How to Take the Stress Out of Vacation Planning (Open Thread)

We haven’t talked about how to plan a vacation in years, so here’s a fun topic for today: how do you simplify travel planning — i.e., take the stress out of vacation planning? Do you repeat trips? Copy a friend’s (or blogger’s) itinerary? Use a travel agent? Do you have any “done and DONE” kind of things where, say, if you know there’s a Kimpton hotel in that town you’ll stay there, or if your friend or a magazine or book series says Y restaurant is amazing you make it a “must do”? Take a specialty vacation package like biking or a family vacation resort something? Do you use social media like Instagram or FB? What are your best tips to take the stress out of vacation planning?

The topic kind of comes up because I just stayed at a Cambria hotel a few months ago for an alumni trip — and I mentioned how nice the hotel was for an affordable, well-located hotel to an acquaintance and she said, “Oh yes, we LOVE Cambria and ALWAYS stay there if there’s one in the city.” Interesting technique, and I could see how that would reduce a lot of the stress of vacation planning if you didn’t have any boutique hotel you were dying to stay at or you were flexible on where in town you wanted to stay. For those among you who travel often for business there’s probably a whole subtopic here — what’s your favorite hotel chain? 

For my $.02, though, in general I STINK at travel planning… so my husband and I usually share this responsibility. We usually start with travel arrangements — sometimes just getting the plane booked is the biggest hurdle! I’ve definitely grabbed a guidebook and said I would figure it out on the plane over, and I also tend to crowdsource things and ask friends on Facebook (and obviously, we get a lot of threadjacks here on Corporette with crowd-sourced vacation questions)! I’ve tried working with travel agents twice in my life (once for my honeymoon and once more recently to try to get ideas for a nice family vacation with 6-8 people) and have yet to feel that “click” with any of the agents I’ve used. For those of you who are pros at this, though, share your secrets — how do you take the stress out of vacation planning? What are your favorite resources, tips, hacks, checklists, or more? 

(We’ve talked about how many people are using their vacation time, how to deal with pre-vacation stress at work, how to travel solo, and how to  early to start vacation planning (over at CorporetteMoms).

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