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How To Plan for a Last-Minute Vacation

The good news is that you have options. You’ll just have to learn to roll with the punches a little bit more, which isn’t that hard.

Contrary to popular belief, I’m not a really last-minute type of gal. I plan the majority of my trips—about 75% of the time—in advance. It’s hard to make broad, sweeping generalizations here, but generally the later you wait, the more you end up sacrificing in terms of options and money. But it’s not like you exactly have no options if you decide to jump off for the unknown, at the spur of the moment.

Destination & Flight

Have fun with it, will you? I mean, you’re already taking off at the drop of a hat. I’ve done a couple of trips this way simply by seeing a super cheap deal to somewhere interesting and deciding on a whim. It’s led to a couple of interesting places — along the way, I fell deep in love with Mexico City while Montreal more than pleasantly surprised me.

Many airlines send out last-minute emails around the middle of the week, often trying to fill up inventory that hasn’t sold out for the weekend. JetBlue used to have the best deals around but sadly that option has dried up over the years. Instead, we’d suggest taking a look at what United and American Airlines have on offer. Buyer beware, I’ve noticed over the years that these “deals” are often much closer to the price that what you’d get in buying a fare in advance rather than heavily-discounted steals.

The data actually shows, that out of all the places to go to, the Caribbean is a great last-minute getaway with the best prices showing about two to three weeks out. Cruises are also another option, because last-minute sales are often geared toward filling empty staterooms rather urgently. Last minute, though, doesn’t mean you have to be stuck by a beach if that’s not your thing.

An open-ended search shows flying to Chicago this weekend is pretty cheap.
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An open-ended search shows flying to Chicago this weekend is pretty cheap.

I rarely use Google Travel, but it’s particularly fantastic for finding last-minute fares. By leaving the destination blank and filling in your desired dates, a Google Map will appear with the prices for different cities around the world. Of course, you can zoom in on a specific region and here I’ve focused in on North America. Departing from a New York airport for this upcoming weekend, I’ve spied that going to Chicago will cost me $221. When I click for more information, I learn the departure and arrival times along with the fact that I’d be flying on United. Suffice it to say, that’s actually a pretty decent deal for that market. (Kayak Explore does the same thing, but it doesn’t let you set specific dates.)

Skyscanner is also another option for scouting open-ended destinations if you’re more flexible with your timing. By setting the destination to “Everywhere” and setting the dates to “Whole month,” it’ll look into the cheapest fares across the widest range of dates possible from your destination. Its organization slightly differs in that it’ll return the cheapest results sorted by country, which is then broken down by city. These are probably your best options instead of running generic, random searches across the web to find a semi-interesting place to go at a reasonable price.

Setting your Skyscanner options.
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Setting your Skyscanner options.


This is the second-hardest thing to sort out because it is usually the second-most (or first) expensive cost of your trip. If you just want to lounge around a high-end resort, we’d highly suggest you book that type of thing far in advance. Your last resort in this scenario is to look at some of the vacation packages that some of the airlines and travel agencies like JetBlue and Travelocity offer. I haven’t had the greatest success is booking last-minute packages in the last couple of years but they’re worth a look if you’re traveling with at least one other person.

HotelTonight and Airbnb can be a great resource, depending on how upscale you want to go. It’s worth it to say that sometimes the results are surprising — last year, an ex-boyfriend and I found that the local Doubletree offered a better deal in the location that we were looking at than any of the options we found above. Research, research.

For those slightly more budget-conscious, hostels are another option frequented by Europeans and other nationalities. These often cater to long-term travelers, who are more likely to be flexible in their plans and aren’t adhering to fast and hard schedules. We’d suggest taking a look at HostelBookers and Hostelworld, two of some of the most popular booking sites around. Snagging a bunk somewhere can often cost $30 or significantly less, depending on the city.

Of course, if you want to be adventurous, you can also just show up at a city, roll into a place and see if they have space available. I haven’t done this for years—results may seriously vary—but the few times I’ve done it haven’t made a huge impact on my vacation either way. I’m a little bit too particular these days to give it a try, but it served me well in my younger years.

Couchsurfing isn’t a bad avenue either for those open to the idea. Utilizing the traveling community usually requires more preplanning, but the key to snagging a last-minute host? Heading to a Couchsurfing mixer in your destination city. You may just find a host willing to take you home.

Itinerary Planning

This is often the easiest part to deal with. Some of the best trips I’ve had never dealt with an itinerary — I just wanted to go out, walk around town, pick a spot on the map and explore. That said, it’s sometimes to have at least one or two things in mind that you’d like to see and build a trip around that.

Activities usually fall into several groups: leisure time, cultural outings, food and outdoor adventure. This will depend on your preferences. It’s generally not hard to get an idea of what museums are worth going to by taking a brief look at TripAdvisor or Wikivoyage. Outdoor activities, such as hiking, are always great but usually require a fairer amount of time because they may involve a fair distance from the center of the city. Leisure time… that’s just relaxing, right?

I usually concentrate on food because, well, I like to eat. I often go out my way to ask a local resident for their suggestions and will do a short precursory search on Chowhound (typing “CITY chowhound” in Google usually works well). My modus operandi is to try to visit the local market once, follow up on at least one restaurant suggestion per day while leaving the rest to chance.

There’s a certain charm in getting lost. On one London trip, I remember staring at the subway map with no idea of what direction to head in. I should just get off the Westminster stop, I thought. I didn’t know what was there exactly, it was just a name I’d heard often. When I emerged I was delightfully greeted by the London Eye and Big Ben, two of London’s biggest attractions. It’s interesting where we end up, and in my case, I was exactly where I needed to be.

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