Winter is now officially here and many Canadians are thinking about a trip to a sunny Caribbean destination to escape the ice, slush and snow.  Destinations like Cuba, Mexico, Jamaica, the Dominican Republic and many more are eagerly awaiting their snowbird clientele.

Many of us will opt for an all inclusive resort where the food and drink flow non-stop.  After all, we’ve worked hard and now it’s time to escape the cold weather, work and just relax!

Related: Snowbirds – What You Need To Know

My question to you though is: how many times have you been to a resort?

Planning a vacation to a resort is effortless.  Everything is taken care of including flight, airport transfer, accommodation, food & drinks, activities, etc.  Resorts make it easy for us to go back over and over again.

While we might get a good tan from sitting on a beach all day, we don’t actually get to see or experience the place we’re visiting.  Many of us get so caught up in all the activities offered by the resort that we come back home feeling like we need a vacation from the vacation!

This year, consider a different approach to the Caribbean winter get away, travel for the experience!


Instead of booking a seven night all inclusive package, consider staying in a hotel, guesthouse or eco lodge.  Vacation rentals by the owner offer a good mix of living like a local and enjoying a sun destination.

AirBnB has hundreds of options to choose from for all budgets.  A search of properties in Jamaica to rent during the winter resulted in options from $13 per night for a dorm bed to $2,000 for a full luxury villa with all kinds of options in between.

Food & Drink

I know, I know, resorts offer up all kinds of food and limitless alcohol.  At the beginning of a trip to an all inclusive you’ll think of all the food you will eat and the litres of exotic cocktails you’ll consume.  At the end of the trip, you’ll look down at the scale and instantly regret your dietary priorities.

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The food gets tiring after about day 3.  A la cart restaurants are often horrendously busy and even having all you can drink gets a little boring.  How many rum punches, daiquiris and other umbrella drinks can you really guzzle down in a week?

By not staying at a resort, you give yourself the option to enjoy real local cuisine in an environment which hasn’t been carefully controlled for tourists.  You’ll be able to experience the local food, not just consume it.


Open any package holiday guide and read up on the activities available at various resorts.  They will include a variety of the following: pool, beach, nightly variety show, beach volleyball, dance classes, bingo by the pool, tennis, gym, spa, snorkeling, scuba diving, golf and more.  With water sports as the exception, all of these can be done in your home country.

When you go to a resort you’re really going to do many of the same activities that you would at home but in a hot country with palm trees!  Granted the setting is more pleasant but you aren’t really experiencing the country.

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If you want to experience a Caribbean country through activities, here are a few options.

Option 1) Go out and enjoy the natural surroundings on a tour or on your own

Option 2) Just hang out with friends and family and practice the art of not doing anything

Option 3) Play soccer with the locals

Option 4) Go to a local market and barter for fun

Caribbean sun destinations are not the most well off economically.  Locals aren’t out hang gliding, golfing or going to a spa!  There’s a reason why the pace of life in these countries is slow, most local people are spending their time doing activity option 2!

Vacations are an investment too

Traveling is an investment just like a bond, stock or GIC.  The more money you invest, the more time you spend researching investments, the better off you will be.

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As I mentioned earlier in the article, booking an all inclusive vacation takes very little time and effort.  So if the comparison holds true, how rewarding would this type of vacation be when compared with the alternative?

Planning a trip yourself and really experiencing a country can pay off for years in the form of great memories and a better understanding of life elsewhere.

Andrew Martin is a personal finance and investing blogger from Toronto, Ontario with a background in technology and a passion for travel.  His blog, She Thinks I’m Cheap aims to help Canadians make more money by sharing facts, stories and advice.

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