I love to travel. I’m not necessarily the best travel planner in the world but I am very organized and a little obsessive when planning a trip. Therefore, my friends and family know if I have been somewhere they are going, I most likely have a document compiled with what I think are some of the best hotels, restaurants and things to do in the area. So, I thought I’d share my trip planning process in a series of posts.

How to Pick Your Destination

Most people have a destination in mind, but if you’re planning a trip from scratch, consider who you’re traveling with and what they like to do. Is it a vacation with your spouse, family with children, another couple, a girlfriend or two, or a large group?

Spouse or Significant Other: I love planning a trip with just my husband. Usually we’ll brainstorm about what we’d like to do or come up with a general destination such as going South for warmer weather, going to visit friends, or going to see a historical landmark or area we’ve never been. Honestly, most people have no shortage of trip ideas.

Family including children: Traveling with children has its own challenges. No one wants to listen to a whiny child on a vacation so it’s worth your time to plan a family trip they will enjoy. When our children were young, we went to an all-inclusive resort in Playa del Carmen with a Kids Program. When we mentioned the Kids Club to our children, neither one wanted to go. The next day we told them if they agreed to go we would come back in one hour and if they weren’t having fun, they didn’t have to go again the entire trip. When we checked in an hour later, we were thrilled to discover our children were having a blast and they promptly told us to leave. The next morning our children were up bright and early and kept asking if the Kids Club was open yet. Win – Win!

Couples: When planning a trip with another couple think about what you enjoy doing together. When planning a trip with our favorite cocktail and dinner companions, I knew good restaurants and cocktails would be important but we also wanted some fun daily activities – Napa Valley was a perfect fit! We also know a few couples where the guys like to golf while the ladies prefer to “spa” or shop. I haven’t found a golf destination that doesn’t have a spa and good shopping. And, I’ve been to A LOT of golf destinations!

Girlfriends: When planning a trip with girlfriends think about how active they like to be; for example, I have one friend who would be happy to sit by the pool all day and go out to a nice dinner every night. I have another friend who would go nuts sitting by the pool all day and has to do something active like going on a hike or bike ride. The common theme with most of my girlfriend trips seem to include some form of relaxation (beach, pool, spa, yoga), some sort of activity (museums, hiking, theatre, concerts) and enjoying great restaurants.

Groups: Typically, a group trip starts with a destination and then the group grows. For example, we are currently planning a group trip to Scotland. This trip started when the men were all golfing one day and discussed how they all wanted to golf in Scotland. And, my smart husband said, “I can’t go to Scotland without my wife.” Or it might have been, “My wife would kill me if I went to Scotland without her…” Regardless, all of the other men quickly agreed and it became a group trip with four couples.

Once you know who you’re going with and have a general idea of where you’re going, it’s time to start your research and finalize your destination. Talk to friends and family who travel, request recommendations on Facebook and search online. Some of my favorite travel information sites include: TripAdvisor, Travel and Leisure, Jetsetter, Thrifty Traveler and Pinterest. I also tear pages out of magazines whenever I read about a fun travel destination and keep them in my travel folder. If I come across a great travel destination online, I’ll add it to my Travel folder on Pinterest. Once you select your destination, you’ll need to get there and you’ll need some place to stay.

Next Up: How to Get There and Where to Stay