Trip Planning Tips and Tricks: How I Plan My Travel
Me, in a common trip-planning setting. Lausanne, Switzerland. February 7, 2022.
When I mention to friends the things I consider and do when planning my travel, I’ve often heard back, “That’s a great point! I never would have thought of that.”
With the good fortune of getting to work from anywhere and the general flexibility that allows me to do so somewhat often, especially in recent years, I’ve learned (and continue to learn) what works best for me when it comes to vacation planning. Alas, I’ve often learned these lessons the hard way.
While all of us have our preferences, including me, I have picked up a few best practices and shortcuts that could help almost anyone who plans to a trip.
Here’s to hoping they help you, too. (And that they save you from learning, as I did, through unnecessarily bad travel experiences!)
P.S.—For even more specific-situation advice, check out my guide to planning a vacation to Europe with teenagers, my tips for avoiding drama while traveling with other people, my four tips for finding the best tour guides, and suggestions for when it makes sense and how you can try to “do as a local” as a tourist.
What Kind of Trip are You Planning?
How I plan a trip depends heavily on the type of trip I’ve planned.
For example, if you’ve planned a trip to see people somewhere, you may not have the same amount of say in what you see, do, or even where you stay. In this case, the pointers I’ve developed in this article may help you, but in a much more limited fashion. Pick out the ones that can help make the trip easier and more fun for you and your hosts and ignore the rest.
If you’ve planned a trip purely for tourism, it will take a different shape from a trip that mixes work with pleasure or a work-from-wherever trip. In these cases, the guidance I’ve given in this article should still apply—though take note of the nuances and caveats I’ve provided for each case, based on my experiences.
When I’ll Choose to Stay in a Hotel
If I plan to stay somewhere for one to three nights or so, I prefer a hotel to a rental apartment or property.
First, the cost of hotels makes longer stays in them often cost-prohibitive and less comfortable. However, for a shorter stay, the higher cost and the benefits that hotels bring make a lot of sense:
Hotels make check-in and check-out much easier than rental apartments do (most of the time).
If you come before your room is ready, a hotel will store your luggage—as it will when you need to check out but still want to spend more time in the area. (Rarely true with a rental property.)
Hotels have spacious lobbies and common spaces where you can relax, work, and meet up with people not staying at the hotel.
Hotels often have on-site bars and restaurants for a quick meal—valuable when you don’t have time to find a café or the energy to create a picnic from stuff you can find at the grocery or market.
If you room issues, a hotel can switch you to another room relatively easily, without you needing to go back and forth via an off-site owner or rental agency (who often has no other property to which you can move, anyway).
Further, with so little time in a place, I don’t plan to eat in much, I won’t need to do laundry, and I don’t need much space as I’d rather use my limited time to visit the area rather than hang out where I sleep. A convenient come-and-go hotel room makes a lot more sense.
If I do need to work a bit during a short stay, though—especially if I have calls planned and a table in the lobby just won’t cut it—I will do my best to ensure that the hotel room I book has at least a minimal workspace, which means a desk or table and a chair.
Otherwise, I don’t need much more from a hotel room than a comfy bed, a clean and well-appointed bathroom, and high-speed internet.
Ah, and another solid reason for choosing a hotel over any other option: If traveling solo, I always feel more secure in a hotel.
When I Prefer to Stay in a Rental Property
If I plan to go somewhere for longer than a night or two and have someone on the trip with me, finding a space where we can spread out, enjoy downtime without sitting on the bed, cook and keep food stored and refrigerated, do laundry, and work without trampling each other matters.
When it comes to vacation rental properties, I rarely need more than an apartment. However, if the trip will involve more than two or three people—a rarity, in my case—a house may make more sense.
Here are my rental-property criteria:
A washer or nearby laundromat: I like to pack lightly, meaning that I only want to bring what I need for a few days—and as I tend to pack things that coordinate easily, I can get by without bringing much. I simply do not love carting around a bunch of luggage—especially not when I have to transport it from the car, train, or bus to the apartment (and possibly up a bunch of stairs).
Comfort, for chill-out and work-from-wherever trips: If I plan to mainly sleep and eat in a place, I don’t worry too much about the comfort or coziness of the common areas. However, if I need to spend time there working during the day or we plan to relax in the place we’ve rented—such as, for example, a trip to unwind in the countryside or in the snowy mountains—then I want a comfortable couch, chairs, and kitchen table. (By the latter, I mean I want more than a bar table with two stools. We’ve seen that often, and I don’t mind it if I plan mainly to eat and run, but I don’t like it for long meals in company.)
Dedicated workspace: Unless I don’t have even a couple of hours of work on the agenda—a rare occurrence—I don’t worry about workspace in the vacation rental. Otherwise—or, in other words, most of the time—I seek a place with at least one desk and chair and a real dining room table-and-chair set, so that at least two people can work in reasonable comfort. (Expecting two desk-and-chair combos in a vacation rental often pushes reality.)
High-speed internet: Especially with work—but really, always—I require high-speed wireless internet and will often even e-mail the host before booking to double-confirm internet speeds. (Alas, I’ve discovered far too often after arrival that a property says it has wifi—and then I arrive and find it inoperable or woefully inadequate. Beware and, as I do, take your precautions.) If I still don’t feel entirely confident, I scope out coworking spaces in the rental’s vicinity to which I can quickly decamp for an hour or two.
Central location: Unless I’ve made hanging out in the middle of nowhere the goal of the trip, I require a place located centrally to all the major attractions and sites and that has all the necessities nearby, such as pharmacies and groceries. It can seem like “no big deal” to stay a mile or more away from the action when you book a place, but you’ll find it an entirely different matter to walk a mile and back every time you need to return to base. Yes, staying in a central location means you will pay more, but I find the cost-to-hassle difference worth the price.
If you’ll use the place where you stay for the night as your base of stay, you will need to include a few other evaluation criteria. What do I mean by “base of stay?” Read on.
How and When to Choose a Base of Stay
You can visit a city and spent your entire time in that city. However, if you plan to explore one or more towns—more of a region in general—you need to choose your base of stay wisely.
When I refer to a “base of stay,” I refer to the place where you decide to search for a hotel or a rental apartment. You may visit the town where you stay—and I hope you do!—yet you can easily launch yourself from there to see interesting things around the area.
For example, we had Tours as a base of stay to see the Loire Valley châteaux, Bordeaux to see the Bordelaise region, and Toulouse to visit the areas around it.
A good base of stay will have easy in-and-out access for a car (and reasonably priced or free parking at or around the hotel or rental apartment) or, if you plan to travel by public transportation, easy access to the bus and train stations.
Further, every good base of stay needs to have plentiful cafes and restaurants, pharmacies, bakeries and patisseries, and everything else you could want or need before you leave for the day, after you get back, and to take with you while you head out to explore. Ideally, so that you don’t have to drive the car while in the base-of-stay location, you will have all these amenities within easy walking distance of the hotel or rental apartment you choose.
How to Find Stuff to Do
Before I go anywhere, I’ve learned that leaning old-school and buying a guidebook often really helps orient me and give me baseline ideas for what a place has to offer and the major things I should do and see while there. Even in the internet era, you can’t go wrong with a good guidebook.
The challenge with guidebooks is that today’s web-focused world has started to gut the industry, and the quality guidebook publishers have started to move away from unbiased advice to pay-to-appear listings. Go to the bookstore and flip though whatever they have on the region you plan to visit, and try to find a guidebook that seems as comprehensive as possible—and as objective as possible.
One of my first stops in any place I visit is the nearest official tourist office. I’ve had hit-or-miss experiences with them, as some tourist-office staff will get creative and think broadly with you to find activities suited to your interest—and some just want to give you the usual spiel. That said, even if you don’t get over-the-top ideas from your visit to the tourist office, the entire reason it exists is to provide guidance—at no cost—to visitors on what to see and do and how best to enjoy the area. Why not take them up on the free offer?
Also, if staying in a hotel, you can ask the concierge or front-desk person for ideas for what to see and do during your visit. (Friendly reminder: Tip them for their help!)
A what-I’ve-learned caveat: Tourist offices and hotel staff can get in ruts. They answer the same questions and provide the same guidance for days on end. Therefore, if you have specific interests, you’ll get a better response if you arrive with questions to orient the person’s answers. Examples: “I love medieval history. What would you recommend I do?” “Do you have a list of the city’s theater productions during my visit?” “While I’m here, I’d love to do something active. Do you have information on biking tours or guided hikes?”
Further, hotel staff and tourist offices often have minimal insight into limited-time opportunities happening during your visit. For that reason, you should do a little grass-roots research ahead of your trip and during your visit to turn up real gems you’ll otherwise miss.
To dig around a little beyond what guidebooks, hotel staff, and tourist offices serve up to every visitor, I try these avenues:
Do an on-line search for local-area event calendars and review their offerings. An important tip: Use a translation tool (I recommend DeepL) to use search terms in the language of the area you plan to visit—searching in the native language always turns up the best results. You can then use the same tool to translate what you find on the web back into English (or whatever language you prefer). English speakers assume that searching in English will turn up everything—as they assume everything on the web has an English translation (or that the search engine will “know what they mean”). It doesn’t, it won’t, and you’ll miss a shocking amount if you search the web only in English.
Check out the area’s magazines and newspapers on-line or in the local news stands for event listings. (See above bullet for an important language tip!)
Look at the posters in public transportation and on the street for special exhibits, tours, performances, and more. I once had someone tell me that the best way to know what’s happening in Paris while you’re there is to go down into the Metro and look at the wall—and that advice could not be more on point for Paris and pretty much everywhere else you’ll visit.
Using the native language, do a web search for classes in the area you plan to visit. I’ve found cooking classes, language classes, pottery and arts classes of all kinds—and beyond. If you find one of interest, you’ll likely meet only locals attending (because tourists rarely think to look up courses to take), and even if you don’t speak the language, you can often muddle through just fine if the class focuses on hands-on, follow-the-teacher learning.
Search Meetup.com and Eventbrite for the place you plan to visit during the dates you’ll be in the area. You’ll find everything from business networking and lectures to happy hours, language exchanges, hikes and yoga sessions, and more.
Though I’ve often found the listings much pricier than what I can find on my own via a web search or other portals, I have had luck finding fun activities through searching the listed local AirBNB Experiences during the dates of my stay. You can search experiences on offer via the company’s main website (regardless of what you’ve used to locate lodging during your stay).
Because while you really should see the can’t-miss attractions in any place you visit, the surprise treasures really make for special memories.
Where to Find What to Eat (Meals, Breads, Treats, and Groceries Galore!)
A common mistake that travelers from the United States make elsewhere in the world: They assume everything will be listed on Google or Apple Maps and in smartphone apps like Yelp and Tripadvisor.
Wrong.
Outside the United States, many businesses don’t bother to create listings on these platforms or they choose other, more locally focused, platforms. Therefore, if you rely on Apple Maps and Yelp or Tripadvisor (and the rest) you’ll likely only find the places that mainly cater to Americans. If you don’t want to end up at the tourist traps, you must look elsewhere for your food and treats.
Better avenues for finding great stuff to eat while on travel:
Scroll through local publications for restaurant reviews. (As mentioned above, you can plug almost anything into translation apps to understand what the article or listing says.)
Check out articles and posts you can find via a web search from travel experts and travel bloggers, who will give you first-hand experience on what they tried and liked.
Go to social media sites known for travel inspiration, like Instagram and Pinterest, and search the platform for posts about the place you plan to visit.
On the grocery and pharmacy front, I recommend that you stick with the country’s or region’s main chains for safety’s sake when visiting a place you don’t know well. You’ll save time trying to find your favorite local grocer and won’t worry quite as much about the health safety of the food you buy.
Yes, go to and buy from markets when you can—I love them—yet you’ll likely have to go to groceries and pharmacies for the staples needed in a rental apartment for a week. Spend less time wandering, looking for kitchen basics, and more time visiting the area.
Planning Your Travel Days (and Weeks)
If you plan to work while traveling and you haven’t yet quite gotten the hang of work-from-wherever, you’ll need to continue to remind yourself that, while you aren’t in your usual working space, you still need to work as much (or almost) as always.
In work-from-wherever cases, you’ll need to plan most of your activity around your work schedule, rather than the other way around. This means you need to expect to see a fraction of what you’d see with the same amount of time than what you’d see on a normal vacation in a place. On a work-from-wherever trip, don’t expect to manage much more than visiting the tourist spots on the weekends and maybe two tourism-focused half-days during the week, which means you’ll need to work extra during the other days.
Either you need to come to terms with this shift in thinking (and planning)—or you need to book your trip for a much longer time.
If you have pretty good leeway in your schedule for touring—in other words, if you’ve mainly planned a vacation, even if you have a little work to do here and there—how do you decide what to schedule and where to schedule it on your calendar of travel days?
Personally, I want one “real” meal per day. This means I want to sit down in a café or restaurant or in the rental property and properly relax and eat a meal, finished off with tea, without rushing. I don’t mind not eating breakfast and having a snack or a picnic in the car or on a park bench for the other food of the day. However, unless something I want to do means I need to eat on the run the entire day—which can happen, if I really want to do an activity and the activity requires it—I prefer planning to have a moment to pause and property eat and digest my food.
Therefore, I budget time for one real meal of about two hours total each day. If your group will want more than one real meal each day—a far more common situation—you will need to budget more time than this.
With one meal per day, I can manage to visit or do two activities in a vacation day. (Maybe three, if the things I’ve planned are small or quick or I find that one can happen on the way to or from another.) After all, you shouldn’t rush through things you visit and you need to factor in travel time between activities.
To choose my daily two things, I aim to schedule no more than one museum per day—because even when you love museums (as I do), you can get museum overwhelm and find yourself wandering through rooms without really taking in anything you see. That’s a waste of time and of a good museum. (And if you have some of the big national museums on your list, read my tips on how to approach landmark museums successfully.)
Fortunately, most places have historical sites, walking tours, and other activities than just museums to see and visit. Count on one of these types of activities plus one museum, plus a meal, and you’ve mapped your travel day.
And if two activities plus a museum sounds exhausting—though I tend to find people overly ambitious about what they think they can do during a trip, rather than the opposite—remember that you have a lot of fun when traveling and touring, so you’ll discover that you have more stamina than you might have at home when it comes to a single day’s sites and museums and activities.
And if you tend to be like more people and want to do more than what I’ve outlined, remember: You don’t want to wipe yourself out in two days, such that you don’t enjoy the rest of your trip. Pacing makes a difference!
Crowd-Sourcing Best Practices for Travel Planning
We all have our priorities when it comes to travel—including priorities that I have that are me-specific enough not to warrant mention here. However, the broad strokes of travel and the best practices we can apply to them often can help us all.
And in that vein, if you have tips if your own to share that can help plan travel, please share them. Help me out—and everyone else reading along, too!
P.S.—And if you’d like a few packing tips for low-volume items to always have in your bag, click here.