Multi-City Trip Planner
Plan Tokyo → Kyoto → Osaka or Athens → Santorini → Mykonos in one itinerary. Add your stops and nights — the AI splits your days per city automatically and stitches everything into a single day-by-day plan.
What is a multi-city trip planner?
A multi-city trip planner splits one trip across several destinations and works out how long to stay in each, in what order, and how you get between them.
The extra difficulty is the joins. Days lost to travel are the ones people forget to count, and a route that looks tidy on a map can still mean a 6am flight that swallows a whole morning at both ends.
MonkeyTravel plans each city day-by-day and keeps the transitions in view, so a three-city trip reads as one continuous schedule instead of three separate plans stapled together.
Rome, Florence and Venice in ten days is not three separate trips. It is roughly seven usable days and three spent moving, and where you put the split matters.
It does not book transport or read live timetables. Confirm the connections before you commit to the shape of the trip.
Live from the planner
- Trips planned
- 3,200+
- Planned in the last 30 days
- 1,100+
- Activities on saved itineraries
- 22,000+
- Median time to a full itinerary
- 24s
Real counts from planning sessions, with bots and automated traffic left out.
Built for Trips That Don't Stay in One City
Everything the single-city planner does, extended across your whole route.
Per-City Day Allocation
Set how many nights you want in each city and the AI plans exactly that many days there — 3 nights in Kyoto means three full Kyoto days, not a guess.
Journey Overview
A city-by-city ribbon shows your whole route at a glance: where you start, how long you stay, where you head next. No spreadsheets required.
Up to 5 Cities & 21 Days
Chain up to five cities and three weeks into one itinerary — enough for Japan's Golden Route, a Greek island hop, or a full grand tour of Italy.
Group Voting
Share the trip with your travel crew, let everyone vote on stops and activities, and lock in the route the whole group actually wants.
How It Works
Add Stops & Nights
List your cities in order and set the nights for each — Rome for 3, Florence for 2, Venice for 2. Done in seconds.
AI Plans Every City in Parallel
Each city gets its own day-by-day plan, generated simultaneously and stitched into one continuous itinerary with the right days in the right places.
Drag, Edit & Share
Reorder activities, swap venues, rebalance days — then share the trip with friends or keep it to yourself. It's your route.
Popular Multi-City Routes
Start from a classic and make it yours — every route opens the planner in multi-city mode.
Japan Golden Route
Neon, temples, and street food — the classic first-timer line through Japan's big three.
Greek Islands
Ancient ruins, caldera sunsets, and island nightlife in one sweep of the Aegean.
Iberia
Gaudí and the beach, then the Prado and rooftop bars — Spain's two heavyweights back to back.
Italy Classic
Colosseum mornings, Renaissance afternoons, canal evenings — Italy's essential trio.
Frequently Asked Questions
How does the AI split days between cities?
You set the nights per city when you build your route, and the AI allocates whole days to match. Each city is generated as its own mini-itinerary, then everything is stitched into one continuous day-by-day plan. Want a different balance? Change the nights and regenerate.
How many cities can I add to one trip?
Up to five cities in a single itinerary. That covers most classic routes — Tokyo–Kyoto–Osaka, Rome–Florence–Venice, or a three-island Greek hop — while keeping each stop long enough to actually enjoy.
Can I plan a trip longer than 2 weeks?
Yes — multi-city trips go up to 21 days, versus 14 for single-city trips. That's enough for a full three-week route without splitting your plan across separate trips.
Is the multi-city planner free?
Yes. Multi-city planning is part of MonkeyTravel's free planner: no credit card, no trial period. Multi-city planning is included at no cost.
Can my group vote on the stops?
Absolutely. Share your trip via link and everyone can vote on activities and stops, propose changes, and reach consensus before anyone books anything.
Ready to Plan Your Multi-City Trip?
Add your stops, set your nights, and get one seamless itinerary across every city — free.