Personal / Travel Planning
Travel that’s already booked when you remember to leave.
Flights, hotels, restaurants, ground transport, family itineraries. Your assistant builds the trip and hands you one document with every confirmation in it.
A trip is dozens of decisions stacked together. Your assistant takes the brief, comes back with options that match your budget and travel style, books what you pick, and writes it up in a single PDF you can hand to your phone or your spouse. No 14 browser tabs, no half-saved itineraries.
Works for solo trips, couples weekends, family vacations, and the multi-stop trips your friend group has been talking about for two years.
What we handle
The work your assistant takes off your plate.
- Flight research and booking, including miles redemptions, multi-leg routes, and same-day rebooking when something blows up at the airport
- Hotels and rentals matched to your taste and price band, with three vetted options instead of forty-seven Airbnb tabs
- Restaurant reservations across cities, including the hard-to-book ones (we’ll keep refreshing OpenTable so you don’t have to)
- Ground transport, transfers, day-trip planning, museum tickets, the small things that make a trip feel sorted instead of scrappy
- One consolidated itinerary document with confirmation numbers, addresses, and contact phone numbers, sent to you and anyone traveling with you
Top 0.1%
Of applicants accepted onto our team. Multi-stage screening, real work as the audition, references called.
100%
Identity-verified and criminal-background-checked. Access scoped to what the work requires, logged, revocable.
2-3 days
Typical match time from intake call. The same dedicated person, every week after.
Questions
Still circling?
Are you a travel agency? Do you take a kickback?
No. We’re not an agency, we’re not on commissions, and we don’t push specific hotels. Your assistant works for you. Whatever rate you find, you get.
Can you book with my points and miles?
Yes. Share your loyalty logins through a shared password manager and we’ll book the cheapest combo of cash and points. Award flights, hotel free nights, transfer partners, the whole game.
What if my flight gets cancelled at 11pm?
Text your assistant. We rebook on the next flight, hold the hotel, and update the itinerary. Same-day support is included on every plan.
Can you plan group trips?
Yes. We’ve planned bachelorette weekends, multi-family Italy trips, and a 14-person ski lodge. We loop in the group, gather preferences, and book once everyone has agreed.
What if I don’t click with my assistant?
Tell your account manager. We rematch. No drama.
Your account manager
A dedicated account manager. The person you actually talk to.
Every account has its own account manager, separate from your dedicated assistant. They run the kickoff, own the match, and are the person you reach if something needs to be rematched, escalated, or just sanity-checked. Every assignment has a quality bar. You aren’t the one chasing it.
Same person, every week. No round-robin queue. No swapping out the contact after onboarding. The match you meet on day one is the match running the work on day two hundred.
From people who hired one of us
They came back for the next year.
“It is really nice having a dedicated assistant and my assistant has exceeded my expectations. They’ve saved me a lot of time dealing with a variety of tasks: canceling and scheduling appointments, booking work trips, researching.”
Roy · OkayRelax client · August 2018
“She checks in about details and keeps me on task, which is quite a tall order. My ADHD makes it impossible to keep up on all my adulting without it.”
Erin Jones · OkayRelax client · Trustpilot, August 2023
The quickest path
Book a 30-minute discovery call.
Talk to a real person first. Bring what’s on your plate, the tools you’re already using, and where it’s breaking. You leave with a scope, a price, and the name of your match, or the honest answer that this isn’t a fit.
No sales pressure. We say if it’s not a fit.
Prefer to write it out
Send the details. One business day to reply.
Drop the basics. We come back inside one business day with a match and a scope.
Reply within one business day · Your details stay private · No sales pressure
Hand off the next trip.
Top 0.1% accepted. Matched within days. Your account manager is waiting.