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Cool Tools for Planning Complicated Trips

trip planningPast surveys have shown us that IndependentTraveler.com 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 Kayak.com, 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.

A Clever Secret to Getting a Cheaper Airfare


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.

Skyscanner.com 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.

International Discount Airlines


Although limited at present to a few handfuls of major cities in North America and Europe, Plnnr.com is an extremely well realized and fun site to use for planning a multi-day itinerary based on your interests, energy level, budget and more.

When you click on one of the listed cities, Plnnr asks for your arrival date and how many days you will stay; pretty routine stuff. Then things get interesting. On the next screen, Plnnr asks "what your trip is going to be like," with the following options:

couple map fall travel- With kids
- Outdoors
- The best of (Great for a first-time visit)
- Culture

The next screen asks how hard you want to charge it, with five choices ranging from "Light -- wake up late, here to rest" to "Extreme -- wake up early, see everything!" Then Plnnr asks how many stars you prefer for your hotel, and coughs up your itinerary.

The result is a day-by-day itinerary that I found to rival pretty much anything I could have put together on my own by slogging through websites and guidebooks. It included hotel recommendations, how much time you need for each attraction, the distance between attractions, and the travel time between attractions complete with maps, rankings and descriptions of each attraction. These itineraries were spot on. Even if you are not inclined to follow the entire schedule, you can get a really good idea of how much time any given attraction requires and deserves, as well as a good sense of the distances involved in a nice selection of potential sights.

The only complaint I had was that in several cities transit times were calculated using taxis, which can be both expensive and counter to the spirit of travel. In London, for example, to spend a week in taxis and never ride the Tube or the double-decker buses seems just wrong.

The site is graphically organized, with each day's itinerary represented on a map, and extremely easy to navigate; all told, very well done.

The Five Worst Trip Planning Mistakes and How to Avoid Them


If you are a Facebook user, particularly one with a lot of friends around the world, Trippy.com 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.

Like IndependentTraveler.com on Facebook


I have mentioned this service before, and I have not found anything that can beat it -- TripIt.com 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 plans@tripit.com 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.

How to Create the Perfect Itinerary


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 nudge@nudgemail.com 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:

To: nudge@nudgemail.com
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.

10 Hardcore Tips for Frequent Travelers

Resources for Traveling Light

suitcase city nightWe 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). You can go even deeper at onebag.com -- or take the No Bag Challenge if you dare. 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.

Travelista.com: How to Do Laundry When Traveling

Wikihow.com: 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!

Go Anyway,
Ed Hewitt
Features Editor


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