What are some good vacation/traveling hacks?

Freeze your drinking water bottles in the motel fridge freezer to use as ice in your cooler the next day. No need to buy ice, keeps your lunch cold, and leaves more room for food in cooler.

Pack pjs that double as workout gear or street clothes to minimize packing.

I travel frequently for work.

I have a separate toiletry kit that stays in my suitcase. Don't have to worry about forgetting something for each trip. Same for laptop and phone/ipad chargers. I keep a travel set in my briefcase.

In my trunk I keep a spare pair of loafers, socks, underwear, undershirt and a set of casual clothes. Since toiletries and chargers are always covered (see above), these are the only things I could mistakenly forget.

I second using hotel lobby bathrooms when in a pinch. Also if there's a publix nearby, that's another good bathroom option.

I also keep a case of bottled water in my trunk. Some hotels provide water, some don't, some charge.

Hilton's digital check-in and mobile key is awesome. You can select your hotel room from a floor plan of the hotel, check-in on your phone, and use your phone as your room key. No interaction with front desk necessary. After a long day of traveling, being able to go directly to your room without having to stop at the front desk is awesome. Marriott is supposedly working on a similar feature.

Load up on napkins.

I was skeptical about them, but the wife converted me to using those packing cubes. So easy to unpack when you get to your destination and have everything organized. Also maximizes space in the suitcase.

I have a dozen or so vacuum bags. They don’t need a vacuum cleaner to vacuum them, you just seal them and roll them up. They have a one way valve. After you roll them up, you unroll them and they lay flat. They are perfect size for an entire outfit for a day. Use one bag per day. Each of my bags contain underwear, shirt, pants/shorts, socks, and T-shirt.

This is 9 outfits, vacuumed, shirt, shorts, socks, underwear, and T-shirt in each

Thought of another one today:

This seems obvious, and it's a muscle memory for me, but adding hotel stays to my iphone/pad calendar straight from the confirmation email is very helpful. Hotel phone number, address, and reservation confirmation number are all conveniently in my calendar. Don't know how to get there? Click the address in my calendar and it automatically pops over into apple maps and I'm on my way.

I’ll add, swinging by the hotel bar for a couple of to go ice waters also works to get you through the night

Packing cubes. They really do consolidate and organize your luggage

Sancho's Golden Rule of Travel:

Bring Twice as much gold (money) as you think you'll need; & half as many clothes...

Not really hacks, but how I go about travel:

Book flights early preferably with SW who doesn’t have cancellation/change fees
Always book the room late (1-2 weeks out) - negotiate that rate.
Be nimble on your destination if you can