This trip was different for us in several ways. First, we committed to staying in each accommodation for five consecutive nights—a big shift from our usual travel style, where we rarely stayed in one place for more than four nights.

Second, we booked both our flights and accommodations for the entire duration of the trip in advance. In the past, we typically only secured our outbound airfare and the first few nights upon arrival, leaving the rest open-ended.

And finally, we planned to rent a car during our island stays. Normally, we either brought our own means of transportation (i.e. our tandem) or relied on local public transport, so having our own set of wheels felt like another new chapter in how we travel. By the way, it dawned on us that our last winter getaway was our Southeast Asia trip back in 2023.

Trip planning

As we began planning the trip, we were pleasantly surprised by how well connected our target islands were by air. While the distances between islands were short—often just 30 to 45 minutes by plane—we quickly ruled out ferries, as those same journeys would have taken far longer by sea.

With plans to spend five nights on each of the nine selected islands, the total length of our adventure settled at 47 days. Although Jamaica was originally part of the itinerary, we decided to postpone that visit after Hurricane Melissa caused widespread damage at the end of October 2025.

The sequence of our island visits was largely shaped by available air links, with a strong preference for direct flights whenever possible. When it came to accommodations, we prioritized apartments with kitchen facilities. While beachfront stays aren’t expected, we’re hoping to enjoy at least a few sea views along the way.

Flight Cancellations Galore

Just two days after we had painstakingly booked all of our flights and accommodations in mid-November, we received a notification from one of the airlines informing us that the flights for our first two island hops had been cancelled. Cue the scramble. Fortunately, we managed to rebook those legs with another carrier—only to later see the departure times for both flights change.

In the final weeks leading up to our departure, things escalated further. We were forced to rebook two additional flights with different airlines after the original carrier arbitrarily changed the flight dates—not just the times.

One particularly interesting twist was being asked by an airline to provide the passengers’ weight. We can only hope that seating assignments aren’t determined by the parachute sizes provided.

Post-Trip Scheduling

We spent a fair amount of time on Google Maps scouting out hiking trails, snorkeling spots, and other tourist attractions on each island. As usual, Jenny did her part by reviewing and bookmarking a selection of relevant travel videos on YouTube for every destination.

For this trip, we were determined to travel with carry-on-only luggage. After initially eyeing some $300-plus backpacks at a local outdoor store, we opted instead for travel backpacks from Decathlon at roughly a third of the price. In addition to our clothes and toiletries, we managed to squeeze in our hiking poles and snorkeling gear—everything fitting neatly into our carry-on and personal item bags.

Other small follow-ups included obtaining an International Driver’s License through CAA and notifying our bank and credit card companies of our travel plans.

World Events

As if our flight-booking challenges weren’t enough, global events added another layer of uncertainty. On January 3, 2026, the United States conducted military strikes in Venezuela. In the aftermath, restrictions were imposed on several flight routes and airspace to and from parts of the Caribbean.

The impact was immediate: many travelers found themselves stranded across the region, while others saw their carefully planned vacations disrupted. All we could do was hope that the skies would return to normal in time for our January 17 departure from Canada.

Being Scammed Even Before Our Departure

Our first accommodation booking on Booking.com quickly taught us to be extra cautious. A few days after making the reservation, we received messages from our host—both on the Booking.com platform and on WhatsApp—reminding us that payment was required before arrival. Naturally, we followed the online payment instructions.

Then, a couple of days later, we got another WhatsApp message requesting payment for a different accommodation. The link looked extremely legitimate, referencing the property name, reservation dates, and even mimicking the Booking.com interface perfectly. Confidently, I started to initiate the payment.

Thankfully, the credit card’s verification process flagged a mismatch—the amount didn’t match our reservation. I immediately stopped the transaction. The credit card company canceled it but, in the process, temporarily locked my card. Since the card had been compromised, they issued a new one which we received only a day before our departure.

Even though we had read about scams via WhatsApp, we never thought we’d almost fall for one ourselves. Painful lesson learned—and a stark reminder to always double-check before hitting “pay.”