I’m excited to kick off proceedings here on the blog, and with a trip coming up later today, the timing couldn’t be better. Let’s jump right into the thick of things with some background on my upcoming trip.

The planning for this trip started in late 2016, when a routine perusal of my travel calendar had illuminated the weekend of February 18–20, 2017 as a tempting option for a quick getaway from the grim Toronto winter.

For those of you who aren’t aware, the third Monday of every February is designated a public holiday here in Ontario (and in a few other Canadian provinces), known as Family Day. Now, I’m not sure what kind of reasoning lies behind that name, since it seems to me that the day serves as little more than tacit acknowledgement from the government along the lines of “Yes, we all have to live through such bitterly cold winters every year and there’s nothing we can do about it, but here’s a random day off in the middle of February so we can all get away a bit.”

Travel junkies working full-time jobs will know that vacation days are a precious commodity, making long weekends a godsend in terms of being able to squeeze out a three-to-five-day trip to someplace not far. Hence, in the spirit of the holiday I began planning a neat little two-person getaway together with my lovely girlfriend Jessy, the only family I’ve got around these parts.

Plan A

Impeccably sunny California was the original plan. I hadn’t been to Los Angeles for a good few years and had a few friends there I could visit. Plus, Universal Studios is always a blast, and I was sitting on a pile of Marriott Rewards points that I could redeem for our hotel stay. I had my pick of the Marriotts at Beverly Hills or Marina del Rey, two very well-appointed properties, and could make full use of Marriott’s fifth-night-free benefit when redeeming points. All the boxes were ticked.

Or so it seemed. You see, my girlfriend had been bugging me for three years now to go on a sunny beach vacation, and each time her pleas had fallen on deaf ears. I’m generally not a huge fan of beach resorts and prefer to go on trips with a more urban flavour. Seattle and Vancouver in a week, London and Lisbon in ten days, that sort of stuff. To be fair to Jessy, though, she was dogged in her desire to frolic and sunbathe, and was therefore thoroughly unimpressed with my Los Angeles plans. I gave it some thought, and since she had indeed been patiently nursing her wish for three years, I decided to go back to the drawing board and see what I could throw together to satisfy this longstanding hope.

The Rethink

I quickly cycled through a few options. Traditional Caribbean vacation packages (in which flights and accommodations are included, with food and drink bundled in as well if it’s an “all-inclusive” deal) for that weekend started at $1,500 per person with no meal plan and mediocre lodgings (and I mean hostel-style bunk beds). Forget it. I then figured I could still make use of my Marriott points, since I knew they had a few superb resort properties in the Caribbean. The Atlantis Paradise Island Resort in the Bahamas – of American television commercial fame and a part of Marriott’s Autograph Collection – had initially caught my eye, with decently priced direct flights from Toronto to Nassau available for my dates. Digging deeper, however, I found that there were resort fees of 53.70 USD per person per night that were payable even on a points booking. So even though I’m spending a small fortune in Marriott Rewards points, I’d still have to pay about 270 USD plus about $600 for the flights. Next. The Marriott resorts in Grand Cayman and Aruba also looked attractive, but reward availability for my dates were nought. Such is life sometimes.

That left the St. Kitts Marriott Resort & Royal Beach Casino as the standout choice. It sits along a gorgeous beach in a relatively secluded part of the island, charges no resort fees, and the islands themselves seemed to have plenty to offer, including a zipline canopy tour to a historical scenic railway. Flights were also relatively cheap, at about $600 round-trip in economy with American Airlines. And of course, I knew my girlfriend would be over the moon.

The Itinerary

There was just one problem. The flights with American had an overnight layover in each direction. Now, for the outbound journey this was no trouble for me, as I had a Category 1-4 free night certificate with Marriott that I needed to burn anyway, and an overnight stay at an airport hotel in Charlotte would be a decent use for it. For the return portion of the trip, however I would hate to take an extra day off of work just because of traveling time. 

As it turned out, while the St. Kitts to Miami flight on February 22 wouldn’t arrive in time for me to catch the last American flight out to Toronto, there was a later flight operated by Air Canada Rouge which that I could feasibly connect to (I know Rouge gets a bad rap, but these were desperate times; think of how precious a vacation day can be!)

Of course, purchasing these two flights as separate tickets would have been disproportionately expensive, but luckily there was award availability on both flights, so I snapped them up for 10,000 British Airways Avios (for the St. Kitts–Miami segment) plus 12,500 Aeroplan points (for the Miami–Toronto segment) per person and a small handful of taxes and fees. 

Our final itinerary was as below, all in economy:

• YYZ-CLT on American Airlines, departing 7:15pm and arriving 9:28pm
• CLT-SKB on American Airlines, departing 11:35am and arriving 4:24pm
• SKB-MIA on American Airlines, departing 4:29pm and arriving 7:02pm
• MIA-YYZ on Air Canada Rouge, departing 9:55pm and arriving 1:05am the next day

Our total out-of-pocket costs per person were as below:

• One-way flight with American Airlines, YYZ-CLT-SKB: $310
• Taxes and fees for Avios redemption SKB-MIA: $70
• Taxes and fees for Aeroplan redemption MIA-YYZ: $45
• Total: $425

Conclusion

We’re super excited to get on the plane for this one. Jessy is obviously pumped to finally get some time on the beach under the sun, and I’ve come to look forward it as well, as it’s something new and different from our previous trips together. Boarding’s about to start so I’ll leave you on this note, but I do endeavor to continue adding a few posts while I’m away, and of course I’ll have the full trip report ready not long after I get back.

By the way, don’t worry if you find some of the miles & points terminology confusing, as we’ll be covering a lot of ground in future posts. Feel free to pipe up in the comments with any questions though, and do let me know if you’ve been to St. Kitts and have any tips to share!