How to plan a trip step by step: a 5-day Lisbon and Sintra itinerary

Before you start: the example trip

Two people leave Madrid on Saturday, October 3, 2026 and come back on Thursday the 8th. They want to see Belém, spend a day in Sintra and leave time to wander around Alfama at their own pace. They haven’t booked anything yet.

The places (Belém Tower, Palácio da Pena, Rossio station) are real and their coordinates approximate. The two hotels (“Hotel Calçada Azul” and “Apartamentos Doca Norte”), the restaurant (“Tasca do Pátio Verde”), the prices and the bookings are made up.

Everything that follows works today in the browser. The iPhone and Android app is on its way to the stores; anything that differs on your phone is mentioned in its step.

The order matters more than the tool: first dates and destination, then what you want to see, then where to sleep, and only then each day’s plan. Planning the days before you know where you’re sleeping means redoing them.

1. Create the trip: name, destination, dates and time zone

In «Tus viajes» (“Your trips”), tap «Nuevo viaje» (“New trip”), or «Crear un viaje» (“Create a trip”) if it’s your first. The «Nuevo viaje» dialog opens:

1. «Nombre» (“Name”): Lisboa y Sintra en otoño. It’s the only required field: a trip without dates is saved as an idea.
2. «Destino» (“Destination”): Lisboa y Sintra. When you leave the field, Kokai looks up each part separately and puts them together. Below it you’ll see what it found, in the form «En el mapa: …» (“On the map: …”). If it says «No lo encuentro en el mapa» (“I can’t find it on the map”), try a city, an island, a region or a country.
3. «Ida» (“Departure”): October 3, 2026. «Vuelta» (“Return”): October 8, 2026. The return can’t be before the departure.
4. «Zona horaria del destino» (“Destination time zone”): Europe/Lisbon. It isn’t deduced from the destination: the selector starts with your device’s zone, so from Madrid you have to change it. Mainland Portugal is one hour behind mainland Spain, and «las horas del plan y de las reservas se leen en la hora de allí» (“plan and booking times are read in local time there”).
5. «Moneda» (“Currency”): EUR. «Viajeros» (“Travellers”): 2 (from 1 to 99).
6. Tap «Crear el viaje» (“Create the trip”).

October 3 to 8 comes to six days and five nights: a night is named after the date of its evening, and on the 8th you no longer sleep there. Kokai stores dates as destination dates (2026-10-03), not as instants, so a clock change can’t shift any day.

With the destination placed, the trip map, the interest maps and the AI plan map already open over Lisbon, search gives priority to what’s nearby, and the «Resumen» (“Summary”) uses the destination on the map as its cover.

If you want the AI to know how you travel, in «Ajustes del viaje» (“Trip settings”) → «Cómo es este viaje» (“What this trip is like”) write something like: Viaje en pareja, sin prisa, nos gusta comer bien y andar; evitamos las colas. (a couple’s trip, unhurried, good food and walking, no queues). It’s optional.

2. Save your places, with their category and priority

Open the «Mapa» (“Map”) tab. There are two ways to add a place: type in «Buscar un lugar para añadirlo…» (“Search for a place to add it…”) and pick a result («Guardar este lugar», “Save this place”), or tap «Añadir tocando el mapa» (“Add by tapping the map”) and tap where it is. Either way you choose «Nombre» (“Name”) and «Categoría» (“Category”), can tick «Imprescindible» (“Must-see”) and tap «Guardar el sitio» (“Save the place”).

Each place has one of seven categories (accommodation, food, sightseeing, nature, leisure, transport and practical) and a priority: «Imprescindible» (“Must-see”), «Si hay tiempo» (“If there’s time”) or «Quizás» (“Maybe”). Priority isn’t decoration: it’s used to compare accommodation and to tell the AI what can’t be missed.

When you create a place, Kokai automatically looks for its photos and links on Wikipedia, Wikidata, Wikimedia Commons and OpenStreetMap. On its card you’ll see them with their author and licence; if a photo isn’t of that place, «No es de aquí» (“Not from here”) dismisses it.

On each place’s card («Dirección, horario, precio y contacto», “Address, opening hours, price and contact”) note the opening hours and price you’ve checked on its official website. It’s the part that changes most from one year to the next.

3. An area interest with AI (optional)

For Sintra, the two people in the example only know about Palácio da Pena. Instead of searching blindly, they create an interest: an area of the map with a question.

Kokai’s AI works with your own key from Anthropic or OpenAI. You set it up in Settings → «Inteligencia artificial» (“Artificial intelligence”) → «Proveedor» (“Provider”) and «Guardar la clave» (“Save the key”). Before sending anything for the first time, the app asks your permission, naming the provider. Without AI, everything else in this guide works just the same.

1. Open «Intereses» (“Interests”; on your phone, inside «Más», “More”) and tap «Nuevo interés» (“New interest”).
2. «Título» (“Title”): Sintra en un día. «Sobre qué» (“About what”): «Una zona del mapa» (“An area of the map”).
3. In «Buscar la zona» (“Find the area”) type Sintra and pick the result. Among the size shortcuts, tap «Una comarca» (“A district”, 40 km radius). The others are «Un barrio» (“A neighbourhood”, 1 km), «Una ciudad» (“A city”, 8 km) and «Una región» (“A region”, 150 km); the control goes from 100 m to 500 km.
4. In the question, write: Qué ver además de la Pena si vamos en tren y a pie, sin coche. (what to see besides Pena by train and on foot, without a car). Tap «Crear» (“Create”).
5. Tap «Proponer sitios» (“Suggest places”). With a radius over 20 km, Kokai asks for 10 places spread across the area (6 up to 2 km and 8 up to 20 km).
6. Go through the «Sitios propuestos» (“Suggested places”) list and tap «Añadir al viaje» (“Add to trip”) on the ones you want, or «Descartar» (“Dismiss”) on the rest.

Say the suggestions include Quinta da Regaleira and Castelo dos Mouros, and both are added. They go onto the map with an approximate location: the coordinates come from a language model and may be off. On their card, drag the pin to the exact spot or tap «Está bien» (“It’s right”). Then change their priority: Regaleira to «Si hay tiempo» and Castelo dos Mouros to «Quizás».

A 40 km radius from Sintra reaches Lisbon and the Cascais coast. If you only want the town and the hills, «Una ciudad» (8 km) gives suggestions closer to each other.

4. Accommodation: compare two options, book and read the PDF

Open «Alojamiento» (“Accommodation”). With the dates set, the «Noches del viaje» (“Nights of the trip”) strip shows the five nights (October 3 to 7) as «Sin alojamiento» (“No accommodation”), with a «Falta alojamiento para…» (“Accommodation missing for…”) notice above. «Buscar en otras webs» (“Search other websites”) opens Booking.com, Airbnb, Expedia and others with the destination, dates and travellers already filled in; more in Searching for accommodation.

After looking at prices, two candidates are left. Each is saved with «Añadir una opción» (“Add an option”; status «Una opción, sin reservar todavía», “An option, not booked yet”), with its «Entrada» (“Check-in”), «Salida» (“Check-out”) and «Precio total» (“Total price”), and placed on the map:

Since there’s no plan yet, Kokai compares each option with your must-sees («de tus imprescindibles», “from your must-sees”); with a plan, it would use what you have planned on those nights and the check-out day. It uses the median and not the average: with Palácio da Pena 23 km from both, the average pushes both hotels away from everything, while the median tells you what will happen almost every day. Here the difference comes from Belém, the castle and the viewpoint: €24 less per night ends up costly in metro rides.

They choose Hotel Calçada Azul and book on the hotel’s website. The PDF confirmation arrives, and in «Alojamiento» they tap «Desde el PDF de la reserva» (“From the booking PDF”):

1. The app reads the PDF’s text on the device, without AI and without sending it anywhere: «Leyendo el PDF…» (“Reading the PDF…”).
2. It recognises that it’s accommodation, check-in on the 3rd and check-out on the 8th, the times, the booking reference, the price and the free cancellation deadline.
3. Since there was already an option for that same hotel on those nights, it turns it into a booking and links the document to it. If there weren’t, it would create a new stay.
4. At the end it says «Leído en este dispositivo: …. Revisa que esté bien.» (“Read on this device: …. Check it’s right.”). Check it: a scanned PDF or a photo has no text and can’t be read.

The apartments option is still there, for the same nights. You remove it from its menu with «Borrar» (“Delete”). If you’d booked without a PDF, «Elegir esta» (“Choose this one”) turns an option into a booking. More on what is and isn’t read in Booking PDFs.

With the booking saved, Kokai schedules three local alerts: «Puedes cancelar gratis…» (“You can cancel for free…”) on September 29 at 10:00, «Hoy es el último día para cancelar gratis…» (“Today is the last day to cancel for free…”) on October 1 at 10:00 and «Mañana duermes en…» (“Tomorrow you sleep at…”) on October 2 at 18:00. And on the 8th, with check-out by 11:00, «Hoy dejas…» (“Today you leave…”) at 9:00 (two hours before, never before 6 or after 9).

5. The day-by-day plan, with estimated journeys

Open «Plan». Each day of the trip is a card; with «Añadir» (“Add”) you choose «Uno de mis sitios» (“One of my places”) or «Otra cosa (una nota, un traslado)» (“Something else (a note, a transfer)”), the «Hora (opcional)» (“Time (optional)”), the «Minutos que dura» (“Duration in minutes”) and «Cómo se llega desde lo anterior» (“How to get there from the previous stop”). From a place’s card, «Añadir al plan» (“Add to plan”) does the same. Anything without a day yet goes to «Sin fecha» (“Undated”).

Because Hotel Calçada Azul is booked, each day starts at the hotel and ends there: a normal day’s card says «Desde…» (“From…”) at the top and «Duermes en…» (“You sleep at…”) at the bottom (on arrival day, «Entras en…», “You check in at…”; on departure day, «Sales de…», “You leave…”), and journeys from and to the hotel count towards the total.

The times don’t come from a routing service: they’re the straight-line distance multiplied by 1.3 (the detour of following streets) at an average speed. That’s why the app always says “about”. If you don’t choose transport, it goes on foot up to 1.5 km and by public transport above that.

With «Ver en el mapa» (“See on the map”), the day is drawn with its stops in order. If a day adds up to too many hours of journeys, that’s the sign to move something to another day with «Mover al…» (“Move to…”) or leave it in «Sin fecha» (“Undated”).

6. The AI plan (optional)

For the remaining days (Alfama on Tuesday, something relaxed on Wednesday), in «Plan» tap «Completar con IA» (“Complete with AI”), or «Crear el plan con IA» (“Create the plan with AI”) if the plan is empty. In «Plan con IA» (“AI plan”) you choose:

• «Desde» (“From”) and «Hasta» (“To”): day 4 to day 5 of the trip, Tuesday the 6th and Wednesday the 7th.
• «Ritmo» (“Pace”): «Tranquilo: dos o tres cosas al día» (“Relaxed: two or three things a day”), «Normal: tres o cuatro cosas y las comidas» (“Normal: three or four things and meals”) or «Intenso: de la mañana a la noche» (“Intense: morning to night”).
• «Qué os apetece» (“What you fancy”): Un día para Alfama sin prisa, fado solo si no hay que reservar, y una tarde en el Oceanário. (an unhurried day in Alfama, fado only if no booking is needed, and an afternoon at the Oceanário).
• «Usar mis sitios guardados» (“Use my saved places”), «Proponer sitios nuevos, que se añadirán al mapa» (“Suggest new places, which will be added to the map”) and «Incluir dónde comer» (“Include where to eat”).
• If those days already have something: «Respetarlas y completar los huecos» (“Keep them and fill the gaps”) or «Rehacer esos días (se sustituyen al guardar)» (“Redo those days (replaced when saved)”).

Tap «Proponer el plan de 2 días» (“Suggest the 2-day plan”). The AI works in batches of three days, in the background: you can leave the screen. It receives the trip, your places (the 60 nearest, with their priority), the existing plan, your interests and where you sleep each night, but never your documents, the booking’s price or reference, or your route.

What it suggests stays as «Propuesta de la IA · sin guardar» (“AI suggestion · not saved”). You review it day by day on the map, remove what you don’t need, ask for «Otra propuesta para este día» (“Another suggestion for this day”) if you’re not convinced and, when it’s right, «Guardar en el plan» (“Save to plan”). New places go in with an approximate location, like those from an interest.

7. Trip documents and wallet

Kokai keeps two things apart: trip documents (tickets, bookings, admission tickets) and the wallet, what’s valid for every trip (passport, ID card, annual insurance, driving licence). The wallet opens from «Tus viajes» (“Your trips”) or with «Abrir la cartera» (“Open the wallet”) in «Documentos» (“Documents”).

1. In «Documentos», «Añadir documento» (“Add document”): type «Billete» (“Ticket”), title Vuelo Madrid – Lisboa, and the boarding pass PDF in «Ficheros (PDF o fotos)» (“Files (PDF or photos)”). If it’s a PDF with text, the app fills in what it finds (airline, dates, booking reference) and says what it filled in.
2. Another document of type «Entrada» (“Admission ticket”) for Palácio da Pena, with «Desde» (“From”) set to October 5 and the related place.
3. In the wallet, each traveller’s ID card and the passport.

Files are stored on the device and open offline, in the boarding queue or with no data. On the eve of a dated ticket, booking or admission ticket, at 18:00, «Mañana: …» (“Tomorrow: …”) arrives with its reference.

Passports, ID cards and health documents don’t leave the device: they aren’t included in your account’s copy and never reach the AI. If you lose your phone, you lose them with it, so it’s worth keeping another copy yourself.

8. The packing list

In «Maleta» (“Packing list”), «Empezar con lo básico» (“Start with the basics”) adds ten things almost everyone forgets at some point, in their groups:

Everything else goes in «Añadir a la maleta…» (“Add to packing list…”), choosing the group. With AI, «Proponer para este viaje» (“Suggest for this trip”) adds what this particular trip calls for (clothes for that time of year, the country’s plugs) and marks it as «Propuesto por la IA» (“Suggested by AI”). Ticking something off takes one tap, and progress shows at the top.

The basic list is short on purpose: nobody goes through an eighty-item list. Remove what doesn’t apply to your destination (the adapter, if they use the same plugs as you) rather than leaving it unticked.

9. Alerts at key stops

Not every place needs an alert. In the example they’re set on four, from each one’s card with «Avisarme al pasar cerca» (“Alert me when I pass nearby”), «A qué distancia» (“How close”) and «Qué quieres que te diga» (“What you want it to say”):

The radius can be set from 75 to 1,000 m. Alerts only go off with the trip on the road, and the app filters out imprecise GPS positions and doesn’t repeat a place’s alert within 45 minutes: the details are in how it avoids false alerts.

10. The first day: start On the road

On Saturday the 3rd, after landing, open the «En ruta» (“On the road”) tab and tap «Iniciar el viaje» (“Start the trip”). The «Antes de empezar» (“Before you start”) dialog explains what the app does with your location and when it stops using it. You can turn on «Marcar como visitados los sitios donde me quede» (“Mark places where I stay as visited”, 8 minutes inside the radius) and, on your phone, «Seguir con la app cerrada» (“Keep going with the app closed”). Tap «Iniciar» (“Start”).

From then on, the On the road screen shows «Esta noche duermes en» (“Tonight you sleep at”) with the hotel’s address («Enseñar la dirección», “Show the address”, displays it in large type for a taxi driver), «Cerca de ti» (“Near you”), «Hoy en el plan» (“Today in the plan”) and the «Avisos» (“Alerts”) that have gone off. The «En ruta» pill is visible from any screen.

• In the browser, alerts work with the tab in front. On iPhone and Android they’ll keep going with the screen off once the app reaches the stores.
• Alerts, the route and the hotel address work without data; the background map doesn’t.
• When you get back to the hotel each night, «Parar el viaje» (“Stop the trip”) saves battery; the next day you start it again.

More about On the road mode on its page and about battery in Battery.

11. When you’re back: stop and export

On Thursday the 8th, at home, tap «Parar el viaje» (“Stop the trip”): the app stops using your location. The trip moves to «Ya viajados» (“Past trips”), with the route and visited places («Este viaje ya pasó. El recorrido y los sitios visitados se quedan aquí.», “This trip is over. The route and the places you visited stay here.”).

To keep a copy of your own, «Ajustes del viaje» (“Trip settings”) → «Exportar» (“Export”) → «Descargar la copia» (“Download the copy”) downloads a JSON file with the places, the plan, the documents (without their files), the interests, the packing list and the stays. The route isn’t included. Exporting works in the browser; on phones it’s still pending.

The recorded route stays on the device. If you don’t want it, use «Borrar el recorrido» (“Delete the route”) on the On the road screen.

Tips for planning any trip, with or without an app

• Two or three must-sees a day, no more. It’s a personal rule of thumb, not a standard: with three big things, meals and journeys, the day is already full. Everything else goes under “If there’s time”.
• Group by area. Belém one day and Alfama another saves more time than any shortcut. If a day adds up to more than an hour and a half of journeys within the same city, something is on the wrong day.
• Check opening hours and closing days on the official website of each monument, and do it close to the date. Many museums close one day a week and change hours with the season; a blog post from two years ago won’t do.
• Book first whatever sells out or has a time slot. Palácio da Pena tickets, for instance, are sold with a date and time, according to the Parques de Sintra website. Put the time in the plan and build the day around it.
• Sleep close to what you’ll do most days, not to the day trip. Compare with the median, not the average.
• Leave a gap. Half a day with no plan absorbs rain, tiredness and whatever you discover there.
• Look at cancellation before price. A non-refundable rate saves little if your dates change. Note down the free cancellation deadline.
• Keep your documents offline and somewhere else too. Phones get lost or run out of battery.
• Treat estimated times as a lower bound. A straight-line estimate knows nothing about hills, queues or waiting: leave slack around trains and timed tickets.

Frequently asked questions

Sources and references

The original documentation for what is cited here, checked on this page’s review date.

1. National Palace of Pena: opening hours and tickets with date and time Parques de Sintra – Monte da Lua
2. Train timetables and tickets CP – Comboios de Portugal
3. Museus e Monumentos de Portugal Museus e Monumentos de Portugal
4. Time zone database (Europe/Lisbon) IANA
5. Travel documents for EU citizens Your Europe, European Union
6. Travel advice by country Spain’s Ministry of Foreign Affairs
7. Haversine formula Wikipedia

Keep reading

• The planHow each day’s plan comes together in Kokai: timed places, notes and transfers, how long from one stop to the next and how to ask the AI for a draft itinerary.
• AccommodationHow Kokai organises accommodation by night: bookings, undecided options, gaps, double bookings, free cancellation alerts and the hotel address offline.
• Travel documentsTravel documents checklist: ID, passport validity, visas and ETIAS, insurance and EHIC, tickets, driving and health, with official sources.
• On the roadHow Kokai alerts you near a saved place: the radii it uses, how it avoids false GPS alerts, what it records of your route and what it does with your location.
• GlossaryTravel glossary: what a geofence, a stay, a booking reference, GPS hysteresis or PMTiles is. 35 travel and map terms, with the figures Kokai uses.