Maximizing Your Chances of Upgrades at Times When Stays are Cheapest

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.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. We often take our kids out of school a few days early from a school vacation — it’s amazing how that opens up possibilities for upgrades, low fares, etc.

  2. I can’t agree more about leaving when the weather is bad. I’m abandoning Colorado for Australia this December. Not exactly a shoulder season, I know, but I do miss a month of winter.

    I was in Croatia (Istrian peninsula) in 2011 October 3-17 and it was great. The coast was deserted, and those hotels that were open were cheap. Inland hotels were cheap and plentiful. The weather was nice, varying between cool at night and hot during the day. The place is a zoo in the summer, crawling with European tourists, but wonderfully quiet in the autumn. I’d recommende going a week or two earlier (last week of September) if you want more selection of stuff to do in the coast.

  3. I completely agree. I live in the DC area as well, and hate the cold weather, too, so I’d much rather have somewhere warm to look forward to in January/February. Unfortunately, that’s my company’s busiest time of year, so I usually can’t go anywhere until late February at the earliest.

  4. Absolutely. Went to Hong Kong, Bali, Bangkok and Macau in late May/early June, and I got great award availability through Hilton and SPG that made my points go considerably farther than they could normally in Bangkok and Macau, and even though that time of year is shoulder season in Bali, it’s also dry season, so the weather is nice.

    I’m also not afraid of tropical heat; not only been to Bangkok and Hong Kong/Macau in full-on hot and sticky season, but Cancun in July… as well as Texas, Florida and DC.

    This year, I’m taking my daughter to London and Paris over Christmas and the New Year. You’d think “oh, ick”… but I’m from Seattle. The weather is pretty much the same, cold, dark and rainy… the difference being we’ll be in Paris and London, and I can actually do things like spend Hilton points at a cent per point. (Not so easy to do post-devaluation!)

  5. Gary, I can’t imagine being in Thailand in July. I was in Koh Lanta and Phi Phi Island in February and it was borderline unbearable. You are one tough cookie.

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