How I Plan a Europe Trip (And Why I Don't Start With Destinations)

When someone tells me they want to go to Europe, they usually expect my first question to be,

"Which countries are on your bucket list?"

But that's almost never where I start.

Because "going to Europe" means something completely different to every person.

For some people, it's finally seeing Paris, London, and Rome.

For others, it's long dinners at sidewalk cafés in Italy, wandering through small towns, hiking in the mountains, relaxing by the water, tasting local wine, or spending days exploring museums and historical sites.

Some people dream about seeing as much as possible.

Others picture themselves slowing down and soaking in one place.

Before I recommend a single destination, hotel, or itinerary, I want to understand something much more important:

What are you hoping this trip feels like?

That answer shapes everything that comes next.

Every Great Itinerary Starts With the Traveler

When I begin planning a Europe trip, I'm thinking about much more than destinations.

I'm thinking about the time of year someone wants to travel, how many days they actually have, where they can realistically fly in and out of, and what routing makes the most sense.

A lot of people start with a list of places they've heard of and try to connect them together.

I'm usually doing the opposite.

I'm trying to figure out what kind of trip they actually want first. Once I understand that, I can recommend the destinations that naturally fit.

I don't want to recommend a place simply because it's popular or because it's all over Instagram.

I want to understand why someone wants to go to Europe and what they're hoping to get out of the experience.

The Questions That Matter Most Usually Aren't About Destinations

People sometimes come to me with a list of ten cities because they feel like if they're flying all the way to Europe, they need to see as much as possible.

But once we start talking, I often discover something completely different.

They tell me they don't like early mornings.

They don't want to change hotels every two days.

They love long dinners.

They want time to wander without feeling rushed.

Those answers immediately tell me that the itinerary they've imagined probably isn't going to give them the vacation they actually want.

Before I recommend places, I want to understand:

• What do you enjoy most when you travel?

• What has frustrated you on previous trips?

• How active do you want your days to be?

• What does a really good vacation day look like to you?

• 
  

Once I understand those answers, the itinerary usually becomes much clearer.

I Plan Around How You Want the Trip to Feel

This is probably the biggest difference in how I approach planning.

Two people can both tell me they want to visit Italy.

One couple wants the trip to feel romantic and slow. They're picturing beautiful hotels, long dinners, wine, small towns, and maybe a few relaxing days by the water.

Someone else wants to wake up early every morning, see the major sights, take a cooking class, hike, and fit as much as they reasonably can into each day.

Neither approach is right or wrong.

They're simply two completely different vacations.

The same is true for families.

If someone tells me they want their family trip to feel easy, that immediately changes how I plan.

I'm probably choosing fewer hotel changes. I'm looking for hotels where they can easily walk to dinner. I'm thinking about whether a train transfer means dragging luggage through multiple stations with kids. I'm not scheduling a three-hour museum tour at 9:00 a.m. the morning after an overnight flight.

When I talk about how a trip should feel, I'm thinking about what it's actually like to live through that itinerary—not just how impressive it looks on paper.

The Same Country Can Become Completely Different Trips

Italy is probably the easiest example because I plan so many completely different versions of Italy.

One client wants the classic first trip: Rome, Florence, and the Amalfi Coast.

Another is passionate about food and wine, so we start looking at Tuscany, Bologna, and Emilia-Romagna.

Someone else is dreaming about beautiful scenery and quieter towns, so the itinerary might become Puglia or the Dolomites instead.

A family traveling with active teenagers is going to have a very different itinerary than a honeymoon couple, even if they're visiting some of the same places.

The country is only the starting point.

Who is traveling, what they care about, how quickly they like to move, and what they want each day to feel like are the things that actually shape the trip.

Sometimes One Conversation Changes Everything

This happens pretty regularly.

Usually it's because someone says one thing during our conversation that reveals what they actually value most.

I worked with clients who wanted to visit the Greek islands.

Like many travelers, they started by talking about Santorini and Mykonos because those were the classic islands they had always heard about.

But the more we talked about what they wanted from the trip, the clearer it became that those islands weren't actually the best fit.

They wanted a more authentic Greek experience.

They valued history, culture, fewer crowds, and a slower pace.

Once I understood that, the itinerary changed.

Instead of focusing on Santorini and Mykonos, we built their trip around Naxos and Paros—two islands that aligned much more closely with the experience they were actually looking for.

When they returned home, those two islands ended up being some of their favorite memories. They loved the laid-back atmosphere of Naxos and felt like they were experiencing the "real" Greece. They also loved the charm and energy of Paros without the heavier crowds often associated with Mykonos.

That's exactly why I spend so much time asking questions before recommending destinations.

Sometimes one conversation changes the entire trip.

The Questions Clients Never Expect Me to Ask

Some of the questions that have the biggest impact on a trip don't sound particularly exciting.

I ask people:

• What time do you realistically like to start your day on vacation?

• Do you actually enjoy museums?

• How do you feel about driving in another country?

• Would you rather navigate train stations or have a private driver meet you?

• Would you rather spend more on your hotel or on experiences?

• Do you like making dinner reservations, or would you rather decide in the moment?

• How many times are you willing to pack and unpack?

  
  

I also pay attention to things like whether someone enjoys nightlife, whether they want to walk everywhere, and whether they need downtime after a busy sightseeing day.

Those questions might not seem as exciting as asking which countries are on your bucket list.

But they have a much bigger impact on whether the trip actually feels good once you're there.

The Best Option Isn't Always the Most Famous One

Whether I'm choosing hotels, cities, or experiences, I'm always looking at the bigger picture.

A hotel can be beautiful on paper, but if you're spending 30 minutes in a taxi every time you leave, it may not be the right hotel for that trip.

A city might be wonderful, but if adding it creates a six-hour travel day just for one night, I'm probably going to question whether it's worth it.

When I'm choosing hotels, I'm thinking about the people staying there.

For families, that might mean finding the right room configuration, kid-friendly amenities, or a location where everything is within walking distance.

If a family is traveling with a stroller, cobblestone streets and endless stairs become much bigger considerations.

The "best" option isn't always the nicest or the most famous.

It's the one that makes the most sense for that particular trip.

More Destinations Don't Always Create Better Vacations

One of the biggest misconceptions I see is the idea that seeing more automatically means having a better trip.

People often tell me they don't know when they'll get back to Europe, so they feel like they need to fit in as many places as possible.

But every additional destination also means another hotel check-out.

Another train station.

Another airport.

Another travel day.

Another check-in.

Sometimes two thoughtfully chosen home bases with a few day trips create a much more enjoyable week than trying to fit four cities into seven days.

For example, instead of changing hotels every few days, I might recommend spending five nights in Paris and taking day trips to Versailles, Giverny, Champagne, or the Loire Valley. Or spending a week in Lisbon while exploring Sintra, Cascais, Nazaré, or nearby wineries.

You still experience an incredible amount.

The trip just feels less like a series of transfers.

The Little Details Matter More Than People Realize

One thing I pay attention to constantly is the timing of the itinerary.

Museums close on certain days.

Markets only happen on certain days.

Some towns are incredibly quiet on Sundays.

Other destinations are much busier on weekends.

I also think carefully about the order of the trip.

The exact same hotels and experiences can feel completely different if they're arranged in a different sequence.

Balancing busy days with slower ones often makes the entire trip feel more enjoyable.

One Piece of Advice Before You Book Anything

If you're planning Europe on your own, my biggest piece of advice is this:

Don't book your flights until you have at least a rough idea of your itinerary.

I often see people find a great round-trip airfare, book it immediately, and then realize they've created unnecessary backtracking or added expensive transportation just to return to where they started.

I recently worked with travelers who had already booked roundtrip flights into Rome. Their dream itinerary included Florence, Tuscany, Milan, Venice, and the Amalfi Coast. Because of those flights, they ended up spending their final day traveling all the way back to Rome and staying near the airport before flying home the next morning.

Had we planned the itinerary first, I likely would have recommended flying into Rome and home from Milan or Venice instead. They would have avoided hours of unnecessary backtracking and ended their trip on a much more relaxing note.

Before purchasing flights, think about the overall flow of the trip.

Would flying into one city and home from another make more sense?

How long does it actually take to travel between destinations—not just the train ride itself, but the entire process?

A little planning before booking airfare can make the entire trip much smoother.

One Final Thought

The best Europe trips aren't the ones where you saw the most.

They're the ones that matched your vibe and felt the most like you.

That's why I don't start planning with destinations.

I start by understanding the people taking the trip.

Europe Trip Planning FAQs

How many cities should I visit on my first trip to Europe?

There isn't one number that works for everyone. It depends on how much time you have, how you like to travel, and what you want your days to feel like. Some travelers enjoy moving every couple of days, while others prefer choosing one or two home bases and exploring from there.

The best itinerary is the one that matches your travel style—not the one that checks off the most destinations.

Should I book my flights before planning my itinerary?

Generally, no.

Having a rough itinerary first can help you avoid unnecessary backtracking and may allow you to fly into one city and home from another, creating a smoother overall trip.

How many days should I spend in each city?

There isn't one answer that works for every destination, but as a general rule, I recommend spending at least two full days (three nights) in most major European cities.

That gives you enough time to explore without feeling like you're constantly rushing from one attraction to the next.

I'm also a big fan of choosing one city as a home base and taking day trips instead of changing hotels every few days. For example, you might spend five nights in Paris while exploring Versailles, Champagne, or Giverny, or a week in Lisbon with day trips to Sintra and Cascais.

You still experience a variety of places without constantly packing, unpacking, and losing valuable vacation time to travel.

The right amount of time ultimately depends on your interests, your pace, and how you want your trip to feel.

Ready to start planning your Europe trip? Contact me today to get started.