Yes, you can plan a fantastic last-minute vacation!!

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Although my daydreams often feature vacations and far-flung destinations the actual trips tend to come together themselves very late in the game. Though I am a planner by nature for some reason our Winter escapes especially seem to be talked about a lot in September, dithered on in December and then brought to fruition in January for a late February departure. This year is no different!

Perhaps it’s due to New York City life, where everyone is so work-focused and it’s considered bragging rights to work 80 hours per week and then have social obligations on the weekend so that there’s hardly time to even consider a vacation, good lord man what are you thinking! (Said in my best haughty voice.)

In reality, vacations are a necessity! Study after study shows that vacations refresh the mind, restore the body and calm the nerves. It’s true that some vacations require tons of planning — I wouldn’t want to try to toss together a last-minute trip to say, Disney World for instance.

But if you’re flexible on destination and timing the Winter is an amazing time to score travel deals, because after Christmas it’s the off-season in many warm destinations. Between January 5 and Spring Break season airlines, car rental companies, hotels, resorts and excursions offer spectacular promotions meant to drive sales. We eat this stuff up!

It should be mentioned that there’s last minute and then there’s last minute. Whether last minute is 3 months out, 8 weeks out, 2 weeks out or 3 days out, yes you can score amazing vacations without a ton of planning. Here are some of the companies who can help you plan your fantastic Winter getaways.


I love traveling anywhere where scooters are a preferred mode of transportation and rentals are available!


When planning a last-minute trip it’s easiest when the flight, hotel and transportation can all be scooped up in one fell swoop. Two of our last three Winter getaways have been planned via Cheap Caribbean, and we’ve been absolutely delighted with the results! The site features tons of vacations around the Caribbean from Mexico to Costa Rica, from Belize to the Bahamas and everywhere in between. In both cases our trip has worked out to be at least a thousand dollars less than quoting the trip our ourselves. We’ve done adults-only all-inclusive resorts both times (read all about our Costa Rica trip and my Cozumel travel guide will be live next week!) and been upgraded to VIP guests at each resort.

The staff at Cheap Caribbean is exceptionally friendly and helpful and can help you design a trip for your wants and needs. If you want a family-friendly trip they have fantastic recommendations. Want to learn to surf? They’ve got connections with resorts and camps for that! Just want a place where you can relax in peace, quiet and the gentle sound of waves lapping at your toes? They can totally do that too. The all-inclusive resorts they work with include ground transportation to and from the airport, your room or suite at the resort, and often meals and alcohol as well. Each resort we’ve stayed in has been clean, modern or charming in its quaintness, with fantastic staff and plenty of activities. And the beaches have been exceptional!

I really can’t say enough good things about Cheap Caribbean. If the beach is where you’d rather be, this is the company to work with on your next Winter vacation.

While many airlines treat customers ever worse, JetBlue continues to be the class of its field. Sometimes the most stressful part of vacation planning is finding a decent flight which is part of why JetBlue’s Vacation Services are so amazing. When you search for a vacation package through JetBlue you already know that the trickiest part — the flight — is taken care of.

JetBlue has worked out deals with some of the most desirable hotels and resorts in the destinations it serves, both at home here in the USA and abroad. They offer trips as low as $195/person (yes, including the flight!) for 3 day/2 night trips at this time of year and cater to the weekend jet-setter looking to get away for just a few days. Longer trips are definitely also available.

There are some additional perks to scheduling your entire trip via JetBlue: you earn JetBlue’s TrueBlue loyalty points, not just on your flight but also on participating hotels and car rentals! You can also use your earned TrueBlue points towards a JetBlue Vacation. There’s 24/7 customer service that’s actually really good and JetBlue offers a limited Price Match guarantee. My cousin found a spectacular deal on Disney World family package through JetBlue. A few days later he came across a special deal on a similar package, and with no fuss JetBlue made up the difference.

I would absolutely use JetBlue Vacations on a future vacation. I’m already a big fan of the airline!


Sun, fun and colorful buildings? Yes, please!


This category is a toss-up between two similarly-named companies.

If you’re looking for worldwide travel options, then I’d recommend going with Last Minute. Last Minute takes the unsold vacation packages from its European-based sister sites and negotiates better last-minute prices with hotels, airlines, car rental companies and more to put together some really sweet packages!

This colorful site has a humorous bent to it that fits in with the London-based company’s cheeky vibe. Note that all prices are in pounds or Euros, but a simple call on their freephone number can help you get conversions to US dollars. This site is ideal if you want to go to Europe but has destinations and excursions all over the world.

If you’re looking for a domestic trip or a trip to Central or South America then you will want to check out Last Minute Travel. This membership-based site ($50/year) buys discounted vacation packages in bulk and then resells them to the public. These types of packages are usually available through other membership-based travel agencies, so even with the $50 annual membership fee you’re getting a better deal than the general public will.

This site is great not only for last-minute vacation deals, but also deals on activities, experiences and such once you’re at your destination! That’s a pretty special offering that most travel sites don’t offer. They have a fantastic app (iPhone and Android versions available!) that can help you plan your trip and keeps you on the hot tip while you’re cruising around your destination.

Last Minute Travel comes very highly recommended from multiple friends of mine, including two travel blogging friends who really know their stuff!

My preferred sites to use when planning last minute vacations are above but this is by no means an exhaustive list. Here are some more options to consider when planning that last-minute, all-inclusive getaway!

  • EXPEDIA has a section of their site specifically catered to last-minute deals. PROS: As a major travel company, Expedia can negotiate additional discounts on vacation packages that are not yet sold. CONS: Although Expedia allows you to pick your airplane seat during checkout, many airlines disregard these selections, which means you may end up in the back of the plane or not together with your entire party.
  • TRAVELOCITY has great travel deals to begin with and their last-minute deals are often even better. Excellent for budget travel. PROS: If you don’t mind mid-range or budget hotels, you can find a package to a highly desirable destination on a shoestring budget. CONS: As a broker, Travelocity doesn’t have direct hotel or car rental company relationships the way some of the sites mentioned above do. So if there’s a problem, you may end up with a voucher or a refund but without the car or hotel room you booked.
  • GROUPON offers last-minute travel deals on flights and hotels that can put part of your last-minute vacation together with ease. PROS: There are hotel rooms for over 50% off and flights around 30% off, both extremely good deals. CONS: They don’t offer much in the way of last-minute packages, so you’re on your own to complete the necessities for your trip.
  • KAYAK is my favorite travel website aggregator, which means this site searches tons of other travel sites for you, saving you lots of work. You can absolutely use it for last-minute deals. PROS: You can see all the pricing options for a trip you’d like to take from a myriad of travel sites. CONS: But that doesn’t include sites behind a paywall or ones that hide their special deals in a special section of their sites.
  • AAA: Travel agents aren’t as sought out as they used to be with the advent of the Interwebs, but AAA still offers amazing vacation-planning services as part of its membership. PROS: You’ll get personalized, one-on-one service that can cater to any special needs or requests that you may have. CONS: You have to be a member, which comes with a somewhat hefty fee. Then again, if you own a car you get lots of additional perks with that membership! AAA has saved me more than once when I’ve had a flat tire or car issues.



Do you plan your vacations way ahead of time, or do you wait for the last minute like me? (Or do you wait for the last last minute???) What other vacation-planning services have you used and liked, beyond the ones mentioned here? When are you planning to take your next vacation?

Now that you know how to plan your vacations, make sure you’re taking along these 7 Travel Essentials and following these 5 Easy Steps to Pack for Any Vacation!!


  1. Kylie Kreischer
    January 11, 2018 / 11:12 am

    Such helpful tips!! Totally going to be bookmarking this – thanks so much for sharing!

    • January 11, 2018 / 1:28 pm

      You're welcome Kylie! So glad you found them helpful.

  2. January 11, 2018 / 11:28 am

    I have planned last minute trips before, they can be the best trips! When they are more spontaneous, there seems to be less stress. Great post!


    • January 11, 2018 / 1:28 pm

      I agree, it's strange how there's a bell curve of stress so to speak, and when you wait until the last minute there hardly seems to be any stress at all.

  3. evb
    January 11, 2018 / 1:20 pm

    Great tips!

    • January 11, 2018 / 1:28 pm

      Thank you evb!!

  4. January 11, 2018 / 1:21 pm

    Wow great tips! I don't like too last minute but maybe 3 months out is my max, I really like planning! But just incase there's a need for a vacation, I can go for these tips.

    • January 11, 2018 / 1:29 pm

      I totally hear you Laura! I'm normally a planner too; our Hawaii vacations for example are booked nearly a year ahead of time! But there's something so nice about waiting until the inspiration hits to plan a Winter getaway. I can't fully explain it.

  5. joevans29
    January 11, 2018 / 1:56 pm

    Thanks so much for this article! I am planning a trip right now with my best friend and we are looking for the best deals!

    • January 17, 2018 / 8:07 am

      Nice! Hopefully this post helps a lot.

  6. Christina
    January 11, 2018 / 2:02 pm

    This post is so very helpful, Roxy! We are actually on a last-minute getaway to Mexico as I write this. I frantically searched flights and lodgings separately, but the process would have gone much smoother had I known about the resources you provided. I will surely make use of them next time!

    • January 17, 2018 / 8:07 am

      I hope you're having a great time in Mexico Christina!

  7. January 11, 2018 / 4:01 pm

    These are all such great ways to book a vacation for cheaper! I am going to have to book mark this for my next trip!


    • January 17, 2018 / 8:08 am

      Excellent Kim, this guide will come in handy anytime!

  8. Anna English
    January 11, 2018 / 7:24 pm

    I'm hoping 2018 is a year of lots of travel! This post is super helpful.

    • January 17, 2018 / 8:08 am

      Thank you Anna!

  9. January 12, 2018 / 12:25 am

    I’ve never thought to use AAA for travel plans, I have to check that out. Thanks for the post!

    • January 17, 2018 / 8:08 am

      You're welcome Sarah! Whenever we go camping we grab maps from AAA. They're a great resource.

  10. January 12, 2018 / 11:28 am

    I've used Cheap Carribean in the past and was super impressed by how speedy the process was! Another benefit to planning last minute is you can often snag great deals (especially off-season!)

    • January 17, 2018 / 8:08 am

      Agreed Kelly!

  11. How 2 Wear It
    January 12, 2018 / 11:37 am

    Vacations are 100% necessary!! And I agree that all-inclusive is the way to go when planning a last minute trip!

    How 2 Wear It []

    • January 17, 2018 / 8:09 am

      Totally, it saves so much time and stress.

  12. anniewearsit
    January 12, 2018 / 12:40 pm

    This was such a helpful post! We are going on a last minute trip this weekend, and I'm so excited to use some of these tips, thank you!

    • January 17, 2018 / 8:09 am

      You're so welcome anniewearsit!

  13. Jessica
    January 16, 2018 / 1:56 pm

    I love planning last minute vacations for my family! They are so much fun!

    • January 17, 2018 / 8:09 am

      Agree, it's very exciting to do a last-minute getaway!

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