How to Plan the Perfect Trip from Scratch

Technology has upended the way young people travel today—it’s a double edged sword that has both the potential to make travel more efficient, or place barriers between you and the culture visiting and interacting with. The multitudes of information available can be overwhelming, but with a well-honed perspective, you can cut through this jungle of info and long to-do lists. First, ask yourself these questions:


Most importantly, you’ve got to have a general idea of your itinerary or purpose of travel. With Malia Obama now publicly taking a gap year before starting at Harvard, many of today’s Millennials are following suit by taking time off to explore the world. I anticipate this worthwhile practice of exploring the world, going on a journey of self-discovery to only get more and more popular. The Aussies have been doing it for years, and I know it’d be a great thing for more Americans to open their minds through Gap Year travel before starting university and careers. Other travelers are seeking volunteering, interning, studying, service opportunities or simply good old-fashioned tourism. Whatever your desire is, nail down the primary reason and goal of your trip to get started. 

Planning vacation


Your next step is to consider seasonality—when you go is just as important as where you go. Southern Europe is mostly shut down in August. October offers less crowds, ‘shoulder-season’ prices and still-acceptable weather. January and February are miserable to slog through the snow and ice in cities like Prague and Edinburgh. If you love visiting the beach, stick to the summer, and remember that swimsuit weather doesn’t roll around until June. Conversely, if you want to experience the slopes in the Swiss and Austrian Alps, February is your prime time to shred them.

Today’s "flashpacker" defines their trip by flight availability and price first rather than dates. Rather than pick arbitrary dates far off in the future, they jump on the cheapest flights they can find. Downloading ‘Hopper’ app will set up price alerts to give you notifications, if your preferred destination has a more affordable option. Google Flight Search is also a great resource to search entire continents for flight prices. Flexibility in dates will reap financial rewards in your long haul flights. Snatch your flight then request your time off. Use these long haul flights to anchor your itinerary, and remember that search engines may get hung up on a final destination if you’re searching all the way to your desired starting point. Instead, focus on the main airline hubs of Europe (Amsterdam, London, Paris, Frankfurt, Copenhagen) and look for connections to your desired starting point (like Dublin, Krakow, Rome or Barcelona) from there. We’ll discuss city-hopping flights in a subsequent blog entry.

As you establish your starting and ending points, it’s up to you to decide on pacing of your trip. Many friends and acquaintances come to me with ambitious lists of cities they plan to visit all the time. My first piece of feedback is nearly always to reduce, reduce, reduce. Aim for an average of one city every 4 days in your trip. That accounts for 3 days in the city and one travel day. Anything less than three full days in a city will really only allow you to scratch the surface and you’ll be spending a lot of time in transit on your trip. Another things to remember: Certain major sights may be closed on a couple days of your visit, and if you have extra time, you’ll have the flexibility for a day trip. 

If there are certain events that you’re dying to see, whether it’s music concerts, festivals, sporting events or otherwise, mark those into your calendar early on and make accommodation reservations around the same time you book your flights. In other words, as soon as you know the trip is happening, make reservations to stay at the events important to you, because prices skyrocket and availability plummets as soon as you near the event and people get around to making plans. The same goes for important holidays like New Years, Christmas, Easter and other national holidays.

Another point I always remind young students and adults alike: be selfish with where you plan to travel. Make sure that you’re going to each destination for your own reasons, not just because it’s ‘the place to go’. Every European city is different. The culture and activity options are different. Food is incredible in certain cities, while the nightlife is the highlight of others. Some are famous for architecture and art, others are famous for graffiti and grunge. Come to terms with the fact you’ll never have time to see them all on your first trip, so make sure drill down to cities that get your most excited based on your interest, not because it’s just where everyone else goes.

Look at your trip like a blank canvas: establish the outlines with your long haul flights, work on your foundation colors and shading with selecting your cities and the order you want to visit them. Map out important event dates well ahead of time and use those as check points in your itinerary. Leave the details like restaurants and sights until later in the process.

As you establish your list of cities to visit, start considering your transportation options now. Group the cities in an order that makes geographical sense, so you’re not zig-zagging back and forth across the continent. The only reason to ignore that advice is if you discover an excellent flight cost. Eurail passes are only a good deal if you really plan on using them. Determine your itinerary and do a cost comparison for cost of a Eurail pass plus about 20 eur for a seat reservation each leg you plan to use that. Compare that against about 100eur/flight that you would plan to take otherwise. That should give you a strong direction based on the cost analysis. Don’t forget to quantify your time en route as well!