“Travel makes one modest. You see what a tiny place you occupy in the world.” – Gustave Flaubert

The summer before my 30th birthday, I decided that if I did nothing else, I was going to Europe. I sent out a mass email to a bunch of my friends the December before my proposed trip, not really caring whether anyone was bold enough to embark on a journey across four countries with me. I was going, even if I had to go alone. This was my dream trip before turning 30. And if you know me, you know that once I put my mind to something, I make it happen. So I did. From London to Paris to Venice to Florence to Rome to Mykonos to Crete to Athens to Santorini.

Initially, I contacted my trusty travel agent, but after reading her calculations, I knew that either I was going to have to find a cheaper route or a stripper pole… But like I said, I was going to Europe by any means necessary. So I sat down and mapped out my trip, the same way I’ve done for the past ten years. In college, my roommates and I discovered that I had a niche for travel planning. While I had never planned a trip this extensive, I sat down and figured it out. Thank God I had two traveling companions that trusted my judgment and didn’t question my lead. Somehow, it all worked out. Below are the steps I took to plan my dream vacation:

your wanderlust — Photo: Courtesy of author

1. Choose your destination (s), and if you are going to multiple places, pull out a map and check the feasibility of your trip. You want to go from Paris to Russia on a budget? Oh ok, let me know how that works out for you. Be reasonable.

2. After you’ve chosen your destinations and have your start and end points, take a look at the price of your round-trip flight. Note that I said check the price of your “round trip” flight. When pricing international flights that are coming to and leaving from different locations, single trip tickets can be more expensive. For example, when pricing a one-way ticket from Greece, it was about $1,200. However, my entire fare to London and back from Greece was only $1,440. You do the math. Pricing your flights when you are at the beginning of planning also lets you know whether your trip is within your budget. The last thing you want to do is plan a trip all the way through and then realize it was never affordable anyway. The app Momondo and sites like Kayak are great tools to help find the best prices. When paying for a flight of this magnitude, either save in advance or use part of your income tax check. Don’t wait until too close to your travel date and risk paying an enormous fare.

3. So, you know where you want to go and have an idea of how much it costs to get there. Now you start the really tedious parts. Determine the best modes of transportation to get from city to city based on the trip that you mapped out. For traveling through Europe, most of your traveling will be done via train, and if going to Greece, via ferry. Use sites such as Rail Europe to get an idea of costs. Although our train ticket via the chunnel from London to Paris was $138, our tickets through Italy were fairly cheap, less than $25 to get from city to city. Mapping out your trip also lets you know which cities are feasible. I really wanted to see the black sand beaches of Sicily, but unfortunately, it didn’t fit easily into the travel plan. Also, decide whether certain cities can be done via a day trip through a tour company. For instance, we didn’t need to spend the whole day in Cognac, France, so we took the early morning train there and came back on the last train that night. However, sometimes you have to accept that you won’t be able to see and do everything, but I will come back to that point a little later.

4. After you’ve decided the easiest transit forms to get from place to place on your trip, you can now start looking into your lodging options. Airbnb was my best friend. However, I have some tips to give you based on our experiences to help you through yours:

5. Remember, reviews are your best friend. Try to stay away from properties with minimal reviews and/or unfavorable ones.

6. Make sure that your selections have Wi-Fi, central air and/or heat, and any other amenities that are important to you being able to lodge comfortably while traveling.

7. Research the area where your lodgings are located. Make sure that the area is safe and near a train or bus station for easy commuting.

8. Although Airbnb was my best friend, I did have to use hotels.com for areas with limited options, such as the Mykonos. Airbnb is a good resource, but not the end all, be all. And be sure that if you have to use a site like hotels.com, verify that you are getting the lowest price by also checking the hotel’s website and other discount sites such as Expedia, Kayak, etc.

9. Feel free to contact either the hotel and/or Airbnb property owner with any questions before booking. Most of them are pretty helpful, and if they’re not, you dodged a bullet anyway.

10. Paying for lodging options all at once can be super expensive. In order to maximize our teacher budgets, we decided to pay for our trip one country at a time. We paid for London in February, Paris in March, Italy w/transit in April, and so forth. I created this schedule way in advance so that everyone traveling had an idea of when we would be making our payment for that location. And because I had researched lodging options while putting the trip together, I was able to give estimates before people agreed to come, so that everyone had an idea of how much they would need to budget for each country. Transportation via train, ferry, etc., was paid with the corresponding country. Because I was traveling in a group, each month I sent out three lodging choices for each city and went with majority vote.

11. Flights, lodging, inner-city travel… The last thing to do is to decide what activities you want to do in each city. This can be tedious. Here I come back to my point that you might not be able to do everything this trip. Don’t crowd your itinerary so much that you don’t have time to just enjoy the scenery and immerse yourself in the culture. Use popular tour sites such as Viator, Google, or consult with either your hotel or Airbnb hosts to decide the best sightseeing options. Almost every major city has a hop-on, hop off bus to see the most popular tourists sites, and depending on what you want to see, that might be a viable option.

I’ve been blessed enough for travel to be a fixture of my lifestyle, but this trip was by far the one that tested my capacity and longevity and whether or not I was really true to this travel life. This trip was full of valuable lessons that I’ve listed below, but all in all, it was an experience filled with beautiful moments that will last a lifetime:

1. Pack wisely. It’s not fun lugging a 50 lb. bag across four countries. I always over pack, and it had never been a problem, but I have also never spent 18 days traveling Europe and having to pack that over-packed bag onto every train, ferry, water bus, down cobblestone streets and everywhere else we had to go.

2. Live. You don’t spend this kind of money to spend most of your time worrying about things and people still in America or staying immersed in social media (unless that’s part of your job). Let your social media time be late at night when your excitement keeps you from falling asleep.

3. Try new things and meet new people. Leave your inhibitions at home. I was nervous that I would starve to death in Greece because their staples are my least favorite, but I opened my mind and ate a hearty meal everyday.

“To my mind, the greatest reward and luxury of travel is to be able to experience everyday things as if for the first time, to be in a position in which almost nothing is so familiar it is taken for granted.” – Bill Bryson

Want more travel content like this? Sign up for our daily newsletter!

travel tips

Get relevant content delivered to you once a week