Points strategy
Know when to use points, when to pay cash, and when a better redemption can put a better trip within reach.
TRAVEL, FIGURED OUT.
You know you
want to go.
We know
which way.
Your interests. Your budget. The points you’ve been saving. We’ll help you figure out where to go—and bring the whole trip together.
Ask WhichWayExplore a sample itineraryYour travel profile comes first.A complimentary 30-minute Strategy Call follows.
A LITTLE DIRECTION.
A WHOLE NEW WORLD.
A WHOLE NEW WORLD.
LESS SEARCHING. MORE GOING.
Somewhere
that feels like you.
THE WHICHWAY WAY
Your points. Your taste.
Your whole trip.
Most travel planning handles one piece. WhichWay brings three together.
Taste + curation
Hotels, restaurants, neighborhoods, shops, and experiences chosen around you. We turn your interests, travel style, and saved finds into a trip that feels like yours.
Execution
Flight and hotel choices, reservation help, transportation, and a stop-by-stop itinerary—with the timing, directions, and practical details that make it all work.
Let the algorithm cook.
Send us the places you’ve saved. We’ll connect the dots.
A $5,000 business-class seat. Sometimes 60,000 points.
Illustrative example. Availability, points required, taxes, and fees vary.
One trip. One point of view.
Everything figured out.
A GLIMPSE OF THE EXPERIENCE
A little Tokyo.
A lot to love.
YOUR PERSONAL ITINERARY ↗DAY 01 / SETTLE INTO THE CITY
BONGEN · coffee and matcha.
+A Ginza pause before exploring the market.
Tsukiji · lunch by discovery.
+A 10 min walk · approx. 0.4 miles.
MADE FOR THE TRIP. NOT JUST THE PLANNING.
Every day,
thoughtfully put together.
A quick overview when you need the big picture. One day at a time when you’re out exploring.
- Short descriptions, with details a tap away
- Walking and driving times between stops
- Maps and Instagram links where available
- Clear reservation statuses
- Save your itinerary for offline access
CUSTOM PLANNING, WITHOUT THE GUESSWORK
A little direction.
A whole trip taking shape.
01
Tell us about you.
Your taste, travel window, budget, points, and saved finds. A destination is optional.
02
Talk it through.
We research possibilities before your complimentary 30-minute Strategy Call with Josh.
03
We bring it together.
Once you approve and pay the agreed fee, we build your trip and help with bookings.
04
Go, with a good plan.
Thoughtful days, room to explore, and the practical details close at hand.
Good reasons to go.
- Couples trips
- Honeymoons & anniversaries
- Bachelor & bachelorette trips
- Friends & group getaways
- Family vacations
- Solo adventures
A LITTLE HELP OR THE WHOLE PLAN
Three ways to go WhichWay.
Follow a thoughtfully built itinerary. Get help putting it into action. Or let’s create something entirely yours.
COLLECTION · COMING SOON
Premade Itinerary
$150 USD
A great plan, ready for you to follow.
- An existing WhichWay itinerary
- Organized days and practical details
- Explore and book independently
COLLECTION · COMING SOON
Itinerary +
Booking Help
$350 USD TOTAL
The plan, plus a little direction.
- Everything in the premade itinerary
- One 30-minute booking-help call
- Guidance putting the plan into action
BUILT AROUND YOU
Custom Trip Planning
FROM $1,000 USD
Your taste. Your pace. Your trip.
- A personally designed itinerary
- Points strategy and cash comparisons
- Booking help included
- Up to 10 days, including travel days
Planning prices are in USD. Flights, hotels, and other travel costs are paid separately. Custom planning starts with a complimentary Strategy Call; the agreed fee is paid before planning begins.
PERSONAL TRAVEL NEEDS A PERSONAL TOUCH
Meet Josh.
Your trip’s editor.
Where to splurge. When to slow down. What’s worth getting up early for.
That’s where I come in. I bring together the stays, meals, and experiences that fit how you like to travel—with an eye on value and a feel for how the days flow.
We start with a conversation. We build from there.
Josh ↗A FEW GOOD QUESTIONS
Before
you ask.
What if I don’t know where to go?
That’s a great place to start. Your interests, travel window, budget, and points help us find the right opportunity. You don’t need a destination picked out.
What if I don’t have points?
You don’t need points to plan with WhichWay. We work with your cash budget and focus your spending on the experiences that matter to you.
Which option is right for me?
Choose a premade itinerary if you want an existing plan to follow. Add the booking-help call for guidance putting it into action. Choose custom planning for a trip designed around you. The $350 package does not include custom itinerary changes.
How does booking help work?
With custom planning, Josh guides flights and points transfers while you complete the steps in your own accounts. For hotels, restaurants, experiences, and transport, he can help you book or make arrangements on your behalf, as agreed. The $350 package includes one 30-minute booking-help call. Travel purchases are paid separately.
How far ahead should I start?
Allow about a month from your Strategy Call for your custom itinerary. Traveling sooner? We’ll discuss what’s possible and agree on timing and any rush fee before you pay.
Can I use my itinerary offline?
Yes. Save it to your device before you travel and refresh the saved copy after updates. Maps and Instagram links need an internet connection. Offline access lasts for the period shown when you save.
TRAVEL, FIGURED OUT.
Your next trip starts
with a question.
Ask WhichWay.
Find my trip