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Watch the Full Breakdown — @smobyday

Most people search for travel recommendations wrong. They type "best restaurants in Lisbon" and get a list of places with 10,000 Google reviews that have been in every travel guide for the last five years. That's not discovery — that's the tourist loop.

AI travel tools are different. The more specific the input, the more useful the output. Here's how to actually use that to your advantage.

Step 1 — Stop Searching, Start Briefing

Think of it like briefing a well-traveled friend who has lived in every city. You wouldn't say "what should I do in Tokyo?" — you'd say "I have four days, I'm obsessed with architecture and modern design, I don't do tourist shrines, I want to eat standing up at counters, and I'll walk 10 miles a day. Go."

That's the energy. Give AI a brief, not a search query.

smobyday tip

The three layers that make AI travel recs actually good: (1) what you're into, (2) what you're avoiding, and (3) your physical context — how much you'll walk, your budget range, what time of day you're usually out.

Step 2 — Add "Anti-Tourist" Filters

One phrase that changes everything: "not in any major travel guide." Or: "where locals go, not expats." Or: "the neighborhood before it got popular." Claude and ChatGPT both respond dramatically differently to these qualifiers — they pull from a much deeper well.

Other great filters: "no English menus required," "off the main street," "that doesn't show up on the first page of Google," "that opened in the last 2 years."

Step 3 — Layer in Time and Budget Context

Context changes everything about a recommendation. "Natural wine bars in Porto" is fine. "Natural wine bars in Porto open after 9pm on a Tuesday in November with no reservation needed and glasses under €6" is a completely different question with a completely different answer.

Add time of day, day of week, season, and price anchors to every request.

Prompt 1 — The Hyper-Specific City Brief
I'm spending [X] days in [CITY] in [MONTH]. Here's exactly who I am as a traveler: - Walking: I'll do [X] miles/day without complaint - Food: I care about [e.g., fermented foods, regional cuisine, street food only, counter dining] - What I'm avoiding: [e.g., places in major travel guides, English-only menus, anything near the main tourist square] - Vibe: [e.g., slow mornings, late nights, market culture, architecture obsession] - Budget per day for food: around [AMOUNT] - Where I'm staying: [neighborhood] Give me a day-by-day structure that reflects this, not generic tourist recommendations. Include backup options for each main suggestion.
Step 4 — Use It for Neighborhoods, Not Just Restaurants

The best travel AI use case isn't food — it's spatial understanding. Ask Claude or ChatGPT to explain a city's neighborhoods in terms of vibe and who lives there, not what they're "known for." The difference: "Pigneto in Rome is known for its nightlife" vs. "Pigneto is where young Romans who can't afford Trastevere anymore actually live and eat."

That second framing changes how you plan an entire day.

Prompt 2 — Neighborhood Vibe Map
Explain [CITY]'s neighborhoods to me not in terms of what they're "known for" in travel guides, but in terms of who actually lives there, what the streets feel like at different times of day, and which ones are worth spending real time in vs. just passing through. I'm interested in [your vibe — e.g., creative communities, food culture, architecture, local markets]. Tell me which neighborhoods match and why.
Step 5 — Verify and Cross-Check

AI recs can be outdated — a restaurant it suggests might have closed. Always cross-check the specifics on Google Maps or local food apps (TheFork in Europe, Tabelog in Japan). Use AI for the discovery layer, not the confirmation layer.

Prompt 3 — Last-Minute Pivot
I'm currently in [NEIGHBORHOOD] in [CITY] at [TIME]. The place I planned to go is closed/not what I expected. Based on where I am, suggest 3 alternatives within 15 minutes walking that match this vibe: [describe what you were going for]. Include address or cross-streets.
smobyday tip

Save your best AI travel conversations as notes or PDFs before the trip. Once you're on the ground with spotty wifi, having those recommendations already pulled and saved means you're not re-prompting from scratch in a foreign city with a dead battery.