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.
Better trips.
Smarter points.
Your travel, figured out.
We plan your trip—from flights and hotels to restaurants and a complete day-by-day itinerary—and help you get more from your credit card points and travel budget.
Start with your travel profile and a complimentary 30-minute Strategy Call.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, and experiences chosen for your taste and the way you like to travel.
Execution
Booking help, transportation, and a day-by-day plan with the timing and directions to make it work.
Let the algorithm cook. Send us the places you’ve saved. We’ll connect the dots.
One trip. One point of view.
Everything figured out.
A GLIMPSE OF THE EXPERIENCE
A little Tokyo.
A lot to love.
YOUR PERSONAL ITINERARY ↗A MORNING IN GINZA / SAMPLE PLAN
BONGEN · coffee & matcha
A Ginza pause before exploring the market. Save your appetite for lunch.
Open map ↗ Walk · 10 min · approx. 0.4 miles
Tsukiji · lunch by discovery
Browse the stalls and build lunch from a few small things that catch your eye.
Open map ↗LESS RESEARCH. MORE BEING THERE.
A great trip.
Already thought through.
Skip the scattered tabs and saved lists. Your days connect naturally, with places worth your time and the practical details close at hand.
- Places chosen around your taste
- Walking times and directions between stops
- Reservations, arrival notes, and useful details
- Your full itinerary, saved for offline access
CUSTOM PLANNING, WITHOUT THE GUESSWORK
A little direction.
A whole trip taking shape.
Let the algorithm cook. We’ll connect the dots.
Share the hotels, restaurants, and experiences you’ve saved on Instagram or TikTok. We’ll turn your inspiration into a trip that fits your taste—with the research, timing, and logistics figured out.
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.
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
THE COLLECTION
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
THE COLLECTION
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
WhichWay vs. a Travel Agent — see the difference ↗
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.
WHAT YOU GET BACK
More out of your budget.
More out of your trip.
Smarter spending.
Compare points and cash, find better redemption opportunities, and spend on the experiences that matter to you.
Your time back.
Let us handle the research and connect the logistics, so your evenings aren’t spent comparing hotels and reading endless lists.
Better days away.
Enjoy thoughtful pacing, memorable places, and a clear plan—with room to explore along the way.
Have a question? Explore the FAQ ＋
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.
Plan my trip