Tips for Planning Your Dream Trip

trip planningWinter is the time when we dream about big trips for the upcoming warmer seasons. The New Year spawns resolutions, and almost everyone says they want to travel more.

What are the trips you dream about? Rafting the Grand Canyon? Trekking in the Andes? Paddling among Alaskan glaciers? A month-long road trip of California’s premier surf spots? Whatever your dream, here’s the way to make it go from dream, to actual trip.

Planning Is Fun
Big trips take a lot of planning: research, figuring out who should (and shouldn’t) be in the group, finding climbing route and river rapid beta, what vaccinations you need, how to negotiate shuttles, small plane flights (potentially in different languages), and how to be sure you get the experience you want when investing a lot of time and money. Planning is work, but the first step is to decide that it’s also fun. It’s a treasure hunt, a puzzle, and a journey in and of itself. I love pouring over maps of distant coastlines and mountains or reading guidebooks to faraway places, even if I may not get there for years.

Write It Down
Keep a list of trips you want to do, from quick week-long and cheap getaways to vast expeditions on the other side of the world. Don’t be too specific and don’t worry about whether or not you know much about the place at all. This list is to keep the juices flowing.

Do Basic Research
Pick the spot on top of your list and start the research. Get guidebooks from the library. Have a beer with friends who have been there and look at their photos. Surf the web. Start to figure out the basics. What time of year? What subregion of big places like Prince William Sound or the Scottish highlands? What’s the main appeal of that place to you and your pals?

Early Adopters
Eventually you’ll find someone you like adventuring with who will say “yes” in a serious way. Now you’ve got a co-conspirator. There may be obstacles that pop up later, but for now you’re plunging into the journey of planning the trip together. Split up things to research—transportation, routes, risks, permits, and get back together. Talk about what the group should look like: size, skills, and personalities.

trip planning
Find the Local Knowledge
Get beyond the guidebooks: talk to locals or people who have done similar things in the same place. They can tell you what it’s really like, and you can learn from their mistakes. Not everyone likes to give up their secrets, so expect it to take some friendly cajoling and reciprocal sharing when the time comes. Spread out the maps, talk specific routes, outfitters, or cultural, technical or logistical challenges.

Trust…But Verify
Don’t take all the info at face value. Not every trip has the same goals, conditions change, and for many remote places, logistical info is spotty. A friend found that a guidebook under-recorded the length of an stretch of arctic by a whopping 100 miles. Another friend sea kayaked in an island chain the charts were last surveyed in 1912. And landscapes change. New rapids form, trails wash out, glacial landscapes in Alaska are still rising as they rebound from the last ice age, creating new islands.

Time and Money
Trips are expensive and take time. Have an open conversation about cost, what people can afford, and what you’re willing to sacrifice if costs come higher along the way. This saves a lot of stress and prevents inter-group tension down the road.

Talk About Goals
Be overt about what you want your trip to be like. Are you driven to climb the peak? Will you be content if weather turns your trip from a summit push to a high-alpine trekking circuit? Do people want to do long miles, and are they willing to train for it beforehand? When you have this conversation, some people will drop out. It might feel like your trip is falling apart, but this is actually a good thing. It’s better to have this happen now then later in the game.

Identify the Crux
Most trips have some sort of crux move: a high-elevation a pass to get over before the weather turns or a big rapid. Others have logistical cruxes—how to get kayaks to a remote set of islands, or how to arrange a food drop and what to do if the weather prevents small aircraft from flying. Then plan the rest of your trip around that crux.

To Flex or Not to Flex
Beyond the crux, decide how much of the itinerary should be planned and nailed down in advance. Some will depend on the destination—permits, outfitter reservations, etc. In some places, great deals are available when you simply go there and take advantage of unreserved spots on transport and travel at the last minute—but you’ll need to be flexible if this doesn’t happen. Every group lives on a spectrum between planning everything and making it up as they go. Decide where on that spectrum you want to be.

group trip
Reform The Group
By now, several members of your group may have dropped out because they can’t afford it, can’t take the time off, or don’t have the same goals. This may a good thing. Big trips require an almost intuitive trust and you’ll have to get along well when things aren’t going as planned. This is the time that your group reforms. Then you’ll take the plunge: buying a ticket, making the core reservation with an outfitter, and locking in the dates on the calendar.

Micro-Plans
On big trips, micro-plans can matter as much as the big idea. The next step is to create them. I like to have a list of things I’d like to do while I’m there, as well as big objectives. This gives me ideas I can work with quickly when things change. They can be as simple as a great side hike if I have time, or a set of contact numbers of outfitters that can provide a diversion if I suddenly have two extra days to kill.

No New Gear
Don’t bring new gear. Even if it’s great, you don’t know it well, and on big trips you want to be able to set up your tent blindfolded. If you have new gear, give it a solid shakedown trip first. And remember, prep always takes more time than you think: planning menus, dehydrating food, repairing gear, and training.

Not All Dreams Come True
A lot of big trips won’t happen. Think of your dream trips like baseball players—many don’t make it to the major leagues, and some take a few years to blossom. But these trips definitely won’t happen if you don’t plan them. And like dreams, often it’s the dreaming that matters. It sparks the imagination and sense of possibility. As Vincent Van Gogh said, “I dream of painting, and then I paint my dream.”


Ready to take your dream adventure? Check out The Clymb Adventures page for an epic selection of unforgettable trips.