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
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."
Their 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
What we 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
What we considered:
- ○ Charleston — Great food, walkable, romantic
- ○ Montreal — International feel, 1-hour flight, excellent restaurants
- ○ Savannah — Similar to Charleston, slightly lower-key
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 added: Reservation at Michelin-starred restaurant ($400)
The Outcome
DIY Research Estimate
6-8 hours
With Otherwhere
15 minutes
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