9 Steps For Planning The Perfect Trip

If you’ve never tried planning the perfect solo trip or if your previous “perfect” solo trips didn’t live up to your expectations, you might feel overwhelmed at where to begin. The following guide leads you step-by-step through the planning process, from figuring out your goals to booking your ticket. The more time you take deciding the Where, When, Why, and How of your trip, the less likely you are to be derailed by What If…?.

There are no right or wrong answers to the questions in each of the following steps. Just be honest with yourself and realistic about what you’re hoping to get out of the experience. If you are, you should end up with a trip tailor-made to your interests, your budget, and your comfort level. Click here to download the PDF worksheet for this guide, which includes space to write your answers.

Step 1: Figure out why you want to travel

Begin by thinking about why you want to travel. What do you hope to get out of your trip?

Do you want to break out of a rut in your normal life? Do you need to get away and relax? Are you looking for comfort and convenience or are you looking for action and adventure? Do you want to do the things you’ve heard about your whole life, like ride in a gondola through Venice? Or do you yearn to experience things relatively few others have done, like stay at a buddhist monastery in Tibet? Are you looking to gain confidence or regain your footing in life? Or is it simply a matter of gathering enough memories to tide you over until your next trip?

Step 2: Calculate your budget

More than anything, your budget will determine the nature, though not necessarily the quality, of your trip. When calculating your budget, don’t forget to factor in all of the one-time and daily expenses you might be faced with. The following are some of the more common ones:

  • Passport application fees
  • Travel visas fees
  • Travel vaccinations
  • Transportation from your arrival point – airport, bus terminal, train station, etc. — to your accommodation and back again
  • A local SIM card for your smart phone, if you want to avoid roaming charges
  • Weekly laundromat visits
  • Public transportation
  • Museum entry fees
  • Tour costs
  • City taxes on hotel guests. These usually run about 1 euro/night in Europe.
  • Alcohol and club entry fees
  • Souvenirs

Step 3: Decide where you want to go

This is probably the easiest one because you’ve probably been thinking about it for a long time already. If not, your answers to Step 1 should have sparked some ideas. Forget what everyone else has told you you “must” go see or do. Ask yourself a simple question, “If I could go to sleep tonight and wake up somewhere else tomorrow, where would that be?” When you have the answer, you’re ready to move on to Step 4.

Step 4: Determine the level of comfort you want

If you can handle sleeping in hostels, traveling by bus, and cooking your own meals, you’ll be able to travel for longer on a lot less money than if you want luxury hotels, airline flights, and restaurant dining. In general, the cheaper your travel, the more social it is, as hostels are much better places to meet fellow travelers than 5-star hotel lobbies. If your budget is limited but you really want comfort, consider shortening the length of your trip. Alternately, plan to spend most of your time living cheaply with the occasional splurge of a nice hotel or meal.

Step 5: Calculate how long you can (or want to) travel

Just because you can afford to travel for three months doesn’t mean you necessarily should. Be honest with yourself and, using your budget, your destination, and your comfort requirements as a guide, determine how long your trip should be. Hawaii always sounds wonderful, but after a week of perfect weather and wide sandy beaches, I always grow restless. The solution for me is to break my trip up into 5 to 7 day chunks, each different from the previous one. This helps me avoid boredom and gives me something to look forward to each week.

Step 6: Decide when to go

Keep in mind factors like cost. Most touristy places have a high and low season, so they’re a lot more expensive during the main part of the tourist season. Going when it’s cheaper will save you money, but you might find attractions closed or with reduced hours. Many stores and restaurants in Europe shut down from the Feast of the Epiphany (January 6) until the end of the month and many stay closed even into mid or late February.

Also factor in the weather during the time you’re planning to visit. Keep in mind that many tourist brochures use the term “Green Season” instead of “Rainy Season.” Make sure your trip is not going to fall during monsoon season, wildfire season, avalanche season, etc. In Spain, for example, Madrid and Sevilla become virtual ghost towns in August when huge segments of the local populations head for the coast to escape the oppressive heat.

Make sure whatever you want to see is not seasonal. You’ll get to experience nearly 24 hours of daylight in Fairbanks, Alaska in the summer, but all of that sunlight means you’re not going to be able to see the Aurora Borealis (the Northern Lights). Yosemite is gorgeous during the warm days of mid-summer, but some of the waterfalls all but dry up. Milan’s La Scala opera house is world-class, but like many opera houses in Europe, it’s closed in August.

Step 7: Decide how you want to get there

A friend of mine once booked a passenger cabin on a cargo ship traveling from Rio de Janiero to Salerno, Italy. The journey took two weeks, there was only one other passenger onboard, and she was only allowed to interact with the captain and other officers. Despite this, she loved the trip because she viewed the journey to her destination as another part of the experience. I personally travel by train whenever possible even though it’s often more expensive and time-consuming than flying. For me, the freedom to wander around, sprawl out, and get comfortable more than outweighs the extra costs involved. Ask yourself, is the journey to get to your destination important to you or do you really just want to get there as fast or as cheaply as possible?

Step 8: Figure out what you want to do when you get there

If you’re more of a nervous traveler, you’ll want to have some sort of itinerary worked out before your arrival. If you’re more adaptive and comfortable with not knowing things, a vague plan might be enough. When I travel, I usually book a hotel or AirBnB** rental for the first day or two. The rest of my trip is unplanned. Each morning I decide what I want to do and where I want to go. In contrast, a great friend of mine isn’t comfortable leaving for vacation until she’s conducted extensive research. She needs to know everything about each city, hotel, museum, and restaurant she plans to visit while away. There’s really nothing wrong with either approach, as long as you’re comfortable with it.

Step 9: Make your booking

Now that you’ve nailed down the why, the what, the when, and the how, the only thing left to do is to book your ticket. For over ten years, I’ve used Orbitz.com** for most of my travel planning. It’s an easy-to-use resource for finding the cheapest hotels and flights available. If you buy a package deal — a flight and a hotel stay — you can usually get a signficant discount. If you become a member of Orbitz before booking your trip, you will get a 1% rebate, called Orbucks, on the cost of your trip. Hotels.com** is another resource I use a lot. Rather than a 1% rebate, they offer one free night for every 10 you pay for. For both sites, sign up before booking if you want your purchases to count toward your rebate or nightly totals.

**Note: I am not affiliated with AirBnB, Orbitz.com, or Hotels.com in any way. I just value and trust their services.

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