Carla Like It Is

How to Plan a Multi-City Europe Trip and Travel Tips from Hammers and High Heels

Kayd Roy4 Comments
Since getting back from Europe and sharing photos of our adventures, I got a few emails from readers and had quite a few friends ask questions like… “How did you go about planning it all?” “Where did you start?” “What hotels did you stay in?” “How did you find the best airfare?” “How much does a trip like that cost?” “What tips do you have for someone going to Croatia?”

After gathering the emails and mentioning the idea of writing up a post on how we planned our multi-city Europe trip, it sounded like writing all this up in one shot was something a lot of you would be interested in… at least I really hope so, this is a pretty dang long post! So here it is- How to Plan a Multi-City Europe Trip and Travel Tips from Hammers and High Heels!

To kick things off, everything in our little ‘how to’ is based on our experience from our two trips to Europe. That said, we know we aren’t Anthony Bourdain or Rick Steves or any other true experienced travel expert. This is just advice from a plain ol’ married couple with a modest budget and saved-up paid vacation time ready to burn.  Planning this kind of trip isn't easy- it takes a lot of time doing research to coordinate dates, flight times, what flights connect to each city that you want, and of course comparing prices to make sure you can budget $.... You bet’cher buns we made an Excel spreadsheet to keep everything straight (that’s tip #1, get crazy organized) it's very necessary and that’s coming from someone who HATES Excel spreadsheets.

For reference, went to London, Split, and Paris in 2011 and then Prague, Milan, Dubrovnik, Kotor (Montenegro), and Rome this past August. This is the order we did it all in when it came to planning and booking to make it all happen…
US to/from Europe Flights
For those most interested in the price tag of our trips, this part is the bulk of the travel budget. Flying to Europe from the US ain’t cheap...$adly!!!  These flights make up about half of your total cost of the trip.
     -We searched on for the US to Europe flight to see which airlines were coming up cheaper, in what timeframe (months and days of the week), in order if cities you want to see (if you are doing one-way flights), and if they had layovers or not. Make sure you take notes as you research, it's a lot to try & just remember once you want to book, especially if you are booking the one-way flights.
     -We flew Delta on our first trip when we went to London, round trip & I think it was around $1,200.00 a ticket per person direct from Minneapolis to London. The bummer there was starting in London and then having to go back there at the end since it was round trip. So we used the high speed train from Paris to get back to London to fly out. If you are able to avoid round trip flights I'd recommend that, it felt like a waste of time & money. The trains aren't cheap, I think it was around $150.00 a person to go from Paris to London.
     -For this trip, we found the cheapest one-way flights out of Chicago that worked for the cities we wanted to visit. We flew from Chicago to Prague with a layover in Stockholm and then Rome back to Chicago with a layover in Denmark. The layovers aren't bad really, one long flight over the pond and then just a one or two hour flight to actual vacation. We used SAS airlines (found on and it was around $1,400.00 a person for those tickets. Higher $ but no waste of time or money when you do a round trip to get back to the first city and really the cost is close to balancing out.
     -Flights seem to be cheapest in the fall or early spring. We always have gone in August because of our wedding anniversary but I don't want to ever again- Read my post about Rome if you want to know why :)

City to City Flights in Europe
     -Now for the city to city once you figure out the US to and from Europe. Best tip I got from a friend that travels a lot, use EasyJet! The flights are crazy cheap if you research days, times, and what city order. Most are around 50 Euro if you look for the cheap ones. EasyJet is a lot cheaper than the trains there but not if you are checking a large suitcase, because their model is carry on only. The cost to check a bag is higher than the plane ticket, so just do a carry on if you can, worked easily for me both times (with a lot of outfit planning and clever packing methods)... 

     -If you go on their site review the route map to see how you can connect city to city. We went from Prague to Milan to Dubrovnik to Rome. We actually didn't have Milan on our wish list but it was the only way to get to Dubrovnik and that was our #1 priority, the Milan flight was cheap so we figured what the hell and did a day and a half there. Other cheap airlines for city to city are Ryan Air and SAS from what my friend said but we never used either for city to city flights.
     -Trains to go city to city where a lot more expensive from what we found and I heard the same from the same friend that travels a lot. If anyone out there thinks differently, let me know in the comments, but hopefully I'm not wrong.

Hotels and Apartment Rentals
     -After figuring out all the flight stuff we moved onto booking hotels. We used all kinds of hotel search engines but booked most through It was nice because we basically searched by looking at the map on the site to pick hotels that were nearby areas we wanted to be in. We stayed on traditional hotels for all cities on both trips except while in Croatia. If you do research for a stay inside the old City Walls of Split or Dubrovnik, you will see that most of the hotels that come up in a search are actually privately owned "apartments". In order to find more traditional hotels and luxury accomodations you often will have to look beyond the walls of the Old Town. Both options have their benefits so you will have to decide what kind of stay you want to have but, we decided that staying within the Old City for our vacation and one of the biggest benefits of being in an apartment is taht you often gain the ability to do your own laundry which makes carry-on only packing easy since you can clean dirty stuff and wear it again.
     -Free in room Wi-Fi was another thing that we checked for with our hotels - Remember, it's much easier to stay connected with your Wi-Fi enabled device then by relying on an expensive calling plan. We always keep our phones on "airplane mode" during vacation just to be certain that we avoid any strange phone charges. Seems to work perfectly and it's fun to Instagram and use Facebook to share pics. Lots of cafes and restaurants have free Wi-Fi too.

Here’s a full list of the hotels we stayed in and recommend:
Other Transportation Tips
This is what "herding" does to you, it isn't pretty
      -If you book a hotel or apartment contact them to see how you should get to the hotel or if you can book a taxi through them. If you opt to use public transportation ask the hotel for directions/instructions, it's much easier than figuring it all out yourself and they will give you the easiest route. If the hotel offers a taxi though and the price is decent (30 to 40 euro usually) I recommend doing it. We've used metro trains from airport hotels and it isn't always awful but it can take long and if you are traveling with a spouse it can result in arguing and crabby attitudes when you are dodging crowds and trying to figure out where to go. The feeling of being herded gets real old after a few flights, taxis are worth the extra money, trust me.

Sightseeing and Tours
     -Alex and I aren't the type that likes going on organized tours with a tour guide so we usually do online research to figure out what we want to see and when. The Frommers website is pretty good and we also like Anthony Bourdain's page on Travel Channel’s website since he is pretty laid back and gives you real advice about what to do and what to avoid.
     -If you buy books to do research beforehand I recommend Frommer’s “Day by Day” type of travel books. I like the way they are laid out and they give you ideas of daily itineraries if you want to sightsee on your own. They also have more trusted restaurant, bar, shopping, etc. recommendations. We had a “Top Ten” type of book, can’t remember the brand, but the 2 restaurants we went to that were recommended in that book were terrible!
     -BOOK TICKETS IN ADVANCE! If there is a sightseeing attraction that you know charges admission and you need to buy tickets for, buy them well in advance!!! Not only will you avoid a long crowded line, you can ensure that you will get to see that attraction. We learned this the hard way, lots of very busy attractions make you book a day and time to see it- we wanted to see Leonardo DaVinci’s Last Supper painting in Milan and didn’t book tickets ahead, when we got there they said that the next open day they had tickets for was two weeks out, it was such a bummer. After that we hopped online and bought tickets for all the other attractions we wanted to see on our trip so that we didn’t have to be disappointed again.

General Europe Tips:
     -If you do go to Italy in August it is true that lots of businesses are closed because they go on vacation at the end of August and return on September. We saw this on our trips but still got by just fine, only a couple restaurants we wanted to go to were closed. Most tourist things are open though.
     -If you go in the high season it is CROWDED, everywhere. That said stock up on patience before you go, I guarantee you or and your hubby will have a fit/ freak out at some point because of crowds. According to my hubby I complained or had a crowd freak out at least 3 times a day on our last trip :) I'm sure it makes me charming.
     -Related to crowds, be prepared to have some of your moments kind of ruined due to crowds and large tourist groups. I think London was pretty bad but Rome was the worst when it came to crowds that I've encountered. The beautiful moment when I laid eyes on the Sistine Chapel for the first time was pretty disappointing considering I was being pushed through a sea of people while security yelled "no photos" and "shhh" constantly. I couldn't even stop and stand still for a moment, such a bummer.
     -Last but not least, if I can recommend any must-visit cities for you, it’d be Paris and Split or Dubrovnik in Croatia. Croatia is a mix of that historic European feel but you also get a gorgeous, relaxing beach vacation! Split and Dubrovnik were both built during the Roman Empire and are inside old palace walls, it is just amazing! Anyone that goes there loves it! And if you haven’t been to Paris you have to go there! Alex and I knew we wanted to see it but had no idea we would really love it so much. It is a beautiful city, clean, romantic, relaxing, chic, and the food everywhere is amazing! You have to get a bottle of wine, a baguette, fruit and cheese and do a picnic on the lawn in front of the Eiffel Tower at sunset- favorite moment of that trip, I think I even cried because it was so beautiful. Ahhh, I want to go back to all three places right now!

PHEW! I think that covers a lot and if there is anything else you want to know just ask, I will be happy to share more! I just loved our trips to Europe, I wish I was still there :) Whether you are planning your first trip to Europe, a family vacation, honeymoon, or a trip with friends I hope some of our tips are helpful! Good luck with your planning and enjoy every moment of the adventure!