Beating the Winter Blues on a Budget

Beating the Winter Blues on a Budget

Are you already counting down the days until you can push those bulky sweaters to the back of your closet and pull out your flip flops and shorts? Well it’s too bad Mother Nature doesn’t feel the same. The short days are giving way to frigid nights and winter storms that blow through at blustery speeds. Each day your skin is probably feeling more and more like Frosty the Snowman’s—pale & flakey. Not to mention we started this work week on Blue Monday, which is supposedly the most depressing day of the year. To me, it sounds like the perfect time to plan a winter getaway for a big healthy dose of natural Vitamin D!

Snowy Upper East Side, New York, NY

For those of us trapped in below freezing weather, a sunny, warm beach is about the only thing that’ll make us voluntarily leave our comfy beds and cups of hot cocoa and tea. But maybe you think it’s not the best time to be spending money on a vacation after finally paying off the holidays? With a little time and creative research, you might be able to land on a beach for no more than the price of a weekend on the town. Here are a few tips for beating those winter blues on a sandy white beach, with minimal effects on your bank account.

Grand Cayman Island, Cayman Islands

1. Now is as good a time as ever to cash in on those free flights, airline miles, or credit card points you’ve been sitting on. Look into redeeming points for flights, hotels, rental cars, restaurants, or even just a Visa or MasterCard gift card.

2. For obvious reasons, December through late April is the high season (aka most expensive) in the Caribbean, but that doesn’t mean you’re totally screwed if you’re on a budget. If you have the flexibility and you’re willing to wait, book something just a couple days outside of the high season. It’ll still give you something to look forward to all winter, and maybe a reason to get off the couch and into the gym for some post-holiday fat busting (double bonus!). The extra exercise will not only help you to look great when the trip rolls around, but the endorphins will help you to beat those winter blues in the meantime.

3. Unless you’re a 19 year old college student, stay away from Spring Break season (late February to early March). You might be able to land a good all-inclusive deal through a student travel site if you’re under 26, but depending on the location, you’ll no doubt be paying a pretty penny to be surrounded by hundreds of underage college kids partying 24/7.

4. Flying on Super Bowl Sunday can give way to much cheaper deals on airfare and significantly less crowded airports since most of America is glued in front of a TV.

5. If you’re going to the Caribbean, try to fly out of a main port on the Eastern or Southeastern coasts. Many places like New York, Orlando, and Fort Lauderdale can see a huge price difference from the next town over.

The Bahamas

6. Check out the websites of small airline carriers for deals. Sign up for their email lists, check out their Twitter page, and keep your eye out for a deal for at least a few days before booking. Usually, airlines such as Spirit Air will run a promotion every couple of days, offering up to $50 off of a roundtrip flight. The cheap no-frills plane ride to paradise will be completely worth it once you’re basking in the sun instead of shoveling yourself out of 3 feet of snow.

7. Go with a bunch of friends, look for group rates, and bunk together. Though it’s nowhere near a budget hotel, places like the Atlantis in Nassau, Bahamas offer Buy One Get One Free roundtrip airfare (but you’ll likely pay for it with the price of a room).

8. Reach out through your social networks to see if anyone knows someone who’s willing to rent you their time share or vacation home.

9. Consider packages, but don’t rely on them. I’ve always been told that buying in a package is a great way to save money on a hotel + airfare trip, but I’ve almost always had better luck saving a few hundred dollars by booking separately.

10. Consider all-inclusive hotels in destinations like Cancun, Jamaica and the Dominican Republic. Many of these beachfront hotels cost around $110-$160 a night, and are much cheaper than one in the Virgin Islands, Aruba, or Barbados, AND that includes the price of food, alcohol, and all tips and gratuities. Not to mention a lot of budget airlines offer much more frequent and cheaper flights to those islands as well.

11. On the contrary, get the facts before purchasing an all-inclusive package. Personally I wouldn’t bother with an “all inclusive (see fine print)” package, or the “all you can eat at _____ restaurant.” The one time I purchased an unlimited food and alcohol package at the now closed Nassau Beach Hotel in Nassau, Bahamas (through a travel organization, not the hotel itself), it turned out the “unlimited alcohol” only included three premixed drinks available at the bars in the hotel, which were closed half the time I was there. One can only take some many sugary frozen drinks with minimal alcohol before busting out their wallets and paying for some hard liquor or beer. And the “unlimited food” was limited to a small cafe and a Sbarro’s pizza. If I wanted pizza or a bagel for every meal I would have stayed in Times Square.

Sunset Beach All-Inclusive Resort and Spa, Montego Bay, Jamaica

12. Take a cruise. Check out last minute cruise sites like for some great savings on ships to the Caribbean and Mexico. If you can limit binge drinking, you’re basically looking at an all-inclusive trip for as little as $199. Cruises have great food too. I’m talking steak and lobster every single night for no extra charge.

13. Tone down your travel experience. Maybe you’re the adventurous type who loves to buy into every possible activity everywhere you go. Cut the length of your trip down this time around, and use those few days just to relax on the beach and you’ll save money in the process. Don’t add on all of those extras like parasailing, off-roading, or swimming with dolphins (or just limit it to one excursion). Not to mention you’ll come back completely relaxed, not in need of a vacation from your vacation.

14. Consider camping. Many camp sites in the Caribbean are decently equipped with plumbing, water, and even electricity. In fact, a lot of the cottages are almost no different than a nice budget hotel. You’ll save a fortune on lodging and see a different side of the Caribbean islands that resorts just can’t offer. Check out Caribbean Inspired for a few recommended camp sites in the Virgin Islands.

15. Can’t afford to island hop in the Caribbean? Stay in the states and visit Florida or the West Coast. If Miami is too expensive, try Panama or Tampa. Though not exactly beachy, Las Vegas usually has pretty good deals on airfare and hotels any time of year.

16. Remember, it’s tax season. If you’re entitled to a tax refund then this time of year can be a great bonus financially. If you can afford it, use part of your refund to pay for your hotel and airfare up front. Setting yourself up with a predetermined budget will keep you from charging a Ritz Carlton on your Mastercard to pay off next tax season.

17. As always, my biggest tip no matter when you plan to go anywhere: research! I always spend as much time as possible doing research here and there so that I know what to expect when it comes time to book. Sometimes the best experience won’t be at that uptight $300/night beachfront resort, but at the $90/night bed & breakfast across the street that usually doesn’t show up in the hotel search engines. Just knowing about it could save you a fortune.

I’ll be using these tips myself to plan a 2-person getaway the first week in May. Do you have any other tips for your fellow budget-minded travelers?


  1. Just Visiting » Sunset Beach Resort in Jamaica: Save Money by Staying All Inclusive February 3, 2011

    [...] off the heels of my last post, Beating the Winter Blues on a Budget, I wanted to follow up with a review on an all-inclusive hotel I stayed at in Jamaica last fall. I [...]

  2. Karen April 11, 2011

    We’re trying to plan a trip for 2 to St. John USVI the week before Christmas. While we’ve got the place to stay pretty much wrapped up, we need to book our flight from Washington, DC. Any suggestions of which carrier to use and when to book for the best fares?

  3. Just Visiting April 12, 2011

    Hi Karen,

    I haven’t explored many of the flight options down to St Thomas yet just because I’m using up some frequent flyer miles from Spirit Airlines to get down there myself. I’m looking to go in August (from NYC) and I can tell you that the average airfare has been around $450-$475 on major sites like Expedia and Kayak. When I went through Spirit I found one for $431 which is slightly cheaper, but they also charge for carryon bags AND checked luggage, so it kind of evens out. My boyfriend is planning on going with me however, and he found one through his airline miles that was originally $371.89 after taxes through American Airlines. They’re also one of the carriers that offer nonstop service down to St Thomas, along with US Airways. I think most other airlines offer connecting service (Delta, Spirit, United, Continental).

    I would recommend keeping an eye on the dates you’re interested in flying for a few days before booking, but definitely book sooner rather than later. I’ve been hearing amazing things about, though I have yet to use it. It lets you track the prices of flights before and after you buy so that you can get a refund if the price of that flight goes down after purchase. I’ve never went wrong with booking a flight early, but I have seen prices go up one too many times because I’ve waited.

    A recent report in the Wall Street Journal said that you should never book a flight on the weekend for the cheapest deals, but rather wait until Tuesday or Wednesday when most sales are running and airfare is at its lowest. Sales expire and airlines bump their rates for the weekend just because more people generally book on those days. I’ve tried checking this out and it’s not always the case though. Also I believe Bing Travel is supposed to give you a predictor on whether or not they believe the airfare will increase based on current trends.

    I usually just research the destinations and any possible dates so that I have an idea in mind of the kind of money I’ll be spending. Once I get a comfortable budget in mind I just keep an eye out for any deals, and book whenever I see a rate I’m comfortable with. At the very least, I think this Yapta site is doing a pretty good job at keeping flight rates in check (or so I hear!)

    Hope I helped some, and I hope you enjoy your time in St Thomas even more! May I ask where you’ll be staying? I’m heading down there in August and still deciding between a few resorts.

    Thanks for stopping by the site!

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