Can it be as easy as simply asking for a room upgrade or asking if there are any extra tickets to a big show that night? Can simply being nice be one of the big secrets no one talks about?

According to USA Today the answer is absolutely. It never hurts to ask especially if you're being genuine. We know hotel staff has seen and heard it all so not much gets passed them and truly nice people shine through.

Now that we have that out of the way, let's talk about when your authentic kindness truly comes in handy for hotel upgrades that have actually worked for me.

jennifer latuperisa andresen/frames for you
jennifer latuperisa andresen/frames for you

Timing is Everything

There's a very good chance a hotel will give you a room upgrade if you ask and even offer it up on their own if it's during off or shoulder season travel when hotels and resorts aren't sold out in that particular destination. According to Jetsetter, even the time of day you check-in or ask for the upgrade makes a difference. The middle of the day is prime because there aren't many people around so the staff is less busy.

My most recent shoulder season travel experience was to St. Barth's and not only did I receive an upgrade but extra spa discounts and comped cocktails every night at dinner.


Milestone anniversaries or birthdays as well as honeymoons are spectacular ways to get upgrades at hotels and resorts however those are often expected, highly used, and usually happen during booking. According to Jetsetter, it's the unexpected events like celebrating a divorce or bestie reunion that can garner excitement for you from the staff. Birthday

I received an upgrade for my mom and I in Bermuda when I told the front desk this our first mother-daughter vacation leaving the hubbies at home.

Arrive Before You Arrive

Booking dinner reservations or a spa appointment days before you arrive puts you on the radar with hotel staff. Even sending the concierge a personal email about your excitement to stay with according to Jetsetter and asking for any ideas can help with upgrades once you arrive.

Be Flexible

When you check in to your hotel or resort, let the front desk agent know that if an upgrade is possible you're flexible to switch rooms in the middle of your stay. According to the Points Guy this is a very popular way to grab a better room, especially if you take advantage of the hotels activities.

Chelsea Gates/eiliv aceron
Chelsea Gates/eiliv aceron

When I was in Tahiti I spent the first two nights in a garden bungalow and was moved to an over the water bungalow for the remaining six nights simply by asking when I arrived.

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