Trip Itinerary Builder

Build a day-by-day itinerary that survives real travel: jet lag, weather, tired feet, and the museum that turned out to be closed on Tuesdays. The craft is mostly restraint and geography — cluster each day around one area, give each day a single timed anchor, alternate intense days with loose ones, and write the contingencies down before they are needed. Criss-crossing a city twice in one day is the classic amateur tell this skill exists to prevent.

When to use this skill

The user names a destination and dates and wants a day-by-day plan
A pile of saved recommendations needs turning into a coherent route
An existing itinerary feels overstuffed and needs pacing surgery
A trip involves multiple bases and the connection days need planning
Someone asks what to book ahead versus decide on the ground

Intake

Gather before building: exact dates plus arrival and departure times; the party — ages, mobility, travel styles; pace preference on a scale from packed to lazy; ranked interests (food, art, nature, history, nightlife); budget band; anything already booked; and where they are sleeping each night.

Workflow

Anchor the skeleton on the travel realities first. Arrival day gets a gentle plan scaled to the journey — after a long-haul flight it is a walk, a meal, and an early night, not a headline sight. Departure day contains nothing that hurts to abandon: no must-sees within four hours of a flight.
Cluster attractions by geography. Put everything of interest on a map, group by neighborhood or area, and assign one cluster per day-part. Transit between clusters happens at most twice a day.
Give each day exactly one anchor — a single timed, booked commitment. Everything else on the day flexes around it. Two timed anchors in one day is how a delay becomes a domino run.
Pace deliberately: cap big sights at two per day, alternate an intense day with a looser one, and respect the party's walking budget. The third big sight of the day is where trips go to die — it gets a fraction of the attention at triple the fatigue.
Triage reservations into three lists: book-before-flying (sells out or has timed entry), book-two-days-ahead (popular restaurants, tours), and walk-up. Note the date each booking window opens where it matters.
Treat meals as geography, not appointments: save two or three options near each day's cluster, book at most one special meal per trip, and leave the rest to appetite and discovery.
Add the contingency layer to every day: a wet-weather swap of similar appeal, and a "cut first" item — the thing that drops without regret when energy runs out. Deciding this in advance turns a bad afternoon into a shrug instead of a negotiation.
Finish with the logistics ledger: transit between clusters with realistic times plus 25 percent, tickets and passes to pre-buy, and a one-line plan for luggage on base-change days.

Day-block template

Day 4 — Old Town + riverfront
morning     Old Town on foot: market square, cathedral (open 9:00)
anchor      12:30 river cruise — BOOKED, gate 15 min before
afternoon   riverfront museum quarter, one museum max
lunch nearby   two saved options by the market, no booking
evening     dinner in Old Town, sunset viewpoint if legs allow
wet swap    covered market + gallery instead of riverfront walk
cut first   the second museum
getting around   tram 4 out, 25 min back on foot along the river

Output format

Deliver the full itinerary as one day-block per day, preceded by a trip summary (bases, anchors, pace) and followed by the booking checklist sorted by deadline — soonest first, with booking-window opening dates flagged.

Common failure modes

Two timed bookings in one day, so a single delay knocks over the whole afternoon
The greatest-hits route that criss-crosses the city because the list was sorted by fame, not geography
Arrival-day heroics after a long-haul flight
Museum days stacked back to back until nobody can look at another framed thing
Every meal booked, leaving no room for the place discovered on the corner
No cut-first item, so fatigue decisions happen at the worst moment with the most guilt
A base change with no luggage plan, spending the best hours of a day dragging bags

Pacing rules

One anchor per day; two big sights maximum; transit clusters at most twice a day
Every second or third day carries visible slack — an unplanned morning or afternoon
Nothing precious within four hours of a departing flight or train
The walking budget matches the least mobile member of the party, not the most eager
If every evening is planned, the trip has no room to be surprised — leave two open