Puerto Rico Trip Review: Just My Boys and I – Part 1 – Planning Our Trip

This is my first post in my series on my trip to Puerto Rico with my oldest two boys. You can find the other posts here:

Puerto Rico Trip Review: Day 1 & 2 Getting to Puerto Rico

Yes, I took my oldest two boys to the Caribbean and yes, we left my wife behind… Ok, so now I sound like an awful husband for not taking my wife. But before you start thinking I went crazy or have a death wish let me explain. Believe it or not, this trip was actually my wife’s idea!

I actually tried to take her to the Caribbean but she declined! With a new baby she decided it would not be much fun going to the Caribbean and she had a point. It is not like we could swim together very easily with a baby and hiking in the rain forest isn’t much fun with a baby on your back either.

Sun Bay Vieques Puerto Rico

Sun Bay – Vieques, Puerto Rico

I had a couple of flight vouchers that I had earned for volunteering to be bumped on prior Delta flights and they were getting ready to expire. So my wife actually suggested I use this as an opportunity to have some quality time with my 6 and 9-year-old sons.

With only $800 in Delta vouchers to spend and three of us traveling I knew I was going to have to get creative. After this long miserable winter I had my mind set on a beach. I searched and searched but couldn’t find a flight out of Sioux Falls to anywhere remotely tropical for under $500 per person. Living in a small city makes finding cheap flights a pain in the butt.

Here in lies the beauty of British Airways Avios points and one of the reasons why I recommend everyone keep a stash on hand! Thanks to Avios distance based award chart I can redeem flights to Chicago for only 4,500 miles one-way and availability is almost always there. Searching for cheap flights out of O’Hare can open a whole new world of opportunities at an affordable level.

Google Flights is a great tool when you want to search simply by region. For example, I plugged in ORD for the departure city and then put Caribbean as my destination and the map displays all the different Caribbean destinations along with the cheapest prices for the dates selected.

Google flights caribbean flights search

The only destination that was going to keep me relatively close to the $800 voucher value was Puerto Rico. Being an US Commonwealth, Puerto Rico is also a cheaper destination because you do not need a passport to visit the island. At the time, flights were pricing out at $311 for a total of $933 for the three of us round-trip.

You cannot redeem more than one Delta voucher at a time online, however it can be done over the phone. After checking to make sure there was award space to get us to Chicago and back from Sioux Falls using Avios, I picked up the phone for a call to the Delta Gold desk. After a 25 minute phone call the tickets were all booked.

Total cost for 3 round-trip flights from FSD to ORD on American – 27,000 Avios & $15

Total cost for 3 round-trip flights from Chicago to San Juan, Puerto Rico – $133 out of pocket

With the flights booked it was time to start looking for hotels. I find it easier to book the flights first and then book hotels as hotel award availability is easier to find than airline availability. Most hotel programs do not have black out dates making it pretty easy to redeem a free night as long as there are standard rooms available… More on that in one of the next posts…..

For some reason I really had a hard time nailing down our itinerary for this trip and as a result I struggled to decide on hotels. I knew I wanted to use as few points as possible as we would not spend much time at the hotel and the majority of my points are already earmarked for specific future trips.

On the way to and from Puerto Rico we were going to have an overnight in Chicago so I needed a cheap hotel within close proximity to O’Hare. The Four Points O’Hare is only 3,000 Starpoints on the weekends and offers free round the clock shuttle service to and from O’Hare so I decided that would be as good of place as any to get a little shut-eye.

I have a huge stash of Club Carlson points thanks to the 85,000 point sign up bonuses on both the business and personal Club Carlson Visa cards which had no specific plans for use. The Club Carlson Visa cards have my favorite credit card perk, Bonus Award nights which give you the last night free on a 2 night or greater points stay. With only one property in Puerto Rico it was pretty easy to decide which property to stay at. The Radisson Ambassador Plaza may be a little out dated but 38,000 points for 2 nights is a pretty solid value considering how easy it is to earn Club Carlson points.

Other than the overnight in Chicago and the two nights at the Radisson in San Juan I had a pretty good idea on where would stay the rest of the nights but I could not make up my mind. I knew we were going to spend a day hiking the rainforest and taking a plunge in its cold waterfalls. I knew were going to spend a few days on some amazing beaches and touring the old Spanish forts. But which ones on which days would determine which hotels we stayed and I was indecisive so I decided to just play the rest of the nights by ear and decide once we got down there, which by the way is completely out of character for me.

In the next post I will cover the first 2 days of the trip and our adventure getting down to Puerto Rico.

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One Response to Puerto Rico Trip Review: Just My Boys and I – Part 1 – Planning Our Trip

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