Start by Asking
Unlike air travel, speaking up (politely) can go a long way toward getting a hotel upgrade. At check-in, ask the front desk clerk if there are any opportunities for upgrading to a higher-class room. This is a particularly good strategy if you're celebrating a special occasion, have arrived later in the day (and the hotel has vacant rooms that won't be filled), or are a frequent guest at the property and/or its parent company's affiliate hotels.
Make Your Loyalty Count
If you do happen to be a frequent guest, start the upgrade process the moment you make your reservation. Book your room directly with the hotel itself, not over a central reservations line, and be sure to mention that you've stayed at the property before. Join any brand loyalty programs, such as a rewards credit card or frequent-guest club. Even if you don't get an upgrade on your next visit, you'll be accruing points that can pay off on a future trip. If you have any other affiliations, such as AAA, military, or AARP, be sure to mention those as well; the hotel staff may have additional perks for other partner organizations.
Tipping Your Way to an Upgrade
Lastly, you can always try to tip your way up. Depending on where you're traveling, an extra $10 or $20, discreetly offered to the check-in staff, may get you a better room. It never hurts to offer, and by doing so you could get a better room for a fraction of its cost.
Car rental upgrades are going to be wholly determined by supply and demand. In many cases, economy and compact cars are the most requested vehicles, so if a given region is busy (say, because of a convention, festival, or peak travel season), this can work in your favor toward getting an upgrade.
Like airfare and hotel, joining a car rental company's loyalty program can sweeten your standing and make it likelier that you'll be upgraded. At check-in, present your loyalty card and ask if any upgrades are available. You can also ask if there are any promotions going on during your rental period that could make an upgrade more accessible and/or affordable.
Do some legwork before you arrive. It never hurts to call and ask about the branch's recommended practices toward getting an upgrade—you may find some insider info that can help you get a better ride.
Is it Worth Upgrading?
Lastly, be an informed consumer. When considering an upgrade, you'll want to take fuel costs into account. A higher-class car may be fun, but you'll probably spend more on fuel than you would with a smaller vehicle. If you're offered an upgrade and choose to take it, be aware that the "free" boost may mean more money in the long run. AAA's Fuel Cost Calculator can help you determine gas prices for your route to help you decide the best course of action.
What upgrading strategies have worked for you? Share your expertise by submitting a comment below!