Travel recommendation and advise from my 20+ years traveling around the world.
Everyone wants to vault to the front of the cabin or to that penthouse suite, but most of us feel that an upgrade is out reach. Not necessarily so. The best way to get upgraded is to join loyalty programs. While it’s hard for many leisure travelers to accrue enough miles for a free first- or biz-class ticket, basic upgrades usually require fewer miles. For hotels and rental cars, points generally add up more quickly and you can get additional free perks just for being a member.
Alternatively for air travel, you can try bidding for upgrades or simply buying your way to more legroom and better service. While it will cost extra, it’ll be much cheaper than purchasing a first- or business-class ticket. Also look for deals; some airlines will launch short-term sales on premium seats.
With hotels, arriving late in the day can increase your chances of a better room, since the hotel might have vacant rooms to fill (and can subsequently open up a cheaper room for another paying customer). Also, at check-in, mention if you are celebrating a special occasion like a honeymoon or an anniversary. At the rental-car desk, asking for an upgrade might work, but make sure you’ve weighed your options: A higher-class car could mean higher gas costs, which can quickly negate any benefit. In any situation, even with the airlines, it never hurts to ask; when you do, dress nicely, be specific with your request, and above all, be polite.
