every ferry passes - the most photographed spot on the island and the traditional first/last sight of a Nantucket trip. A flat, easy walk from town to a small beach below it. Free.
Official source ↗Siasconset ("Sconset") village & bluff walk
The quiet east-end village of rose-covered cottages, a small market, and the Sconset Bluff Walk - a public footpath between hedges and the sea past grand summer houses. The classic Nantucket day-trip-within-the-island. Free.
Official source ↗Cisco Beach
A big south-shore Atlantic surf beach popular with surfers and older kids, near Cisco Brewers. Lifeguarded sections in summer; real waves and undertow, so watch younger swimmers. The teen-and-surf reunion beach day. Free; parking fills early.
Official source ↗Jetties & Children's Beach (calm swimming)
The calm north-shore beaches a short walk or shuttle from town - Children's Beach (playground, bandstand, shallow water) and Jetties (snack bar, calm harbor swim, watersport rentals). The little-kids and grandparents beach. Free.
Official source ↗Island bike paths
Flat, paved bike paths connect town to Sconset, Surfside, Madaket, and Cisco - the best way to see the island car-free. Rent in town; tag-alongs and trailers available. The active multi-gen half-day. Rentals ~$30-40/day.
Official source ↗Sankaty Head Light
The red-and-white striped lighthouse on the bluff above Sconset, moved back from the eroding cliff in 2007. A scenic stop on the east-end ride or drive, with big ocean views. Pairs with the Sconset Bluff Walk. Free to view.
Official source ↗Great Point Light & Coskata-Coatue refuge
A remote lighthouse at the island's northern tip, reached by a guided over-sand tour or a 4WD oversand permit through the Coskata-Coatue Wildlife Refuge. Seals, shorebirds, and empty beach. The adventurous-group outing. Tour fees apply.
Official source ↗Maria Mitchell Association (science & stargazing)
Named for the pioneering Nantucket astronomer, the association runs a natural-science museum, an aquarium, and public observatory stargazing nights. The rainy-afternoon and curious-kids win. Modest admission; combo passes available.
Official source ↗Cisco Brewers (brewery, winery & distillery)
A laid-back outdoor compound combining a brewery, winery, and distillery with food trucks and live music - bikeable from town. The relaxed adult afternoon; food trucks keep kids fed. Tastings and drinks pay-as-you-go.
Official source ↗Nantucket lightship basket weaving & shops
Nantucket's signature handcraft - the woven lightship basket - is sold and demonstrated in town shops and at the Lightship Basket Museum. A short, distinctive cultural stop and the island's classic keepsake. Museum admission modest.
Official source ↗Harbor sailing, kayaking & seal cruises
Sailing charters, kayak and SUP rentals out of Jetties and the boat basin, and seasonal seal- and lighthouse-watching cruises from the harbor. Calm protected water for first-timers. The on-the-water splurge. Charters and rentals vary.
Official source ↗Surfside Beach
A wide south-shore Atlantic beach reachable by bike path or shuttle from town, with lifeguards, a snack shack, and room to spread out a big group. More surf than the north-shore beaches but family-manageable. The reunion big-beach-day option. Free.
Official source ↗Find more things to do for your Nantucket, Massachusetts reunion
The picks above are general. Inside the Reunly app, Rosi tailors local activities, meals, and printables to your actual dates, group size, ages, and budget - and saves them straight to your reunion plan.
Where to hold your reunion near Nantucket, Massachusetts
Outdoor pavilions, county parks, fairgrounds, and event grounds within driving distance - places where your group can actually gather, not just visit.
The Nantucket Hotel & Resort - Function Space
🏨 Resort / LodgeA large family-focused in-town resort with pools, kids' programs, ballroom and function space, and full catering, walkable to Main Street and the harbor. The easiest single anchor for a large Nantucket reunion. Inquire about group blocks.
Reserve / info ↗White Elephant - Harbor Lawn & Event Space
🏨 Resort / LodgeThe premier harbor-front hotel with cottages, suites, lawn and event space, and harbor views steps from town. A polished base-plus-gathering option for a mid-to-large reunion. Inquire about group reservations and events.
Reserve / info ↗Jetties Beach - Town Pavilion & Picnic Area
📍 VenueA town beach with a bathhouse, snack bar, tennis and volleyball, and picnic/event space the town rents for gatherings - a calm, accessible spot for a big group beach cookout near town. Inquire with the town for event use.
Reserve / info ↗Nantucket Historical Association - Whaling Museum Events
🏛 Event CenterThe Whaling Museum and its rooftop deck and galleries host private group events - a distinctive, history-rich venue for a milestone reunion dinner or gathering in the heart of town. Contact the NHA events office.
Reserve / info ↗Cisco Brewers - Outdoor Compound
🏛 Event CenterThe brewery-winery-distillery compound with an outdoor yard, food trucks, and live music hosts relaxed group gatherings - a casual, all-ages reunion-party venue away from the in-town formality. Inquire about group events.
Reserve / info ↗Maria Mitchell Association - Group Programs
📍 VenueThe Maria Mitchell Association runs guided natural-science walks, aquarium tours, and observatory stargazing nights bookable for groups - an educational add-on and quiet gathering option for a multi-generation reunion.
Reserve / info ↗👥 With Reunly
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Good for
- Walkable, car-free island reunions (bikes and shuttles)
- Classic New England whaling-history multi-gen groups
- Harbor-town-and-beach long weekends
- Quiet, upscale, slow-paced reunions
- Shoulder-season (June / September) value reunions
- Lighthouse-and-village photo reunions
Practical logistics
- Closest Airports
- Nantucket Memorial Airport (ACK) on-island with seasonal direct flights. Cape Cod / Hyannis (HYA) at the Hyannis ferry terminals. Boston Logan (BOS) ~1.5 hr to Hyannis plus the ferry. T.F. Green / Providence (PVD) ~1.5-2 hr to Hyannis.
- Drive Times
- Hyannis ferry terminal: Boston ~1.5 hr · Providence ~1.75 hr · New York ~4.5 hr to Hyannis, then a fast ferry (~1 hr) or the car ferry (~2 hr 15 min). On-island, no point is more than ~30 min from another.
- Group Lodging
- White Elephant (harbor-front, the premier in-town hotel, cottages and suites). The Nantucket Hotel & Resort (family-focused, pools, large). Jared Coffin House (historic, town center). The Wauwinet (up-island luxury inn). Vacation rentals are the heart of the group market - gray-shingled cottages in town to 5-8 BR houses toward Sconset and Cisco, on Vrbo, Airbnb, and local agencies.
- Rental Companies
- Fisher Real Estate, Congdon & Coleman, Great Point Properties, and Lee Real Estate handle most managed island rentals; Vrbo and Airbnb cover the rest. Book group houses by January for July and August; the best in-town houses go first.
- House Size
- 3-5 BR gray-shingled cottages are the standard in-town inventory. 6-8 BR houses exist out toward Sconset, Cisco, and Monomoy (limited, $10,000-30,000+/week peak). For 25+ people, the play is two or three adjacent rentals plus an in-town inn block at the White Elephant or Nantucket Hotel.
- Peak Season
- Late June through Labor Day. July and August are the single most competitive and expensive; book houses 6-9 months ahead and ferry car space the moment the schedule opens. The Fourth of July and the August weeks are the tightest.
- Shoulder Season
- June (water warming, fewer crowds) and September through Columbus Day (warm ocean, lower rates, restaurants open); the Nantucket Wine & Food Festival (spring) and the Christmas Stroll (December) are off-peak draws. Late September is the locals' favorite.
- Restaurants
- The Brotherhood of Thieves (whaling-era pub, casual, family) · Black-Eyed Susan's (breakfast institution, expect a line) · Cru and the Straight Wharf (upscale harbor dining, milestone dinners, reserve ahead) · Millie's (Madaket, casual Mexican and sunset) · Something Natural (the giant-sandwich picnic stop) · the Juice Bar (the after-dinner ice-cream line). Reserve group dinners 2-3 weeks ahead in summer; the best tables book further out.
- Kid Friendly
- Children's Beach (playground, shallow water, bandstand), Jetties Beach, the flat bike paths, the Whaling Museum, the Maria Mitchell aquarium and observatory, Brant Point Light, and the Juice Bar are reliable wins for ages 3-15. Children's and Jetties in particular suit younger kids - calm harbor-side water.
- Accessibility
- Nantucket Town is walkable but the cobblestone streets and brick sidewalks are uneven - plan for that with wheelchairs and unsteady walkers. Children's and Jetties beaches have accessible areas and beach wheelchairs (reserve through the town). The White Elephant and Nantucket Hotel have elevator/ground-floor rooms; historic inns and cottages vary - confirm when booking. NRTA shuttles are accessible.
- Weather Window
- Summer 72-80°F days, 58-66°F nights, cooler and breezier than the mainland; water 64-70°F by August. June and September 62-76°F days, warm ocean in September. Fog is common and can linger. Hurricane-season awareness late August through October.
- Park Fee
- No island entry fee. All beaches are free; some have paid parking in season. Great Point oversand access requires a permit or a guided-tour fee. Museums (Whaling Museum, Maria Mitchell) charge admission.
- Official Site
- https://www.nantucketchamber.org/
When to go
Late June through Labor Day for full beach season; July and August are the most competitive and expensive, so book houses 6-9 months ahead and ferry car space the moment the schedule opens. For the best value-to-weather ratio, target September through Columbus Day - warm ocean, lower rates, and restaurants still open. June is the spring sweet spot.
Best for your group size
Small group · 10–25
10-25 fits in a 4-6 BR gray-shingled house in town or near Sconset, or a block of rooms at the White Elephant, Jared Coffin House, or Nantucket Hotel.
Medium group · 25–60
25-60 should book two or three adjacent vacation rentals plus an inn block at the White Elephant or the Nantucket Hotel, splitting families between in-town and Sconset/Cisco bases.
Large group · 60+
60+ groups combine multiple vacation rentals with a hotel block (the Nantucket Hotel & Resort and the White Elephant are the largest properties) and use a beach, a restaurant's private room, or an event venue for the big group meals. No single property absorbs 60+ rooms easily, so plan a multi-property island reunion - and book the ferry first.
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Sample 5-day Nantucket reunion (summer)
A starter agenda you can copy into Reunly's Schedule and customize for your group.
Friday - Ferry Over & Nantucket Town
- 11:00 AM Hyannis fast ferry to Nantucket (reserve car space far ahead if bringing a car)
- 12:30 PM check-in at the rental or White Elephant; pass Brant Point Light on the way in
- 2:30 PM explore cobblestone Main Street and the wharves
- 4:00 PM Children's Beach - shallow swim and playground
- 6:30 PM group dinner at the Brotherhood of Thieves
- 8:30 PM the Juice Bar for ice cream
Saturday - Whaling Museum & Jetties
- 8:30 AM breakfast (or the Black-Eyed Susan's line)
- 10:00 AM Nantucket Whaling Museum and rooftop deck
- 12:00 PM Something Natural sandwiches for a beach picnic
- 1:00 PM Jetties Beach - calm swim, watersport rentals
- 4:00 PM Brant Point Light walk and photos
- 7:00 PM dinner at the Straight Wharf
Sunday - Sconset & the Bluff Walk
- 8:30 AM breakfast at the rental
- 9:30 AM bike or shuttle out to Siasconset
- 10:30 AM Sconset Bluff Walk past the rose-covered cottages
- 12:00 PM lunch in Sconset
- 1:30 PM Sankaty Head Light photos
- 6:30 PM cook night at the rental
Monday - Cisco, Beaches & Brewers
- 9:00 AM breakfast at the rental
- 10:00 AM Surfside or Cisco Beach (surf for the teens, lifeguarded sections)
- 1:00 PM lunch at the Cisco Brewers food trucks
- 3:00 PM Maria Mitchell aquarium (cooler indoor break)
- 5:00 PM Millie's in Madaket for an early dinner and sunset
Tuesday - Town, Keepsakes & Goodbyes
- 8:30 AM breakfast at the rental
- 10:00 AM in-town shopping - lightship baskets and gray-shingle storefronts
- 11:30 AM last walk to Brant Point Light
- 12:30 PM goodbye lunch in town
- 2:00 PM afternoon ferry back to Hyannis
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Build the Nantucket, Massachusetts reunion schedule in minutes
Drag the sample itinerary above into Reunly's Schedule, add per-event RSVPs, and share one link with the whole family. Rosi (our AI) fills in gaps from your group size and dates.
Reunion organizer tips
Book the ferry before you book anything else. Car space on the Hyannis - Nantucket Steamship Authority boat sells out months ahead for summer and is expensive; reserve the moment the schedule opens. Most reunions skip the car entirely - park in Hyannis, take a fast passenger ferry, and use bikes and the NRTA shuttle on-island.
Plan to be car-free. Nantucket is only ~14 miles long, flat, and laced with paved bike paths and shuttle routes. Skipping the car saves the priciest ferry slots and the town's scarce, expensive parking. Reserve one taxi or rental on-island for any heavy grocery or up-island runs.
Book group houses by January for July and August. The best in-town gray-shingled houses and the larger Sconset and Cisco houses are the scarcest inventory and go first. For 25+ people, plan two or three adjacent rentals plus an in-town inn block rather than one giant house.
Pick your base to match the group. In-town for walkability to restaurants, the museum, and Children's Beach with kids and grandparents; out toward Sconset for quiet, rose-covered-cottage charm and the bluff walk; near Cisco/Surfside for surf beaches and the brewery, with bike or shuttle access to town.
Use the calm north-shore beaches for little kids. Children's Beach (playground, shallow, bandstand) and Jetties are the toddler-and-grandparent beaches; save Cisco and Surfside's Atlantic surf for teens and strong swimmers. Having both within a short shuttle ride is Nantucket's flexibility.
Rent bikes for a Sconset day. The flat path out to Siasconset, the Sconset Bluff Walk, and Sankaty Head Light make the best low-effort multi-gen outing. Shops rent trailers and tag-alongs. Plan it for a cooler morning and pack a Something Natural sandwich.
Reserve group dinners 2-3 weeks ahead in summer. The Brotherhood of Thieves and Millie's handle big casual tables; Cru and the Straight Wharf are the harbor-side milestone splurges. Black-Eyed Susan's breakfast line is worth getting one person in early for.
Stock the rental on arrival day. The Stop & Shop in town is the big food run; prices run high on-island and selection thins. Bring or buy enough for the first day before you settle in. Order ahead online if you want a delivery slot in peak summer.
Mind the fog. Sea fog rolls in even in high summer and can ground flights and gray out a beach day. Keep an indoor backup ready - the Whaling Museum, the Maria Mitchell aquarium, or in-town browsing all work, and the fast ferries usually still run.
Build a sunset tradition. Millie's in Madaket, the Brant Point beach, and the Sconset Bluff are the classic golden-hour spots. Pick one as the group's nightly or farewell gathering - an easy, mostly free evening ritual.
Consider a Great Point or seal cruise for the adventurous half. A guided Great Point lighthouse over-sand tour or a harbor seal-watch cruise gives the active part of the group a memorable half-day while others stay in town. Book ahead in summer.
Let Reunly handle the logistics. Use the budget tool to split lodging and the steep ferry costs across the houses, the polls feature to vote between the Sconset day and the Cisco beach day, and the itinerary to keep everyone synced on ferry times and shuttle plans.
How Reunly helps you plan it
Reunly is the all-in-one app made for family reunion organizers. Free to start. No credit card. Cancel anytime.
Smart guest list
Drop in any spreadsheet - Rosi (our AI) reads multi-sheet, color-coded family groups, even handwritten exports. RSVP, dietary, T-shirt, paid status all in one row.
Open in Reunly →Public RSVP link
Share one link with the whole family. They RSVP per event (Friday BBQ, Saturday dinner) without making an account. You see live counts.
Open in Reunly →Budget that adds up
Track estimated vs. actual, who paid, who still owes. Auto-creates per-guest fee rows from your registration cost.
Open in Reunly →Day-by-day schedule
Friday welcome BBQ, Saturday photo, Sunday brunch - with location, meal flag, and per-event RSVPs.
Open in Reunly →Name tags + printables
Avery 5160 sheets color-coded by family, programs, welcome packets, packing lists - auto-filled from your data.
Open in Reunly →Rosi the AI helper
Stuck on a reminder email? A budget? A timeline? Click Rosi anywhere in the app - she drafts it from your live data.
Open in Reunly →Plan your Nantucket, Massachusetts reunion with Reunly
Free to start. Build your guest list, share an RSVP link, track payments, and print name tags - no spreadsheets.
Frequently asked
What's the best time to book Nantucket for a family reunion?
Late June through Labor Day for full beach season; July and August are the most competitive and expensive, so book houses 6-9 months ahead and ferry car space the moment the schedule opens. For the best value, target September through Columbus Day - warm ocean, lower rates, and restaurants still open. June is the spring sweet spot.
How do we get to Nantucket, and do we need a car?
You reach Nantucket by ferry from Hyannis - either the slower car-carrying Steamship Authority boat (~2 hr 15 min) or a fast passenger-only ferry (~1 hr; Hy-Line also runs fast ferries). Bringing a car is expensive and books out months ahead. Most reunions go car-free: the island is only ~14 miles long, flat, and laced with bike paths and NRTA shuttle routes.
What is the closest airport to Nantucket?
Nantucket Memorial Airport (ACK) is on-island with seasonal direct flights. Otherwise, Boston Logan (BOS) and Providence (PVD) are about 1.5-2 hours to the Hyannis ferry, and Cape Cod/Hyannis (HYA) is right at the ferry terminals. Most mainland-Northeast families drive to Hyannis and take a fast ferry over.
How big a house do we need for 25 people on Nantucket?
A 6-8 BR house out toward Sconset or Cisco (limited, $10,000-30,000+/week peak), or two adjacent 4-5 BR in-town cottages. For 40+ people the standard play is three or four adjacent rentals plus a block of rooms at the White Elephant or the Nantucket Hotel & Resort.
Is Nantucket good for little kids and grandparents?
Yes - Children's Beach (playground, shallow water, bandstand) and Jetties Beach are calm and family-friendly, the bike paths are flat, and the Whaling Museum and Maria Mitchell aquarium suit ages 3-15. Note that the town's cobblestone streets are uneven, so plan routes carefully for wheelchairs and unsteady walkers.
Should we base our reunion in town or out by Sconset?
In-town for walkability to restaurants, the Whaling Museum, and Children's Beach with kids and grandparents; out toward Siasconset (Sconset) for quiet, rose-covered-cottage charm and the bluff walk; near Cisco or Surfside for the surf beaches and brewery, with bike or shuttle access back to town.
How much does a week-long Nantucket reunion cost per family?
Nantucket is among the pricier Northeast islands. Peak July/August: roughly $5,000-10,000+ per family of 4 (lodging and food run high, plus the ferry). Shoulder season (June, September): noticeably lower. Going car-free saves the priciest ferry slots and town parking. Beaches, the bike paths, and the village walks are free.
What is there to do on Nantucket besides the beach?
The Nantucket Whaling Museum and cobblestone historic town, Brant Point and Sankaty Head lighthouses, the Siasconset village and bluff walk, the Maria Mitchell aquarium and observatory, Cisco Brewers, lightship-basket shops, harbor sailing and seal cruises, and a guided Great Point lighthouse over-sand tour.
Other reunion-friendly spots nearby
Helpful planning guides
The complete family reunion checklist
12-month, 6-month, and day-of checklists organizers actually use.
Read the guide →Family reunion budget guide
How to estimate, track, and split costs without spreadsheets.
Read the guide →Family reunion on a $2,500 budget
A real budget breakdown for a destination reunion under $2.5K.
Read the guide →