Everything from Lucy's list, placed into actual days, around the things that can only happen on certain ones. Booked items are marked. Tap a leg to jump.
Leg one
Honolulu
Fri 28 Aug β Thu 3 Sep Β· 6 nights Β· Castle Ilikai Tower, Waikiki Β· all three of us
Two things fix the shape of this week. Hanauma Bay is closed Monday and Tuesday, and the Aloha Stadium Swap Meet only runs Wednesday, Saturday and Sunday. Both want the same three days, so Saturday and Sunday are spoken for before anything else gets a look in.
01Fri 28 AugLand, and do nothing much
08:25Land at HonoluluNine hours in the air and you gain a day crossing the date line. Bags to the Ilikai, but the room won't be ready until mid afternoon.
Late morningBreakfast, then Waikiki BeachDon't drive anywhere. Don't book anything. Sit down.
AfternoonKaimana BeachLucy's listTwenty minutes' walk east along the sand, past the aquarium. Quieter than the main strip and good for a first snorkel. Lucy's note: "good beach for snorkelling."
EveningEarly dinner, early nightEveryone will be wrecked. Fighting it makes the next three days worse.
02Sat 29 AugHanauma Bay
β Thu 27Book it two days before, 7am Hawaii timeAlarmReservations open exactly 48 hours ahead and go within minutes. This is the single most likely thing on the trip to be missed.
MorningHanauma Bay Nature PreserveLucy's listThirty minutes east. A flooded volcanic crater and the best snorkelling on the island without a boat. There's a short mandatory briefing video before you go down to the water.
AfternoonBack to Waikiki, nothing plannedSecond day of jet lag. Leave it open on purpose.
03Sun 30 AugDiamond Head at dawn, then the flea market
05:40Out the doorBus route 23 from Waikiki, about 15 minutes. Water and a hat. Mum's sitting this one out.
06:00β07:00Diamond Head CraterBookedLucy's listEntry-only reservation, 2 people. The bus stops outside the crater, so allow 15 minutes to walk in through the tunnel before the trail even starts. Sunrise is about 6:15, so you'll summit after it β but the low sun behind you lights up Waikiki, which is the shot anyway.
09:00Aloha Stadium Swap MeetLucy's listOpens 6:30 on Sundays and runs to 3pm, so there's no rush. About 25 minutes across town. Hundreds of stalls β this is the souvenir run, and it's a fraction of Waikiki prices. Lucy's note: "flea MARKET!"
AfternoonHome and horizontalYou'll have been up since before five.
04Mon 31 AugThe windward coast β the big one
Hire carOne day's rental covers all of thisBook aheadEverything below is on the far side of the island and none of it works on buses. Anticlockwise loop, roughly 5β6 hours of moving and stopping.
EarlyLanikai Pillbox TrailLucy's listLucy's note: "short but steep" β she's right. Twenty to thirty minutes up to old concrete bunkers with the Mokulua islands laid out below. Best light early. Not one for Mum.
Mid morningLanikai Beach + Kailua BeachLucy's listThe two best beaches on Oahu and it isn't close. Lanikai has no facilities and street parking only; Kailua next door has both. Swim here, not at Waikiki.
LunchKailua townProper local lunch away from resort pricing.
AfternoonHoΚ»omaluhia Botanical GardenLucy's listFree, ten minutes inland at Kaneohe. The KoΚ»olau cliffs rise straight up behind it β this is the famous mountain-backdrop shot. Easy flat walking, so this is a good one for Mum.
LateMakapuΚ»u LookoutLucy's listOn the way home round the southeast point. Lucy wrote "maybe whales" β no whales, humpback season is December to May. Still the best coastal view on the island.
05Tue 1 SepPearl Harbor, then something green
β Mon 31Pearl Harbor tickets drop 3pm Hawaii time, day beforeAlarmUSS Arizona Memorial tickets are free with a $1 reservation fee, on recreation.gov. The eight-week batch has gone; this 24-hour release is the remaining route.
MorningPearl Harbor + USS ArizonaAllow three to four hours. Bags aren't allowed in β there's a paid store, but travel light. Same side of town as Sunday's swap meet.
AfternoonFoster Botanical GardenLucy's listSmall, shaded, downtown, on the way back. An hour is plenty and it's a gentle landing after a heavy morning.
NoteHanauma is closed todayWhich is exactly why Pearl Harbor sits here.
06Wed 2 SepLast full day β pick one
Option ANorth Shore, full dayNot on Lucy's list, but it's the other Oahu. Haleiwa town, Waimea Bay, the Pipeline lookout, shrimp trucks at Kahuku. Needs the car again and it's a long day.
Option BMΔnoa Falls Trail, then WaikikiLucy's listLucy's note: "scenes from Jurassic Park shot here." Fifteen minutes from the hotel, an easy rainforest walk to a waterfall, about 90 minutes round trip. Genuinely muddy β real shoes. Leaves the afternoon free for the beach and packing.
VerdictTake BTomorrow starts at 4:30am. A full North Shore day the night before that is a mistake you'll feel all the way to San Francisco. MΔnoa Falls also clears one more thing off Lucy's list.
07Thu 3 SepFly to San Francisco
β07:00HNL β SFOVery earlyLands San Francisco 15:13, and Hawaii is three hours behind β which means an early-morning departure and a 4:30am alarm. Pack Wednesday night, not Thursday morning.
Leg two
San Francisco
Thu 3 Sep β Mon 7 Sep Β· 4 nights Β· Labor Day weekend Β· all three of us
Three and a half days, not four. You land mid-afternoon Thursday and leave early Monday, so Friday, Saturday and Sunday are the whole leg. Everything below is walkable or a short ride β no car needed.
What got cut, and why. Lucy's list had Apple Park, the Google visitor centre, Silicon Valley Bank and Muir Woods. The first three are an hour south and amount to two gift shops and a bank that collapsed in 2023. Muir Woods is 45 minutes the other way and needs a parking reservation. Lands End, the Palace of Fine Arts and the Presidio give you the same coastline for free, in the city, with nothing to book.
08Thu 3 SepLand, eat, sleep
15:13Land at SFOBART or a ride into town. Check in, then don't go far.
EveningDinner in North BeachThe Italian quarter, next door to the Wharf. Eat here rather than on the waterfront β same walk, half the price, better food.
PackAn actual jacketFog rolls in most afternoons and it's cold by New Zealand standards. After six days in Waikiki it will genuinely bite.
09Fri 4 SepThe classics, then Alcatraz after dark
MorningPowellβHyde cable car + Lombard StreetBoard at a mid-route stop rather than queueing at the Powell turntable. Ride it over the hill, get off at the crooked block.
AfternoonFisherman's Wharf, Pier 39, the sea lionsTouristy and worth an hour. Keep the legs fresh.
EveningAlcatraz Night TourBookedLucy's list3 adults, USD 178.95, paid. Departs Pier 33, not Pier 39 β they're a 15-minute walk apart and people miss sailings over it. Allow three hours door to door. You land on the island and tour the cellhouse at your own pace with the audio guide.
10Sat 5 SepMarket morning, Mission afternoon
08:00β14:00Ferry Building farmers marketLucy's listSaturday is the big one and your stay covers exactly one of them. Best single food stop in the city. Walk the Embarcadero afterwards.
AfternoonThe MissionA burrito at La Taqueria, murals on Balmy Alley and Clarion, an hour lying in Dolores Park looking back at the skyline. The most alive part of the city and the least like the postcards.
EveningFreeLong day tomorrow.
11Sun 6 SepThe coast, the bridge, and the best half day here
MorningBike the Golden Gate to SausalitoRent at the Wharf, ride the waterfront, cross the bridge, coast down for lunch, ferry back past Alcatraz. Mostly flat β the ferry does the hard part. Far better than looking at the bridge from a car park.
On the wayPalace of Fine ArtsLucy's listFree, twenty minutes, and it sits right on the route out to the bridge. A leftover Roman rotunda on a lagoon in the middle of a suburb. Odd and lovely.
AlternativeLands End TrailLucy's listIf nobody fancies bikes: free coastal path along the cliffs, Sutro Baths ruins at one end, the bridge framed through cypress at the other. Then Baker Beach and the Presidio. Same feeling, no pedalling β and the better call if Mum's coming.
12Mon 7 SepFly to New York β Labor Day
β08:00SFO β JFKEarly againLands 16:26 New York time. Another dawn start β the day's gone.
Leg three
New York, together
Mon 7 Sep β Sat 12 Sep Β· 5 nights Β· Radio City Apartments Β· Mum and Lucy fly home on the 12th
Four full days, built by neighbourhood so you're not crossing the city twice a day. All eight of Lucy's New York places fit without a single detour.
Read this before booking anything else. Your hotel checks out Saturday 12 September β the morning the biggest weekend New York will have all year begins. US Open women's final on the 12th, men's final and the NFL season opener on the 13th, a three-game Subway Series across 11β13 September, and the 25th anniversary of 9/11 on the 11th. Fashion Week runs 10β15. The recommendation is to stay through Monday the 14th.
13Mon 7 SepArrive, and see one thing
16:26Land at JFKLabor Day, so traffic is lighter than a normal Monday. Just tap your phone on the subway β MetroCards are gone.
EveningTimes SquareLucy's listWalkable from Radio City and best seen at night, which is all you'll have energy for. Fifteen minutes is enough for anyone.
14Tue 8 SepMidtown and the park
MorningCentral ParkLucy's listIn from the south end, up through the Mall and Bethesda Terrace. Walk it, don't tour it.
MiddayThe Metropolitan Museum of ArtLucy's listOn the park's eastern edge. Pay-what-you-wish is for New York, New Jersey and Connecticut residents only β budget full price. Two hours, not five.
β17:00Top of the Rock, sunset slotBook aheadBook the slot about an hour before sunset and you get daylight, sunset and the lit city in one visit β and unlike the Empire State, the Empire State is actually in your photos.
15Wed 9 SepThe harbour and downtown
09:00Statue of Liberty + Ellis IslandBook nowLucy's liststatuecitycruises.com only β it's the sole authorised seller. Crown is sold out; General Admission is fine and still includes the ferry, Liberty Island and Ellis Island. The monument itself is free β you're paying for the boat. Take the 9am: the security queue at Battery Park is the real bottleneck.
Early afternoonWall StLucy's listFive minutes' walk from the ferry terminal. The Exchange, the Charging Bull, Federal Hall. Half an hour.
Afternoon9/11 Memorial + MuseumTimed entryDo this today, not Friday. The 25th anniversary falls on the 11th and the whole Financial District becomes difficult.
16Thu 10 SepBrooklyn β the best day of the four
EarlyWalk the Brooklyn BridgeFrom the Manhattan side, before it fills. Later in the day it's shoulder to shoulder.
Mid morningDUMBOWashington Street for the Manhattan Bridge framed between the warehouses, then the waterfront park underneath.
AfternoonWilliamsburgLucy's listLucy's note: "vintage shopping" β this is her day. Bedford Avenue and the streets either side. Smorgasburg if it's running.
17Fri 11 SepWest side, then the anniversary
MorningThe High LineLucy's listAn old elevated railway turned into a linear park. Walk it north from Gansevoort.
LunchChelsea MarketLucy's listSteps off the High Line. Old biscuit factory, now food halls.
AfternoonWest VillageNo plan. It's the part of the city best wandered.
EveningThe 25th anniversary of 9/11Memorial ceremony downtown in the morning, Tribute in Light after dark. Watch the beams from across the water β Brooklyn Heights Promenade or Liberty State Park β not from underneath. Alternative: Subway Series game one at Yankee Stadium, 19:05.
18Sat 12 SepMum and Lucy fly home
DaytimeAirport run, then Daniel's on his ownHotel changes here. Lower East Side, East Village or Long Island City all work and all cost less than Midtown.
16:00US Open women's finalArthur Ashe Stadium, 40 minutes on the 7 train. Or watch it in an East Village bar, which is its own kind of New York night.
Leg four
The seven nights
Sat 12 Sep β Sat 19 Sep Β· solo Β· flight home from JFK at 21:55 on the 19th Β· undecided
Nothing here is booked and no plan is chosen. This is the last real decision, and it's the expensive one β Manhattan rates climb into Fashion Week, which runs 10β15 September.
Plan
Shape
Why it works
Why it might not
A Β· Finals then Falls
NYC 12β14 Niagara 14β16 NYC 16β19
Keeps the biggest weekend in the city, gets Niagara at the right length, and puts you back in New York with three unhurried days before a night flight.
Three accommodation blocks, two booked late during Fashion Week.
B Β· Falls and Toronto
NYC 12β14 Niagara 14β16 Toronto 16β18
Toronto is 90 minutes from the falls and is a real city, not a viewing platform.
The border twice, and you fly back to New York the day before an international departure.
C Β· Northeast corridor
NYC 12β14 Washington 14β16 Philadelphia 16β17 NYC 17β19
Most new city per hour of travel, all by train, no airports. Smithsonians are free.
No Niagara.
D Β· Boston run
NYC 12β15 Boston 15β18 NYC 18β19
Simplest version with a second city in it.
No Niagara, and a smaller payoff than DC.
E Β· Don't move
NYC 12β19
Cheapest, one bed, no packing. Queens, the Bronx, Governors Island, Coney Island.
You fly home having seen one American city properly.
If you want one answer: Plan A. It's the only version that keeps the 12β13 September weekend, gets you the falls at the right length, and leaves slack in New York before a 21:55 international departure. Crossing into Canada by land needs only your passport β no eTA. That's only true by land; flying into Canada would need one.
Sun 13 Sep
US Open men's final at 14:00, then Giants vs Cowboys at 20:20 β the NFL season opener at MetLife. Both in one day is ambitious. Either is a good day.
Mon 14 β Wed 16
Fly to Buffalo, cross the Rainbow Bridge on foot, two nights on the Canadian side in the Fallsview district. Maid of the Mist, Journey Behind the Falls, Cave of the Winds.
Thu 17 β Fri 18
The city on your own terms β the Bronx, Queens food crawls, Governors Island, Coney Island, a Broadway rush ticket, the Met done properly.
Sat 19 Sep
Out of Manhattan by mid-afternoon for a 21:55 flight. Nothing outside the five boroughs on this day.
What's left
The booking board
In deadline order. Ticks save in your browser.
0 of 14 done
Official sellers only. Alcatraz β alcatrazcitycruises.com Β· Statue of Liberty β statuecitycruises.com Β· Diamond Head β gostateparks.hawaii.gov Β· Pearl Harbor β recreation.gov. Anything else selling these four is adding a markup. statueoflibertytickets.com adds about $7 a ticket simply to forward your order.
Money
NZD 5,500β7,000 spending across 22 days, excluding flights and beds. Add 20% to every sit-down meal and rideshare when you do the mental maths β the tipping tax catches New Zealanders out for the whole first week.
Cards
Revolut for everything β you avoid roughly 2.5β3% in FX fees a NZ bank card charges, which is NZD 150β200 across the trip. Convert to USD on a weekday to dodge the weekend markup. Carry USD 100β200 cash for food trucks and tips.