The custom itinerary, built for your crew.
- A timed itinerary, every stop, every move, in order
- Stops matched to your crew's energy, not a tourist list
- A route that keeps the night moving, no dead time
Get my $19 plan
After checkout, I'll email you for your city, date, budget & vibe.
Here's what lands in your inbox.
A real Go With Leon plan: timed stops, smart routes, zero debating. Example format, yours is built from scratch for your city, date, budget, and crew.
Girls' night out, Denver
A buzzy spot with shareable plates and a patio, reservation handled, table for six, no waiting around.
Skyline views timed for golden hour. A 6-minute ride from dinner, ordered while you finish dessert.
Live music and dancing in RiNo, the venue matches your crew's energy, and you're in before the line builds.
The taco truck everyone talks about, two blocks from the venue. The night ends on a high note, not a search for food.
Ride timing between every stop · ~12 minutes total travel · backup options if the vibe shifts
Date night, Chicago
West Loop dinner where the food is the event → a Riverwalk stroll to shake off the table → a speakeasy nightcap in Wicker Park.
Birthday, Atlanta
Bites and browsing at Ponce City Market → Midtown cocktails with the crew → Buckhead dance floor to close it out.
Or the whole weekend, planned end to end.
Some crews want one perfect night. Others want the full trip, flights, hotel picks, restaurant reservations, day parties, nightlife. This is a real sample format: every stop timed, every address included, built around your crew.
$39 NOW $19
Halloween weekend in New Orleans?
Arrive with a plan. This is the haunted weekend done right: French Quarter nights, a ghost tour, House of Blues, and ZooBoo, Oct 30 to Nov 1. Booking window closes soon, so lock in your custom itinerary now.
$39 NOW $19
Whatever the night is for.
Date nights
Impress without the spreadsheet. Just show up and shine.
Girls' / boys' nights out
The whole crew, one plan, zero "so what are we doing?"
Birthdays & anniversaries
Milestone nights deserve better than the usual spot.
Food crawls
Eat your way through the city like you live there.
Weekend escapes
New city, no research rabbit holes. Land and go.
Group trips
Herder of cats? Hand me the group chat.
Any city. This energy.
Real nights, real routes, built for real people.
Atlanta
Ponce City Market → Midtown cocktails → Buckhead late-night
San Juan
Old San Juan golden hour → La Placita → Condado
Miami
Wynwood → Little Havana → South Beach
Chicago
West Loop dinner → Riverwalk → Wrigleyville
Richmond
Carytown → Scott's Addition breweries
Alanna's Indianapolis weekend
Dining, downtown discovery, and a custom city challenge in one connected game plan.
Going bigger than one night?
Full travel planning, flights, hotels, cruises, group trips. You pack your bag. I'll handle the rest.
People went. People loved it.
My birthday itinerary was the best thing I could've bought. It was all thought out and I didn't have to do any planning. I definitely will be purchasing for my next vacation.
, ZellyonaMy work trips to Seattle were the same every time until I found Go With Leon. Now I go out and explore the city and eat in restaurants that I would have never even known of.
, TomFAQ
What do you need from me?
Four things: your city, your date, your budget, and your vibe. That's the whole brief.
How fast is delivery?
Tell me your date, turnaround is confirmed before you commit, and rush delivery is available when the night is close.
What cities?
Any U.S. city. If people live there and go out there, I can plan it.
Is it really custom?
Yes, every plan is built from scratch for your crew. No templates, no copy-paste.
Questions? Call or email Leon.
Real person, real answers, before or after you book.