Vacations are expensive, and your vacation time is a precious, limited resource. Therefore, there is only one correct way to vacation: with meticulous planning and detailed scheduling aimed at making every moment of your trip as good as it can be.
Spontaneity on vacation is wildly overrated. “I just want to go with the flow,” you might say. In practice, spontaneity means wandering aimlessly, waiting in lines you could have avoided, and discovering that your desired restaurants and attractions are closed or booked solid. You came to Rome to visit the Vatican Museums, not to stand in line for hours at the Vatican Museums. Having a good plan that helps you enjoy all your time is far more relaxing than not having a plan and wasting your vacation.
A good vacation starts with buying and reading a good guidebook. This assignment is not a chore, because planning and researching a trip is a major part of the fun! For Europe, I’m partial to Rick Steves’s guidebooks since he expresses strong opinions: Far from just giving you a list of attractions, Rick tells you which he thinks are most important and which you can skip. The best Hawaii guidebooks are Andrew Doughty’s Hawaii Revealed series. For elsewhere, I like the Rough Guides.
It is almost never truly necessary to wait in line. At a museum, the long line at the front is usually a line to buy tickets, not a line to enter. Can you buy tickets on the internet or on your phone? Is there a multi-museum pass that will save you both time and money? Guided tours may enrich your cultural experience while allowing you to skip the general-admission line. At the Palace of Versailles, for example, this is well worth the extra €10, but you have to book in advance. If you have disregarded my advice to plan ahead and have no choice but to stand in a ticket line, consider whether you’re looking at the only entrance available; the Louvre has some less famous entrances with less daunting lines than those you’ll see in front of I.M. Pei’s pyramid.
Plan your sightseeing around avoiding crowds. Your guidebook should tell you what days the most popular attractions are most crowded and unpleasant. If you’re visiting an attraction that’s popular with locals, go during the week while they’re at work. And of course, make sure the attraction is actually open on the day you’re trying to visit.
Have a plan to pay for transportation. I hate standing in line to buy subway tickets; standing in that line might cause me to miss a train and lose several minutes of my vacation. Investigate: Can you skip the machines and pay at the turnstile with a contactless credit card or Apple Pay? In Chicago, London, and Singapore, you can. Throughout Japan, you can use Apple Pay for transit — it’s especially important because you’ll otherwise probably need to stuff cash into a ticket machine — but if you want to use your phone to pay, you’ll need to set up a special card in your phone wallet ahead of time.
Consider the pros and cons of the various modes: Is Uber widely available and reasonably priced in the city? Do taxis take credit cards? Is there a lovely walk to your next sight that counts as a vacation activity unto itself? I am personally a fan of bike shares even in unfamiliar cities, but consider whether you are the sort of person who finds biking in an unfamiliar city with possibly aggressive drivers to be invigorating or stressful. If you do want to use the shared bikes, set up the relevant application on your phone ahead of time so you don’t waste time at a kiosk. A general rule of thumb is that you should use kiosks as infrequently as possible; if you’re interfacing with a kiosk, you probably failed to plan something in advance.
If you want to eat at restaurants that take reservations, make them well in advance. Lunch is often a better value than dinner at high-end restaurants; consider more casual places for dinner. Sometimes, I worry that I have prebooked too many of the meals on a trip; in the end, I usually wish I had reserved everything ahead of time. If you want to go to a hot spot that doesn’t take reservations, consider the right time to try your luck. Often the answer is right when the establishment opens. I particularly find this is the case for cocktail bars, which tend to open at 5 or 6 p.m., just in time for a well-deserved drink after a busy day of sightseeing.
If you’re staying at a nice hotel, have a breakfast strategy. You will find the sumptuous hotel breakfast has two price extremes: exorbitantly expensive or free. Try to get breakfast for free. You will sometimes find deals on the internet that include breakfast at a regular room rate; you may also be able to get free breakfast by booking through a travel agent in a program like Virtuoso, American Express Fine Hotels & Resorts, or Hyatt Privé. These programs come with additional benefits like late checkouts and room upgrades.
If you’re traveling in a group, someone should be in charge. One major group-travel time suck is when everyone stands around politely expressing to the others that they’re happy to do whatever you want to do next. Polite deference may leave you without plans at a time when you need them. If you’re standing at the top of a well-chosen ski mountain discussing where to go next, all the runs down are probably pretty good; a group leader who simply picks one is helping everyone maximize their vacation. (You did buy your lift tickets or passes in advance to get discounted pricing and avoid waiting at a ticket window, right?)
A plan to do nothing is still a plan that should be made in advance. Of course, you may just want to sit around and relax on your vacation. But have you chosen the right place to relax? If you’re going to a resort, does it have the right amenities for your children or your lack of children? Read the TripAdvisor reviews. Know whether you’re going to need to come down before 9 a.m. to snag a good pool chair. Wear sunscreen.
Most of all, don’t forget to have fun. I am not proposing that a vacation should be a death march. Downtime is an appropriate part of any vacation schedule, and your meticulous planning should be aimed at achieving the pace of travel you enjoy, not at spending every waking hour checking off every sight you can possibly see. If you’re going someplace where aimless wandering is part of the fun — Venice, for example — you should put some aimless wandering on the schedule. Just make sure your stroll is designed to terminate where you’ve made a reservation for lunch. You’ll probably be hungry.