Five Weeks in Europe: How to Create the Best Itinerary

Since Jeremy and I got married at the height of the COVID 19 pandemic, we didn’t have a chance to take any kind of real honeymoon. We both wanted to spend more time traveling in Europe, maybe even months. So, we knew from before the wedding that at some point in the future we would make an extended trip across the pond.

The real question was, for how long and to which destinations. We also wanted to travel light (See Minimalist Packing for One Week to a Season in Europe), make some splurges on luxury hotels and experiences, and get the most bang for our buck (See Budget Luxury Travel Doesn’t Have to Be An Oxymoron). In this post I’ll share with you

my planning process, how the itinerary worked out, what I would change, and how you can create your own perfect-for-you itinerary.

When to Go and How Long to Stay

The first step in making an itinerary was choosing when to go and how long we would be gone. We knew Jeremy would be quitting his job for our future move abroad to Taiwan. So we wanted to take advantage of the time between his quitting and the move to enjoy a really substantial trip. However, because of obligations at home, we decided to limit the trip to about five weeks rather than being gone for several months. I was concerned that we would get tired of traveling if we went for too long, especially with a big move abroad planned as well.

Additionally, though we had both been to Europe more than once, there were many things we had not had a chance to do or see. We hoped this trip would serve as a good exploration into areas we might want to visit again in the future, possibly on a longer trip or even for a move.

Our other considerations in when to go and how long to stay were the weather and the prices. We were already sure we didn’t want to travel in the summer. Not only was the timing poor for our other plans, summer is peak tourist season, which means more crowds, higher prices, and less flexibility in planning. Summer requires much more booking in advance and premium rates. We both hate the heat (ironic living in southern Arizona and now Taiwan ) and I have a hard time with crowds.

On the flip side, winter in Europe was both colder than we wanted and is a time when a lot of the big tourist attractions close for the season. Therefore, we settled on either spring or autumn, what is known as “shoulder season”, as the ideal travel time for us.

I began researching prices and found there was a sharp dip in airfare starting around the last week of October. Skyscanner and Google Flights are excellent tools for researching flight prices. Skyscanner will allow you to do general searches with flexible dates and “Everywhere” as a destination. On Google Flights, try typing in a flight from your desired departure city to a city you want to visit in Europe. If you open the map feature (click Explore) you can see prices for other major cities in Europe as well.

Using these tools, I was able to pinpoint a departure date for the last week of October with an amazing price. As it happened, that meant our trip also encompassed our wedding anniversary at the beginning of November, which was a nice bonus!

Something else to keep in mind with a long Europe trip, is the possibility of flying into one city and home from another as a way to extend your travel time. This means not having to return to the first city of your visit in order to fly home. You can easily experiment with the multi-city feature of Google Flights or look at one way flights in each direction and compare roundtrip prices. We found that flying into Paris and out of Barcelona at the end of our trip was about the same price as a roundtrip ticket in and out of Paris. And booking this way eliminated the added time and expense of returning to our starting point.

Choosing Destinations

Choosing which cities to visit is without a doubt one of the most fun parts of planning travel and also highly personal. On his previous visit to Europe, Jeremy really loved his time in Paris. I had never been there except for a layover almost twenty years prior. So, we decided to start our itinerary there. It was also one of the most expensive places we went, which turned out to be a bit of a mistake in retrospect. More on that later.

Since there were so many places we wanted to go, we started by narrowing down a geographic area. Then picking the countries that made the most sense by location and interest level. The weather would be increasingly cold, so we focused more on the Southern part of Europe and visited our furthest North locations at the beginning of the trip. If we visit in Spring, we would probably reverse this, visiting the warmer destinations first.

Another consideration for us were the holidays and events taking place in the locations we wanted to visit. There are quite a few holidays that are common in certain European countries but not celebrated in the United States. These can affect prices and conditions while traveling. For example, autumn vacation from school in France means many French families travel to Paris to tour, driving up prices, and increasing crowds.

I thought this crowd predicator site was a great tool to get a feel for busy times across the continent. Some sites may be closed on certain holidays as well. You can check out holidays in various countries here or look on the specific website of the attraction. On the other hand, you may also want to plan to be in a certain location at a certain time if you have a special interest in an event. For example Oktoberfest in Munich, Germany or fashion week in Milan, Italy.

Our Itinerary

We knew we wanted to get a broad overview of several countries for future return visits. So, we tried to fit as many destinations in as possible, without rushing to the point we couldn’t enjoy our time. Besides France, Belgium was on my bucket list and we both really wanted to get a taste of Italy. We were also seriously considering moving to Portugal or Spain at some point in the future. Therefore, we wanted to explore what we could there as well. In the end, our five week itinerary consisted of the following:

Travel day

Week 1 – Paris & Versailles, France

Week 2 – Brussels & Bruges, Belgium; Nice, France

Week 3 (part I) – South of France (Nice, Cannes, Eze, Grasse, Monaco)

Week 3 (part II) – Milan & Venice, Italy

Week 4 – Florence, Tuscany & Rome, Italy

Week 5 – Lisbon & The Algarve, Portugal; Barcelona, Spain

Travel day

As you can see we packed a lot into what was actually a thirty-seven day trip.

Avoiding Travel Fatigue

Travel fatigue is real. No matter how amazing the sights you are seeing or the food you are eating, there comes a point when it starts to blur. You miss your bed, your bathroom, your pets or friends. Being in a foreign country is exciting, but it can also be exhausting. For me, as an introvert, even at home I need rest days.

To combat the inevitable travel fatigue we tried to spend two nights or more in each city we chose to explore. We also built in days of rest, with no reservations or specific activities planned or even suggested. On a few days we didn’t really leave our room for most of the day, just relaxing, reading or napping. Since we had built this time in, we felt less guilty about “wasting” our vacation. I highly recommend doing this.

I like to create a framework of “must do” activities with reservations and set rest days and fill in the remaining times with suggested activities. Be sure to book really popular, high volume tourist activities like going to the top of the Eiffel Tower in advance. Then build your framework of other activities around your reservations. Stay flexible, don’t lock in too much. Otherwise, you may end up not enjoying the activities because of being overbooked. Or you may miss them altogether and lose your money, like we did with our Paella Workshop in Barcelona (See How Serially Late Flights Cost Us Money and Dreams)

Choosing the Best Activities

Much of your enjoyment from traveling will come from a good balance of planning and spontaneity. Again, your choices will vary greatly depending on your personal preferences, budget, group size and time available. However, there are some good guidelines I would suggest. If you haven’t seen the most popular tourist sites in a city, don’t skip them just because they are “tourist” spots.

There is a reason attractions like the Colosseum in Rome,  the Louvre museum in Paris, and Park Güell in Barcelona draw millions of visitors from hundreds of countries each year. Major attractions like these are worth seeing at least once. Take a look and form your own opinions. Do choose to eat away from these major tourist areas if you want better prices and quality. (See How to Avoid Eating Mediocre Meals At Tourist Traps)

Something I like to do in each major geographic area we visit is search for hands-on activities/experiences that are unique to the region. These usually prove to be the highlights of our trips. Sometimes I already have an idea in mind, like taking a pastry making class in Paris (See Why Croissants Made in Your Paris Pastry Workshop Will Be the Best You Ever Eat) or a glass-blowing workshop in Venice. I found by scanning ideas on Trip Advisor or Viator.

Once I find ideas I like, I compare tours, companies, and prices across different websites. Sometimes booking directly with the vendor has a better price, but insurance and cancellation policies on booking websites may be better if you need more flexibility.

Our Unique Experiences

Paris – cruise on the River Seine and St. Martin Canal with Canauxrama and pastry making classes at Patisserie à la Carte

South of France – perfume making workshop (See Secrets to A Beautiful Scent According to a French Nose) at the Les Studio des Fragrances Galimard in Grasse

Venice – kayaking tour with Venice Kayak and glassblowing workshop

Tuscany – Vespa and winetasting tour (See Adventures By Vespa in the Picturesque Tuscan Hills) with Fun in Tuscany

Florence – pasta making class at In Tavola

Portugal – food tour with Secret Food Tours

Barcelona – Paella Making Workshop with The Paella Club

After our experiences in Europe we highly recommend food tours when arriving in new cities, even though they can be pricey. Why? If you have any interest in food, or you just aren’t sure what to eat, a food tour will guide you to the best local choices in cuisine.

Though you can certainly design your own food tour, if you are traveling single or as a couple you will end up spending more than you want. You will also sometimes get food you don’t enjoy and some food will probably go to waste. On a food tour, you get to try small portions of everything. So you can decide what you like and don’t like without wasting food or money. Usually food tours also include some nice facts about local history and culture as well.

What you choose to fill your trip with will be highly individual- if you love museums, history, and/or art, Europe will not let you down. Hiking buff? You are in for a treat. Foodies, you’re headed to paradise. Traveling with kids or older folks? There are so many accessible and enjoyable opportunities for all ages and physical abilities.  Just be sure to remember the tips discussed above and adjust for your own tastes and circumstances.

What I Would Do Differently

There are definitely things I would do differently if I was planning our first five week trip to Europe again. Although we enjoyed everything we were able to do, we had some snafus that could have been avoided.

The first was due to a storm that caused us to miss our connecting flight to Paris and left us stranded in Dallas, Texas for twenty-four miserable hours. (See Our Nightmare Flights to Europe: Why American Airlines is Out). Due to that delay, we arrived in Paris completely exhausted.

We also missed our first night at the very expensive and luxurious Waldorf Astoria Versailles, which was meant to be a luxury splurge. See Best and Worst Hilton Hotel Stays in Europe. Our Chase travel insurance covered our expenses for the 24 hours. But we started our trip off in less than stellar condition. Because of this we didn’t use our Paris Museum Pass to the full and even chose not to use our pre-paid Eiffel Tower entrance because we were just too tired.

Later, we missed the nonrefundable paella workshop we had booked in Barcelona because our flight from Lisbon was delayed more than three hours. Actually, almost all of the flights we took both on the European continent and to and from Europe were significantly delayed.

In the future, we would probably focus more on train travel rather than flying between countries. We would also definitely not book anything important or expensive within the first few days of our trip or scheduled within a few hours of getting off the plane. Going forward, I actually book separate travel days and do not schedule any other activities on the transit days.

Our trip to Europe had quite a few hiccups. You can find out more about what we learned and how we dealt with them in these posts:

Best and Worst Hilton Hotel Stays in Europe
How to Deal With a Dental Emergency Abroad
How to Deal with Traveling While Sick or Injured
Why Heathrow is In the Running for Worst Airport.
Our Nightmare Flight to Europe: Why American Airlines is Out

In spite of this, good planning meant we still got to see, do, and eat a lot of amazing things! We hope our experience is valuable in your own planning – feel free to share your own tips below!