Why Cuba is a Canadian favourite — and what makes it different
Cuba's appeal is easy to understand: it's close (Varadero is well under four hours nonstop from Montreal), it's affordable, and the beaches are genuinely world-class. Add a one-of-a-kind culture — Havana's vintage Chevrolets, live music spilling from every doorway, rum, cigars and a warmth that's impossible to fake — and you have an escape that feels both easy and exotic.
Where Cuba differs from Mexico or the Dominican Republic is in expectations. Because of decades of economic constraints, resort food variety and some amenities can be more limited, and the country runs on its own rules — most notably, Canadian bank cards generally don't work, so you bring cash. None of this should stop you; Cuba is wonderful. But it means choosing the right resort and arriving prepared matters more here than anywhere, which is exactly where a knowledgeable advisor earns her keep.
Cuba's regions, decoded
Cuba offers several very different beach areas plus unmissable cities. Here's how they compare.
- Varadero — the classic and easiest choice: a 20-km ribbon of white sand on the Hicacos Peninsula, the biggest resort selection, and just two hours from Havana for a day trip. Best for first-timers, families and anyone who wants the most options.
- Cayo Coco & Cayo Guillermo (Jardines del Rey) — stunning, more remote cays off the north coast with postcard beaches and calmer, quieter resorts. Reached by a long causeway; great for couples and beach purists who don't mind being farther from a city.
- Cayo Santa María — another beautiful north-coast cay, upscale and serene, connected by a scenic causeway. Lovely for a relaxed, disconnected week.
- Holguín & Guardalavaca — the greener, hillier east, with beautiful beaches and a more local feel; a good choice for repeat visitors.
- Havana — the capital and the soul of Cuba: colonial plazas, the Malecón at sunset, classic-car tours and live music. A must-see day trip from Varadero, or a city stay on its own.
- Trinidad — a gorgeous UNESCO colonial town of cobblestones and pastel houses near the south-coast beaches of Playa Ancón; the best culture-plus-beach combination.
Best time to visit Cuba (month by month)
Cuba is warm year-round, but the dry winter season is markedly better for beach time. Use this quick reference, then let your dates guide the resort.
Cuba travel seasons at a glance
| When | Weather | Crowds & price | Good to know |
|---|---|---|---|
| Dec – Feb | Warm, dry, low humidity | High season; book early | Best beach weather; Christmas & New Year sell out months ahead |
| March | Warm and dry | Peak (March break) | Busiest and priciest weeks — book 6+ months out |
| April – May | Warm, getting humid | Shoulder; good value in May | Lovely, quieter weeks before the heat |
| Jun – Aug | Hot, humid, brief showers | Lower prices; family season | Rainy/hurricane season begins; still plenty of beach time |
| Sep – Oct | Hottest, wettest | Cheapest of the year | Peak hurricane risk — insurance is essential |
| November | Warm, drying out | Value before high season | An underrated sweet spot |
Cuba vs Mexico or the Dominican Republic
If you're deciding between Cuba and the other big Canadian sun destinations, here's the honest comparison. Cuba wins on the short flight, on price, on beaches (Varadero and the cays are exceptional) and on culture — nowhere else feels like Havana. Mexico and the DR generally win on resort food variety, amenities and the breadth of luxury and adults-only options, and their banking works normally for Canadians.
Put simply: choose Cuba for the beach, the value and a genuinely different experience, and go in with realistic expectations about the resorts and the cash-only reality. Choose Mexico or the DR if polished resort dining and seamless payments matter most. Lisa will tell you straight which fits your priorities — she's not interested in selling you the wrong trip.
Money in Cuba: bring cash (this is the big one)
This is the single most important thing to know: Canadian credit and debit cards generally do not work in Cuba, because most are tied to the US banking system that Cuba is cut off from. You cannot count on withdrawing cash from an ATM or tapping a card at a shop. Plan to bring enough physical cash for your entire trip — Canadian dollars or euros are both easy to exchange.
Exchange your cash at the resort or a bank into local currency for off-resort spending; avoid bringing US dollars, which historically face a penalty on exchange. Bring a mix of small bills for tipping and incidentals, and keep your cash secure. Your all-inclusive covers meals, drinks and most activities, so the cash is mainly for tips, excursions booked off-resort, souvenirs and Havana day trips. This one detail derails more Cuba trips than any other — and it's exactly the kind of thing Lisa makes sure you know before you fly.
What you must know before you go
- Travel medical insurance is mandatory to enter Cuba — keep proof with you. Lisa arranges the right coverage as part of your booking.
- Canadians need a Cuban Tourist Card (tarjeta del turista) to enter; it's commonly arranged through your tour operator, and Lisa handles it so it's not left to chance.
- Internet is limited and slower than you're used to: resort wifi can be paid and patchy, and travel eSIM/data coverage in Cuba is restricted. Plan to genuinely disconnect — many travellers come to love it.
- Bring any specific medications, and a few basics (over-the-counter remedies, etc.), as pharmacy supplies can be limited.
- Pack small gifts or toiletries if you like — it's a kind gesture many travellers make, though never expected.
Choosing the right all-inclusive in Cuba
Resort quality in Cuba varies more than in Mexico or the DR, so choosing well matters even more. The newer and higher-tier properties — and certain well-run brands in Varadero and the cays — deliver excellent food, service and rooms; others can disappoint on dining variety. The label on the brochure tells you very little.
What matters is current, on-the-ground knowledge of which specific resorts are performing well right now — and that changes. This is precisely where booking with an advisor beats a website: Lisa knows which Cuban resorts are genuinely delivering this season for your type of trip, and steers you away from the ones that look fine online but disappoint in person.
Cuba for families
Varadero is the easiest base for families, with the widest selection of family-friendly resorts, a long calm beach perfect for kids, and short transfers. The best family resorts offer kids' clubs, pools and connecting rooms; as always, the quality varies, so the choice of property is everything.
Beyond the beach, a catamaran cruise to Cayo Blanco, a dolphin encounter, and a day trip to Havana in a classic convertible make for memories kids talk about for years. Lisa knows which resorts genuinely work for families and pairs them with the right excursions.
Couples, romance and Havana
Cuba is wonderfully romantic — long quiet beaches on the cays, sunset on the Malecón, live music and a slow, unhurried pace. Adults-only and higher-end resorts in Varadero, Cayo Santa María and Cayo Coco offer lovely, intimate stays at gentle prices.
For something unforgettable, pair a few beach days with a night or two in Havana or Trinidad — colonial charm, rooftop bars and that singular Cuban energy. It's the kind of two-centre trip an advisor designs well and a booking site can't.
Beyond the resort: Havana, Trinidad and excursions
Cuba is one of the few beach destinations where leaving the resort is genuinely worth it. A day in Havana — Old Havana's plazas, a vintage-car tour, a mojito where Hemingway drank — is the highlight of many trips. Trinidad, with its cobblestone streets and nearby Playa Ancón, is pure colonial magic. From the resorts you can also catamaran to offshore cays, swim with dolphins, or explore the countryside and tobacco farms.
Lisa builds these experiences in thoughtfully — the right balance of beach and culture, booked through reputable operators, so you see the real Cuba without the hassle.
What a Cuba vacation costs from Canada
Cuba is among the best-value sun destinations from Canada. For a one-week all-inclusive package (flights + resort, per person), value resorts are often very affordable, with higher-tier and adults-only properties costing more. The short flight and competitive winter charter market keep prices attractive.
Remember to budget separate cash on top of the package for tips, excursions, souvenirs and Havana day trips, since cards won't work. As always, your dates (Christmas, New Year and March break cost the most) and how early you book move the price the most — and Lisa finds the resort where value and quality actually meet.
How far ahead should you book?
For peak dates — Christmas, New Year, March break and reading week — book four to eight months ahead. Cuba is in heavy demand from the Canadian market on those weeks, and the best resorts and flight times go first. For value season you have more flexibility.
Booking early at a fair price and letting Lisa watch for price drops generally beats gambling on a last-minute deal, especially when you also need to arrange insurance and the tourist card — details that are far easier handled in advance than in a scramble.
Mistakes to avoid
- Assuming your Canadian cards will work — they generally won't. Bring enough cash for the whole trip.
- Skipping travel insurance — it's mandatory to enter Cuba, not just a good idea.
- Forgetting the tourist card, or leaving it to the last minute.
- Booking the cheapest resort without checking how it's actually performing this season for food and service.
- Expecting constant, fast internet — plan to disconnect.
- Booking March break or the holidays late and overpaying for what's left.
Practical tips: tipping, water, packing and connectivity
- Tipping in cash is genuinely appreciated — small bills (CUP, Canadian dollars or euros) for housekeeping, bartenders, servers and tour guides.
- Drink bottled or resort-filtered water; reputable resorts use purified water.
- Pack any specific medications and a few over-the-counter basics, as supplies can be limited.
- Bring sunscreen and toiletries you rely on — selection in shops can be thin.
- Plan for limited connectivity: download maps, books and entertainment before you go.
- Keep at least six months' passport validity beyond your return date, and confirm entry requirements with Lisa before you travel.
Why book Cuba with a Montreal travel agent
Cuba is the destination where booking with an expert pays off the most. A website will happily sell you a resort and a flight — but it won't warn you that your cards won't work, that insurance is mandatory, that you need a tourist card, or that the lovely-looking resort in the photos is having a rough season for food. Get those wrong and a great-value trip turns stressful fast.
Lisa Salter does this for a living. Based in Montreal with 20+ years of experience, IATA-compliant and a proud partner of Voyages Cap Evasion, she sets honest expectations, arranges your insurance and tourist card, knows which Cuban resorts are genuinely delivering right now, and is on the phone if anything comes up. It usually costs the same as booking online — and in Cuba especially, it's the difference between a trip that goes smoothly and one that doesn't.
