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1. Figure out when you can travel & for how long
2. Determine what climates you want to be in
3. Determine the "feel" or the vacation (city/restaurants/museums; outdoorsy/hiking/nature; resorty/spa/beachy)
4. Figure out how much you're willing to spend, and then explore options in that price range (hotels, airbnbs, couch surfing, camping) + evaluate travel options (flight prices, rental cars, etc)
Then go from there :) or just pick a spot you've always wanted to check out and work backwards!
Thank you for the detail!
Great advice here, one thing I want to add.
Plan in a half day to a full day of “open” time. Once at your destination, you will always find something new to do that didn’t come up on your research. Having this open time allows you to fit the activity in w/o bumping something else.
Pro
Trip planning is one of my favorite things in the world. I enjoy it almost as much as the trip itself. I probably should have done that for a career. Since I can't go anywhere myself (locked down in CA with an immuno-compromised spouse, so not flying or hotelling anytime soon), if you want to DM me your time constraints (when, how long) and any vague ideas you have for what you want the trip to look like, I would love to send you some resources and ideaaaassss
Usually I pick a location after I see how much I have to spend since my priority is traveling when I want to over going to a certain place (sometimes...I saved 10k+ for my honeymoon in Japan and it was worth it).
I'm also stuck home with my immunocompromised spouse and would love to throw travel ideas your way, so send us your preferences/constraints: time of year and do you want cold/hot weather), budget range, of these which do you want from your trip nature/cities/beaches/museums/food, do you want to relax or see/do a lot?
I pick the city I want to visit first and then search “top things to do in xyz” in TripAdvisor. Gives you a list of the most popular things to do in that city.
I usually look for what type of experience do I want? That combines with safety level, budget and how much time is available. Once ready to plan I begin looking at sites like TripAdvisor.com and booking.com for flights. If you plan on traveling to Europe (once safe of course) for example, you’ll get cheaper deals if you use European sites.