How can you improve your last-minute booking experience?

For the most part, I wait & book solo urban hotel stays until 1-2 days beforehand. With very few exceptions, I book on a discounted or semi-opaque website: either Priceline, Hotwire or occasionally Hotel Tonight. Expedia owns Hotwire, and you can usually use it to figure out their opaque hotel array: if Hotel Q has a cumulative 4.5* rating based on 773 total reviews, it'll have a similar figure as Hotwire's rate. Priceline functions a bit differently: if you hit even their lowest "VIP" level, you're generally shown deeply discounted rates including their names. Except in instances where a given place is almost entirely sold out of hotel rooms, I typically save at least 50% this way: last stay was a $199/night hotel for $85.

A problem you might encounter in choosing accommodations is one defined by Malcolm Gladwell as "the paradox of choice": given a seemingly endless number of options, consumer may very well being wholly overwhelmed & not choose at all. Continuing with my example above: if I'm booking on a semi-opaque site, I quickly narrow down the options. I specify preferred areas of town, guest ratings, hotel star ratings, and accommodation quality. If no 4* hotel are available in my preferred areas & price range, I either expand my search areas and/or include 3* hotels. If I get stuck with a not-great hotel, I make the best of it & ask nicely upon check-in if they have any high-floor, well-lit rooms away from the elevators (for quiet / privacy).

I was an Airbnb host for nearly seven years (though I'm currently on hiatus due to the still-going market downtown), and if I'm going somewhere for at least a week, I usually book an Airbnb. As a host I'm sensitive to overly high-maintenance guests, and I try to be as communicative and trouble-free as possible. Airbnb has upgraded both its website & app considerably over the past couple of years, and you can convey everything at left within either. The app makes it very easy to pull up the most essential need-to-knows: how to get there, how to get in, and special requests such as late checkouts or suggestions for local eateries or nightlife. (I stock my own Airbnbs with a detailed city guide.)

The fine print can be irksome for either a hotel or Airbnb/short-term rental. I'm most careful about cancellation fees: given how common it is nowadays for inbound travelers to be delayed or otherwise forced to postpone or cancel a trip, I always try to avoid booking fully nonrefundable stays, at both hotels & STRs. For Airbnbs, the parts guests most often overlook are the cleaning fees & house rules, along with extra fees for things like pets. Also, nearly all hosts prohibit large parties or excessive noise after 10pm. At hotels, my primary focus is avoiding my least-favorite tacked-on charge: so-called "resort fees" or "amenity fees." Last week in Vegas I had a $52 fee on a room that only cost $34! (Also note any parking fees.)

As a former road warrior, I can fully pack for a two-month trip – in as many as three climates – in under 20 minutes, all in a carry-on bag. (Yes, even on European budget airlines, despite their miserly carry-on allowances.) Unless it's the summertime, I stick with an all-black-and-white palette (mostly black). It's versatile and, more importantly, hides stains while traveling. Even before the term "athleisure" existed, my go-to "dress" shoes for trips were solid-black Prada Sport ones: up top they look dressy, but they have supportive (and hidden) black rubber soles. Finally, I may use different luggage depending on the trip, but I always use the same backpack. I always stash my absolute essentials there: passport, emergency phone, etc.