How to Create the Perfect Travel Itinerary

Ever noticed how some folks make the toughest trips seem like a leisurely walk in the park? We’ll wager that nine out of 10 times, those travelers created a near-perfect itinerary before they even started packing.

Modern itinerary-making tools, from websites to mobile apps, allow travelers to build colorful trip timelines and share their travel plans with loved ones. But the ability to engineer an effective, seamless itinerary requires more than just bells and whistles—and well-laid travel plans are an integral component of any successful trip.

So what’s the secret to creating a great itinerary? After you’ve snagged a solid airfare deal, arranged for a car rental, and even managed to pack light, there are some less obvious—but equally important—tactics you can use to put together a seamless trip.

Be Realistic

Sure, you’d like to milk your trip for all it’s worth by booking a red-eye flight and then scheduling a full day’s worth of activities on day one, despite an eight-hour time difference. But by the end of the trip, you’re likely to look and feel as if you’ve spent the week in correctional boot camp. If you really want to squeeze in every tour, meal and excursion you’ve typed into your itinerary, but as it currently stands you’re getting six hours of sleep a night with no room for a time adjustment, you need to add a day—or cut an activity.

Choreographing all you want to get done into a seamless schedule, especially if you’re visiting multiple cities or countries, can be a massive challenge. Make it easier by creating a list of everything you want to see or do in your locale. Then put the list in priority order. To help estimate how long an activity will take, or how long it will take to get there, consult a guidebook or check out online forums or reviews for perspectives from other travelers who’ve been there and done that. This will make it easier for you to feel out what you can and cannot accomplish during, say, three nights in Montreal.

Research events happening in your destination while you’ll be there (tourist board websites are good for this—they usually have events calendars), and plan accordingly. There may be a nifty festival that you want to slot into your schedule, or, at the opposite extreme, you may want to avoid a certain part of town if it’s going to be crowded or blocked off.

Also note local holidays coinciding with your trip, which can affect transportation schedules, business opening hours, etc.

Ambitious travelers who plan to embark on a weeklong tour of Europe (yes, we’ve actually heard of people who attempt to see a continent in less time than it takes to learn the Thriller dance) should do some serious planning. In a case like this, a map is your best friend as you prioritize activities. Look at a map and start grouping the different attractions you want to see by neighborhood or region—this will help you minimize transit time between one part of your itinerary and the next.

There’s more to consider than just time and location. Planning to search for sunken treasures? Most scuba experts agree that divers should allow at least 24 hours between scuba diving and flying (so that your body can adjust to changes in altitude). If you have a cruise or a prepaid excursion planned, arrange for your flight to arrive no less than a day prior to your departure date. Otherwise, a missed or severely delayed flight could cost you. A good rule of thumb, regardless of what you have planned: The more space your itinerary allows between activities and transportation, the better.

Get It Right, from Door to Door

Is it me, or are economy parking lots are getting farther and farther away? Beyond just the length of your drive to the airport, it’s important to account for time spent schlepping from the economy parking lot a few towns over. Allow yourself plenty of time to make it through the security checkpoint’s snaking line.

Ask yourself a few questions: How far from the airport do I live or work? Will I have an opportunity to eat before driving to the airport? If I miss the parking or rental car shuttle by seconds, will I have enough time to wait for the next one, or am I going to be sprinting across the lot trying to hail down the driver?

The same thing goes for your arrival. Although travelers may sometimes save by booking flights to smaller, more out-of-the-way airports (especially in when flying on discount airlines in many European countries), it’s important to weigh thrift against travel time. One of our editors saved some money by booking a Ryanair ticket to Barcelona’s secondary airport in Girona (instead of Aeroport de Barcelona, the city’s main hub). But she ended up taking an hour-long bus ride to get from the Girona airport to Barcelona’s city center—an inconvenience that eclipsed what she saved on the ticket.

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Connections Are Key

Add a connection to your itinerary, and plenty could go wrong that wouldn’t have happened had you booked a nonstop flight. Connections mean additional planes and additional opportunities for delays. Connections also mean that your bags are being moved and mauled, which creates more occasions for your property to be lost or damaged. God forbid you make a connection and your bags don’t—or vice versa.

A connection will disrupt your sleep too. If you’re the type to take a sleep aid in transit, you know that there’s nothing more miserable than surfacing from the depths of a Dramamine-induced slumber to slouch off the plane, lumber through the airport to a new gate and endure another complete boarding process.

If you simply can’t avoid a connection, make sure not to cut it too close. Allowing at least a couple of hours to change planes (longer for international connections) will give you a little wiggle room in case of delayed flights.

Useful Websites and Apps

Various websites and apps have facilitated the creation of itineraries, and the ability to share those itineraries, for thousands of tech-savvy travelers. Here are a few of our favorites:

TripIt.com allows users to create complex online itineraries and email them to themselves or to friends and family. The site will automatically insert tons of useful information into your itinerary, including maps, directions and weather. TripIt is free, but you can buy extra perks, like a mobile service that alerts you if your flight is changed or canceled, for an annual fee.

TripCase.com is a similar service to help you organize your trip. Forward your air, car, hotel and other confirmations, and the site will arrange them in an orderly timeline. You can share your itinerary with friends and add restaurants, shops or other relevant attractions.

TripHobo.com is less about organizing your itinerary and more about helping you populate it. Put in your starting point, your desired destination(s) and ending point, and the site will offer recommendations for how to get between places and which activities you may want to do in each city on your list. For each attraction you’ll see info like opening hours, ticket prices and the estimated time it will take to see it. You can view other users’ itineraries to get ideas.

The Itinerary app for iPhone helps you organize your trip by plotting each day’s stops on a map and letting you add notes. Another itinerary app worth a look is TouristEye, which allows you to get ideas and map attractions.

The Best Laid Plans…

Your itinerary is not a legally binding contract. It’s more like a rough draft written in sand. Things will go wrong. Restaurants will be closed. Buses will be late. Animals will attack.

Consider scheduling a free day into your itinerary. During your trip, it’s likely you’ll discover some worthwhile attractions you didn’t know about prior to your departure. This will also give you some wiggle room in case you don’t see everything you had originally planned.

All in all, the most flexible itinerary is often the best. Our final advice? Opt out of the hour-by-hour detailed timeline that factors in bathroom breaks and photo ops. Instead, expect the unexpected, and leave plenty of room for upsets. If you know where the bumps in the road might be, you can steer around them. And if you’re really lucky, you can put it all together for the perfect itinerary.

More from SmarterTravel:

• Planning a Trip to Europe: Your 10-Step Guide
• 5 Ways to Make the Most of Your Vacation
• 10 Things to Do When You Get Home from a Trip

Ed Hewitt contributed to this story.