The Best and Worst Vacations We've Ever Taken

Where to go and how to plan, based on these editors' worst and best vacations.

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*Sometimes* It's Good to Plan Ahead

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Stefan Marolachakis, senior editor, @stefanmymind

The Trip That Never Actually Happened

My Worst Trip Ever Was… The one where I rented a car, drove down to the French Riviera, one of the most gloriously scenic stretches of coast on the planet, and never stepped out of the car.

Why It Sucked So Much: We'd planned enough to book flights and reserve a rental car, but then made the devastating mistake of not securing a hotel room. Much to our surprise, we were visiting during peak tourist season, and there wasn't a single room available on the entire coast.

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The No. 1 Thing I Learned: Well, there are two things that stay with me. One is the phrase c'est complet (French for "no vacancy"), a statement I heard more times that night than I'd care to remember. But, more importantly, to paraphrase the words of Wallace Shawn in The Princess Bride: Never get involved in a spontaneous vacation to the French Riviera!

It's all about the offseason, friends. If your desired destination happens to be the exact same place the rest of the hemisphere is dreaming of spending their free time, make sure to get a little creative about when you're going to visit.

The Road Trip With a Lot of Detours

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My Best Trip Ever Was… A trip my girlfriend and I took to a friend's wedding in Milwaukee that was initially just meant to be 36 hours long, but turned into a 5-day long road trip with our dog.

Why I Loved It So Much: Because I never get tired of a good road trip, and because for once we didn't have to leave Nutty (our pitbull rescue) at home.

The No. 1 Thing I Learned: Doing the tiniest bit of research before a trip can open up a lot of doors. When we got the invite to this wedding, we quickly learned that the hotel where it was happening was pet-friendly. If we rented a car, we could bring our dog and even have time to plan some fun stops along the way. Those included burgers at an old-school roadside restaurant on the bank of a river in Western Pennsylvania, and a stop at the Capri Drive-In, one of the oldest operating drive-in theaters in the U.S. As much as I tend to want to rebel against this kind of advice, getting some of the annoying logistical stuff out of the way on the early side does actually let you do more of the fun stuff once the trip is underway.

Pro Tips: Have a Backup Plan, Take Short Trips

Rebecca Bates, senior editor, @re.beccabates

The Trip Where the Car Broke Down

My Worst Trip Ever Was… The drive from Dallas to Chicago to visit my grandparents, circa summer 1993.

Why It Sucked So Much: My mom's little sedan overheated and nearly bit the dust in what can't even charitably be called a small rural town. All that was there were a gas station/garage and a few nearly identical cheap motels. We spent the night at a Scottish Inn, where a drunk trucker mistook our room for his (why else was he trying so hard to break down the door) and raccoons were nesting in the A/C system.

The No. 1 Thing I learned: Even a very loose contingency plan is necessary: If you're on a road trip, familiarize yourself with the lodging options in the towns you'll be passing through. Learn what the best restaurants are, too, so if one is full, you're not stuck eating Dairy Queen Blizzards for dinner.

The Trip That Opened Up More Trips

My Best Trip Ever Was… The long weekend my husband and I spent in Amsterdam in the middle of our honeymoon.

Why I Loved It So Much: We were in Paris for most of the trip, but those three days in Amsterdam offered a different kind of urban expedition. There's basically no language barrier, so we were able to explore the city more casually, with fewer maps and schedules. We spent an entire day only walking up and down the Nine Streets, going into shops we didn't read about in guidebooks, eating at cafes where we could actually ask the staff for recommendations. It was all so lovely that we're already going back next month.

The No. 1 Thing I Learned: Short trips, only a couple of days or so, are a great way to get a teaser of a city you don't know much about without having to commit to a ton of planning. Once you've done enough trips like that, look back over your experiences and ask yourself: When I think about going back to all the places I've traveled recently, which place fills me with the most joy on an instinctual level? Then book a longer stay there immediately.

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