Booking travel is always rife with questions - Am I getting the best deal out there? Is the hotel REALLY that fantastic if it's less than $100 a night? What charges AREN'T included in this that I need to know about? Should you add "What hotel am I staying at and what airline will I be flying?" to you list when you're staring at the BOOK NOW button on the screen, credit card information entered?
I'm all for playing the part of Adventure Girl when I travel. Sometimes, that means taking off up a mountain "path" (which really means hike) in the wrong shoes without sunscreen and thinking that everything will be okay - which it was but the shoes didn't survive much longer. Sometimes it's a solo camping trip. Other times, I never leave the spa or hotel, preferring to sink into the deliciousness of doing nothing except focusing on doing nothing. But plunking down money and booking a flight and hotel without knowing what airline or where I'm staying takes a bit of courage. So here are the rules I use.
1. Never pay for anything through a site that doesn't have "https" at the front of the URL. HTTPS means that what you're sending to that company is going through an encrypted system, so in theory, the information cannot be accessed by any party other than who you intend.
2. I always ask myself, "how comfortable am I with getting around the city?" If I have never been to a particular city, I generally don't book an "anonymous" hotel. If I'm relatively comfortable with where I'm going and want to have a bit of an adventure, I may book a hotel without knowing precisely where it is. However, as snobby as it sounds, I do look at the star ratings of the hotels. They are in no way a guarantee, but I never book anything that has fewer than 3 stars in their rating.
3. If I'm making a concerted effort to build up frequent flyer miles, I rarely book flights without knowing who is operating it. I am dedicated to a certain frequent flyer program, and rarely travel outside of its network. I've found in 13 years of traveling there are also airlines that I would crawl across broken glass to avoid. Being picky about who I fly comes with additional increased expenses, but loyalty, as they say, also has its privileges. How important is the cheap ticket?
4. If there's ANY chance that your trip could be canceled or changed, do not book anonymous hotels or flights. Generally speaking, once you click "Buy Now," your credit card will be charged the cost of the trip, and there are no refunds. Know the policies of the site you're using before you buy it.
5. If the cost savings is worth it to you and all of the above factors have been weighed, book it. Anonymous bookings can save you up to 50% on hotels and 40% on flights, which can give you some spare cash to bring back some great souvenirs.