How Not to Get Upgraded When You Travel 

Kit and Ace Ambassadors share their get-lucky getaway tips.

By: Taylor McKinnon | Illustrations: Spencer Pidgeon

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When travelling, be sure to always ignore the friendly advice of strangers.

You know that friend, the one who seems to constantly travel with a horseshoe in their suitcase – the person who stumbles upon luck around every corner? Then there’s the person who just can’t catch a break, from bad meals to plugged toilets.

While vacation plot twists can be unpredictable, we spoke to some well-travelled Kit and Ace Ambassadors who argue that good fortune is often within your control. If you’re looking to conjure up some of your own travel luck, here’s what they recommend you NOT do.

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"I was promised PEANUTS!"

Lose Your Cool When Things Go Off-chart

If you’re looking to get bumped to the absolute last spot on an overbooked flight, get loud and angry at the ticket counter. There’s nobody travel-industry professionals love more than the red-faced tourist spouting vitriol five inches from their face. Much like ankle socks and a fanny pack, it’s not a good travelling look – and a little patience will get you much farther, literally and figuratively. The Ante editor Michael Small recently found himself amidst uncertainty – and a throng of angry flyers – when his flight home from LA was cancelled. Instead of losing it, he did a simple thing: asked the airline attendant how she was holding up. “Eventually, everyone was told we had to move to make room for the next flight. I was getting ready to line up all over again when the attendant grabbed my arm and said ‘stay with me,’” he says. “She walked me to the new terminal, bypassed a giant line and got me my stuff.”

Lesson learned: Staying cool is cool.

Snub the Locals

If you’re hoping to avoid insider tips, shun any and all interaction with the locals. It’s way more fun to depend on other clueless tourists anyways, right? Oakville Ambassador and B&W Wines rep Mark Klevinas argues otherwise. During a recent trip to Costa Rica, he stumbled upon a local surf school while running on the beach and found himself chatting with the founder. “He wound up basically acting as our tour guide, and took us to a bunch of secluded beaches we wouldn’t have found with a tour company – he even offered to let us stay at his place the next time we visited,” Klevinas recounts. “I guess he just connected with us and wanted to show us a good time.”

Lesson learned: Love thy local.



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Pink slippers are the international travel sign for being an asshole.

Roll Through in Pajamas

If you’re seeking a first-floor room with a scenic view of the brick wall next door, check in wearing your old college sweatpants. If you’re looking for something a little more “lap of luxury,” Hayes Ambassador (and co-creator of The Mermaid Diary) Ryan Hanson Swaner swears by dressing the part. “When I fly, I make sure I’m washed and in an outfit that’s comfortable – but not workout clothes,” she explains. “It’s a little old school, but it affects how you carry yourself – and people are perceptive of that.”

Lesson learned: Dress for success – or extra leg room.

Stick to Your Plan, No Matter What

8AM run, 11AM brunch reservation, 3PM museum visit – it’s OK to keep your schedule jam-packed when on a trip. But being married to said schedule is a surefire way to ensure you’ll never find something unexpectedly awesome. Bethesda Ambassador and Secretly Fancy founder Candace Ourisman found a “super cool” San Francisco spot through a vacation rental site, and she and her partner wound up hitting it off with the host, who lived upstairs. “He and his girlfriend invited us up for wine one evening and we were having so much fun that we eventually decided to give up one of the best dinner reservations in the city,” she recalls. “We wound up talking all night, and when we left, we not only had new friends, but they let us know that the next time we visited, we could set up our own agreement to avoid the crazy rental site fees.”

Lesson learned: Go with the flow.