It never hurts to ask

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This is one of those cases where you’ve got nothing to lose if you make a special request, so it absolutely is worth asking the tour company, cruise line, or hotel/resort whether they’ll drop their single supplement fee for you.
Now, if you’re traveling at the height of the tourist season and visiting a popular spot, you’re not likely to hear a “yes” to that question (they’d be polite to at least wait until they hang up the phone to laugh out loud at the very idea). But if you’re traveling in the off-season, or to a less-visited place, or last-minute – it’s a good idea to ask. Maybe the cruise isn’t as full as they wanted it to be. Maybe the tour is one person shy of being able to actually go on the trip. Maybe the hotel or resort would rather have the room occupied for a lower rate than sit empty for the weekend. You just never know, which is why it’s good to ask.
By all means, however, ask nicely. And don’t get your panties in a knot if they say no. Know whether the single supplement is the only barrier to you taking the trip, and be prepared to walk away from it if they won’t back down.