Vacation Planning: How to Plan a Month-Long European Holiday

Let’s be honest, vacation planning can be really fun but it is A LOT of work. Particularly if the planner is “a little OCD” about optimization and has a mile long list of “must-sees”. I spent a lot of time planning for my month-long trip to Italy, Spain, and Portugal — and I mean an excessive amount of time researching, comparing, organizing, and preparing. Now that I’m back from my trip, I can honestly say it paid off. But at the same time, I’ve learned some valuable lessons and tricks that would have saved me many hours of confusion and made the trip more enjoyable.

While there are many travel planning tips and recommendations out there, here are my personal top five:

1. Get a GOOD Guidebook

If you take anything from this post, do this! Unless you’re hiring a personal trip planner, the money you spend on a good guidebook will more than pay for itself in the amount of time it saves you alone.

I was not a believer of guidebooks. I’ve always thought of them as a little bit of information that I can Google myself with a lot of advertisements. I spent many long hours/days in front of the computer reviewing itineraries, recommendations and attraction details for every city. Then a week before leaving for the trip, I decided to pick up a couple of guidebooks. Why didn’t I do this as soon as I decided on the destinations?!?! I would have saved so much time.

I was blown away by the two Rick Steves guidebooks I got. Besides the typical info such as attraction costs, opening hours, how to get there, and handy maps, they also provide tips on which attractions need to be booked ahead of time either due to requirements or to avoid long lines. The best part is, they include self-guided city walking tours and museum tours that highlight the points of interest and provide concise but interesting history/background. Wait for it… there is also a free audioguide app (you don’t have to buy the book to get the app by the way) that goes with the tours so you don’t even have to read! How cool is that?? Even though we didn’t take any guided tours in any city, we got just as much out of our visits. (Okay… I’m done gushing over guidebooks… it’s not like I’m getting paid to talk about these or anything…)

Bonus tip, have a cheat sheet for opening hours handy either in print or stored on your phone. This was super handy when we needed to adjust the plan, double check the time, and didn’t want to flip through the guidebook every time or didn’t have good internet.

2. Choose Home Bases For Exploring

Over 27 days, I visited 3 countries and a total of 14 cities (not counting the Vatican). It was the longest continuous traveling I’ve done, but because we didn’t constantly move around, I didn’t get super tired by the end of it. And logistically, there are just way too much to see in and around each of our destination cities that required at least 3-4 days to fully enjoy. Here is an overview of the trip:

A big lesson I learned from the New Zealand trip was that a different city every night is exhausting. The constant unpacking/repacking, check-in/check-out and the traveling (even with a rental car) just got to be way too much. Having a base allowed us to make each place a home rather than a stop. Day trips from these central cities were super easy and quick by train.

3. Always Take the Trains

They are super fast. The stations are always in or near the city center. You are less likely to get motion sick. You can walk around. There is a dining car. There are power outlets. There are bathrooms. The seats are more comfortable. There is practically no luggage limit because no one checks. And if booked at the right times, can be super affordable. Need I say more?

4. Not All Airbnbs (and Hosts) are Created Equal

I’m pretty late to the Airbnb scene and this trip was the first time I used the service extensively. We were four adults who wanted to immerse ourselves in the local culture, cook our own food and do laundry. Convenience and cost considered, Airbnb was a clear choice for us. Besides the obvious things like location and good reviews, here are what I learned after staying at these places:

• If you struggle to pack light like I do, consider filtering by the availability of an elevator, which is not always a given for higher stories in Europe.
• Superhosts really make a difference. It guarantees the places are well stocked with all the necessities (shampoo, body wash, laundry detergent, TOILET PAPER), as well as prompt and clear communication. They also helped with booking reservations and calling taxis when we couldn’t speak the language and didn’t have a local phone.
• We only stayed in one Airbnb where we didn’t have two bedrooms because the options were limited by the time we booked. For four adults (my parents, Sam and I) on a longer trip, personal space is essential. Everyone rests better when there are doors. And sofa beds are really better suited for children.
• Photos and descriptions can be unclear. Sometimes you get there to find out the only bathroom is through the bedroom…

5. Leave Free Time

The trouble with these European destinations is there are always so much to see. As much as I try not to, I always end up packing the itinerary quite full. As a first-time family vacation planner for this trip, I needed to adjust the pace and the amount of walking that I’m used to doing on trips.

If possible, leave a couple of hours to half a day in every location free. This time can be used for optional attractions, shopping (oh the cute clothes, awesome skincare, and quality leather goods…), naps/rest, laundry, but also just enjoying some tapas and beers on a random square.

I would say approximately 80% of things went as planned, and that should be as good as any planner can expect. The bottom line is, once the homework is done, relax, enjoy, and be flexible with the unexpected.

Actual trip blog posts coming soon!!

C.