I’m a big fan of optimizing, and sometimes that takes the shape of combining one trip with another. When I wrote this, I was away for a four-day anesthesia meeting in Hawaii, but we actually enjoyed the tropical paradise for 23 days, visiting three different islands.
My flight to Hawaii was reimbursed by my employer, and the other three round-trip flights (for my wife and 7 & 9-year old boys) were booked with miles thanks the sign-up bonus miles from a pair of American Airlines credit cards from Citi that my wife and I opened. If you have a business, you can also consider obtaining the Citi Business version with an equal or larger bonus.
When we returned from FinCon17, we immediately made plans to attend the 2018 conference in Orlando. We usually take a cruise about every other year, and our boys really enjoyed our last cruise, which was their first.
I was delighted to learn that there was a perfectly timed cruise to a destination I’m pretty excited to see: Havana, Cuba. [post-publication edit: You can no longer take a cruise to Cuba. I’m soooo glad we went when we did!]
The Havana portion is a twelve-hour stop, which isn’t a vast amount of time to explore, but it’s more than you get at your average port of call.
Saturday, 9/22/2018: Departs from Tampa at 4:00 pm
Sunday: Arrives in Key West at 1:00 pm. Departs at 7:00 pm
Monday: Arrives at Havana, Cuba at 8:00 am. Departs at 8:00 pm
Tuessday: Day at Sea
Wednesday, 9/26/2018: Arrives at Tampa at 7:00 am
We opted for 6 pm dining, which Royal Caribbean considers early dining, which more closely resembles our family dinner time at home. It’s nice to go straight from dinner to the evening’s entertainment or other activity.
Cruise for Free with Travel Rewards?
While I have been known to give away Bitcoin, I’m not about to give away a cruise. You’re going to have to do a little bit of work to get your free cruise, but there’s plenty of time to make that happen with bonus rewards from credit cards.
Unlike many of the airlines, you won’t find credit cards with bonus miles that can be directly redeemed for a cruise. There are, however, several cards with bonus offers that can be used to reimburse you dollar for dollar for any travel, and of course, a cruise counts.
Currently, a family of four in an oceanview stateroom can book the cruise for about $1,800. For a couple, it’s about $1,300.
Bonus offers for meeting minimum spending requirements on some of these cards are valid for $500 or more in travel. Also keep in mind that for a couple, both couples can apply for the same card (smarter than getting a companion card for a spouse) which allows you both to receive the lucrative reward points, potentially resulting in $1,000 or more in free travel for each card you both acquire and meet the minimum spend.
Some of the best options for flexible travel reimbursement (such as cruising) include:
I’m not allowed to link directly to the last two cards, but they can easily be found via the left sidebar on CardRatings when viewing other card offers. With our normal spending, we’ve been easily able to meet the minimum spending requirements of $3,000 to $4,500 in the first three months to earn the thousands of dollars in travel rewards available through the above cards.
Several of the cards mentioned above specifically reimburse travel. You can also consider any card that rewards you with money, and there are some great cash back credit cards that offer 2% back on all purchases and up to 6% or more back on specific and common spending categories. How’s that for passive income?
Why Cruise to Cuba?
Based on the offers I’ve seen, cruising is easily the most affordable way to visit the country. Tours of the country are very expensive compared to its neighbors in the Caribbean.
In twelve hours, we were able to take in many of Havana’s highlights, including the beautiful streets, antique cars, expansive churches, plazas, and quite possibly a mojito or two.
I also like the fact that someone who is only able to take one week off can take this cruise and also attend all of FinCon while only burning one week of vacation. If you’re not into FinCon (the Financial Conference where media & money meet), I’m sure you could find something else fun to do in Florida, home of the happiest place on earth, among other things.
Why cruise in general? To be perfectly honest, I have a bit of a love / hate relationship with cruises, but when we do them about every other year and combine them with another event, it’s mostly love.
Our prior two cruises were taken after attending a nearby wedding and the other after taking our boys to Universal Orlando. It’s hard for me to justify flying across the country only to jump on a cruise ship.
If I’m going to fly far away, I want to do something else while I’m there. Similarly, if we’re going to be near a port for a different reason, and have the time to spare, it makes sense for us to look for a cruise.
What I love about cruises:
Very good, unlimited food
Quality entertainment is included
Visits to a variety of ports
No need to drive
Variety of onboard activity (trivia, a capella troupes, comedians, and main stage shows)
Childcare often included or well worth the cost
Friendly staff from around the world
What I hate about cruises:
The same crappy stores near every port (I’m looking at you Del Sol and Diamonds International)
The pound a day I’ll gain if I overindulge in the very good, unlimited food
The ridiculous people that complain about the very good but not perfect food and service after getting a last minute deal on the cruise for a couple hundred bucks.
The way it can get a bit crowded, and your only escape is a tiny stateroom
When it’s over and we have to start taking care of ourselves for a change.
If you’re going to explore using travel rewards to travel for free, please use these links to explore those cards to support this site and its charitable mission.