Forget The Resort! Why You Should Travel For The Experience This Winter

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.

Related: Travel Medical Insurance – Don’t Leave Home Without It

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.

Related: 6 Free Mobile Apps That Make Travel Easier

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.

Related: Best Credit Cards For Travel Rewards

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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  1. Robert on January 11, 2013 at 7:42 am

    I went to a resort once for a destination wedding. A bit like skydiving, everybody probably tries it once In general I don’t see the appeal – they are boring if you like to explore. My best foreign vacations have been when I left with a ticket, a map, and a bicycle, and didn’t stop riding down the road.

  2. Echo on January 11, 2013 at 8:28 am

    We went to Mexico for our honeymoon and stayed in an all inclusive resort. It was a nice break from the hectic days leading up to the wedding. But after a few days, you’re right, it was a bit boring. We both decided that for our next big trip we’ll go to Europe and explore.

  3. Rosemary Wells on January 11, 2013 at 9:47 am

    Been to many resorts over the years and never spend much time at the resort. The packaged vacations tend to have the cheapest airfare so we fly down, maybe spend a day or so, then hire a car and off we go. Usually spend the last day at the resort before returning home. Works for us.

    • Andrew @ She Thinks I'm Cheap on January 11, 2013 at 4:07 pm

      Interesting way of using a resort as a jump off point for your travels. I never thought of going to a resort as a way of gettin a cheap flight!

      • Rosemary Wells on January 11, 2013 at 4:35 pm

        Yep, it’s true. The package deals (hotel and airfare) are sometimes cheaper than if you purchase just flights depending on the country and the time of year. Dominican Republic and Cuba are two that I know of but have heard St. Martin mentioned as well.

  4. Joe on January 11, 2013 at 11:19 am

    And don’t forget that, when Canadians go to Cuba, they’re visiting a terrible regime that still brutally oppresses its people.

  5. Rosemary Wells on January 11, 2013 at 12:31 pm

    LOVE Cuba and make sure I share my good fortune with as many people as possible. As the government is opening up it is encouraging more entrepreneurial endeavors. Still free education, free health care (and some of the best in the world) is nothing to sneeze at. The basic social safety net is there for everyone. They do need some work in other areas. The US embargo has caused irreparable damage in terms of denying them construction materials, etc. Other countries help but have to be careful not to go against the US or suffer the consequences. At least that was the situation the last time I was there. I hope things are getting better.

  6. John on January 11, 2013 at 2:43 pm

    I would suggest a cruise. You can find a good cruise with airfare for about the same price as staying at an all-inclusive. Plus everyday is a new adventure as you get to visit and explore 3-6 different islands during a 7 night cruise.

  7. Jane Savers@ The Money Puzzle on January 11, 2013 at 7:33 pm

    I think that lots of people choose all inclusives because they feel safer in a confined area with a fenced beach.

    How do you know what areas are safe to visit once you leave the safety of the resort? Those news reports from Mexico are pretty scary stuff.

    • Andrew @ She Thinks I'm Cheap on January 12, 2013 at 4:47 am

      This is where common sense and awareness come in. Generally speaking if you don’t go looking for trouble (ie: drugs) you’ll be ok. Also don’t go wandering about looking lost, or flaunting your wealth. Ask local staff where are good safe places to go.

      Learning a little of the local language goes a long way as well so you could communicate with a taxi driver, read street signs, etc.

  8. Dustin Small on January 11, 2013 at 8:19 pm

    Almost every year I go on an all-inclusive vacation to the carribean. We enjoy it because it’s hassle free. Once you book your trip there’s literally zero other expenses or things to worry about once you’re there. This past year we decided to opt for a change and booked a trip to Atlantis in the Bahamas to see if the quality is that much better than a typical all-inclusive.

    The place was amazing – everything was themed much like a high-end theme park like Disney, however EVERYTHING had an extra price to it… restaurants, parks, golf, dolphins, etc. While very nice, I am going to stick to the all-inclusive haha.

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