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Planning Your Next Getaway



I'm blessed (and cursed) with endless curiosity, and so, travel, with all it’s newness, is one of my favorite ways to spend time. When I was working in Corporate America, it wasn’t always easy to secure vacation time, or at least, not three weeks at a time, which I felt necessary to really go somewhere far away and make the most of it. Thankfully, with much negotiation, I was often able to get the time off I wanted and travel to distant lands. As a single parent, I raised my children to appreciate the unexpected, unknown, and unusual.


As you look ahead to 2023, and think about your vacation time, now is a good moment to narrow down the list of possibilities and start to plan. I’m now location independent, and spend much of the year traveling all over. People often ask me how I decide where to go. The truth is that I have a running list of places I want to visit. I add to this list all the time, because I read an article in an inflight magazine, or I see an Instagram post from a beautiful locale, or a friend visits somewhere and blogs about it, or I just see a gorgeous picture on my laptop and think “yes!”. My current list has at least 25 countries that I want to see.

 

If you, too, have a long list and need to make a decision, I’ll share my process in the hopes it may help you pick the perfect spot for your 2023 sojourn. I always start by asking myself a variety of questions:

  • When can I go? I do a lot of research on weather because the last thing you want is a beach vacation where it rains every day, or to land somewhere stunning but it’s too hot and sticky to spend the bulk of the day outside. When I was working for others, I landed on my month first, and then picked an appropriate destination. Now that I work for myself, I do the opposite, I research when is the best time of year to visit a place, and plan for that month.

  • How long can I go for? My rule of thumb is that you always need at least two consecutive weeks to really relax. The problem with one week is that by the time you start unwinding from the office, it’s time to start ramping back up again. Sometimes I think you can do a one-week vacation if two things apply: you don’t have a long flight to get there and you stay in one spot. Otherwise, you need two weeks, and if you are flying longer than 12 hours, you really need three because you will lose at least 4 days in the air/recovering.

  • Who am I going with? I’ve traveling with all types of companions: small children, aging parents, a partner, solo, a single friend, a group of friends, and total strangers on a tour. Because the goal is that everyone has fun, the companions often dictate the destination. I found little point in dragging children through a city that is rich in museums and fancy restaurants, although it’s a great trip for a group of friends. I love an active vacation, but others want to relax, so that has to be taken into consideration too.

  • How experienced a traveler am I/is my group? While you can usually find English speakers in most tourist places, once you go a little further afield, that may not be the case. Can you navigate without necessarily understanding the language? Are you comfortable with a very different diet than your one at home? Are you willing to adapt accordingly to fit in a culture that is very different from home? How do you handle mishaps, because they always happen: a reservation that isn’t honored, getting lost in a city, missing luggage, a cancelled flight? If navigating one of these events makes you overly nervous, I’d recommend starting with places in Europe or where you speak the native tongue.

  • Lastly, I’ve learned to consider the pacing of the trip. When I was younger, my curiosity would drive me to see everything and do everything whenever I traveled. Usually this meant a list of must-see sites that I wanted to check off. As I’ve matured, I spend longer in places and get a feel for the location, rather than racing around the country. Most organized tours move at race speed: no more than two nights in a location. I like to stretch this out to 3, 4 or even 5 nights in a place so I can absorb more and also allow myself and my group to take a rest day if needed. I used to think – well, I’ll never be in Greece again, so I have to see it all – but actually, you do have the option of returning to somewhere you love again and again. You’ll still eventually see a lot, but not all at the same time.

 

I hope this series of questions helps you determine where you might travel in 2023. The world has opened up again, and if we want the best prices, we need to book early especially for next summer. Over the next few weeks, I’m going to write about certain places, and what a first-time vacation there might look like to get the most out of the trip. As always, I’m very happy if you choose to add your feedback to this post. Bon voyage!

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