skip to main content
Suitcase and Heels Suitcase and Heels

Winter Vacations for Canadians (That Aren’t All-Inclusives)

This time of year it feels like everyone I know is planning their winter vacation to an all-inclusive resort in the Caribbean. I’ve looked into them myself but my own personal travel taste is leaning more towards the independent aventure style as time goes on. Mind you, I still love sun, sand, and surf so I wanted to provide you with some alternative warm weather destinations that you can easily visit for a week.

San Juan, Puerto Rico |

Puerto Rico

Here’s one that Americans are already really familiar with, but Canadians have yet to catch on. If you want warm weather, cool buildings, great food, and good beaches head to Puerto Rico for your winter vacation. I spent a week there a few years ago and loved it. I split my time between Old San Juan and Vieques.

Old San Juan has lots of great photos ops, is very walkable, and you can try tasty foods like mallorcas, mofongo, and the best rice and beans in the Caribbean. Marvel at the blue paving stones and pet the friendly cats at the home of Ponce de Leon.

Vieques and Culebra have beautiful white sand beaches and great snorkelling. My favourite moment in Vieques was driving to the beach and watching the wild horses graze underneath palm trees. Magical.

The island is still rebuilding after Hurricane Maria but the economy would welcome your tourism dollars. Vieques was especially hard hit so it’s best to check with local inns and tour operators before you book but as soon as they’re up and running, I know they’d love to see your smiling faces.


Most vacationers will head to Cuba’s many, many beachside all-inclusive resorts for their week of sun and sand. But if you want to shake things up a bit, try exploring Cuba independently. Resort vacations are great but they’re pretty isolating unless you manage to get off the resort several times.

Instead, why not visit the tobacco region of Vinales for their gorgeous scenery and hikes. You can also take a tour of a farm and buy your cigars directly from the farmer instead of a government business.

Or check out the pretty colonial town of Trinidad on Cuba’s southern shore. Lots of great Instagram walls there. You can also take a steam train to the Valley of the Sugar Mills to feast in the views and explore the ruins. Horseback riding, hiking, and beach bumming are just a few more things you can do in the area.

Learn to salsa in Havana. Visit art galleries in Cienfeugos. Scout out delicious bbq in Baracoa. There are so many things to do outside of a resort.

I haven’t made it to Cuba yet, but I’m pretty sure this is how I’m going to spend my time on the island nation.

Four Bloggers Share Their Favourite Winter Vacations


Costa Rica

Costa Rica

Costa Rica just might be my favourite place in the world. Abundant wildlife, beautiful beaches, and adventure activities are found all over this gorgeous country. Even in the rainy season – and even during a hurricane – there is so much beauty to immerse yourself in. Fortunately, bad weather (if you get it) never lasts long. If you are looking for a break from the winter blues, Costa Rica is lined with more beaches than you could ever hope to visit. With the Pacific Ocean on one side and the Caribbean Sea on the other coast, you will be spoiled for choice. Personally, I love the Caribbean side. Cahuita National Park has an easy hike that will drop you at -sometimes deserted – beaches along the way. What could be better than sitting with the turquoise Caribbean Sea in front of you and a jungle for of tropical animals behind you? The food in this little town is also some of the best I’ve ever had (check out Mama’s for a great jerk sauce). If you want to get away from the crowds even more, head further south of Puerto Viejo. Playa Chiquita has to be the best beach in the world! Secluded, calm waters, and horses traipsing by as you unwind in the sun – magical!

Jennifer Riley – The Rainbow Route


Isla Holbox Pier

Isla Holbox – Mexico

An island with no paved roads, no high rises, very few cars, endless fruit stands, and shallow, crystal clear water that stretches on as far as the eye can see lining its beaches: welcome to Isla Holbox.

This little island set in the Mexican Caribbean requires a tiny bit more effort to reach than Riviera Maya staples like Isla Mujeres, but the distance has kept tourism to a quieter level: instead of the all-inclusives that are popular on the Riviera Maya, you’ll find boutique properties. Instead of bustling traffic, you’ll find a leisurely walk along a dirt road as you go to hunt down breakfast.

Isla Holbox doesn’t have too many year-round things to do (though kite-surfing and kayaking are popular): it’s more of a place to hang out, to eat good food while staring out at the sea, to watch a killer sunset, to meander around without a final destination in mind, and to get up the next morning and do it all over again.

In short, Isla Holbox is incredibly relaxing… with the occasional adventure thrown in.

During certain times of the year, whale sharks and flamingos come to visit Isla Holbox, so we definitely recommend timing your visit around theirs if you can–seeing a flock of flamingos in the wild or swimming with whale sharks is sure to make your time on Isla Holbox a trip that you’ll never forget!

Kate Storm – Our Escape Clause


Leon, Nicaragua


If you are looking for a warm weather winter destination with beautiful beaches, interesting wildlife, a rich culture and a plethora of adventure activities, look no further than Nicaragua.  This Central American country is often described as “Costa Rica before it got popular” and your money will go further here.

Nicaragua has something for everyone.  If you are into beaches, you can explore the black sand beaches of the Pacific Coast or the tranquil white sand beaches of the Caribbean coast.  The Corn Islands offer sleepy beach side cabins and beautiful calm, blue waters to explore.  The colonial cities of Nicaragua, Granada and Leon are rich in history and culture.  Explore the many churches, colourful streets and markets of these quaint cities.  If you are into adventure activities, Nicaragua’s 19 volcanoes offer incredible hiking, sand boarding, and zip-lining.  Nicaragua also features the largest lake in Central America with the twin-volcanic island of Ometepe.  This island has many excellent small eco-hotels and lots of adventure activities.

Nicaragua is a great destination to escape winter, but also experience the rich culture of the region.  The cost of travelling independently in Nicaragua is very reasonable.  While the country was thought of as unstable in the 1980s and rarely visited by tourists, that has well and truly changed.  Nicaragua is now one of the safest countries in Central America.  Plan a visit before tourism explodes in this beautiful country.

Dawn Nicholson – 5 Lost Together




This gorgeous Caribbean island is well known for its pristine sands perfect for topping up your tan, and with miles of beautiful beaches to choose from you’ll be able to find one where you’re the only visitors! Aside from the beaches there’s plenty more fun and exciting activities to do when you get bored of sunbathing (or have a boyfriend who is pasty white and therefore has to shadebathe).

Barbados is an awesome place to chill out on deck with a rum punch and some reggae music playing in the background. There are some awesome catamaran tours you can take around the island where you’ll visit a couple of amazing snorkelling spots where you can hopefully catch a glimpse of one or two of the island’s famous turtles!

There are also a number of great dive locations around the island as well for both beginners and those looking for something more challenging. There are a number of purpose sunk wrecks to explore inside of Carlisle Bay; the island’s protected Marine Park. Alternatively the Stavronakita, a 350 foot freighter that sunk in the 1970s, offers an exciting dive with some opportunities to explore inside its hull.

The East coast of the island is a much more rugged environment to explore, best done on horseback. Your equine companion will lead you through lush sugar plantations, across the clifftops and even wading through the coastal shallows (your feet might get a bit wet!

One of your evenings must be spent at the island’s famous ‘Fish Fry’ at its market town of Oistins. The event is extremely popular with both tourists and locals alike and you can meander through the large number of stalls offering up delicious grilled fish fresh from the barbecue.

Laura – The Travelling Stomach

Where will you be vacationing this winter?



  1. Carly | Fearless Female Travels says:

    February 16th, 2018 at 6:20 pm (#)

    I did a two-week trip to Nicaragua (from Canada) this Christmas. It was lovely – the flights were easy, the weather was fantastic and there was so much to see and do. I will say, though, that San Juan del Sur practically felt like just another Canadian city with all of the expats living there now!

  2. Melissa Hogan says:

    February 18th, 2018 at 3:06 pm (#)

    Did you try the poutine at the Canadian bar? It’s not the same as home but certainly a good try given local ingredients.

  3. Lena says:

    February 18th, 2018 at 5:59 am (#)

    (A European here thinking of moving to Canada, and who cannot live without traveling.) So, in Europe it is easy, everything is close by: European countries of all weather conditions, Middle East, Africa, Asia, etc. So my question is, is it common to travel from Canada to other places than the Caribbeans? Or is it simply getting way too costly?

  4. Melissa Hogan says:

    February 18th, 2018 at 3:04 pm (#)

    There are flight deals to be had (especially out of Toronto) but Canada is such big country that travelling outside of the USA or the Caribbean can just take a lot of time. London, for example, is a 5 hour flight from the eastern edge of Canada, 8h flight to Toronto, or 13h of flying time to Vancouver. That being said, there are tons of people who travel internationally.

    You won’t find the same kinds of budget airlines that you do in Europe. We have Air Canada, WestJet, Porter, and WestJet’s new discount airline Swoop, and that’s pretty much it.

Leave a Comment