How to Plan a Multi-Destination Trip (Step-by-Step Guide)

When it comes to travel, there are so many options that make it hard to choose where to go. You want to see Paris, Barcelona and Rome in two weeks. Or maybe it’s Amsterdam, Bruges and Berlin. The idea sounds perfect until you open Google Flights and your brain starts to hurt.

Planning a trip with multiple destinations doesn’t have to be overwhelming. I’ve been addicted to multi-stop travel for years, and I’ve learned that the secret isn’t working harder at planning. It’s having a repeatable method that works every time.

Whether you’re planning a trip to two cities or five countries, this guide will show you how to plan a trip with multiple destinations that feels relaxed rather than rushed.

Step 1: Choose your anchor destination and trip style

The biggest mistake people make when planning a route with multiple stops is trying to pick everything at once. Your brain gets overwhelmed, and suddenly you’re reading 47 blog posts about whether Slovenia is worth it.

Pick one “must-see” and build around it

Start with your anchor. This is the one place you absolutely want to visit. It could be a specific city like Lisbon, or a region like Tuscany, or even one particular experience like seeing the Northern Lights. Once you have that anchor, everything else becomes easier. You’re not choosing from every city in Europe. You’re choosing from places that make sense near your anchor.

When we decided Croatia would be our anchor, we had to choose which part of the country to focus on. That decision helped us determine the remaining stops. The same thing happened with Portugal. We needed that anchor to organize the whole trip.

The anchor stays fixed. Everything else is flexible. This approach cuts your decision-making time in half.

Decide what kind of multi-stop trip you’re planning

Not all trips with multiple destinations are the same. The planning changes based on how you’re moving between places.

• Train-based city hopping works well in Europe, Japan, and other places with good rail networks. You can book a rail pass or individual tickets, stay in city centers, and move between different locations in a few hours.
• Multi-day road trips give you the most freedom. We did this in Iceland, stopping at a different town each night. You control the pace and can add spontaneous detours, but you need to factor in driving time and fatigue.
• Multi-city flights make sense when distances are considerable or time is tight. This is where open-jaw tickets (flexible flight booking where you fly into one city and depart from a different one) come in handy.

Pick your style based on distance, time, and what sounds fun to you. Each one changes how you book transport and where you stay.

Step 2: Build a route with multiple stops that minimizes travel time

This is where most people either nail it or create a nightmare schedule for themselves. The goal is simple: see what you want without spending half your vacation travelling from one place to another.

Start with a map, then check real travel times

Open Google Maps and drop a pin at every place you’re considering. Look at the big picture. Are these places clustered together, or are you trying to connect dots across an entire continent?

Now here’s the part that saves you from disaster: check actual travel times before you fall in love with your route. That cute medieval town might look close on the map, but if it takes four hours and two transfers to get there, it might not be worth it.

I often rely on Google Maps to check train times, flight durations and drive distances. If a connection takes more than four hours, I think twice about whether both stops belong on the same trip.

Use “one direction” logic to avoid backtracking

The best order for visiting multiple cities with minimal travel time is almost always a line, not a circle. Pick a direction and stick with it. Go north to south. Coast to inland. East to west. Whatever makes sense for your destinations.

Bad route: Fly into Barcelona, take the train to Paris, fly to Rome, then fly back to Barcelona to fly home.

Better route: Fly into Barcelona, take the train to Paris, fly to Rome, and fly home from Rome.

See the difference? The second route doesn’t make you retrace your steps. You’re always moving forward, which saves time and money. The only time you backtrack is when your anchor destination is genuinely in the middle, and you want to use it as a base for day trips.

Add one buffer night for long transfers

If you have a transfer day with a flight or train ride longer than three hours, don’t plan a full day of sightseeing on either end. Build in a buffer night. Arrive the night before a long trip so you’re not stressed about making your train. Or arrive at your next stop with enough time to settle in before you start exploring.

We learned this the hard way in Palermo. Our flight was scheduled to land around midnight, but delays meant we didn’t arrive at our destination until 2 a.m. We were useless the next day. If we’d planned that as a “rest day,” it wouldn’t have felt like a waste. Flight delays happen. Trains get cancelled. Roads close. That extra night gives you room to breathe when things go wrong.

Step 3: Decide how many days per city for a relaxed pace

You’ve picked your cities. Now you need to figure out how long to stay in each one. Get this wrong, and your whole trip will feel like a race.

A simple pacing formula (and when to break it)

Most European cities can be seen well in 2-4 nights. That’s enough time to hit major attractions, wander neighbourhoods, eat good food, and not feel like you missed everything.

Big cities like Paris, Rome or London can easily fill four or five nights. Smaller cities such as Porto, Bruges, or Salzburg may require only two nights. Tiny towns you’re using as a base for day trips might need one.

Here’s my rule: if I’m moving every single day, I’m doing it wrong. At least one stop on your trip should be three nights or longer. That gives you time to do laundry, sleep in, or sit at a cafe without a set plan.

If you’re travelling with kids or anyone who doesn’t travel often, add an extra night to most stops. The pace that works for me might be exhausting for someone else.

Don’t count travel days as sightseeing days

This is the number one reason multi-destination trips feel rushed. People count the days wrong. For example, if you take a train from Paris to Amsterdam at noon, that’s not a Paris day, and it’s not an Amsterdam day. It’s a travel day. You lose half a day on each end.

When I plan, I mentally cross out any day where I’m moving between cities. If I want three full days in Rome, I need to book four nights. The first day I arrive doesn’t count because I’m tired and it’s probably afternoon. The last day I leave doesn’t count because I’m checking out and trying to get to the train station or airport.

This is why a two-week trip often only leaves you 10 real days of exploring. The rest is moving, recovering, or catching flights.

Step 4: Budget trips with multiple destinations per person

Budgeting multiple destinations feels complicated because costs keep popping up in weird places. But if you break it into two buckets, it gets easier.

The “fixed vs variable” budget method

Fixed costs are things you book ahead and know the exact price: flights between cities, train tickets, hotels, any pre-booked tours or museum entries, and travel insurance.

Variable costs are everything else: meals, local transport, taxis, attraction entries you buy on the spot, souvenirs, or that extra gelato.

When I’m planning, I total up the fixed costs first. That gives me the baseline cost per person before we leave home. Then I estimate variable costs at about $50-100 per person per day for Europe (depending on the country and our eating habits).

If the fixed costs are already high, I look for ways to cut variable costs. Maybe we can stay in an Airbnb with a kitchen so we can cook breakfast. Perhaps we can skip the hop-on-hop-off bus and walk instead.

Don’t forget to plan for “transfer costs”

Multiple destinations have hidden costs that single-destination trips don’t. They’re small, but they add up fast. This can include everything from baggage fees for flights between cities and seat selection fees to taxi fares and luggage storage.

I usually budget 10-15% of my fixed costs to cover surprise expenses. It’s better to overestimate and have money left over than to blow through your budget by day four.

Step 5: Book transport the smart way

This is where planning a trip with multiple destinations either saves you money or costs you way more than it should. The key is booking smart, not booking everything at once.

Tips for booking flexible multi-city flights

If you’re flying into one city and out of another, book it as a multi-city or open-jaw ticket. You can do this directly on airline websites or through Google Flights. Sometimes it’s cheaper to book one ticket that includes both flights. Sometimes it’s cheaper to book them separately. You have to check both options.

Look at the fare rules before you book. Some tickets let you change dates for a fee. Others are locked in. If your trip is more than four months away, paying extra for flexible fares might be worth it.

Pay attention to connection times if you’re booking flights between cities. If you miss the connection because the first flight was late, you might have to buy a new ticket or have your suitcase arrive on a different flight.

And check which airport you’re flying into. Some cities have multiple airports. Flying into the one that’s an hour outside the city might save $50, but cost you $40 in transport and two hours of your day.

When trains beat flights for multi-stop itineraries

For short distances, trains often win. When we were going from Lisbon to Porto, the flight was shorter, but we also had to consider getting to the airport early, waiting to board, and getting from the Porto airport into the city. The train was longer, but we saved time overall, and it was cheaper.

Trains also give you flexibility. If you miss your train, you can usually catch the next one for a small fee or sometimes for free. Miss your flight and you’re often starting over.

In Europe, rail passes can save money if you’re doing lots of train trips. But sometimes individual advance tickets are cheaper. Compare both before you commit. Don’t forget to compare basic fares with premium or first-class tickets, as they might be cheaper.

One last thing: overnight trains can save you a night of accommodation. If you’re okay sleeping on a train, it’s a clever way to cover long distances and save money at the same time.

A quick checklist before you click “buy”

• Connection time is realistic.
• The airport or station is actually convenient.
• Baggage rules work for your packing style.
• Arrival time doesn’t force you to check in at 1 a.m.
• You have a backup plan if one segment gets cancelled or delayed.
• Screenshot or save every confirmation in a folder on your phone.
• Keep a backup on Google Drive. It sounds like overkill until your email stops working and you need to show your train ticket.

Step 6: Choose lodging that makes multi-stop travel easier

Where you stay matters more on a multi-destination trip than it does on a normal vacation. Location isn’t just about being near attractions. It’s about reducing effort.

Stay near the station when you move every few days

If you’re moving between cities every two or three days, book hotels or Airbnbs within 10 minutes of the train station or main bus terminal. This saves you time and taxi money every time you arrive or leave. You’re also not dragging luggage across cobblestones for 20 minutes. You’re not stressed about missing your train because your Uber got stuck in traffic.

If you’re staying somewhere for four nights or longer, you can choose based on which neighbourhood you want to explore. But for short stops, stay close to your exit point.

One-night stays can cost you more than you think

Every time you change hotels, you lose time. Checking out, getting to the station, travelling, finding your new place, checking in, unpacking. Two nights is my minimum for most stops. Three nights are better. That gives you one full day in the middle where you’re not coming or going.

One-night stays feel efficient on paper, but they’re exhausting in practice. If I’m only staying one night somewhere, it’s because there’s literally nothing else to do there or because I’m using it as a sleep stop between two longer stays.

Constantly moving hotels is also exhausting. You’re always thinking about the next connection, the next check-in time, and whether you remembered to pack everything. This makes your trip less enjoyable.

Step 7: Keep your itinerary organized (without overplanning)

You need to be organized when you’re planning a route with multiple stops. But you don’t need to plan every single hour. There’s a sweet spot.

Create one master itinerary you can access offline

I keep one document that has everything I need, in the order I need it. Dates, hotel names and addresses, confirmation numbers, train times, flight info, and any notes about check-in instructions.

I don’t include restaurant lists or detailed daily plans. Just the stuff that gets me from point A to point B without panic. The format is simple. Each day gets a heading. Under that day, I list where I’m sleeping, how I’m getting there, and any critical info like “hotel check-in is after 3 p.m.” or “train leaves from platform 7.”

Step 8: Pack light for a multi-stop itinerary

Packing light isn’t just about fitting everything in a carry-on. It’s about not hating your life every time you move to a new city.

Pack for laundry, not for every day

Bring fewer clothes and plan to wash them. Most hotels have laundry service. Most Airbnbs have washing machines. Even if you’re in hotels the whole time, you can hand-wash basics in the sink.

I pack one week’s worth of clothes, no matter how long I’m gone. I plan one laundry stop halfway through. Laundry can add an hour to your trip. Dragging a 50-pound suitcase through cobblestone streets in five cities adds stress to every single day.

Use a “carry-on capsule” list

Pack clothes that all work together. Stick to two or three colours so everything matches. Bring layers instead of bulky single items.

Here’s what I pack for two weeks:

Three tops, two pairs of pants, one dress or nice shirt, one lightweight jacket, one pair of walking shoes, one pair of dressier shoes or flip flops (depending on destination), underwear and socks for five days, one swimsuit if it makes sense, and one small daypack. That’s it. Everything fits in a carry-on.

Common mistakes that make multi-destination trips exhausting

You can do everything right and still burn out if you make these mistakes. I’ve made all of them, so I’m speaking from experience.

• Too many one-night stops. This is the big one. If more than half your trip is one-night stays, you’re going to be tired and annoyed by day five. Slow down. Cut a city or add nights.
• Early flights after late arrivals. Don’t fly into a city at 10 p.m. and then book a 7 a.m. train the next morning. You’ll be useless. Give yourself at least one night to recover.
• Ignoring jet lag. If you’re flying from North America to Europe, you’re losing a day to jet lag, whether you admit it or not. Don’t plan major sightseeing on day one. Sleep, walk around, eat, and go to bed early.
• Skipping buffer time. Trains run late. You get lost. Museums take longer than you think. If your schedule is packed with back-to-back plans, one delay ruins everything.
• Trying to see everything. You can’t. And trying to cram in every church, museum, and viewpoint will make you hate travel. Pick three things you actually care about per city. Skip the rest without guilt.

Multi-destination trip checklist

• A valid passport. It needs to be valid for at least six months after your return date for most countries. Check now, not two weeks before you leave.
• Visas. Some countries require them. Some don’t. Don’t assume. Look it up based on your citizenship.
• Plug adapters. Europe uses different outlets than North America. Asia uses different ones than Europe. Bring the right adapter or buy one when you land.
• SIM card or eSIM. You need data for maps, confirmations, and communication. You can get a local SIM at the airport or set up an eSIM before you leave.
• Travel insurance. Don’t skip this. Medical emergencies, cancelled flights, lost luggage, all of it can happen. Insurance is cheaper than paying out of pocket for a hospital visit abroad.
• Key bookings saved offline. Hotels, trains, flights, and car rentals. Download or screenshot everything. Store it in a folder you can access without wifi.
• A buffer fund. Keep an extra $200- $500 on hand for unexpected expenses. Missed trains, emergency hotel nights, and medical costs. If you don’t use it, great. If you need it, you’ll be glad it’s there.

Other ways to enjoy multi-destination travel

If you’re not quite ready for planning your multi-destination trip or just can’t be bothered, there are a few ways you can still get a taste of it.

• Cruises: Cruising can be a great way to see the world. Everything is pretty much planned for you.
• Group tours: Another great way to visit multiple destinations while someone else does the planning.
• Use a travel specialist: There are many travel experts who can plan your entire trip for a fee.

Final thoughts

Multi-destination travel can be fun, and it offers a great way to see the world. It can sharpen your research skills and challenge your mind. For me, it’s like solving a problem, and it gets addictive. What makes multi-destination travel so appealing?

• You get to see more places in less time.
• It’s more cost-effective than visiting each place on separate trips.
• Your travel planning skills will be challenged and tested.
• It will be an adventure.
• You won’t be bored.

However, there is a fine line between visiting multiple destinations and your trip turning into a nightmare. I hope this post has provided valuable tips for planning your trip so you can make the most of it and enjoy it.