People live and breathe by their schedules. “If it’s not in my calendar, it doesn’t exist”. This logic easily applies to short term planning, but when it comes to planning months or years in advance, we start to ease up a bit. These days, planning further ahead is harder than ever before.

One reason is that humans can be emotional creatures. We all groan at the sight of someone’s countdown-to-departure on Facebook, but that doesn’t save the previous 6 to 8 months where we barely can contain the built up stress. How do we properly manage ourselves during that time? Balance, of course. And fun, spontaneous getaways.

The majority of people lack the resources to go anywhere in the world at any given time. When it comes to booking a vacation, you typically have a choice between the following three options. Most will only be able to choose two.

Booking travel is based on the three pillars above. If your preferred time is a last minute getaway, that leaves you with one other choice between price and destination. A lot of this has to do with availability, and unless you have Lady Luck on your side, this evidently leaves you with choosing between a last minute getaway that (1) is inexpensive and not in your top two destinations of choice, or (2) you paid a little more to go where you want to go.

In order to help you tilt the balance of luck in your favor, we have put together a list of 25 travel tips for finding the ultimate last minute getaway.


1. Last minute vacations are meant to be fun, impromptu getaways. Not milestones.

If your idea of a last minute getaway includes the words, “honeymoon”, “March Breaks”, “Christmas”, or anything that overlaps a national holiday, you’re doing it wrong. Vacation package availability is at its lowest during peak seasons, so unless you’re looking for a hole-in-the-wall leftover, the pricing on packages for places you’ll want to go will be much higher. Also, if your last minute getaway happens to be your honeymoon, I fear how poorly you planned your wedding.

The best type of last minute getaway is the type that is centered around feelings. If you need to get away to relax, find a beach. If you need to break the monotony of work life, find a popular and exciting excursion. Make the getaway about what you mentally need right now.

2. Don’t get your mind set on a particular destination.

I used to be a vacation guide at RCI, a timeshare exchange company. I had to break people’s hearts every day. For whatever reason, poeple have their mind set on the perfect destination with the limited resources they have. Scoring the perfect vacation within your budget last minute is absolutely possible, and if you do, I suggest hitting the lottery booth pronto. In most cases, the place (or places) that are on the top of your list may not be available in your price range – so keep your options open. There’s no guarantee a vacation will drop in price before it’s time to go either – if it’s a popular package and you’re waiting for someone to cancel, you may end up staying home and watching Anthony Bordain’s Parts Unknown on Netflix instead.

3. Most tour operators offer the same price.

I love researching the best fares and destinations. One thing that I’ve noticed is that each tour company will usually offer the same price for the exact same flight and hotel package, give or take a few dollars. I’m not saying to skip searching all together – if you have the time to, go for it – but it may be more beneficial for you to find a tour operator that you enjoy the service and experience from, and sticking with them. Some will offer bonus points and other neat things to keep you coming back.

4. Sign up for all the travel newsletters and follow them on social media.

Sales and awesome deals happen all the time, and you may as well get told of them first. Besides, there’s no better feeling than seeing deals to Maui in your inbox when you’re feeling the itch to escape. Good deals and newsletters can be found with Skyscanner, Kayak, Redtag, and Sunwing.

As a perk for following them on social media, travel accounts such as United Airlines, JetBlueCheeps, and Quikbook offer discounted deals on flights, hotels, and vacation packages sporadically. Deals on Twitter, Facebook, and Instagram can be platform specific, and may not reach the website or newsletters – whether as a surprise or a last minute stock blowout.


5. Travel deal sites are still relevant and have decent packages.

The days of daily deals are past us, but larger deal sites such as Groupon, WagJag Travel, and TravelZoo still host exclusive vacation packages in limited quantity and at highly competitive prices. This includes 3 to 14 day tours, cruise ships, hotel stays, and all-inclusive getaways. Just do your research on hotel and tour company ratings; if a price is too good, there might be a logical reason why.

6. Leave mid-week instead of weekends.

Weekend travel is chaos. Long airport lineups, busy flights, and lots of screaming babies. While travellers of all sorts do vacation during the week, it may be best to consider leaving for a few days mid-week. You’ll also find better pricing on hotel rooms and flights. Stop following the crowd and create your own vacation mid-week.

7. Off-peak seasons are easier to book, obviously. Except..

While it’s pretty obvious that pricing is cheaper in the off-peak times of the year, remember that the supply is also lower for vacation packages. You see, tour operators realize that they won’t make a lot of bank off off-peak, so they scale down on the number of seats. This keeps prices profitable for them, and will leave you scratching your head as to why your favorite destination didn’t drop in price yet.

8. Let the internet search for flight price drops for you.

One useful service is Airfare Watchdog, which notifies you when the price of a specific destination drops to your price range. The watchdog will do a search for you every day, and when the price appears lower than your stated range, you’ll get an email or SMS notification so you can book it immediately. Put the internet to work for you!


9. After Christmas, the first sign of good pricing begins in the second week of January.

You know the drill – there’s Christmas, Boxing Day, New Years, then the first week of January when people still have time off work. The second week of January is your first potential breath of fresh air, so book last minute getaways just after the week if you need post-holidays relief.

10. Last minute getaways appear around 4-5 weeks from departure.

Don’t quote me on this, but I’ve read on multiple sites that the best price drops happen around 4 to 5 weeks from date of travel. It might be the time where the nervous tour operators find the most profit. You may luck out and find a cheaper price even closer, but their seat availability has to be pretty bad to have that happen. Get confident enough to book it 4-5 weeks away just in case, and save yourself the buyer’s remorse by not checking the price after.

11. Never write off hunting a hidden gem less than a week away.

If the availability is too great, you might luck out and grab a deal days from departure. However, you really need to get your expectations in check, as this directly relates to availability. While it is worth checking, never wait too long or you’ll miss out on a getaway completely.

12. Just say no to transfers. Go direct.

If your time off is limited, spend the extra and fly direct. Multi-transfer and long layovers are the biggest waste of time ever, and if you’re on the clock, it’s better to spend that extra $50-150 on a beach than on an uncomfortable airport lounge chair. Your time is more valuable than anything.

13. Don’t forget to check your miles (and exchange them if needed).

A popular service is UsingMiles, which allows you to exchange existing miles to other point programs. However, be warned: the loss in points for converting them may not be worth it. Do the math and see if the loss in miles is better than just paying for the extra miles, or just not using your miles at all.


14. Install a last minute getaway mobile app and check it regularly.

Hopper’s GTFO app (Get the Flight Out) app has not only the most hilarious app name ever, but it’s also the most popular app for last minute flights. You can also grab Fareness (iOS) and check Kayak’s Explore Tool to test the waters. If booking last minute hotels is more your thing, I’ve used Hotel Tonight quite frequently and have had great experience with it.

15. Haggle prices with vacation rentals.

Maybe not for vacation packages, but if you’re building your own trip and looking at vacation rentals on Homeaway or VRBO, you may want to message the owner directly and see if they’ll do any better on the price. If it’s the off-season or they’re looking to fill up their rooms, you may be able to squeeze into a nicer place within your budget. Depending if you’re good at bargaining, of course.

16. Carry-ons only: Leave the check-in luggage at home.

If fun is your focus, then you need to snip away at the areas that stress you out. The process of checking your luggage is stressful: from extra lineups to broken locks to mishandling to losing it completely can seriously destroy a vacation. Do a mobile check-in to skip the lines and do your best to fit your life into your carry-on bag.

17. Have a designated pet and house sitter ready.

There’s nothing worse than scrambling last minute for someone to take care of your pet and watch your home for a few days. If you have someone in mind that is trustworthy, reach out to them in anticipation of a getaway.

If you’re caught in a bind, you can always reach out to a professional house and pet sitter (yes, a service exists)!

18. Load up your Kindle with good reading material.

Vacationing is the optimal time to get caught up on reading, and while I do very much enjoy the feel of a book in my hand while I’m on a beach, bringing multiple books across the world can be a chore. I suggest loading up your Kindle or other reading device with books from Amazon. Saves space, keeps travelling neat and tidy, and lets you you easily switch between different genres of books. Because there’s nothing worse than forcing yourself through the only book you brought and don’t want to read.

19. Fellas: Invest in a good quality duffle bag or carry-on travel luggage.

As a style guy, I’m natural gravitating towards beautiful travel bags. If getaways are becoming a frequent thing for you, invest in a good one and use it all the time. It’s your home inside a bag, isn’t it? Herschel travel bags are a good start.

20. Ladies: Pack light for light stress.

If you’re heading somewhere hot, if it’s less than four days, bring two of everything: 2x bikinis, 2x shorts, 2x dresses, and 2x tops. If it’s a week, double it. Besides, you can always shop for more stuff while you’re there!

21. Stuff your bag with travel accessories. Then leave it there.

Stock up on travel sized accessories such as shampoos, body washes, toothbrushes, and whatever else you’ll need on your journey. When you’re not out scouring with world, leave all your travel accessories in your bag so that you don’t have to go on a manhunt prior to your flight.

22. This old army trick is great for packing shirts.

I’ve used this technique while backpacking across Europe. Probably the best method I’ve seen for packing your shirts, this video below demonstrates how to fold your shirts up, saving space and making a neat trick to show your friends.

1. Smooth out your shirt

2. Fold up the bottom of the shirt on both sides by 2 inches

3. Fold each side of the shirt over top each other

4. Roll the shirt as tightly as possible

5. Tuck the roll from the original folds from the bottom of the shirt

Source: GQ

23. Don’t forget to check the weather first!

It’s known that August to November is hurricane season down south, which deter people from booking at that time. That low low price just may be a trap. Be diligent and check online for travel suggestions during that time and see if the weather is going to be good or not. I’m not even going to get into the downsides of traveling during rain season.


24. Bringing work with you? Pack a lighter device.

I understand it’s necessary to bring along your work – while a getaway is a getaway, life still continues to operate back home regardless of whether you’re thinking about it or not. Instead of bringing that heavy Macbook Pro or chunky PC laptop along with you, invest in something lighter, such as:

25. Seriously, have fun!

Remember that last minute getaways are spontaneous, exciting, and will break your regular routine. Monitor your needs and when you feel like you need to balance your stress, gear yourself down and enjoy your getaway. You deserve it.