My Personal Guide to Trip Planning

Some find trip planning to be a daunting task. Yet research shows that people are generally happier in the time leading up to a trip than on the trip itself. I find that trip planning enhances the happiness that comes with anticipation. Daydreaming about trying that wood-fired pizza joint whose rave reviews you've read, or imagining yourself wandering through Central Park gives you little bursts of happiness before you even board the plane.

To help you with the planning process, I've compiled some of my top tips.

Planning for Vancouver (three weeks away!) in full swing

Do some research
Whenever I travel, I always begin by researching my desired location. You can go as shallow or deep with this process as you like.

If you're a travel nerd like me, you can get a stack of travel books on the city or country you're interested in and start reading. Some of my favourite guidebook companies are Rick Steves', Time Out, Frommer's, Rough Guides, and Lonely Planet. If you want to go into greater depth, get guides that are designed for future or current residents (like Time Out or Explorer's The Complete Residents' Guide). These generally include a lot more information about neighbourhoods and local customs than typical travel guides do. Rick Steves' is also good for going pretty in depth, but it's exclusive to Europe. If you don't feel up to dropping cash on a guide for a place you're only going once, check out your local public library. Most have a travel section, and you can often borrow the guides for long stretches of time.

If you're not looking to go as in depth, Frommer's, Rough Guides and Lonely Planet all have websites where they offer a lot of guidebook information for free. You can also follow travel companies and tourism boards on Twitter, where they'll tweet articles and information about what to see and do in select spots. Rough Guides and Lonely Planet both tweet more consistently, but I find Frommer's website to be the most comprehensive.

Proof of how much I love reading travel books: taking out books on London a full year before we're thinking about going

Book hotels that get you where you want to go
The money you save by staying in a remotely located hotel isn't worth it. First, you'll probably make up the difference in transportation costs, and second, time is your most valuable resource in your travels. Don't waste it on a hot bus to save a few bucks. Instead, choose more modest accommodations if you want to save money. You'll also get more of the local flavour by staying in locally-owned over chain hotels. 

I've used Expedia and Hotwire for hotel deals, or I'll book online directly with the hotel. Generally, I try to choose a hotel that's been reviewed by Frommer's, but if that's not an option, I'll read customer reviews. Always take them with a grain of salt though, since people generally review to complain rather than rave. If the majority of reviews are negative, don't book it, but a handful of mediocre reviews isn't really cause for worry.

Chris looking out over Wrigley Field from the Press Box (an in-depth tour there was one of the few things I booked in advance on our trip to Chicago)
Book a few of your major plans ahead
Some people like to wing it while travelling, and others prefer to have every minute planned out. I find a combination of the two to be most satisfying.

Before I leave, I generally make reservations for the popular museums, shows or restaurants I know I want to see. More often than not you have to pay a small fee to book in advance, but when you're waltzing past the winding line into the Vatican with pre-paid tickets, it's definitely worth it.

I aim to have 1-3 events (dinner at a special restaurant, a museum visit, a tour or show) booked in advance, depending on the duration of the trip, size of my party and travel destination.

Have a list of recommended restaurants organized by neighbourhood with you when you travel

There are few things I hate more than ending up starving at an awful restaurant after hours of walking. To avoid this, I generally keep a list of 3-4 restaurants in each of the neighbourhoods I plan on visiting. That way, I'm free to be spontaneous if I choose, but I also have some options for meals if nothing's catching my eye. 

Keep all your plans in one place

To avoid confusion, I generally make a complete itinerary for my trips. This includes flight details, transit directions to and from the airport, hotel address and reservation information, a day-by-day plan of activities (this can be as loose or as structured as you wish) including addresses and hours of the sights I'm planning to visit and tickets to shows or museums. This may be a bit Type A of me, but I find it extremely helpful to have all the information I need in one place. I also give a copy to a family member at home in case of emergency while I'm away. I prefer to keep a paper copy, but there are also travel apps like TripIt that you can use to keep track of this information.
Snapped during a spontaneous afternoon walk by the Chicago marine

Build in time for relaxation and re-visiting
It can be tempting to try to pack in as many sights as possible, but don't. Accept that if you're going to a major city, there's no way you'll see everything. It takes months or years to fully explore any city. Figure out what's most important, make sure you see those things and allow unstructured time to flow in around that. Don't feel guilty about taking a walk with no specific destination or napping in the middle of the day. You're on vacation, afterall!