Our family has never been to the Caribbean, and with my youngest son dying to do his first scuba dive once he turned 10 in January, a spring break getaway was on our radar.
From on our radar to reality took some work, but as you read this, we are vacationing in the Cayman Islands, 1,459 miles from our Zionsville, Indiana, home. We left behind the cold (Indianapolis seems unable to shake winter this year with 2 inches of snow falling the night before we left) and wet (flash flooding and tornado warnings) for the sun, the beach and snorkeling.
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Here’s how we did it
Our general travel strategy is to try to stretch our points on Southwest, our favorite airline, as far as possible. We do this by trying to book destinations that are no more than about 15,000 points round-trip per person on Southwest, and if we can find some that are much less, all the better.
We also always try to book flights during Southwest sales, when the points prices drop along with the cash prices.
For example, the first year we started flying on miles and points, we stretched 160,000 points across six trips in the U.S. for four people, spending less than $100 for all us per flight.
Lyn Mettler’s family in the Cayman Islands on spring break.
With the Caribbean on our radar, we started looking for flight deals.
When Southwest had a super cheap sale in February with flights out of Fort Lauderdale, Florida, to the Caribbean starting at around 2,100 points or $59 per person, we did a double-take. Flights from our home airport of Indianapolis to the Caribbean go for about 10,000 points per way at the cheapest.
So, how could we get to Fort Lauderdale to take advantage of this incredibly low-cost way to fly to the Caribbean?
We could drive or fly to Fort Lauderdale, but two days on the road from Indy to Florida was a bit more than we were willing to bear.
The best fares we could find to Fort Lauderdale were on Allegiant, a discount airline that offers lots of flights out of Indy. While I usually avoid no-frills airlines like the plague (I’ve had terrible customer service issues with the likes of Frontier), I had never flown Allegiant, so I figured it was worth a try.
Total cost for our flights to Fort Lauderdale: Allegiant flights for four of us with seat selections and three checked bags totaled $680.
To reduce the cost of the flights, we used my husband’s Chase Sapphire Reserve card, which includes an annual $300 travel credit. Another bonus of the Reserve is that travel expenditures earn 3x points, so our $680 turned into about 2,000 Chase Ultimate Rewards points that we will likely transfer to Southwest to help with our summer flights.
Belize, Turks and Caicos, or Grand Cayman?
Next, we had to decide where in the Caribbean we were going – Belize, Turks and Caicos, or Grand Cayman.
My husband and I were leaning toward Turks and Caicos, as we’d heard it’s less touristy and more natural, but ultimately we decided Grand Cayman (see aerial picture atop this blog post) might be a better fit for kids who are picky eaters and to give us more options of things to do.
Our family tends to be active and adventurous. While hanging at the beach is great for a day or two, then we get antsy to do something.
The Mettlers at Stingray City.
In the Cayman Islands, we may get antsy to see stingrays, which are people friendly, even “kissing” you. Since I’ve written about Stingray City in the past (a spot off Grand Cayman where wild stingrays come in search of food that used to come from fishing boats, but now comes from humans) and definitely wanted to check that off my bucket list, Grand Cayman it was!
We also found more accommodations options in the Caymans during the busier spring break period than on the Turks and Caicos.
Booking our Southwest flights
While we used points to book our Southwest flights (2,160 points each way), there are still mandatory fees for returning flights from any of these three destinations, ranging from about $70 to around $110, with Grand Cayman landing in the middle at $90.
We paid for these fees using our Southwest Rapid Rewards Premier credit card, earning 2 points per dollar on Southwest expenditures to net us more Southwest points for free flights. These points also qualify for the 110,000 points needed to earn our next Southwest Companion Pass, which lets one of us always fly free, aside from the mandatory security fees.
My family currently holds a Southwest Companion Pass, so I booked flights for me and my kids using points, for a grand total of just less than 13,000 Southwest points for four people to fly to Grand Cayman from Fort Lauderdale! I added my husband as my “companion” for only the cost of the security fees.
While we like to try to fly as close to free as possible, we decided to spend some money on this trip to get our family to the Caribbean for the first time. Our trip ended up costing us $260 per person round-trip to leave the cold behind for the warmth of Grand Cayman. Not bad!
Next up? My son’s first scuba dive – and, when we get back, planning our next trip on points!
See related: Redeeming miles, points for a spring break trip, 5 money-saving credit card tips for savvy family travelers