My Family Spent ~$480 Each for Flights + 7 All-Inclusive Nights in Cuba: Part 1 – Introduction and Planning

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Jasmin:  Last summer, my boyfriend, 3 kids, and I enjoyed an all-inclusive beach vacation in Cuba after a long (and grueling) school year.  We really needed a trip with NO agenda, non-stop tourist attractions, or pressure to see as much as we could – just sunshine and ocean!

I did NOT use miles and points to book the trip (yikes!).  But we saved a LOT of money by stacking discounts and choosing the right season for Cuba travel.

Because of the kids’ other summer plans, our travel dates weren’t very flexible, and I had trouble getting award flights and hotels in the Caribbean to line up with our schedule.  If you’ve ever found yourself in that situation, don’t despair!  There are ways to book paid travel with flexible points and no blackout dates – even package vacations.

My Family Spent 480 Each For Flights 7 All Inclusive Nights In Cuba Part 1 Introduction And Planning
Hola, Cuba! I Booked a 7-Night Trip to Cuba With My Family and Saved Big by Stacking Discounts

In this series, I’ll share how I booked the trip and our flight and hotel experiences.  And give you tips about traveling to Cuba, especially with kids!

Note:   Currency conversions in this post applied around the time of the trip, but are slightly different now.

A Family Vacation to Cuba Trip Report Index

  • Part 1 – Introduction and Planning

Booking a (Paid, Gasp!) Last-Minute Vacation Package

When I couldn’t find award flights and rooms in the Caribbean for the 5 of us, an airline friend suggested checking out cheap last-minute vacation packages through Canadian tour operator Sunwing.  The kids and I live close to the Canadian border in Western New York, and often fly from Toronto anyway because I’m originally from there (and we’re all Canadian citizens).

Luckily, I found an amazing all-inclusive resort deal to Holguin, Cuba – just 5 days before our departure.

1.   Sometimes It’s Better to Pay Cash

It’s important to be flexible if you want the best shot at finding award seats and nights, especially when you’re traveling as a group.  But unfortunately this time we had a fairly short window (~2 weeks) in which we could travel.

I was frustrated for weeks looking for a combination of award flights (for 5!) and hotels in the Caribbean that worked for our travel dates.  Even searching from 3 airports (Buffalo, Rochester, and Toronto), I didn’t have much luck.

Hint:   If you’re willing to look beyond the airport closest to you, you’ll find more cheap flights!

When I discovered that Canadian tour operator and airline Sunwing offered discount last-minute vacation packages to the Caribbean from Toronto, I began monitoring their website to see what kinds of deals were coming up.  Cuba hadn’t really been on my radar (because there aren’t many hotels where you can use points) until I saw just how cheap the deals were.

My Family Spent 480 Each For Flights 7 All Inclusive Nights In Cuba Part 1 Introduction And Planning
I Stalked the Sunwing Website for Several Weeks to Figure Out Which Destinations Typically Had the Best Last-Minute Prices

After keeping an eye on the website for a few weeks, I discovered the best last-minute deals typically appeared 5 to 7 days prior to departure.

If you live near the Canadian border (or can easily get to a major Canadian airport), you might consider checking out deals like this from Canadian tour operators.  But because the US government has since tightened restrictions for US citizens traveling to Cuba, it’s more difficult to find US companies offering similar deals.

2.   Kids Stay Free?   Sign Me Up!

Sunwing offers family-friendly “Smile Resorts,” where kids stay “free.”  As it turns out, it’s not entirely free (kids still pay taxes, fees, and the airfare portion) but it still equates to a very big discount.  So I looked for cheap packages at those hotels.

The Memories Holguin Beach Resort caught my eye.  They advertised a kids club, numerous cascading pools, and a white sand beach with lots of activities.  In the winter, this resort costs as much as ~1,765 Canadian dollars (~$1,410) per adult.  But because it was low season, I saw prices in the weeks leading up to our stay between ~750 and ~900 Canadian dollars (~$600 to $720).

These prices included:

  • Round-trip, non-stop airfare between Toronto and Holguin on Sunwing Airlines
  • Transfers (air conditioned coach) to and from the resort
  • 7 nights all-inclusive accommodation (meals, snacks, alcoholic and non-alcoholic drinks, activities, and non-motorized water sports like sailing)
  • Cuba tourist card
My Family Spent 480 Each For Flights 7 All Inclusive Nights In Cuba Part 1 Introduction And Planning
Memories Holguin Advertised a Kids Club With All-Day Activities Like Talent Shows, Cooking Classes, and Character (Toopy and Binoo) Themed Events

I showed the hotel to the kids and they gave their thumbs up (well, except for the eye-rolls at the costumed characters from my pre-teen daughters!). 😉

3.   Pulling the Trigger

I booked our vacation 5 days before departure.  The price wasn’t quite as cheap as I’d seen the previous ~3 weeks, but that’s likely because our dates were right after school let out.  Between the last-minute discount, kids stay “free” deal, and a 5% discount I got for booking a friends and family rate (luckily I have a buddy working for Sunwing), we paid:

  • 2 adults – ~859 Canadian dollars (~$647) each or ~$1,294 total
  • 3 children – ~489 Canadian dollars (~$368) each or ~$1,104 total

So in total, I spent ~$2,398 for round-trip flights, airport transfers, and a 7-night all inclusive stay for 5 people.  Or an average of ~$480 per person ($2,398 total cost / 5 people).

My Family Spent 480 Each For Flights 7 All Inclusive Nights In Cuba Part 1 Introduction And Planning
We Paid Less Than $500 Each for Round-Trip Flights and a 7-Night All-Inclusive Stay

If you’re looking to book a vacation package deal in general, consider using a card like the Capital One Venture Rewards Credit Card.  You should be able to “erase” the purchase with Venture miles within 90 days at a rate of 1 cent per mile, as long as the tour operator or travel agency codes as a travel purchase.

I don’t have the card, so instead, we made the booking on a new card to meet a minimum spending requirement and unlock the sign-up bonus.  So not only did we get a great deal, we used the expense to get closer to the card’s bonus!

4.   What About Cuba Travel Restrictions?

I’m not a US citizen, so I wasn’t worried about the US travel requirements to Cuba at the time (which have since changed).  Current restrictions have made it harder (but certainly not impossible) for US citizens to visit Cuba on package deals like this.

Apart from having current passports, the only other documentation we needed were Cuban tourist cards.  These were included in the price of our package and were handed out on the airplane enroute to Holguin.

My Family Spent 480 Each For Flights 7 All Inclusive Nights In Cuba Part 1 Introduction And Planning
Sunwing Included the Price of the Cuban Tourist Card in the Vacation Package

The tourist card comes in 2 parts.  The first part is collected when you arrive, and the second stays with you until you leave the country.

Bottom Line

It usually gives me hives to pay cash for a vacation.  But in this case, the deal was too good to pass up.

We stayed at an all-inclusive resort in Holguin, Cuba and had an incredible time.  And saved a ton of money by stacking a last-minute vacation package discount with a kids stay free deal.

By flying from Canada with tour operator Sunwing and traveling in the low season, we only spent ~$480 per person including round-trip, non-stop flights, airport transfers, and 7 nights at the all-inclusive Memories Holguin resort.  Stay tuned to find out how this turned into 8 nights thanks to one crummy passenger.  🙂

Next, I’ll share a quick review of Canadian airline Sunwing.  They do fly to certain US destinations (especially in Florida), so let me know if you’ve seen them!

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Jasmin Baron was an editor at Million Mile Secrets. She covers topics on points and miles, credit cards, airlines, hotels, and general travel. Her work has appeared in The Points Guy and Business Insider.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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