The Honeymoon Couple
Puglia, Italy
Newly engaged couple, both 32, working in tech. Budget: $6,000 total (7 nights). Here's how we turned their vision into a booked trip.
22 minutes
Time to book
3 weeks until trip
Planning window
$4,200 for 7 nights (under budget)
Final price
10-15 hours
Time saved
The Brief
"We want somewhere romantic but not basic. Not Cancun or an all-inclusive. Good food matters more than a beach. We're foodies."
Their requirements:
- • Must have: Great restaurants nearby, romantic vibe, walkable
- • Can't do: Long-haul flights (max 8 hours from NYC)
- • Dealbreaker: "Resort feel" or tourist crowds
Our Process
What we ruled out:
- × Caribbean islands — Too "honeymoon cliché" for them
- × Bali — 20+ hour travel time
- × Santorini — Peak season crowds, overexposed on Instagram
What we considered:
- ○ Portugal (Lisbon + Sintra) — Great food, romantic, but they'd been before
- ○ Amalfi Coast — Stunning but crowded in their window
- ○ Puglia, Italy — Off-the-radar, incredible food scene, authentic
The Booking
Masseria (restored 17th-century farmhouse)
- Why it won: Private, romantic, farm-to-table meals included, trulli architecture they'd never seen
- Price: $4,200 for 7 nights (under budget)
- Extras added: Cooking class ($150), truffle hunting experience ($200)
The Outcome
DIY Research Estimate
10-15 hours
With Otherwhere
22 minutes
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