Five Two-City Options in Southern Europe for a week-long vacation — Letter to Sons

Doug Keating
5 min readMar 22, 2024

Congratulations, you’re going to Europe this year, 2024. The even better news is that you have an entire week of vacation to use for your trip. Today, I will share five two-city options in Southern Europe for a week-long vacation. If you want to visit the north, check out my previous video about that topic.

Who should read this blog or watch the video?

I’m designing this content for North Americans who want to spend 5 to seven days in Southern Europe. If you already live in Europe, or it’s easy to get there, I doubt this content will be helpful.

The criteria used to create this list

here are the three criteria I used to create this list.

  1. The two cities have to be generally close together. You don’t want to spend an entire day traveling from one city to another.
  2. I define Southern Europe as anything south of Paris.
  3. These cities have to be relatively easy to get to from the US.

Sample schedule for a week-long trip to Europe

Let me start with a sample schedule (shown below) of how you could spend the week visiting these two cities. You will fly out Friday night from the States. Get to City 1 on Saturday. You’re going to stay there for three days. While there you will take a day trip. Next, you will travel to City 2. Once again, you will remain there for three days and take a day trip. Saturday, you’re flying back to the States. Sunday, You’ll recover, sort through all your pictures, and wonder why you came back. You can easily modify this schedule as much as needed. I followed this plan for previous trips, and it worked well.

Southern Europe Option #1 — Rome and Florence

I’m going to call this the best of Italy option. Both these cities are popular and super packed with tourists. It is easy to get between them via high-speed train. One factor to consider is that Florence’s airport is not that large. You may have some challenges getting back to the States from there.

Option #2 — Munich and Salzburg

Both these cities are fantastic. Getting between them is easy. The other nice thing is that they offer tons of day trip options. If you read this blog’s end, I will identify some day trip ideas.

Southern Europe Option #3 — Barcelona and Madrid

This option is perfect for anyone going to Spain for the first time. I also highly recommend it if you’re taking your children with you. Kim and I went with two American teenagers, and they even confessed that they had an awesome time. These two cities are linked via high-speed rail, or you can fly there.

Option #4 — Lisbon and Porto

If you want to go to Portugal, this is the perfect option. I highly recommend both of these cities. They are linked by High-Speed Rail. The only challenge might be that Porto doesn’t have as many flights back to the States as Lisbon, so you might want to consider that when planning this option.

Southern Europe Option #5 — Madrid and Lisbon

I love both of these cities — well, I love all the cities on this list. I can guarantee you that you will eat like a king on this option. One challenge you may face is the rail between these two cities is not great. Flying is probably going to be a better option for you.

One thing you may not like about these options

Let’s shift gears and talk about one thing you may not like: flying back from a few of these cities, specifically Salzburg, Porto, and Florence. None of them have huge international airports. If you factor this piece into your plan, you’ll be fine. I don’t want you to be surprised.

You will not go to Southern Europe during high season

I will foot-stomp one thing you won’t do when planning this vacation. That is traveling there during the high season. All the cities listed are popular. Some of them will be packed during the summer months and even September. Instead, go during the shoulder season. You’ll have a better time, and you don’t want to fight all of these tourists to get your photo taken at the Trevi Fountain.

Five ideas for day trips from Southern European cities

Let me finish this blog by listing some ideas for day trips from these places.

  1. Florence — Tuscany is magical.
  2. Salzburg — Hallstatt is a picturesque Alpine village.
  3. Barcelona — Girona is a medieval marvel.
  4. Lisbon — Sintra is full of palaces.
  5. Madrid — Segovia has an aqueduct, Cathedral, and castle.

I am Doug Keating, and this is my letter to my sons.

Originally published at on March 22, 2024.



Doug Keating

Leader and learner. husband and father. Novice blogger,, Founder of All The Way Leadership!