Ten Steps for Planning the Best Trip Ever

From my experience reading various online travel forums, I get the sense that many people start their planning at this step. But if you really want to get useful and valuable guidance from others, you need to have gone through these first four steps. If you are able to tell people why you’re going and what you already understand, you are far more likely to get meaningful answers to your questions.

And of course, if you have friends and family who have been where you are considering going, seek their advice. There’s one great advantage to getting help from people who know you: they know you! They can tailor their advice to you. But there’s also a potential pitfall: they may not want to share negative experiences. So when you get recommendations from friends, it’s still a good idea to follow that up with independent research.

Getting travel advice from strangers is low risk, because you won’t hurt anyone’s feelings if you don’t take their advice. But given that there are many varied opinions about every destination in the world, expect a wide range of responses if you’re asking for suggestions. That range of opinions can be useful if you just want to get some perspectives other than your own before you make up your mind. But they can also muddy the waters and make it harder to settle on a good itinerary.

For itinerary help, you may want to consider working with professionals. I’ve used online travel agencies and used their advice to settle on my itinerary. It means paying a little extra, but depending on the complexity of the trip and my familiarity with the language and culture of the destination, this can be a worthwhile investment. I’ve also used the Rick Steves Trip Consulting service, which I have found very helpful and quite inexpensive (at this writing, they have suspended this service while they work on getting their tours back on the road post-Covid; previously it was $50 for a half-hour consult). Sometimes you don’t really need a lot of opinions. You just need a conversation with an experienced traveler to help you make up your mind.

But do your homework first!

Of course, if you’re going to Hawaii or the Caribbean or another tropical resort, or on a ski trip, or a week in Rome, or anywhere that doesn’t involve lots of detailed planning, the only help you might need is to select a hotel. If you aren’t sure where to stay, asking for help is going to work out so much better if you’ve done your homework. Instead of asking, “Where should I stay in Honolulu?” do your research, find two or three places that appeal to you, and ask people about those specific places. Or at the very least, state your budget, the general area you want to be, and specific amenities you’re looking for. “I’m looking for a hotel with a pool, easy walking distance to the beach, under $150 a night.” 

The help you’ll get from online forums is best if you need objective answers to your questions. Last year I was planning a trip to Mexico. I wanted to find someplace quiet where I could relax and enjoy tranquil surroundings, but I didn’t want to go to a beach or resort teeming with Americans. I posted on the Thorn Tree forum (which no longer exists) at Lonely Planet. I had to weed through some replies that were not so helpful, but I did get some good advice and was able to make a decision. And Tepoztlán, which one person suggested, was wonderful, though not a very quiet town.

On the other hand, if you ask open-ended questions looking for help without having done some homework first and with no ideas of your own about what you are looking for, you’re likely to get advice that’s all over the place and muddies the waters rather than steering you toward a decision. Plus, if you haven’t done your homework, you might not get the kind of responses you are hoping for.

There is a tendency among humans to think of everything that’s far from where we live as close together. We just aren’t good at appreciating the distance between two places that are far from us but in the same general part of the world.

If we fly 6 or 8 or 12 hours or even longer to visit a distant corner of the world, it is tempting to want to see as much as we can. On a first trip to Europe, people often want to see Rome, Paris, London, and more. Or on a trip to Southeast Asia, you might want to go to Vietnam, Laos, Cambodia, and Thailand. And then you look at a map and discover that Vietnam alone, from north to south, is tall enough to stretch from Canada to the Gulf of Mexico. Or you look at trains from Rome to Paris and discover how long it takes, even on one of those high-speed European trains.

It takes time to get from place to place

Covering a lot of distance takes a lot of time, and that is time you could spend doing what you came on vacation to do: see stuff. Unless riding on trains was one of the goals you identified (and if it is, it’s a perfectly worthy goal), you don’t want to spend your limited vacation time getting from one city to another. If you already spent the better part of a day getting there, you should select destinations that allow you to maximize your time fulfilling your goals.

If someone told you they were coming to visit the USA and had one week and wanted to go to New York, San Francisco, and Chicago, you’d probably tell them they were crazy. You’d suggest they cut San Francisco, and probably Chicago as well. But I regularly read about travelers from the US who are going to Europe and want to see London, Paris, Rome, and Amsterdam in two weeks, or some such thing. And then they want to know if they can squeeze in a side trip to Bruges! Don’t spend your limited travel time checking in and out of hotels, waiting in airports and train stations, or moving from point A to point B.

But there’s another reason to limit yourself regionally: a trip in a single region will allow you to learn and understand more about that place. If you have two weeks, you could jump from Italy to Norway to Scotland. When you’re done, you’ll see a variety of places, but you won’t remember the difference between Trevi Fountain, Geiranger Fjord, and Loch Ness. Depth makes for better travel than breadth.

Although I think the best trips are done within a limited geographical area, I don’t think you should limit the kinds of activities you undertake while traveling.

The best itineraries involve a combination of big cities, small towns, countryside, and nature. Fortunately, you can get all these things without traveling long distances between them. Norway in a Nutshell, an independent itinerary between Oslo and Bergen that can be done in as little as a single day, offers all four experiences with connections on trains, boats, and buses. Similarly, you could go from Paris to the Loire valley, from Las Vegas to the National Parks of Arizona and Utah, from Tokyo to any of the surrounding prefectures. In fact, pretty much any city in the world can be used as a base for exploring nearby villages and to get away into rural and unspoiled settings. So if you have just a week for your vacation, you can still break things up while staying in the same hotel the entire time.

I love art and love visiting art museums. But after a few days in Florence, I was ready to go to the Cinque Terre and enjoy hiking. And when I stayed in Amsterdam for five days, I needed one day to visit some rural communities north of the city, and also spent some time just enjoying wandering through Vondelpark.

If you’re planning a multi-week itinerary, consider varying things. If you’re traveling by air, fly open-jaw, into one city and out of a different one. And find a route between them that will give you opportunities to see many different kinds of things.

Of course, if you want to spend a week lying on a beach drinking piña coladas, who am I to argue? But maybe order a mojito at least once!

One of the greatest pitfalls in trip planning is the tendency to add too many “must-sees” into your itinerary.

You can’t fit your entire bucket list into every trip. You can’t see every museum in Berlin, or every hilltown in Tuscany, or every waterfall in Iceland, or every windmill in the Netherlands. Not only that, but sometimes you will have to make a very hard choice among a few of your top picks. Something you were really looking forward to might end up on the cutting-room floor.

Having made these hard choices, you have another choice: you can be disappointed about what you didn’t get to see, or you can concentrate on enjoying what you see.

Don’t be that guy.

You can actually skip this step and still have a great trip.

But you won’t have the best trip ever. And skipping this step will make it harder for future travelers—including you, assuming this won’t be your last trip ever—to have brilliant adventures all over the world.

Responsible travel means a lot of different things, and there are many ways to travel responsibly. But the main reason to travel responsibly is to preserve the planet in general, and travel destinations all over the planet, for the next generation.

Travel involves many activities that increase carbon production in the atmosphere. A simple web search will help you find many resources on how to reduce your carbon footprint when traveling. Other terms you might search for are “sustainable travel” and “ecotourism.”

The environmental impact of travel is only part of the story. Travel also has economic, social, and cultural effects on the places we visit. Part of your homework as you plan your trip should be to understand these impacts and consider ways to make them more positive than negative. Try to avoid contributing to the adverse effects that tourism brings to many parts of the world. Be sensitive to local cultural norms. Support the local economy. Be a good ambassador for your homeland and your hometown.

On the perfect trip you fly first class, you eat all the best food, meet all the most interesting people, see all the most extraordinary sights, and stay in the most delightful accommodations. There are no crowds. No graffiti. No lines to get into any attractions. You don’t suffer from jetlag. You never get lost. You never get tired or sick. Your feet never hurt. You pack exactly as much as you need, and your luggage is lightweight and easy to carry. You go on the most fascinating tours. It never rains. There are no delays, no missed connections, no traffic, no noisy neighbors keeping you awake. When you get home, you are invigorated, refreshed, energized, and loaded with wonderful memories, spectacular photos, and meaningful souvenirs you bought from charming vendors in quaint village markets.

The perfect trip only happens in your imagination. When you are planning, none of that bad stuff ever happens. Everything goes smoothly. There is evidence that planning your trip is the happiest part of it.

If you try to have a perfect trip, you are bound to be disappointed, and one disappointment can easily sour your entire experience if you let it. Good planning maximizes your ability to be adaptable and flexible, so when things don’t go according to plan, you can recover and get on with the adventure.

Follow the first nine steps, and your trip won’t be perfect. But your experience will be. And you are sure to enjoy the planning!