Plan a trip honestly.
Not the top-10 tourist list. The day-by-day plan that respects your constraints — jet lag, budget, what you'd actually enjoy.
You have five days in a city you don't know. Every guide has the same top-10 list. You want the plan tuned to how you actually travel — how much walking, how much food, whether you like museums, how you handle jet lag. This prompt asks for the constraints and then plans around them.
THE PROMPT
Plan a trip for me with the following constraints. Do not generate a generic itinerary; take the constraints seriously. **Destination**: [CITY, DATES] **Days on the ground**: [NUMBER, e.g., 5 full days] **Travelers**: [WHO — solo, couple, family, notes] **Energy budget**: [HIGH / MEDIUM / LOW — e.g., "medium, want to sleep in most days, one day I'm okay with a 20K step count"] **Food priority**: [HIGH / MEDIUM / LOW] **What I don't want to do**: [SPECIFIC — e.g., "no walking tours, no queuing for major museums, no Michelin dinners"] **What I care about most**: [ONE OR TWO SPECIFIC THINGS] **Rough daily budget for food and activities**: [NUMBER, per person] Return: **Day-by-day itinerary** For each day: morning / afternoon / evening. Each slot names one specific thing (not "explore [neighborhood]" — the specific café, the specific viewpoint). Include actual place names, and mark [BOOK IN ADVANCE] on anything that needs a reservation. **Where to base yourself** The specific neighborhood, with one sentence on why for these travelers. If two neighborhoods work and the choice is real, name both. **Reservations to make now** Bullet list of the specific things that need booking more than 2 weeks out. **Days I've deliberately underplanned** Name which days have breathing room built in, and why. Great trips are not fully scheduled. **One thing I've cut that most itineraries would include** Name what and why — respecting the constraints often means saying no to a "must-see". Own it.
**Day-by-day itinerary — 5 days in Lisbon (medium energy, medium food priority, no queues)**
Day 1 (Arrival):
- Morning: sleep in — you'll be off a red-eye.
- Afternoon: pastel de nata + coffee at Manteigaria (Chiado). Slow walk down to Ribeira market.
- Evening: casual dinner at Prado. In bed by 22:00.
Day 2 (Alfama):
- Morning: coffee at Fauna & Flora, take the 28 tram east one way to Alfama.
- Afternoon: wander the Alfama backstreets. Miradouro Portas do Sol for the view. No São Jorge castle (queues, overrated).
- Evening: fado at Mesa de Frades [BOOK IN ADVANCE, ~2 weeks].
Day 3 (Belém, easy day):
- Morning: Uber to Belém. Jerónimos Monastery early or skip (queues).
- Midday: Pastéis de Belém (worth the small queue) then walk the riverfront.
- Afternoon: back to your neighborhood, nap.
- Evening: dinner near your base — Taberna Sal Grosso or Damas.
Day 4 (Sintra day trip — the high-energy day):
- Train from Rossio at 09:00. Full day. Pena Palace [BOOK ADVANCE TICKET, ~2 weeks], Quinta da Regaleira, back to Lisbon by 19:00.
- Evening: light dinner near your accommodation. Early bed.
Day 5 (Departure day, no plans):
- Morning: breakfast at Dear Breakfast. Buy pasteis to take home from Manteigaria.
- Airport by [flight-appropriate time].
**Where to base yourself**
Príncipe Real. Central, calm, walkable to Chiado and Bairro Alto, but not in the noise of them. Alfama is beautiful and I considered it — I ruled it out because it's genuinely hilly and the medium-energy constraint makes daily hill climbing miserable.
**Reservations to make now**
- Pena Palace Sintra timed-entry ticket (day 4).
- Mesa de Frades fado (day 2).
- Dear Breakfast (day 5) — walk-in works but Saturday morning gets tight.
**Days I've deliberately underplanned**
Days 1 and 5 (arrival and departure) are effectively free days — you'll want them. Day 3 (Belém) is a half-day plan on purpose to let you rest before the Sintra full day.
**One thing I've cut that most itineraries would include**
The Time Out Market. It's the number-one thing every Lisbon guide mentions. It's fine, but it's a mediocre food-court version of what neighborhoods around it do better, and it's crowded in a way that trades against your "no queues" constraint. Skip it.