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Cool Tools for Planning Complicated Trips

Past surveys have shown us that readers are much more likely than most folks to plan and execute exceptionally complicated trips, often to remote locations, sometimes involving multiple stops in multiple countries. Not only are you independent-minded, but you are also ambitious.

As such, you are also much more likely to need to look beyond the standard booking sites and popular websites to find the information to make your trip come together. Following are a handful of sites to help you realize your ambitions on your next trip.

Kayak’s Price Trend

Most travelers get started fairly early when planning a complicated itinerary, which can make you wonder if the flight prices you are seeing are likely to go down as your travel dates get closer. Sure, many airlines will refund significant price reductions, but they usually also apply a stiff change fee, and most often you will find the change fees to be greater than the price drop.

When you do an airfare search on, the “Price Trend” feature shows whether the fare for that route has been rising or falling of late, and makes a prediction of whether you should buy now (because prices may go up within the next seven days) or wait.


For the past decade or so, budget airlines have been cropping up worldwide, but not all of them are easy to find or book. Many also fly from so-called “alternate airports,” which don’t always show up on the typical flight search. The two sites below focus on routes flown by budget airlines, and, taken together, can greatly expand your options when building highly customized itineraries. covers a huge variety of airports and airlines around the world, and I really like how broadly it allows you to search. You can put in “United Kingdom” as your departure location and “France” as your arrival location, and it gives you back heaps and heaps of options, with prices; talk about being able to see the forest for the trees, whew.


If you are a Facebook user, particularly one with a lot of friends around the world, can help you tap into the hive mind of your friends list for tips and information on the area, and lets you message them with questions as well. This way, you can find out almost instantaneously if someone you know and trust has visited a spot, and get their impressions and tips pretty easily. If none of your friends have been there (or they’re not members of the site), Trippy returns heaps of comments and tips from all public Facebook postings of Trippy members. This service does depend on folks signing up to use it, so it could improve or decline over time.


I have mentioned this service before, and I have not found anything that can beat it — is the place to keep track of every piece of your itinerary. I have used it for a few years now, and find that the service keeps improving — I can forward almost any type of information in any messy format to from any of my multiple designated email addresses, and TripIt pulls it in and organizes it into a tidy line item. Talk about cleaning up well. Beyond the typical airline and hotel reservations, I have sent TripIt tour times, concert ticket times, taxi pick-up times, hotel room change notices and more, all with great success. TripIt continues to upgrade its services, and now offers the ability to share itineraries, which can be helpful when you are meeting up with folks, or your family or office needs to know where you are.

TripIt has both paid and free account levels. I have a $49/year “Pro” account, and have found that the one Pro-level feature that I would miss on the free account is the mobile alerts, which are text messages about flight delays, gate changes and the like. That said, when traveling overseas, you will want to turn these alerts off, as they start pouring in and racking up international texting fees if you turn on your phone. You can see all the different program features here.


I am also a big fan of NudgeMail, a service that lets you schedule reminders to be sent to you via email at a designated future date. On any long, complicated trip, there will be multiple occasions when you need to confirm upcoming reservations, check in for flights, pay bills back home, get in touch with family or work, etc.; you can use NudgeMail as a powerfully simple reminder service that requires no logins, apps (save for email) or other encumbrances.

With NudgeMail, you send an email to with a time or day/date in the subject line and anything you want in the body of the email. At the time designated in the subject line, NudgeMail will send back an email reminder.

So an example NudgeMail might look like this:

From: Ed Hewitt
Subject: September 15
Body of email: Confirm hotel reservations for September 17, phone number 555-555-5555; confirmation number 12345678.

On September 15, NudgeMail will send your own email back to you. If you receive the alert at an inconvenient time, you can send it back to NudgeMail with a new time, and the site will send it to you again.

Before a long trip, I usually send out a number of NudgeMails, all marked with critical dates during the trip, and then forget about them until NudgeMail sends the reminder.

Resources for Traveling Light

We have our own collection of tips for traveling light (see What Not to Pack and The Carry-On Challenge: How to Pack Light Every Time). But for me, the main challenge of packing light for a long trip is not choosing what to bring, but keeping it clean — and these resources for doing your laundry while traveling will help nicely. How to Do Laundry When Traveling How to Do Laundry While Traveling

Want to deal with packing the easy way? Check out our Interactive Packing List, email it to yourself, and then forward it on to NudgeMail to arrive the day before your trip — done!

We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.

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