Multi-City Trip Planner: The Best Apps for 2026

A multi-city trip planner has one job a single-destination planner doesn't: keeping the pieces in line. Every city adds a flight or train in, a stay, and a flight or train out, and each one has to start where the last one ended. A planner that just lists bookings won't tell you that you land in Lisbon on the 12th and your Lisbon apartment starts on the 13th.

Short answer, by what you need most:

• Ordering a lot of places on a map, free: Wanderlog.
• Bookings you already have, from email: TripIt.
• Finding the flights themselves: Google Flights' multi-city search.
• Checking that flights, stays and entry rules fit across countries, on iPhone: NomadPoint.

Disclosure: we make NomadPoint. Each app below is described from its own official page, checked on 3 November 2026.

What makes a multi-city trip hard to plan

Three things go wrong on multi-city trips that rarely go wrong on a single-city holiday.

1. Gaps and overlaps. Two stays that overlap by a night, or a night with no stay because a flight arrives a day before check-in. With five cities you have at least four handovers like this.
2. The order of the cities. Five cities can be visited in 120 orders. Doubling back costs time and money. Most people pick an order once and never question it.
3. Border rules that add up. If several stops are in the Schengen Area, the days in all of them count toward one 90-days-in-any-180 limit, not a separate limit per country. A three-week trip followed by a two-month stay a few weeks later can go over without anyone noticing.

A good multi-city trip planner helps with at least one of these. None of the apps below does all three equally well, so it comes down to which one you're most likely to get wrong.

The apps, and what each is best at

Wanderlog: best for working out the order of the stops

Wanderlog's App Store listing says you can "add unlimited stops for free, optimize your route, view times & distances between places", and every place you add is pinned on a Google Maps-based map. Plans are available offline. You can import reservations by forwarding emails. The listing says linking a Gmail account and exporting a trip to Google Maps need Wanderlog Pro, which the listing sells as monthly and annual plans at several price points.

Pick it if the hard part of your trip is deciding what to see in each city and in what order. It's weaker at checking that bookings across cities line up. For a full side-by-side see NomadPoint vs Wanderlog.

TripIt: best if your bookings live in your inbox

TripIt's how it works page is simple: forward a booking confirmation to plans@tripit.com "and we'll automatically add it to your trip." For a multi-city trip booked on several sites, that's the quickest way to get everything in one place. TripIt Pro costs $49 a year and adds real-time flight alerts, alternate flight suggestions, fare and seat tracking, check-in reminders and risk alerts.

Pick it if you've already booked most of the trip and want one list of it. TripIt shows what you've booked. It doesn't help much with what you haven't. If you're looking at other options, we keep a list of TripIt alternatives.

Google Flights: best for pricing the flights between cities

Google Flights isn't a trip planner, but it's where most multi-city trips start. Google's help page says you can "find and book round trip, one-way, and multi-city tickets", choosing a flight for each part of the trip.

Use it for the search, then put the result into one of the planners here. It won't hold your stays or tell you about a missing night.

NomadPoint: best for checking that the whole route fits

NomadPoint treats a multi-city trip as one journey: the flights, stays and activities sit on one timeline, city by city. That's where the handover problems show up. A night with no stay booked is shown as a gap, and an unbooked leg between two cities is marked so you know a ticket is still missing.

It also checks the border side, which a general planner doesn't. For each country it shows visa and entry rules for your passport (and a second passport, if you have one), counts days left per country, and adds every Schengen stop into one 90/180 count. Move a flight and the counts move with it. You can try that part on the web with our Schengen calculator without installing anything.

What's free and what isn't, from our pricing page: unlimited journeys and multi-city routes, the day-by-day itinerary, entry rules, Schengen counting, documents, forwarding booking emails, and imports from your calendar, Tripsy, TripIt, Flighty and Google Maps lists are all free. NomadPoint Pro ($29.99 a year or $7.99 a month in the US) adds flight delay, gate and cancellation alerts, the travel-day Live Activity, and alerts before a visa or stay allowance runs out. It runs on iPhone, iPad, Mac and Apple Watch. It has no Android app.

Pick it if your route crosses borders, or has enough cities that you're likely to miss a gap. It's newer and smaller than the apps above, and it doesn't optimize the order of your stops the way Wanderlog does.

How to plan a multi-city trip, step by step

Whichever app you use, this order avoids most problems.

1. Fix the first and last city. Those are usually your long-haul flights and the most expensive tickets. Price them as a multi-city ticket and as two one-ways before you decide.
2. Put the middle cities in geographic order. Draw the route on a map. If a line crosses itself, swap two stops. Wanderlog's route optimizer does this for places inside a city. Between cities, a map and five minutes usually do it.
3. Decide the nights per city before booking anything. Write it down as dates: Lisbon 12 to 15 November, Seville 15 to 18. A stay ends on the same date the next one starts.
4. Check the border rules for each country. Visa-free in one country doesn't mean visa-free in the next. If you have several Schengen stops, add their days together and check them against everything you've spent in Schengen in the past 180 days.
5. Book the legs between cities, then the stays. Transport times decide which night you actually arrive. A late flight might mean you need the stay from the day before.
6. Look for gaps once more before you go. Every night should have a stay and every city change should have a ticket. This is the step a planner should do for you.

For keeping the finished plan in one place, our guide to the best app to organize a travel itinerary goes deeper. For a wider look at planners, including AI ones, see the best travel planning apps.

For two worked examples, see the 2-month Southeast Asia backpacking route and the 4-week Vietnam route from north to south.

Frequently asked questions

Is there a free multi-city trip planner?

Yes. Wanderlog's core planner, including unlimited stops and route optimization, is free according to its App Store listing. NomadPoint's journey planner, multi-city routes and entry rules are free too, and the paid tier is only for alerts. Google Flights' multi-city search is free to use.

Is a multi-city ticket cheaper than separate one-way flights?

It depends on the route and the airlines, so price the trip both ways in Google Flights before you book.

How do I plan a multi-city trip in Europe?

Order the cities geographically, set the nights per city as dates, and then check the Schengen 90/180 rule across all your Schengen stops together, since they share one limit. Non-Schengen countries such as the UK or Albania have their own rules for your passport.

What is the best multi-city trip planner app for iPhone?

It depends on the hard part of your trip. Wanderlog is best at ordering places on a map, TripIt at collecting bookings from email, and NomadPoint at checking that flights, stays and entry rules line up across countries.

Plan the whole route in one journey. NomadPoint shows every city, flight and stay on one timeline and flags the nights and legs still missing. Free on iPhone, iPad and Mac.

Download NomadPoint on the App Store