THE ANNIVERSARY TRIP
Montreal, Canada
Couple, late 30s, two kids under 5, haven't traveled alone since 2021. Budget: $3,500 max (4 nights). Here's how we turned their vision into a booked trip.
15 minutes
Time to book
6 weeks out, tied to grandparents' availability
Planning window
$2,100 for 4 nights + flights
Final price
6-8 hours
Time saved vs DIY
THE BRIEF
"We have 4 days without kids. We don't even know what we like anymore. Just... not a theme park and not exhausting."
REQUIREMENTS
- • Must have: Good food, walkable, feels special but not stuffy
- • Can't do: Adventure travel, long travel days (wasted time)
- • Dealbreaker: Anywhere that feels like it's "for young people"
OUR PROCESS
RULED OUT
- × Vegas
They specifically said "no Vegas"
- × Caribbean
Feels like a "family resort without the family"
- × NYC
They live 2 hours away, doesn't feel like an escape
CONSIDERED
- ○ Charleston
Great food, walkable, romantic
- ○ Montreal
International feel, 1-hour flight, excellent restaurants
- ○ Savannah
Similar to Charleston, slightly lower-key
OUR RECOMMENDATION
Montreal — feels European, incredible restaurant scene, easy flight, feels "adult"
THE BOOKING
BOUTIQUE HOTEL IN OLD MONTREAL
- Why it won: Feels European, incredible restaurant scene, easy flight, felt "adult"
- Price: $2,100 for 4 nights + flights
- Extras: Reservation at Michelin-starred restaurant ($400)
THE OUTCOME
Booked. They extended by one night (grandparents agreed). Called it "the reset we needed."
DIY ESTIMATE
6-8 hours
WITH OTHERWHERE
15 minutes
YOUR TURN
WANT THIS FOR YOUR TRIP?
We turn overwhelming options into effortless bookings. Text us to get started.
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