10 Days in Cuba with My Teenager

Some trips are about adventure. Some are about culture. Some are about ticking boxes on a bucket list.

This one was about my daughter and me, a Caribbean beach, and ten days of doing absolutely nothing on purpose.

Last summer I took my 15-year-old to Varadero, Cuba. It was her latest in a long line of Caribbean trips we’ve taken together — because when you’re a solo parent for a large portion of your child’s life, you get creative about how you give them the world. A week on a beach in Cuba all-inclusive is genuinely cheaper than a long weekend in Niagara Falls. That’s not an exaggeration. And while I could have spent those years staying closer to home, I chose to give her plane rides, swim-up bars, and crystal clear oceans instead. Those are memories she’ll carry forever — and they cost less than people assume.

We swam, we sunbathed, we ate lobster for $30 USD, we rode through Havana in a vintage car, and we came home having made memories that will last a lifetime.

Before we get into the trip — a quick, honest update on what’s happening in Cuba right now, because a lot has changed since we travelled. Then it’s straight into the good stuff.

Now that getting there has become so much harder, I find myself longing for Cuba even more than usual — that safe, reliable, affordable getaway we always counted on. Writing this brings back all the nostalgia from our trip last summer, the kind that makes me want to just pick up and go again. My hope is that the situation resolves soon, for the Cuban people as well as for families like ours hoping to return — and that packages and direct flights come back the way they used to be.

Why Cuba for a Mom and Daughter Trip

Cuba holds a special place in Canadian travel. We’ve been going for decades. We know the beaches, the resorts, the quirks, and the warmth of the Cuban people in a way that’s uniquely ours as Canadians.

Americans do technically have access to Cuba, but they face significant additional hurdles to get there — specific licence categories, restrictions on tourist travel, and the ongoing complications of the U.S. embargo mean it’s far from a straightforward booking. For Canadians, it has historically been as simple as picking a resort and packing sunscreen.

I say historically — because the current situation is worth acknowledging (see the update above). Cuba is navigating serious economic challenges right now, and that’s affected the tourism experience at various resorts and across the island. This doesn’t mean Cuba isn’t worth visiting — it absolutely is — but it means going in with accurate expectations matters more than ever.

That said — the beaches haven’t changed. The people haven’t changed.

For a mother-daughter trip with a teenager, Cuba still ticks every box:

• All-inclusive — no decisions, no budgeting at the bar, no stress
• Safe — Cuba is one of the safest travel destinations in the Caribbean
• Affordable — genuinely remarkable value especially in summer
• Beach and culture — you can do nothing OR do Havana. Both options are on the table

That affordability has always been one of Cuba’s biggest draws for Canadian families — at least, it was until recently. My hope is that it holds true again once tourism finds its footing.

---

Why Varadero Over Cayo Coco This Time

I’ve stayed at both Hotel Playa Coco and the renowned Iberostar Playa Pilar in Cayo Coco on previous trips. Both are beautiful. Playa Pilar in particular consistently ranks among the best beaches in Cuba — and for good reason.

But this time I chose Varadero deliberately. The reason: Havana. Varadero is approximately 140 km from Havana — close enough for a feasible day trip. From Cayo Coco, Havana is a much longer journey. I wanted my daughter to see Havana. Varadero made that possible.

And Varadero itself deserves a moment. The beach is quite remarkable — a long, uninterrupted stretch of powdery white sand. It photographs beautifully, but the real thing is better. If you’ve only ever seen Caribbean beaches in resort brochures, Varadero will confirm that the photos weren’t lying.

If you’re going purely for beach and resort with no interest in a Havana day trip — Cayo Coco is arguably the more beautiful destination. If Havana is on your list — Varadero is the right base.

The Pre-Trip Strategy — Marriott Bonvoy Points

The night before our early morning flight we stayed at a Marriott near the airport — paid for entirely with Marriott Bonvoy points.

This is the same strategy I used in Jamaica with Aeroplan points for the Holiday Inn. Hotel loyalty points aren’t just for fancy aspirational stays — they’re incredibly practical for airport nights where you’re essentially paying for proximity and convenience. Using points for that night means zero dollars out of pocket for accommodation you’d otherwise have to pay full price for.

If you’re not building a hotel points balance alongside your airline points, you’re leaving free nights on the table.

The Package — What $1,400 CAD Actually Includes

We booked a 10-day all-inclusive package from Toronto for $1,400 CAD each.

I’ll be honest — people look at me like I’m a little crazy when I say we’ve gone to Cuba in the summer multiple times. Everyone assumes Caribbean travel means winter. But here’s my math, as a solo parent: summer rates are quite a bit cheaper than winter pricing across the board. As a single mom paying for two people instead of one, that difference matters. Booking in summer is how I was able to show her the world and give her unforgettable memories and experiences that she’ll remember her whole life.

Here’s what that covered:

• Return flights from Toronto
• 10 nights at Playa Vista Azul, Varadero
• All meals and drinks
• Checked baggage
• Airport transfers both ways

$1,400 CAD each. Everything included. In summer. For context — that’s less than many Canadians spend on a long weekend in a Canadian city. For ten days in the Caribbean with flights. Prorate that out and it’s about $140 CAD a day — flights, hotel, all meals and drinks included. The value of Cuba as a summer destination for Canadians is genuinely extraordinary — under normal travel conditions to Cuba.

The Resort — Playa Vista Azul, Varadero

The Playa Vista Azul is a five-star resort located on the first line of Varadero beach, with white sand and crystal clear waters, featuring a spectacular infinity pool — the only one of its kind on the Varadero Peninsula.

That infinity pool overlooking the ocean is exactly as impressive as it sounds. It became our daily anchor — morning coffee with the Caribbean stretching out below, afternoon swims, evenings watching the light change over the water.

What we loved:

• The infinity pool — genuinely spectacular
• The beach — outstanding. White sand, clear water, pristine
• The two beach restaurants — where we found the best variety and our favourite meals
• The main lobby bar — the best drinks at the resort by far
• The Cuban staff — warm, genuine, and proud of their resort

The honest truth about the food:

It was pretty decent for Cuba — and that’s meaningful context. This was actually my sixth trip to Cuba, and I’d already been to Varadero before, so I know the pattern well by now: Cuban resort food has a reputation for being repetitive, and by day 6 or 7 I’m always feeling it, no matter which resort I’m at. It’s practically a running joke at this point. And yet every single time, I want to go back — because the beaches are that beautiful, the people are that warm, and the value is genuinely remarkable. Six trips in, that hasn’t changed once.

The buffet cycles and by the end of the first week you’ve seen everything it has to offer. The beach restaurants saved us — better variety, more casual, genuinely enjoyable.

If you’re staying 10 days, lean heavily on the à la carte restaurants and beach spots rather than the main buffet. Variety is your friend by week two.

The Havana Day Trip — The Highlight of the Trip

This is the section that makes the entire Cuba article worth writing — because what we did in Havana is completely different from what most tourists experience, and it cost less than the alternative.

How We Found Our Driver

Through a Cuba travel Facebook group, I connected with someone offering private vintage car day tours to Havana. I’d encourage anyone planning a Cuba trip to join these groups — they’re full of real travellers sharing genuine recommendations, drivers, and tips that you simply won’t find on a resort excursion board.

The Cost — $170 USD for Two People, Full Day

A bus tour to Havana from Varadero typically costs more than this per person. We paid $170 USD total for both of us — a private vintage car, our own driver, our own schedule, our own pace. No group. No rushed timeline. No waiting for 40 strangers to finish their souvenir shopping.

That’s the math that makes private tours in Cuba make sense every time.

Havana — What It Actually Looks Like

I’ve visited 20 countries. Havana stopped me in my tracks.

The architecture. The colours. The vintage cars everywhere you look. There is simply no city on earth that looks like Havana. It’s breathtaking in a way that photographs don’t fully capture — you need to be standing in it, watching a turquoise 1955 Buick roll past, to truly feel it.

We saw all the major sites — Plaza de la Revolución, the Malecón, the Capitol building, Old Havana’s cobblestone streets. Our driver knew exactly where to take us and when, navigating the city with the ease of someone who has done it a thousand times.

The Lunch — $30 USD for a Feast We Couldn’t Finish

Our driver took us to a beautiful outdoor courtyard restaurant in Havana — the kind of authentic local spot you’d never stumble upon on a bus tour itinerary.

We ordered a shared platter: lobster, fish, shrimp, chicken, rice, beans, and salad. The bill was $30 USD for the two of us — and we couldn’t finish it. We tried. The portions were generous in a way that felt almost comical given the price, and we sat back at the end of that meal in the kind of satisfied disbelief that only happens when a meal dramatically exceeds every expectation.

In Canada, $30 USD gets you an appetizer at a mid-range restaurant. In a Havana courtyard, it gets you a shared feast you’ll talk about for years — with leftovers.

This is why private tours with local drivers in Cuba consistently outperform organized resort excursions — they know where locals actually eat, and they take you there.

The Beatles Bar — An Unexpected Evening Out

One evening we ventured off the resort and found our way to the Beatles Bar in Varadero — a Cuban institution dedicated entirely to the Fab Four. It’s an open-air outdoor courtyard with a proper stage and bar, and live music fills the space every single night. The whole setup has a great energy — warm evening air, cold drinks, a crowd that’s genuinely there for the music.

We had a few drinks, listened to the band, and watched the courtyard come alive around us. A spontaneous, genuinely fun evening that cost next to nothing and gave us a glimpse of Cuban nightlife beyond the resort bubble.

Worth seeking out if you’re in Varadero and want one evening that feels different from the pool bar.

The Honest Teen Travel Assessment

Here’s the part every parent planning a trip with a teenager needs to hear.

What my daughter loved: Sunbathing. Swimming. Listening to music on her AirPods. Watching the Caribbean. I arranged a private vintage car tour through Havana — one of the most culturally rich experiences available in the Caribbean. Her personal highlight of the entire 10 days was sunbathing with her AirPods in.

Teenagers.

That’s not a complaint — it’s the most honest and useful piece of travel advice I can offer any parent. A teenager’s definition of a perfect vacation and yours may be completely different. And that’s okay. She was happy. I was happy. The trip was a success.

The honest recommendation on trip length with a teen:

7 days is the sweet spot. 10 days was a little much. By the end she was genuinely ready to go home — and I understood completely. The all-inclusive formula, wonderful as it is, has a natural cycle. Two weeks of unlimited buffet and pool time works beautifully for adults who want complete decompression. For a 15-year-old in summer, a week delivers everything the experience has to offer.

If I were doing this trip again — 7 days. Same resort. Same Havana day trip. Same Beatles Bar evening. Just three fewer days of “are we going home soon?”

Your Complete Cuba Trip Cost

Category	Cost CAD per person
All-inclusive package (flights, hotel, meals, drinks, baggage, transfers)	$1,400
Marriott night pre-trip	$0 (Bonvoy points)
Private Havana vintage car tour	~$115 (half of $170 USD)
Authentic Havana lunch	~$20 (half of $30 USD)
Beatles Bar drinks	~$20 est.
Tips, odds and ends	~$100
GRAND TOTAL	~$1,655 CAD

Ten days in Cuba — Varadero beach, a private vintage car tour through Havana, an authentic Cuban feast, live music at the Beatles Bar, and an infinity pool overlooking the Caribbean — for approximately $1,655 CAD per person.

That is the most affordable international trip I’ve documented on this site. (Booking conditions have changed for 2026 — see the update near the top of this post before you plan your own budget.)

Cuba Practical Tips for Canadians

• Internet: Forget about consistent WiFi. Cuba’s national internet is limited and this applies everywhere — not just your resort. Embrace the disconnect. It’s actually one of Cuba’s greatest gifts to a traveller.
• Cash: Bring USD or Euros. Canadian dollars are not widely accepted or exchanged at good rates. USD is the most practical currency for tips, private tours, and local restaurants.
• Tipping: Cuban hospitality workers depend on tips in a way that’s meaningful given Cuba’s economic realities. Tip generously and consistently — at the bar, at meals, at the beach. It costs you little and means a great deal.
• Facebook groups: Join Cuba travel groups before you go. The best drivers, private tours, and local restaurant recommendations come from fellow Canadian travellers in these communities — not from resort excursion desks.
• Food expectations: Go in knowing Cuban resort food has limitations. It’s not a Jamaican or Mexican resort food situation. Use the à la carte restaurants, find your favourite beach spot, and manage expectations on the buffet after day 5.
• Summer travel: Cuba in summer is genuinely hot and humid. The upside — prices drop significantly and crowds thin compared to peak winter season (more on why that’s my personal strategy earlier in this post).
• Flights in 2026: Direct Canadian flights are suspended for most of 2026. Read the full update near the top of this post before booking — check connecting-route costs and your airline’s current status before you commit.
• Current conditions: Cuba’s ongoing economic situation means the experience can vary more than it once did. Power outages, fuel shortages, and supply challenges have affected different resorts in different ways. Do your homework before booking — recent reviews and active Facebook travel groups are your best real-time source of truth.

Would I Go Back?

Absolutely. Cuba holds something genuinely irreplaceable — the warmth of its people, the beauty of its beaches, the staggering uniqueness of Havana, and a simplicity that forces you to actually rest.

For a mother-daughter trip — yes, with the adjustment of 7 days instead of 10. For a couple or a girlfriends’ trip — I could easily do 14 days and not be ready to leave.

Cuba is a destination that rewards the Canadians who choose it. And when direct flights are running at full strength again, the value is simply unmatched anywhere in the Caribbean. For now, I’d just go in with eyes open about the current situation — for your own trip planning, and for the country and the people you’ll be visiting.

Have you taken a teenager to Cuba? Drop your experience in the comments — I’d love to hear what worked for other families.

Planning a Cuba trip? Read my guides to Jamaica and Greece for more honest Canadian travel cost breakdowns.