Be curious -- and humble.
It may sound morbid, but one of the most interesting (and usually free) ways to learn about a city is to explore its cemeteries. These spaces are often beautiful and can offer insights into the history, architecture, art and religious beliefs of a city. Major cemeteries are usually full of elaborate monuments, interesting folklore and even celebrities (their headstones at least).
The hotel you want is sold out? Find out when cancellation penalties set in for the date you want to arrive, then call the property on the morning of that day. You can scoop up rooms made available by people who've just canceled.
I put almost every dollar I spend on my Discover card that gets me cash back.
When going out of the country you should always carry a copy of your passport, but more important is keeping that copy safe. In the event your bags are lost or stolen, what are you going to do if your passport is in the bag? Keep a copy of your passport in the sole of your shoe. Most tennis shoes have removable inserts - tuck the copy of your passport under the insert. You won't lose your shoes if you're wearing them, and if you're robbed in a foreign city, the mugger won't go after your tennis shoes - so you'll still have a copy of your passport.
Always pack zip-lock bags. They are ideal for packing things tighter, separating wet from dry and managing small items like batteries. I always pack a few bags in a variety of sizes before every trip.
Question charges like resort fees or valet parking at hotels. Often they will be removed from your bill if you question them at check-out.
You will always get more in-depth information in the guidebook with the narrowest scope. If you're going to Rome, the Rome book will be better than the Italy book, and that will be better than the Europe book. Guidebooks are not necessarily updated every year, so choose the one with the most recent publication date and know that the book was written at least six to nine months prior to publication (i.e., things may have changed). Also, three guidebooks are better than one - consider bringing only one or two travel guides and photocopying pages out of the rest, which you can toss when you move on to the next destination or head home.
Don't assume your way is the only way.
Saving money on a rental car has to be the most mundane and least thrilling secret I could offer, but there's nothing dull about saving a dozen to a few hundred dollars every time you travel -- money that can be put toward something a whole lot more exciting. I learned that rental car rates behave unlike almost any other sale in the travel business. Whatever price you are quoted at first, you can work the system such that you pay a mere fraction of the quoted price.
Before you start your trip, take a photo of your luggage. Put yourself into the picture, standing next to the bag. (This will give a good idea of the bag's size.) Keep the shot in your camera, and also print out a copy. When your bag goes missing, hand over the copy (or show the in-cam shot) to the baggage folks at the airport. This can really help with finding your luggage.
Take an extra, minimalist outfit in your carry-on. Luggage, inevitably, will get lost at some point.
Divide each person's belongings amongst all luggage. This is especially important for traveling with a baby, but good for everyone too. That way no one is out of luck if one bag is lost.
Book your accommodations directly on the hotel's own web site. Join the hotel's mailing list and reward program. You'll get the guaranteed lowest rates without booking fees and burdensome cancellation polices. When booking packages, you can sometimes save a few hundred bucks by using a travel agency web site.
Place a plastic bag under the screw caps of soaps and shampoos and tie the bag around the bottle. This way if the cap opens, the bottle spills into the bag, not on your clothes.
Book your flight on a Monday, Tuesday or Wednesday. Most of the airlines roll out their online sales in the beginning of the work week - especially the domestic discount airlines - so this is the best time to take advantage of limited-time fare sales. And if you see a good sale from an airline, keep an eye on its competitors. Airlines regularly publish similar promotions at the same time.
To prevent leaving your phone charger in your hotel room when you check out, unplug the charger every time you remove your phone and put it back in your luggage. On a similar note, ensure that you don't leave anything in your room safe when you check out by putting something essential for your day of travel (purse, coat, shoe) on top of the safe.
Be ruthless with your shoes. It's no secret that shoes are a major space hog, and with outdoor and sporting stores suggesting a different shoe for each activity, it's easy to believe you need an arsenal of footwear. Trust me, you don't. One pair of broken-in walking shoes and a street-friendly sandal are usually all you need.
Low-cost airlines aren't always the cheapest. The ticket price may appear to be a bargain, but take a minute to tally the additional expenses. These include items such as booking fees, check-in baggage fees, advance seat reservation fees, and food and drinks on board. In addition, low-cost airlines often fly to secondary airports that are much further from the final destination than the main airports. This adds an extra transport cost, not to mention the inconvenience. Take the time to do a bit more research, as there may be a better deal out there.
Remain FLEXIBLE and have BACK-UP PLANS. Expect things to go wrong - the rental agent not to answer his phone; delays that keep you from getting to town before the restaurants close; your wallet to be stolen; your passport to be lost. That way you won't spend precious hours freaking out - you can simply move to Plan B.
Never forget that it's your vacation and there's no wrong way to do it. There's no such thing as a must-see attraction. If you want to travel all the way to Paris and order room service, that's your business. Do what feels fun to you.
