
Man invented tents because there just weren’t enough good caves to go around. I mention this in case you have forgotten; so many event planners think tents were invented so they can throw a party wherever the hell they want.
I was reminded of the limitations of tents last summer in the Hamptons, where an adventurous wedding planner plunked down a 40-footer for a twilight ceremony on the beach. It was a simple structure, with 50 or so folding chairs arranged in a semicircle and those fake arched windows made of plastic—if you want to see out, why not just order clear sides?—one of which framed the ocean behind the couple as they exchanged their vows. It should have been idyllic. The only problem was that the tent was set up at low tide, and high tide that day was particularly high. By the time the crowd was assembled, the tide had ebbed but left all the chairs buried three inches in wet sand. The couple tried to make light—“No shoes, everybody!”—but the older people were not amused, and three hours later, with sandy feet still moist in my loafers, neither was I.
Weddings seem particularly prone to this type of mistake, since couples so often fall in love on cliffs or rolling hills overlooking the water, accessible only by four-wheel-drive vehicles. My cousin Meagan wanted to get married in my uncle Ted’s backyard on Block Island, which was all of the above. As we sat there on a sunny summer day, all I could see were rain, wind, and muddy dirt roads—which is what the weather is like 50 percent of the time, making Block Island great for sailing and reading Wuthering Heights. Somehow I convinced her to go for higher, smoother ground. At least I like to think I convinced her.
Likewise, everyone who plans a multiday retreat at some resort becomes convinced that one of the evenings has to be some exotic “off-site” affair. I have been to so many magazine sales meetings where “night two” involved some unusual type of transport to some remote spot—where food and entertainment and blowups and such had to be carted up and carted down—all while there’s a perfectly nice hotel pool we could have been sitting around. The travel magazines are particularly fond of this “hike and eat” formula. I planned one of these sales-meeting evenings for Elle Decor in its inaugural year. (It was the publisher’s idea.) Night two in Aspen involved a horse-drawn hay-ride up to a mountain cabin where we square-danced with a fiddler, then rode bumpety-bumpety back in the dark. Everybody loved it—because it didn’t rain.
I’m not saying not to plan your events on mountaintops, ship decks, train terminals, or what have you—it can be a blast. But here are helpful questions, many of which you can answer just by taking a good look around.
Do you have to get there by gondola? Substitute the word launch, ferry, jitney, rickshaw, ladder, or donkey for the word gondola. If the answer is “yes” to any of the above, you are just inviting bad weather, so budget for ponchos.
Are you the first to hold an event there? Didn’t Avis teach us that being No. 2 wasn’t bad? How much are the bragging rights really worth to host a dance party on top of that Indian temple? Why hasn’t anybody else thrown a party there?
Do you have to bring the bathrooms? No matter how fancy restroom trailers get, you know that there is a percentage of people who just won’t use them, myself included. Now think, what will those people do? Eventually they’ll have to do something, and usually it’s leave.
What size generator do you really need? Whatever size you pick, it will never be big enough. Some wise-guy caterer plugs in an undeclared hotbox without telling you, and presto! Break out the marshmallows and spook stories because you’ve got yourself a night around the campfire now.
Are you thinking of putting copy on the invitation to let guests know what kind of footwear they’ll need? Always a bad sign.
What kinds of permits are required? If you have to get all kinds of permission to do whatever it is you want to do, wherever it is you want to do it, ask yourself why. I learned this by setting up a working shower in Bryant Park. You’re not supposed to shower in a public park, and now I know why.
Is there any chance of guests being attacked by wildlife? Remember to include bugs and locals when answering this question.
Are you breaking a Guinness Book of World Records record? Nobody cares. I don’t think they even publish a book anymore. I proudly built the “World’s Largest Crib” in Central Park. It was 40 feet high and cost a gazillion dollars. Then we tore it down.
Do you need to establish communications? If cell phones don’t work there, what else won’t work?
Are you having trouble getting insurance? And don’t think Lloyd’s of London is the answer; they probably won’t take you either. I’ve tried.