Trip Planning: We’re Going to Cuba!


2015 has been another great year of travel for the Michael W Travels family. We visited lots of new places and had many wonderful experiences.

We’ll be ending the year by visiting a destination I’ve long wanted to visit- Cuba!

I first thought about going to Cuba when I worked at CBS News. The show I worked on, 60 Minutes II had done a segment about Cuba called La Isla De Musica. Seeing footage of the island made me want to get there at some point.

I looked into one of the trips offered by religious organizations around 8-9 years back and the prices were pretty ridiculous. Figure something like $4,000 for a 5 or 6 night trip. No thanks.

When full diplomatic relations were restored between the US and Cuba, it seemed like the time might be right to go. The US government expanded the categories for travel to Cuba to 12 earlier in the year. We will be visiting with a general license under one of these categories.

Since we are budget travelers, it will be interesting to see what Cuban Casa Particulars (basically homestays) are like. I’ll most likely be unplugged during the visit since internet  doesn’t exist all over and when it does I’ve read it can be pricey and slow.

I hope that we’re not taking on too big of an itinerary. Travel around Cuba can be very slow so I guess we’ll see how that goes and adjust accordingly…

Areas in Cuba we plan to visit:

  • Havana
  • Santa Clara
  • Trinidad
  • Cienfuegos
  • Possibly more?

Trip Planning:

Getting There:

I considered taking a charter flight from NYC but the prices are definitely a bit rich for us. I believe a charter flight to Cuba from NYC runs from $800 (or at least for when we were looking to visit.)

Our second option was to fly from Mexico, Panama or one of the Caribbean islands. The problem with this was two-fold. Award flights weren’t available for the dates we needed plus flights from the countries listed above were not cheap, around $400-$500.

The best and final option.

Getting from Montreal to Havana:

I came across a deal from Secret Flying for a flight from Montreal to Havana back in October for $357CAD  which comes to around $270 US.

The dates we needed to fly were not listed on their deal page. I went over to Air China and did a search and found availability for dates which (kind of) fit our break. I was ready to book but Kim needed to check with work the following day. This would cost us…

When I went back to Air China early the following day, the flight had gone up in price. I was still waiting for Kim to see if the dates would work. By the time I tried to book, Air China was showing no availability!

I did some searching and found availability on the flights through a site called (The confirmation e-mail lists an address in Athens, Greece.)

For our flights from Montreal to Havana, Cuba (roundtrip), I paid $1,388.52 Canadian Dollars which comes to $1052.47 US or $350.82 per person.

By waiting a day to book, it cost me around $250 extra but still a good price as far as I’m concerned.

Silver Lining: I called Air China a while back to get seats assigned. I recently called again to confirm the flight times. I decided to check our seats again and was told we were flying business class from Montreal to Havana!

Getting to/ from Montreal (from NYC):

I was able to book an American Airlines flight with British Airways Avios to go from New York (LGA) to Montreal. The flight will get us there early afternoon, giving us a half day or so to wander around the city.

The Cost: 13,500 Avios (4,500 each) + tax coming to $16.80 ($5.60).

Getting home was a bit trickier. There was no availability through British Airways or other programs that I checked.

Our options were limited to buying a flight home or using Amex Membership Rewards points. I didn’t want to shell out more money for the flight back so I made what I’d consider not the best redemption option. I booked a flight on United from Montreal to LGA, paying with Membership Rewards points.

The Cost: 43,194 Membership Rewards points. (If we paid, it would’ve cost $431.94.)

Lodging/ Hotels:

  • Night 1: Montreal- Le Square Phillips Hotel & Suites- cost: $0 (I used a $50 off $100 Orbitz promo code along with $87.55 Orbucks which made the night free.)
  • Nights 2-7: Havana, Trinidad & Cienfuegos- Casa particulars booked through Airbnb- cost: $87.50  (The cost should’ve been $175 for the 6 nights. Thanks to the Airbnb $50 off $100 Amex Offers, our stays came to the price listed above.)
  • Nights 8 & 9: Havana- Casa Buena Vista- cost: 82.40€ ($90US)

Total Budget:

  • Airfare: $1069.27 +13,500 British Airways Avios + 43,194 Amex points
  • Lodging: $177.50 + $87.55 Orbucks which I got for free through a promo

Total Costs: $1,246.77 + 56,694 points

We’re all really excited to be heading to Cuba. After years of hoping and dreaming of visiting, I can’t believe that we’ll be on the island soon enough!

Are you interested in visiting Cuba?

Some Other Trip Planning Posts:

13 thoughts on “Trip Planning: We’re Going to Cuba!

  1. Which of the general license conditions are you planning to use to validate your family trip? And are you planning any travel with a tour group, or will you travel solo? Very interested in the kind of arrangements you found for touring.

  2. Paul B- We’ll be traveling based on journalistic activities. My wife edits my site and we travel as a family not individuals. My plan is to write about our experiences & traveling around with a young child.

  3. I think Cuba is 10-15 years away from being a nice tourist attraction . I felt this way after visiting Punta Cana and being disappointed in the poverty of the community . I picture Cuba as an even more under developed country .

  4. I went to Cuba this past July and cannot wait to get back. I flew through Mexico but flying through Canada seems to be a great deal too (especially I if I can find a flight deal soon and buy the Montreal leg for 4500 Avios before they change it to 7500). Have a great time!

  5. I visited Cuba in January. Cuba is charming and vibrant to say the least. It’s poor and stuck in the past but that’s what makes this country different from others. I can’t wait to return. My route was JFK to grand Cayman then Cuba on the outbound. I returned via Mexico City then back to JFK.

  6. Unless procedures have changed, you’ll be passing through U.S. Customs and Immigration in Montreal. I would imagine they will require some confirmation of your and Kim’s “general license condition”.
    Let us know if U.S. authorities or the airlines require any pre-departure documentation. Thanks ——-

  7. Chanel & Carlyn- Awesome! Which parts of Cuba did you visit?

    Rich A- For a general license there is nothing to get at this point. It used to be that you applied for one. I’ve been told by a bunch of people that no questioning was done.

    Traveler- Thanks!

  8. Thank you for the detailed planning, everything fits my budget! I will definitely do the same(have already book marked this). Can’t wait to read your trip report. Have a great time.

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