How to build a multi-stop vacation: Research and Planning

In the last blog we started talking about what it looks like to go on a vacation with multiple stops and experiences.  I suggested that you think of it in the same way you might read a great novel, and thinking about your travel experiences having a beginning, middle, and end. 

By now we should be comfortable about where we are going, what order we will be visiting each destination, and the overall experience we are looking to have at each stop. Now that you have looked at your vacation in a big picture sense, it’s time to get started on the nitty gritty details. 

Research and Planning Timeline

9 - 12 months out

This time is spent getting to know your destination. I like to immerse myself in a place through books, blogs, magazines, etc. That way, once it’s time to make real decisions about where I’m going to stay and what I want to do, I am making educated guesses. I already know the type of things that speak to my heart and excite me. 

how to plan a multi-stop vacation

This is also where you begin to understand what your vacation actually is going to cost. You need to know what you are able to allocate for the trip, and compare that budget with what it actually costs to go there and experience it like you want. I’m all about saving on the front end, versus credit card payments after the fact. If you are armed with this knowledge a year out from your trip, that allows you to make smart saving decisions and prepare wisely.

3 - 6 months out

This is the time you commit to the actual dates you will be gone, and block this precious time off in your calendar. Especially if you are traveling to a popular destination or during high season, I suggest starting to book the nuts and bolts of your trip sooner rather than later. This means your international flights and your hotels, as well as any visas you might need.

Your itinerary is now beginning to take shape. You have the time you will be gone and your flights to get you there, as well as the time you will be in each destination and the awesome places in which you will be staying. The masterpiece that is your vacation now has the broad strokes down on the canvas.


**PRO TIP: When choosing hotels, it’s best to save the best for last, so to speak. Make sure that the accommodations are getting nicer as you go, and ending with a splurge if possible. It’s easy to compare when you land at a new place if it’s better or worse than where you just came from, so always try and build on your previous digs.

1 - 3 months out

It’s now time to put together all the details that are going to make your trip special and unique. During this part of the planning process you take care of all your inter-trip transportation needs. That might be domestic flights, trains, or setting up transfers or rental cars as needed. You’re going to make sure any tours or special activities you know you want to do are booked and reserved. 

Depending on your desire for a well-laid out, detailed itinerary, or a loose idea of possible things to see and do, will determine what your version of a perfect plan is. You’ll want to do some more research on social platforms or blogs to find any upcoming events or see where the best place for cocktails on a rooftop at sunset might be. Organize all these details in one place, and consider creating an overall itinerary you can have on your phone to refer to at all times.

timeline for vacation planning

My hope is that this outline helps you see that proper planning and research will lead to a better outcome. Travel is always going to be filled with surprises and unexpected experiences, but planning well ensures that the trip of your dreams is that much more likely to be a reality.