How I travel plan

The tips, tools, and rules I swear by for every type of trip

Hello from Vicenza, where I am very behind on planning an Italian Riviera trip. We’re supposed to leave on Saturday. Nothing is booked or planned except for a general idea of which towns to visit.

That probably doesn’t give you a lot of confidence in my expertise on this week’s topic: how to plan an amazing trip. But, bear with me. There’s a time for planning ahead (most international trips) and a time for spontaneity. There’s a time for perfection and a time for booking whatever hotel is still available and winging it. We are extremely lucky to travel often, especially in Italy, so there’s less pressure for a trip to be perfect.

Nearly 20 years of international travel have taught me a lot. I know which destinations and types of trips need more research and which ones can be more spur of the moment. And I have a system down that helps even last-minute travel planning result in fantastic trips.

These are the things I always do ahead of picking a destination, how I choose what to do once I get there, and how I keep it all organized.

Let’s go!