How much do you need to plan?

chaotictravelsblog
Mar 10
5 min read

Updated: Mar 13

ny schools of thought when it comes to planning for recreational travel, each with their own merits. Some travelers prefer to know what they are going to do minute-by-minute, while others enjoy the thrill of never being entirely sure what’s coming next.

Key Travel Elements

Regardless of preference, there are a few elements of travel that always can be pre-planned. Familiarizing yourself with these is a helpful starting point. You can then decide how you want to plan for each aspect depending on your preferred level of planning.

Travel Documentation: Ensuring you have the proper documentation for your trip is essential. Some destinations require visas, permits, or proof of vaccinations, and securing these ahead of time prevents last-minute stress or, worse, being denied entry. No matter how lightly you plan, this is a non-negotiable step.
Primary Transit: Getting to and from your destination is one of the biggest logistical pieces of travel. Flights, trains, and long-haul buses often have fluctuating prices and availability, so booking these early can save money and hassle. If your trip is flexible, leaving this open-ended can provide room for spontaneity, but securing at least a one-way ticket ensures you have a starting point.
Lodging: Where you stay impacts both your budget and overall experience. Some travelers prefer to book accommodations in advance, while others enjoy the freedom of finding a place upon arrival. If you’re traveling during peak season or to a popular destination, booking early prevents unexpected lodging shortages and higher last-minute rates.
Commute Method: How you navigate a destination can shape your experience. Will you rent a car, rely on public transport, or walk everywhere? In cities with well-established transit systems, minimal planning may be needed, but in rural or spread-out areas, knowing your options can prevent frustrating delays and unnecessary expenses.
Activities: The experiences that define your trip fall under this category. Some attractions require advance reservations, while others can be explored spontaneously. Having a shortlist of must-sees ensures you don’t miss out on key experiences, while leaving space in your schedule allows for unexpected discoveries. - Check out this post on how I find stuff to do.
Food & Drink: Food can be a trip highlight or an afterthought, depending on your approach. For those with dietary restrictions or must-try restaurants on their list, a bit of planning ensures you don’t miss out. While some travelers prefer to explore and eat on a whim, securing reservations at high-demand spots can prevent disappointment.
Sequencing & Timing: Not every trip needs a rigid itinerary, but some level of planning can help optimize your experience. Knowing the best time to visit a landmark or whether an attraction has limited hours can prevent wasted time. Some travelers prefer a structured schedule, while others only plan around key activities.
Alternatives: Travel is unpredictable, and having backup options can save a day from being wasted. Whether it’s an alternate activity in case of bad weather, a different restaurant if your top choice is booked, or a plan B for transportation delays, flexibility ensures you can adapt without frustration.

Other Considerations

On top of your personal comfort with more / less planning, there are a few key aspects of a given trip that should be considered. The most common being budget, duration, accessibility, and group size.

Budget: Are you traveling as a broke college student, a DINK couple, somewhere in between? The amount of money you’re willing to spend will likely dictate how much you need to plan and pre-book. A trip where you’re trying to be super thrifty often needs a bit more planning and research vs. a no holds barred trip where you plan to live in luxury.
Duration: How long is your upcoming trip? Are there some things you absolutely want to do? You should ensure that your must-haves will fit into your time horizon! Generally, a longer trip requires less time for planning; and vice versa.
Accessibility: Is this a trip that you could repeat tomorrow, or would this classify more as a once-in-a-lifetime bucket list trip? You should probably treat those differently. My advice, let your ‘easy to replicate trips’ enjoy a little more flexibility and save your minute-by-minute spreadsheet(s) for the trip that you may never get to do again.
Group size: How many people do you have on your trip? Is it more than one? If so, you’re probably going to need to plan a bit more than if you were traveling solo. It may be more difficult to get reservations and you’ll likely need to accommodate for more preferences/priorities. You should expect that the bigger your group, the more you’ll need to plan.

While I’ve typically seen these rules of thumb ring true, there are certainly exceptions to every rule. For example: a larger group that is comfortable with breaking up and doing different things can often follow similar levels of planning as a smaller group. Or a shorter trip where ‘success’ means you did one or two key things (e.g., beer and brats at Oktoberfest) might afford more flexibility. The most important thing for any trip planner is to take these criteria into account.

General Tips & Tricks

Prioritize booking primary transit and lodging: Unless you’re really flying by the seat of your pants, booking your primary transportation and lodging should be knocked out first, and early, to minimize unnecessary costs. My rule of thumb is to book both transit and lodging as soon as I’ve confirmed the location I’ll be visiting and the related dates.
Book for flexibility if it’s affordable: Travel is fluid. Things come up and even the best laid plans can get derailed. When that happens, it can be easy to lose a decent chunk of change without the right level of flexibility in your bookings. Personally, I don’t book the prepaid rates for hotels, and I typically don’t book the basic economy tickets for flights.
Don’t book fully refundable flights: I’m sure there’s some study out there somewhere, but the payoff for booking fully refundable, which I’ve seen to be 25%+ more expensive, isn’t typically there. Not only do most airlines allow you to change flights at cost or with a minor change fee, but there are also plenty of credit cards that provide solid cancellation coverage if you need to fully cancel a trip (be sure to read up on the specific terms and conditions for your card).
Find some useful memberships: Depending on where you typically travel and/or how long you plan to be in your location, it might make sense to join certain memberships. I tend to leverage those included with my credit cards the most (see my credit card strategy here). These can be helpful sources for you to book certain excursions, get free meals, and in some cases provide free or discounted bookings!
Focus on what’s most important to your group:When traveling in larger groups, its near impossible to get people to agree on everything. My recommendation is to poll the group for the top 1-2 things that they want to do and do your best to incorporate those activities into the travel plans. Don’t forget, your travel mates are also independent. If they don’t want to do something on the agenda, they can always go find something on their own!

Conclusion

So, how much planning do you need? I know it’s a bit of a non-answer, but you should do what best fits your situation. Bigger groups, tighter budget, personal affinity towards knowing exactly what you’re doing… Maybe you should plan a bit more. But if you’re traveling solo, feel comfortable spending a little more on last-minute bookings, and love waking up not knowing exactly what’s going to happen today… You could probably get away with a list of activities on a sticky note and a chat with a few strangers in a bar.

My take: Less is more when it comes to planning. The stories I tell friends about my travels are often not the ones I spent hours planning.