The Rain Vortex falling through the lush indoor garden at Jewel Changi Airport
2026–27 Likes

Asia

Lily · Dylan · Maddy · Taylor

Spring 2027 · 12 nightsTokyo → Taipei → SingaporeMar 21 — Apr 3, 2027 · ≈ $5,330 / person
See what we’d do

What we’d actually do

Heart anything you’d want to do.Missing something? Add it.

Tokyo

Tokyo · Mon Mar 22
1 / 8
Tokyo · Wed Mar 24
2 / 8
Tokyo · Thu Mar 25
3 / 8
Tokyo · Tue Mar 23
4 / 8
Tokyo · Thu Mar 25
5 / 8
Tokyo · Tue Mar 23
6 / 8
Tokyo · Tue Mar 23
7 / 8
Tokyo · Mon Mar 22
8 / 8

Taipei

Taipei · Sun Mar 28
1 / 9
Taipei · Sat Mar 27
2 / 9
Taipei · Mon Mar 29
3 / 9
Taipei · Mon Mar 29
4 / 9
Taipei · Mon Mar 29
5 / 9
Taipei · Sun Mar 28
6 / 9
Taipei · Fri Mar 26
7 / 9
Taipei · Sat Mar 27
8 / 9
Taipei · Mon Mar 29
9 / 9

Singapore

Singapore · Thu Apr 1
1 / 8
Singapore · Thu Apr 1
2 / 8
Singapore · Wed Mar 31
3 / 8
Singapore · Wed Mar 31
4 / 8
Singapore · Fri Apr 2
5 / 8
Singapore · Tue Mar 30
6 / 8
Singapore · Thu Apr 1
7 / 8
Singapore · Fri Apr 2
8 / 8

Day by day

One main plan each day, with room around it.

12 nights routeTokyo → Taipei → Singapore
DepartSFOSan Francisco
4 nightsTYOTokyo
4 nightsTPETaipei
4 nightsSINSingapore
TYO

Neighborhoods, food, and one mountain day.

TRUNK Cat Street · 4 nights

Tokyo → TaipeiFlight~3h 45m
TPE

Temple courtyards, tea hills, hot springs, and a table for four.

Regent Taipei · 4 nights

Taipei → SingaporeFlight~4h 45m
SIN

Skyline, pool time, and warm nights.

Mondrian Singapore Duxton · 4 nights

About $5,330 each

Spring 2027 · 12 nights · Tokyo → Taipei → Singapore
Flights, two rooms, food + drinks, getting around, and things we do.

Likely range $4,700–$6,150 each · 4 travelers · 2 rooms

TWO VERSIONSSpring / 12 is the working trip

+$1,490 adds TaipeiBaoan Temple · mahjong · tea hills · hot springs · 4 Taipei nights + 1 more in Singapore

WHERE IT GOESThe trip, at a glance
Flights$1,700
Hotels$1,900
Getting around$350
Food + drinks$1,020
Things we do$360
See full cost details
FULL BREAKDOWNWhat each category includes
Flights3 flight legs$1,700
Long-haul flightsEconomy · SFO → Tokyo / Singapore → SFO$1,190
Tokyo → TaipeiRegional one-way economy$240
Taipei → SingaporeRegional one-way economy$270
Hotels12 nights · 2 rooms$1,900
Tokyo4 nights · 2 rooms · ~$320/room/night$630
Taipei4 nights · 2 rooms · ~$270/room/night$540
Singapore4 nights · 2 rooms · ~$370/room/night$730
Getting around3 cities$350
Tokyo movementRail, airport links, and selected taxis$110
Taipei movementMRT, gondola, airport links, and selected taxis$130
Singapore movementMRT + selected rideshares$80
Transfer bufferBags, airport timing, and fare variance$30
Food + drinksAbout $90 / day / person$1,020
Everyday mealsBreakfast, casual lunch, and snacks · 12 days$510
Planned dinnersShared plates and the main evening meals$330
Coffee + drinksEstimated · ~$20/day$180
Things we doTickets + activities$360
Views + ticketsTimed entries and paid attractions$150
Views + ridesGondola, cable car, boat, or outdoor access$110
Wellness + playHot springs, games, and flexible activities$100
UPGRADESOptional extras
Estimate + 10% cushion$5,860
Everything except flights / night$303
Four-person set-aside incl. cushion$23,440
Optional planning cushion10%
$530 beyond the estimate for exchange rates, taxis, and unplanned extras. It does not change the headline.

Estimate, not quote. Economy airfare allowance with estimated taxes; two hotel rooms with a fee cushion; four travelers. Baggage, insurance, shopping, and points are excluded. Last reviewed Aug 24, 2026.

Make it real

Working trip: Spring 2027 · 12 nights. Still to decide: confirm 12 vs. 7. Flights are the first thing to book.

THEN WE BOOK

Flights first, then two refundable rooms in each city.

01
SeptemberBook long-hauls

Compare multi-city fares before adding the regional legs.

Book soon
02
Oct — NovHold refundable stays

Hold two rooms in each city; keep cancellation terms flexible.

Refundable
Later milestones
03
Jan — FebReserve the must-dos

One dinner, the favorite activities, and timed-entry picks.

Later
04
Mar 21Depart SFO

Pack one light layer; keep the daily plan loose.

Departure
IF SOMETHING’S BOOKEDBackup options
Tokyo · Mar 22–26TRUNK Cat Street

Tokyo combines strong food neighborhoods, walkable design districts, and a Mount Takao day without changing hotels.

Explore Tokyo teamLab Borderless Tokyo hotels · Mar 22–26
Taipei · Mar 26–30Regent Taipei

Taipei changes the pace: a living temple, neighborhood food, Maokong, Beitou, and one low-key game night.

Explore Taipei Taipei taster guide Taipei hotels · Mar 26–30
Singapore · Mar 30–Apr 3Mondrian Singapore Duxton

Singapore finishes with warmer weather, hawker food, skyline routes, and a rooftop pool built into the stay.

Explore Singapore Garden Rhapsody times Singapore hotels · Mar 30–Apr 3
Tokyo · Mar 22–26 · 4 travelers / 2 rooms

Availability and budget fallbacks only.

HOTEL · Shibuya
Hotel Indigo Tokyo Shibuya

Five minutes from Shibuya Station, with skyline views, a terrace, and straightforward airport access.

EAT + DRINK · Daikanyama
Hacienda del cielo

High-rise terrace, shareable plates, and an easy Daikanyama dinner.

Checked Aug 24, 2026. Reconfirm hours, inventory, prices, and reservation rules before booking.