By Molly Chester, Certified Travel Advisor and Scarborough resident
By February, most of us are done with winter, or at least ready for a little reprieve. The question I hear most often at this time of year isn’t, “Where should we go?” It’s some variation of, “What is the easiest way we can travel to feel warm again?” The good news is that when starting from our own Portland International (ish) Jetport, a change of scenery does not have to mean an all-day travel slog! When helping people plan winter trips from Maine, I often start with the travel day itself, because sometimes the breeziness of the travel experience matters just as much as where you end up, especially when the idea is a relaxing escape.
For some travelers, especially couples looking for a quick reset or families with younger kids, ease is the name of the game. Florida is the most natural fit in this case. In winter, there are a fair few nonstop options from the Jetport on various airlines to cities like Orlando, Fort Lauderdale, Tampa, and Fort Myers, with even more additional options available with a short connection. These routes don’t always fly every day, but with a flexible-ish schedule, you can make a nonstop, inexpensive, Sunshine State voyage happen with minimal headache. Travel days are short, predictable, and forgiving. You land, grab a car or shuttle, and are usually beachside within an hour.
For others, the sweet spot is a little farther south. Much of the Caribbean works well from Portland with a single connection through hubs like New York, Atlanta, Miami, or Charlotte. The travel day is longer than a Florida hop, but still very manageable for trips of 5–7 nights. February and March can be an amazing time to go, with warm water, reliable weather, and fewer crowds than the holiday season. For couples, this can mean quieter resorts and more relaxed dining options. For families with older kids, it opens the door to snorkeling, boating, and more availability for last-minute excursions on a day when everyone wakes up and wants to do something awesome.
If you have a full week or a bit more flexibility, parts of Mexico and Central America can also make a lot of sense from PWM. These trips typically involve a connection through a similar major U.S. hub, and this is where planning the travel day well really matters. Flight timing, layover length, and arrival time can have a big impact on how the trip starts, especially when traveling with kids. And when done well, these more far-flung destinations can offer a lot of value in terms of warmth, culture, variety, and activities once you arrive.
A lovely warm-weather escape does not need to be ambitious to be worthwhile. Sometimes a few days of sunshine and remembering what it feels like to eat outside are enough to reset for the rest of winter. From our own little Jetport, we can reach the sunshine with surprising ease, and get back home refreshed, sun-kissed, and without feeling like we’ve run a travel gauntlet.
Molly Chester lives in Scarborough and plans trips to destinations near and far as the founder of MChesterTravel.com.
Photo by Yoori Koo
