Arrive, Wander the Cobblestones & First Oysters
You're on an island 30 miles out to sea. The moment the ferry pulls into the harbor and you see the grey-shingled rooftops and the Brant Point Lighthouse, something shifts. Today is about settling in, exploring the town on foot, and eating your first lobster roll.
🌅 Morning/Midday — Arrival
Ferry to Nantucket
Take the Hy-Line High-Speed Ferry from Hyannis (~1 hour, ~$45/person one-way) or the Steamship Authority fast ferry (~1 hour). As you pull into the harbor, watch for Brant Point Lighthouse on the left — it's the second-oldest lighthouse in America and your first "we're really here" moment.
Drop your bags at your accommodation and head straight into town. Everything in Nantucket Town is walkable.
If you're flying, Cape Air and JetBlue run seasonal flights to ACK from Boston, NYC, and other hubs. The approach over the ocean is stunning.
🍽️ Lunch — First Lobster Roll
Lunch
Cru Oyster Bar
Right on Straight Wharf with harbor views. Start with a dozen raw oysters and a glass of rosé, then get the lobster roll — warm butter, perfectly sweet meat, on a toasted split-top bun. This is the quintessential Nantucket lunch. Sit outside if the weather cooperates (it should — it's late May).
📍 1 Straight Wharf · $$$ · Reservations recommended for dinner, lunch is more flexible · Opens seasonally late May
🚶 Afternoon — Explore Town
Cobblestone Main Street & Whaling Museum
Stroll up Main Street — the wide cobblestone avenue lined with elm trees, brick storefronts, and galleries. This is the heart of Nantucket and it looks like it hasn't changed in 200 years (because it mostly hasn't). Browse the boutiques, peek into art galleries, grab a coffee.
Visit the Whaling Museum — a beautifully curated museum in a former candle factory that tells the story of Nantucket's whaling era. The 46-foot sperm whale skeleton suspended from the ceiling is jaw-dropping. The rooftop observation deck has panoramic views of the harbor and town.
📍 Whaling Museum: 13 Broad St · $20/person · 10:00–17:00
🌊 Late Afternoon — Brant Point
Walk to Brant Point Lighthouse
A 15-minute walk from town along the harbor to Nantucket's most iconic landmark. The lighthouse is small but photogenic, and the little beach next to it is a perfect spot to sit and watch the ferries come in. Throw a penny in the water on your way off the island (tradition says it guarantees your return).
📍 Easton St, end of the road · Free · Always open
🌙 Evening — Dinner
Dinner
The Proprietors
A stylish cocktail bar and restaurant on India Street with inventive New American dishes. The craft cocktails are some of the best on the island. Try the Nantucket Bay scallops if they're on the menu — sweet, tender, and impossibly fresh. The atmosphere is buzzy but not loud — perfect for a first-night dinner.
📍 9 India St · $$$ · Reservations strongly recommended · Opens 17:00
Beach Morning, Farm Stand & Craft Brewery Afternoon
Today is the perfect Nantucket day — morning at the beach, a stop at the island's legendary farm stand, and an afternoon at Cisco Brewers with live music and cold drinks in the sun. This is island time at its finest.
🍳 Morning — Breakfast
Breakfast
Something Natural
A Nantucket institution. Massive sandwiches on homemade bread — the kind of thick, hearty, fresh-baked bread that ruins you for store-bought forever. Get a breakfast sandwich or a classic turkey on herb bread for a packed beach lunch later. The chocolate chip cookies are legendary. Eat in the garden out back.
📍 50 Cliff Rd · $ · Cash or card · Opens 8:00 · Closed in winter
🏖️ Late Morning — Beach Time
Surfside Beach
Nantucket's most popular beach, and for good reason — wide sandy shore, good waves, and a classic beach shack for snacks. It's a 15-minute bike ride from town (flat, paved bike path the whole way) or take the NRTA shuttle. In late May the crowds are still manageable. Bring a blanket, sunscreen, and the sandwiches from Something Natural.
The water will be brisk (~59°F/15°C) but the brave take a dip. The beach itself is beautiful even just for lounging and listening to the waves.
📍 Surfside Beach, end of Surfside Rd · Free · Lifeguards on duty from Memorial Day · Bike path from town
"Surfside is the go-to beach but honestly in late May it's not crowded at all. Bike there on the bike path — it's flat and beautiful. The beach shack has decent food if you didn't pack lunch."
— r/Nantucket
🌿 Early Afternoon — Farm Stop
Bartlett's Farm
The island's oldest and largest farm — a gorgeous farm stand with fresh produce, prepared foods, flowers, baked goods, and everything you need for a picnic. Grab some local cheeses, fresh bread, and whatever looks good. Even if you don't buy much, it's a beautiful stop and a reminder that this island grows its own food.
📍 33 Bartlett Farm Rd · Free to visit · 7:30–18:00
🍺 Afternoon — Cisco Brewers
Cisco Brewers
This is not just a brewery — it's a whole campus. Cisco Brewers (craft beer), Triple Eight Distillery (vodka, gin, whiskey), and Nantucket Vineyard (wine) all share one sprawling outdoor space with picnic tables, food trucks, and live music most afternoons. It's the island's unofficial gathering place.
Order a flight of Cisco beers (the Whale's Tale Pale Ale is the classic), try a cocktail with Triple Eight cranberry vodka, and settle in. The vibe is laid-back, sunny, and perfectly Nantucket. You could easily spend 2–3 hours here without trying.
📍 5 Bartlett Farm Rd · Free entry · Beer flights ~$12–16 · Live music most days in season · Opens 12:00
"Cisco Brewers is an absolute must. We went planning to stay an hour and ended up spending the whole afternoon. Great beer, great vibes, food trucks, live music. Don't miss it."
— r/Nantucket
🌙 Evening — Dinner
Dinner
Lola 41
A sushi and global-fusion restaurant that's become a Nantucket favorite. The sushi is excellent (fresh island fish), the tuna tartare tacos are a must-order, and the cocktails are creative. The vibe is upscale-casual — perfect for a date night. Sit at the bar if you didn't get a reservation.
📍 15 S Beach St · $$$ · Reservations recommended · Opens 17:30
Bike to 'Sconset, Rose-Covered Cottages & Jetties Beach
Today you'll bike across the island to Siasconset ('Sconset) — the tiny village on the eastern shore with rose-covered cottages that looks like a movie set. It's the most charming ride on the island, and the village at the end is worth every pedal stroke.
🍳 Morning — Fuel Up
Breakfast
Black-Eyed Susan's
A beloved Nantucket breakfast spot with creative dishes — think sourdough French toast with caramelized pecans, or eggs with spicy chorizo and peppers. It's small and popular, so arrive early or expect a short wait. Worth it. Cash only.
📍 10 India St · $$ · Cash only · Opens 7:00 · No reservations
🚲 Morning — Bike Ride
Milestone Bike Path to 'Sconset
Rent bikes and take the Milestone Road Bike Path — a flat, paved, dedicated cycling path that runs 6.5 miles from town to 'Sconset. The ride takes about 40–50 minutes at a leisurely pace, passing through moors, grasslands, and the occasional pond. It's one of the most scenic bike rides in New England.
The path is well-maintained, flat (Nantucket has essentially no hills), and separated from car traffic. Pack water and sunscreen.
📍 Starts near Rotary off Orange St · Bike rentals: Young's Bicycle Shop, $30–40/day
You can also take the NRTA 'Sconset shuttle if biking isn't your thing, but the ride is genuinely beautiful and easy. Electric bikes are available at most rental shops too.
🏘️ Late Morning — 'Sconset Village
Siasconset ('Sconset)
A tiny village of grey-shingled cottages draped in climbing roses (they'll be just starting to bloom in late May). The village is impossibly charming — narrow lanes, white picket fences, a general store, and a bluff walk with ocean views. Walk the 'Sconset Bluff Walk — a path along the eroding bluff with sweeping views of the Atlantic. It's short but stunning.
The 'Sconset Casino (not a gambling casino — it's a tennis and cultural club from the 1800s) hosts movies and events in summer. The building itself is beautiful.
📍 Siasconset, eastern shore · Free to explore · Bluff Walk: open dawn to dusk
🍽️ Lunch in 'Sconset
Lunch
'Sconset Café
A charming little café in the village center. Fresh salads, sandwiches, and baked goods. Sit on the patio in the sunshine. It's simple, fresh, and exactly what you want after a bike ride. If they have the lobster salad, get it.
📍 Post Office Square, 'Sconset · $$ · Seasonal hours
🏖️ Afternoon — Jetties Beach
Jetties Beach
Bike back to town (or take the shuttle) and spend the afternoon at Jetties Beach — the closest beach to town, with calm waters, a playground, and a beach bar. It's more sheltered than Surfside, making it perfect for a mellow afternoon. The Jetties Beach Bistro serves drinks and food right on the sand.
📍 4 Bathing Beach Rd · Free · Lifeguards on duty · 10-minute walk from town
💆 Late Afternoon — Spa
White Elephant Spa
Treat yourselves to a couples massage or treatment at the White Elephant Resort spa. It's one of the island's premier spas — serene, beautifully appointed, with harbor views. Book a 60-minute couples massage to recover from the bike ride. Pure indulgence.
📍 50 Easton St, White Elephant Resort · $$$ · Book ahead: (508) 228-2500
🌙 Evening — Dinner
Dinner
Ventuno
Northern Italian with Nantucket flair — handmade pastas, local seafood, and a romantic candlelit atmosphere in a historic building. The pappardelle with short rib ragu is comfort food perfection. Great wine list. One of the island's most romantic dinner spots.
📍 21 Federal St · $$$ · Reservations required · Opens 17:30
Lazy Beach Day & the Best Sunset You've Ever Seen
Your last full day. No agenda, no rushing. A beach, some tacos, and the legendary Madaket sunset. This is the day you'll remember most.
🍳 Morning — Slow Start
Breakfast
Provisions
A gourmet deli and café on Straight Wharf. Excellent coffee, breakfast sandwiches, and pastries. Grab provisions for a beach picnic too — their sandwiches and salads are perfect for packing in a cooler.
📍 3 Harbor Square · $$ · Opens 7:00
🏖️ Late Morning — Cisco Beach
Cisco Beach
The locals' beach. Wider, wilder, and less crowded than Surfside. Great waves, big sky, and a raw Atlantic energy. Spread out your blanket, read a book, nap in the sun. This is the kind of beach day that recharges your soul. You're 10 minutes by bike from Cisco Brewers if you need a mid-day drink.
📍 End of Hummock Pond Rd · Free · No lifeguards (swim at your own risk) · Bike path available
🌅 Late Afternoon — Head to Madaket
Madaket Beach — Sunset
This is the main event. Madaket Beach faces due west and has what many consider the most spectacular sunset on the East Coast. The sky turns every shade of pink, orange, and purple as the sun drops into the ocean. It's a 20-minute bike ride or shuttle from town — take the Madaket Bike Path (flat, beautiful, 5.5 miles).
Arrive at least an hour before sunset to grab a good spot. Bring a blanket and a bottle of wine. Watch the sky change. This is the kind of moment that makes a trip.
📍 End of Madaket Rd, western tip of island · Free · Sunset ~8:10 PM in late May
"Madaket sunset is not overhyped. We've watched sunsets all over the world and this was genuinely one of the best. The sky just goes insane with color. Get there early with a blanket and wine."
— r/Nantucket
🌮 Dinner — Madaket
Dinner
Millie's
A beloved Madaket institution right near the beach. Famous for their fish tacos, lobster tacos, and frozen margaritas. The vibe is casual, beachy, and fun — paper plates, picnic tables, and the smell of the ocean. It's the perfect post-sunset dinner. Get the fish tacos and a marg. Don't overthink it.
📍 326 Madaket Rd · $$ · Seasonal · Can be a wait — put your name in before sunset · Cash and card
Millie's can have long waits on summer evenings. Strategy: put your name in before walking to the beach for sunset, then come back for dinner. Perfectly timed.
One Last Morning Walk, Then Home
A gentle final morning. Soak in the last of the island before catching the ferry back to the mainland. No rush — just one more walk, one more coffee, one more look at those cobblestones.
🍳 Morning — Farewell Breakfast
Breakfast
Handlebar Café
A cute café with great coffee, smoothie bowls, and avocado toast. Light, fresh, and perfect for a last morning. Sit on the patio and watch the town wake up one more time.
📍 15 Washington St · $ · Opens 7:00
🚶 Morning — Last Walk
Morning Stroll Through Town
Take one final walk through the cobblestone streets. Wander down Centre Street and India Street, peek into the shops you missed, and grab any last-minute souvenirs. Pick up saltwater taffy, Nantucket-themed goods, or a jar of beach plum jam from one of the specialty shops.
Walk back to Brant Point Lighthouse one more time. Throw your penny in the harbor. You'll be back.
✈️ Midday — Departure
Ferry Back to Hyannis
Head to the Steamship Authority or Hy-Line dock for your ferry back. Grab a seat on the upper deck for one last look at the island as it shrinks into the ocean behind you. The hour-long ride is a nice decompression before heading home.
Don't forget to throw your penny at Brant Point as you pass by on the ferry — tradition says it guarantees your return to Nantucket.
🐚 Nantucket Tips for Couples
A few more things to make your trip perfect.
Nantucket is expensive. Budget roughly $150–250/day for food for two at a mix of casual and nice spots. Accommodations in late May run $250–500+/night for a good hotel or B&B. The island is worth it.
Bikes are the best way to get around. The island is flat and has dedicated bike paths to all major beaches. Rent for the whole trip (~$30–40/bike/day) and you'll never need a car or Uber.
The NRTA shuttle is $2/ride and runs to Surfside, Madaket, 'Sconset, Jetties, and the airport. Great backup if you don't feel like biking.
Pack layers. Days are warm but evenings get cool, especially at the beach. A light jacket or sweater is essential for sunset at Madaket.
If you want to try Nantucket Bay scallops — the island's signature delicacy — ask at any restaurant. They're sweet, tender, and unlike any scallop you've had. Season runs fall through winter, but many restaurants feature them year-round when available.
For a romantic splurge, book a sunset sail from Nantucket Harbor. Several companies offer 2-hour cruises with drinks. Seeing the island from the water at golden hour is magical.