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How do you plan an 8.5 month trip across the world?

Hello, everyone! It’s AJ here, offering some thoughts on what goes into the planning of an eight-and-a-half-month trip. You may be wondering why I’m flying solo on this one, and the short answer is that I handled 99 percent of the planning for our family’s sabbatical. But don’t worry: Natasha will be writing a first-person post of her own, and it’s bound to be interesting!

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So what do I mean when I use that word planning? Well, I was the one who determined where we were going, and how long we’d stay in each city. I booked the flights and the accommodations, and once we were in a specific destination, I’d be the one to decide what we were doing there and in what order. It’s a lot to consider, especially when you’re doing all the planning for such a long stretch of time.

At the Great Wall of China

How Much Should You Plan Ahead?

Something people ask me is, did we have the entire itinerary planned out in advance? The answer to that is no. I’m sure some people do it that way, but to me it seems like a bad idea—and I’ll tell you why. Until you actually start the trip, you may not have a clear idea of what your family does and doesn’t like. For instance, what happens if you plan several short boat trips in advance, only to do the first one and realize your family just doesn’t like boat trips? Maintaining flexibility is key. Additionally, you may reach a particular destination, see what all is there, and suddenly have a clear sense of what you want to do—but you won’t know until you actually arrive.

What we thought we’d do, before we left on the trip, ended up being pretty different from what we actually did. A lot of the planning happened on the fly. So then the question is, how do you do that? How do you do so much planning by the seat of your pants?

Natasha enjoying some Chianti in Florence

How We Started

We started with bucket lists. Natasha and I both wrote out the things we absolutely must see and do, and we used those lists to structure the trip. For instance, I really wanted to see China, and to swim in the Great Barrier Reef. I wanted to see live cricket and soccer matches. Natasha wanted to spend some time in Italy. We were able to do all of those things. A few things we couldn’t do—going to the Tomatina Festival in Spain, which isn’t especially child-friendly—but I’d say both of us completed around 70 percent of our bucket lists during this 8.5-month trip. (One cool thing about the trip: Many of my highlights were things that weren’t on the bucket list, and I know Natasha would say the same.)

Once we had our bucket lists made, we shaped them into an itinerary; initially, it spanned about seven months or so. Now, when you plan the itinerary for a trip, you have to decide whether you want to spend long periods of time in a particular place (Natasha wanted to really get a feel for Italy, so we spent three weeks there), or to try to cram in as much stuff as possible in the amount of time you had. Another variable to consider is the season; for us, it was important to chase summer, and we structured our trip to ensure that we’d have reasonably nice, sunny weather as often as possible.

Our initial wish list that we came up with a few months before our trip

What We Booked First

Once we had that basic itinerary in place, I booked the first two weeks: A trip to Anchorage, a cruise, and then accommodations in Vancouver. Most everything else we booked as we went. (Thanks to T-Mobile and our data plan, which allowed us to book things on the fly, even from on the cruise ship!)

If you’re planning a long trip, there are a few things I’d recommend booking in advance—including cruises and long, inter-continental flights, simply because these things tend to fill up pretty quickly, and you want to make sure you get the seating and the flights you want. For our trip, I booked a flight from San Francisco to Iceland before we left, and a cruise on the Mediterranean. This brought a little structure to our trip: Even though we were booking on the fly, we knew we had to be in certain places at certain times.

Other things I’d recommend booking on the fly, such as Airbnb. Not only can you find great rentals fairly last-minute, but as reservations are cancelled, Airbnb will offer discounted prices—meaning that by booking later, you can actually save money. (Just make sure you check in every couple of days to make sure enough accommodations are available which they typically are.)  One exception is if you’re staying in a place for a long period of time—say, a week or more—in which case, you may wish to book them early just to make sure you get exactly what you want.

Beautiful cricket stadium in Cape Town to watch India play South Africa

What to Do in Each City

That’s flights and lodgings—but what about the activities we did in each city? I’d divide this into three buckets:

  • Cities where we stayed for more than three nights. (We tried to do this as much as we could.) Typically, when we landed in these cities, we were all tired and ready to get groceries for the week and then crash in the Airbnb. I’d always use that first day to plan out what we’d do in the city. Resources like TripAdvisor makes it so easy to find the top things to see and the top places to eat in the area! My philosophy was to try to see the top 15 things in each city, unless it was something that simply didn’t interest us whatsoever. When possible, I also think it’s good to plan rest days, or days to walk around and explore without any set agenda. Just enjoying the vibrancy and atmosphere of an unfamiliar city can be really enjoyable.
  • Cruise days. When we were on cruises, we mostly avoided “excursions,” because we found them to be rip-offs (that’s a whole another post). Basically, we just planned our days ourselves, whenever possible.
  • Places where we weren’t sure how to get around. There were some places where we just weren’t as sure what to do or how to get around—specifically a on a safari to Botswana and a trip to Victoria Falls. Here, we used tour guides to arrange things like safaris and private drivers. In hindsight, I could have booked these things myself, but having tour guides helped give us some peace of mind. They helped us get started, and next time I think we can handle all the arrangements ourselves.
Getting ready to snorkel the great barrier reef

To wrap this up, I recommend having one person shoulder the load for planning—ideally someone who really enjoys it, like I do! But also keep the lines of communication open and adjust as your trip goes on. You may both decide that you’re really just not that interested in a particular city, or your spouse may want to have a spa day. It’s important to remain open to these things. Always talk things out before you book: Make sure you’re taking the trip you both want, not the trip that just you want!

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4 years ago

Wonderful, you make a trip across the world just in 8.5 months, it’s truly amazing!

Southwest Airlines
Southwest Airlines
4 years ago

Great post, keep up the good work!!