Requested by @lizthewiz
Wow, thanks for this request! This is my most favorite thing to talk about! This is going to be long as hell. And I must say, I'm a very particular traveller and this may not work well for others. I'll present in chronological order and basically include everything I do before I leave home, since I consider all that to be planning.
  1. First, make sure you have enough money to be able to take the trip you want. I personally don't plan a trip unless my trip fund has $5000 in it. I know I can do 2-3 weeks in Europe traveling by myself for that amount of money or less. But I don't eat expensively and I like staying at little inexpensive bnbs.
    I want to be able to be there and do or but whatever I want when I'm on vacation without having to worry about it. I listed about saving for travel here: HOW I'VE BEEN ABLE TO AFFORD TO TRAVEL
  2. Make sure your passport is good for long enough. Many countries require your passport be valid for three to six months AFTER when you plan to exit Europe.
  3. Yay, you have the money! But where to go? Make a list, in preferential order, of your top destinations
    If you can't decide, do a little research and ask people so you can decide your top spot
  4. When I planned my first trip to Europe (my top ten cities in seven countries), I made a list. I said if this is the only trip I can ever take to Europe, these are the places I have to have seen.
    Since I know you want to know, those cities were: Stratford upon Avon, Lisbon, Barcelona, Brussels, Amsterdam, Copenhagen, Vienna, Venice, Florence, Rome
  5. Decide which destination works best for your budget, time of year you want to go, how long you have, etc.
  6. I personally recommend one country per trip if it's 2-3 weeks in length or shorter. That ten city trip was fun but insane. A lot could've gone wrong and I was lucky. It's quality over quantity, which will come up a lot on this list.
  7. So you decided what country to go to, but how long do you have? My advice: take the longest trip you can afford and are able to get off work.
    I'm coming from the west coast so to me, anything less than two weeks would be a waste of 8-10 hours in jet lag and a 12+ hour flight that uses up over 25% of my trip budget. Sure, one week in Europe is better than none, but I think you need a long time to immerse yourself, cleanse your mind from your life back home, and really absorb the experience. I'd rather go less often for longer periods of time. Quality over quantity again!
  8. Now the itinerary. I have rules that I try to stick by. Big cities 3-5 nights or more, small cities about two nights. And on each trip I like to have a mix of big and small cities for variety.
    I've stayed one night a couple times before and it's fine, but if you do it more than once a trip you're packing, unpacking, checking in, checking out, and using transportation more than you're seeing anything. And that's not good!
  9. Having enough time to really unwind in and experience each city is so important. You don't want to just check of the list of sights, you want to SEE the place and FEEL its culture. It's quality over quantity again!
  10. Look at transport options between your cities. Make sure there are good connections between your stops without having to unnecessarily backtrack
    I'm a big fan of picking one region in a country and really focusing in on that region. You spend less time on the train or bus and more time having a blast.
  11. Think about what you want out of the experience. Do you want to hit a bunch of museums? Do you love history? Food and wine? Architecture? Shopping? Nature? Etc. Research to find out what cities and towns have qualities and activities you think you'd enjoy!
  12. For example here's my itinerary for a trip to Portugal I'm taking in May. It's similar to many of my other trips
    Lisbon-5 nights, Porto-5, coimbra-1, leiria-3, evora-2, Lisbon-1
  13. So you know where you want to go, but when? Personally my favorite time in Europe is May. Nice weather, not toooo busy yet, long days. but everyone's different and your schedule may be more limiting. If your budget is very tight, consider off season. I did central Italy at the end of October and everything was much cheaper and quieter.
    But the days were much shorter, everything closes much earlier, etc. It's a trade-off.
  14. Accept that you can't see everything.
    But the goal is to maximize and get the most out of what you do choose to see. If you try to see everything, you'll be on the move all the time and you won't actually see anything.
  15. Now it's time to book stuff. There are different opinions, but these are are the things I personally book in advance
  16. Flight: I've had good luck booking from lax about 2-3 months in advance. In fact I've usually booked all my accommodation before my flight.
    If your travel dates are more flexible, play around with flights to get a good deal, then plan your itinerary around the flight. Just depends on your situation and what works best for you. My dates are typically not at all flexible.
  17. Don't stop over in the US. Someone told me this once and it made sense
    For example I'd never take a flight from LA to stop over in nyc or dc. I always make it somewhere in Europe. From the east coast, there's probably only one flight out that night and if you miss it you're toast. But if you can make it to London or Paris or Frankfurt there are a ton more options to your final destination if you missed the first flight.
  18. Check all the main airline sites for a while to see the trends. It's hard to know when to book but if you're seeing prices go up or down, etc. it may be time to pull the trigger. I usually spend about 1100-1300 to travel in May. When I traveled in October it was about 600!!
    There are a ton of websites that give advice for researching airfare, especially to Europe.
  19. Fly open jaw if you can. this is huge. It's not usually more expensive and it can save a ton of backtracking.
    That means into one city and out a different one. For example, the last time I went to Italy I flew into Venice and out of torino. As you could see above though, I'm flying both into and out of Lisbon on my upcoming trip, bc open jaw didn't work with my itinerary and some other reasons. But if you can make it work, it's way better.
  20. Ahhh! You have a plane ticket and an itinerary! It's real!
  21. Now, accommodation. This is a very personal choice. Some people even wait till they arrive to find places to stay. I'd never be able to do that and why would I want to waste precious vacation time finding a place to stay?!
    As I said above, most of the time I actually book all my accommodation before my flight. I stay in small places that tend to book up quickly.
  22. I prefer small b&bs and guest house type places. You get to interact with both the owners and other guests. They're less expensive and it adds to your experience. Usually the breakfast is local and great. If you want American hotel standards, go for it. You do you.
    I also like doing airbnb in bigger cities where I'm staying longer, might want some groceries, hotels are more expensive, etc.
  23. For accommodation, after safety and cleanliness, the single #1 important thing for me is location location location
    Staying as central as possible is worth the extra cost imo. I've been to cities twice where the first time I stayed less central and when I went back I stayed more central and my experiences in those cities were night and day. Europe also lights up at night and if you're staying really central, you can enjoy that much more easily.
  24. I do hours of research for each city
    Teipadvisor reviews, though that site has serious issues, have always helped me a lot. Also and venere have good reviews. I've been lucky and honestly never had a bad accommodation experience in Europe and I think that's due to the research I put in
  25. I like booking directly with the property where possible
    They pay steep commission fees to booking sites. Small places sometimes only use them so you have no choice, but I've booked a lot of places just via email with the owner. You get to know them a little before you leave home. I love that.
  26. The next phase of planning, daily itinerary planning, is controversial. I'm a big planner and I figure if I have a few days in a place I might never return to, I really want to make the most of it. So I plan a lot.
  27. A note on guidebooks. I use them in my planning and I buy the e-version of at least one to have on my iPad mini when I'm there. Rick Steves books are popular and I find them to be far superior for practical information (opening times, how to get to a sight, walking tours, etc.)
    But he is selective about what he includes. He completely ignores some of my favorite places in Italy, for example. So I always supplement with lonely planet, rough guide, etc. Also his guides are so popular that I personally try to avoid his restaurant and hotel recs.
  28. I plan every day of my itinerary. This is what's controversial. I start early and plan morning heavy so that I have afternoons to relax, people watch, be spontaneous, etc.
    I use an app on my iPad called tripplannerpro, you can do your itinerary day by day. Makes it so easy. And it's free!
  29. I plan days to make geographical sense. Imo this is critical for big cities with spread out attractions and neighborhoods.
    For example, in Rome, do all the ancient sights, which are close together, on one day, and do the Vatican on another.
  30. Get city maps before you go. So that when you land, you're already a little familiar with what the city looks like and you're not wasting time getting your bearings.
    I am a HUGE huge fan of CityMaps2Go, and it is worth the $4.99 and more! You can add pins for your points of interest. Also, it magically pings wifi in every city so even on my wifi-only iPad, once I've connected it to wifi in a certain city, then when I'm out and about with no connection, the app can still pinpoint my location. In other words, it's basically impossible to get lost. It's MAGIC.
  31. Research research research. Research the sights you want to see. Restaurants that sound good. Shops that sound special. Stuff off the beaten track.
    Again, you have limited time and don't know if and when you'll be back. I use and local bloggers for restaurants mostly, and I leave some flexibility for recommendations from locals once I'm there or for places I stumble upon. I love buying one special souvenir in each city I stop in so I like to know of special shops to seek out that sell really typical, preferably handmade stuff.
  32. I buy high speed train tickets in advance.
    You can sometimes save up to half, and it can be a significant amount of money saved.
  33. Reserve any private or day tours
    I'm sure this can be done more last-minute but if I'm going to invest a significant amount of money on a small group or private tour, I want to go with the company I like the most based on my research.
  34. Reserve or pre-purchase any museum tickets you can
    Some, like the last supper in Milan, you absolutely have to. Some, like the uffizi and accademia in Florence, you save a boat load of time waiting in line if you reserve in advance. Guidebooks that are recently updated and current are good for this info.
  35. Before you leave, get enough money to get you from the airport to your first accommodation, a meal, and a change of clothes (think 100€ per person or so)
    Now I take out euros from an ATM on my last day of my previous trip, and store in my travel wallet as seed money. Many people suggest taking no currency and using an ATM upon arrival. What if the ATM in the airport is broken or empty? What if your debit card is denied? No way. I'd never fly thousands of miles to a foreign country where I don't speak the language without a little paper money in my pocket. The few dollars fees I might pay stateside would pale in comparison to that inconvenience.
  36. Get a credit card and a debit card that don't charge foreign exchange fees
    It used to be that capital one was the only credit card that didn't charge foreign exchange fees so that's what I have. But there are others now. Check your bank's foreign atm fees. Chase is my bank and their fees are steep. I use an Ally account when I travel, their atm exchange fees are minimal. A couple friends use a Schwab account. The fees can be significant and can add up over the course of a trip.
  37. Learn a few basic words
    It's amazing how much please, thank you, where is...?, Etc will get you. Being kind, smiling, and pointing will often get you the rest of the way. No one has ever been mean to me in Europe and I think it's because I go with a friendly, open minded approach to their culture.
  38. Learn a little bit about the culture of the place where you're going. That's why we travel, right?
    Tipping is a big one, but also just local customs. For example, Italians don't eat eggs at breakfast or have a cappuccino after 11 am. It's also cheaper to stand and have coffee at the bar rather then sit. This helps you have a more authentic experience. It's good to learn that during the planning phase do you can have an authentic experience and avoid touristy places.
    I cannot stress this enough. I don't check my bag unless they make me. Trust me there's nothing more satisfying than getting off a multi-stop flight after traveling for 16 hours then grabbing your suitcase from the overhead bin, grabbing a taxi, and immediately starting your vacation! make a packing list and make SURE you need everything you're taking. I hand wash in the sink as I go and that doesn't bother me. Maybe I'll list about packing light one day.
  40. Break in your shoes so you know you can walk 10+ miles a day and not get blisters
    Invest in good walking shoes. Seriously. I can't overstate this enough.
  41. Tell all your banks and credit card companies about your travel
    Some you can do on their website with a travel alert form, some you have to call. If you don't, your cards may not work
  42. Store copies of your passport and credit/debit cards in the cloud so if the worst does happen, you have access to copies anywhere in the world.
  43. Go and have the most amazing, life-changing vacation you can imagine!
  44. 🛫🚖🚝⛴🗼⛲🚊️⛰🛬💜💜💜💜💜💜