Maximizing Your Chances of Upgrades at Times When Stays are Cheapest

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  1. BoardingArea

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    When readers shared their own travel tips and several really stood out as worth highlighting.


    Chelsea said,

    Traveling to places during off peak times greatly increases the chance of getting an upgraded room and also usually allows the hotels to offer better service.​

    Wee Willie Keeler was an early baseball great, and one of the best singles hitters of all time. His advice was to “hit where they ain’t.”

    I’m a big fan of ‘shoulder season’. I like to stay where they ain’t.

    Prices are lower, and often not just room rates — resorts will often run across-the-board discounts on food and beverage, and activities like spa.

    Most important to me, though, is that properties are less crowded. I hate the sort of resort where you have to go downstairs at 8am to try to ‘reserve’ a beach chair with a book or else you’ll be shut out for the day. I don’t find that relaxing.

    I don’t necessarily mean that I want to be in the Northern part of the Caribbean during hurricane season. But I don’t actually mind brutal heat, in fact I like it. I don’t mind one bit being in Thailand on the beach in July. It’s hot, but that’s part of the point. And in many places ‘rainy season’ means an hour of rain a day or every other day, preceded and followed by sunshine.

    I live in the Washington DC area and everyone leaves town in August. That never made sense to me. I certainly don’t want to make the drive to the Maryland shore or Deleware beaches on a Friday afternoon. I’ll spend as much time in the car as relaxing.

    Besides, it’s hot in DC in August. I want to be gone in January or February, when it’s freezing cold, and I’ll be in search of the heat. Why run from it when I have it for free?

    I realize this advice applies not at all to many families trying to ‘maximize school vacation’ … but that’s precisely also why it works.


    The post Maximizing Your Chances of Upgrades at Times When Stays are Cheapest appeared first on View from the Wing.

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