Category: Travel

Whether your New Year’s resolution was to travel more or you’re just hoping to get ahead of the game – January is always my favorite time to start to dream about and ultimately begin to plan travel for the coming months. Since I follow a pretty specific game plan when it comes to making my far-flung fantasies a reality, I thought it might be helpful to share.

Step One: I like to begin here – on my Pinterest board of bucket list destinations near and far. I try to start to pick out a few that seem fairly doable (based on distance, expense, etc.) and one or two ‘reach’ destinations (that will require more savings, travel and time off work). I call these top picks my “wander-list” for the year.

Step Two: Next I look to my calendar and hone in on any locked in dates (this could be a friend’s upcoming wedding or a business trip) and also any locked out dates (a month that will be particularly busy at the office for instance).

Step Three: Begin to make matches between your “wander-list” and your calendar. I always do this with Google Maps open. Is that wedding only a short driving distance from a new city you’ve been meaning to check out? If you’re taking a long international flight, is there a day trip you could make while you’re there? This is also a good time to think strategically about scoring off-season prices or overlapping your trip with major local events (like Jazz Fest in New Orleans or Oktoberfest in Amsterdam).  Weather is also a huge factor here.. think New York in the Fall or Paris in the Spring. I always take the time to research things like average rainfall for my destination during the month I’m looking to visit. While rainy days don’t necessarily equal a bad trip, I like to know what I’m getting into ahead of time.

Step Four: Once I’ve made matches and decided on destinations, I use Google Docs to make a to-do list and Google Calendar to create a coordinating time frame. The Google Doc makes it easy to add names of accommodations and additional details such as transportation or activity reservations as I make them (and share them with your travel buddies).  And the Calendar is helpful for setting reminders on when to actually pull the trigger and book. Is it an international flight? I’ve found between 3-4 months out to be the sweet spot for finding the best deals while I allow no less than 1 month for domestic flights. Plus, if I know I’ve got 6 more months to save before I need to book a flight it makes it so much easier for me to make a realistic plan for doing so.

Step Five: Book away. I like to use Google Flights for initial searches and then usually hop over to Expedia to compare actual flights/book. As far as accommodations, I’m a huge fan of AirBnB for access to a more ‘local’ vibe and you usually get more space for your buck. Plus things like a kitchen or washer/dryer (if you’re going to be gone for more than a week or are traveling with little ones) can really come make all the difference. However if a luxe resort at a tropical locale or a hip little boutique hotel downtown are the style you’re shooting for – I love searching Tablet for ideas first and then comparing prices and reading additional reviews at Trip Advisor.

Happy travels!