If "points," “miles," and "transfer partners" make you shake your head, you're not alone. It can be complicated. There’s a lot of small print, but the basics are simple, and you can get real value without becoming an expert.

We all remember our first time, racing through an airline terminal, luggage in tow, chasing a connection when a salesperson jumped from the shadows, grabbed our attention, and relentlessly started pitching a credit card.

Maybe it was on the plane, when, after a long flight, the attendants began passing out flyers promising thousands of free miles to sign up before leaving the plane. Yes, there are advantages to credit cards tied to travel rewards, but there’s always some trade-off or commitment. If you feel pressured, just say no and move on. Your time may be better spent looking for a restroom or grabbing an overpriced burger.

There was a time when I had way more airline credit cards than I needed. I didn’t want the credit, I just wanted the free sign-up miles and points - it was becoming an addiction. Those bonuses were very compelling, often worth multiple free flights. I soon learned that once those miles were spent, I was stuck with another high-interest credit card. It became a chore tracking which cards had the best benefits, or which one had the most accumulated miles. Finally, I just cancelled all but two.

Carrying credit cards from three or more airlines makes little sense unless you are a frequent flyer for business or a dedicated world traveler. For those of us who fly just a few times a year, it’s easier to score free flights and upgrades by flying consistently with one or two airlines. The same is true for hotels. Focusing on one or two chains that meet most of your needs is a good way to enjoy the best benefits.

In addition to airline and hotel credit cards, there are “reward cards” that allow you to convert everyday purchases into travel benefits. These cards offer the greatest flexibility. When you use a rewards credit card for things you're already buying, you earn points, and you can spend those points on travel. If the financial institution that issued the card is also the same one that issued your airline and/or hotel card, it can make bookkeeping and transferring points that much easier.

If you don’t fly a lot, a flexible points card is probably the best fit. You’ll have an excellent choice of hotels and when you do fly, just use the card to pay (dollars or points) for your tickets. You aren't locked into one airline or hotel.

Like with any credit card, you accumulate points through everyday spending on groceries, gas, dining, bills, etc. Many cards will pay extra when you spend in certain categories.

Sign-up bonuses are a favorite hook with airlines and can often equal a free flight. These cards promise a whole lot of miles if you spend a set amount in the first few months. This is great if you'd be spending that money anyway. If you don’t spend the minimum and miss the deadline, it can be quite a disappointment. This happened to a lot of folks (self-included) who signed up for a card just prior to the pandemic.

An easy way to turn points into dollars is with cash back or gift cards, but this is usually the lowest value, often as little as 1 cent per point. Booking direct through the card's travel website is a simple way to apply your points to your next flight or hotel stay, and often worth a bit more. Transferring points to airline or hotel partners can be more work, but is often the best value for flights and hotels. Transfers are one-way, so you can't move points back once they're sent.

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Photos by Craig Lindquist

While much of North America is prepping for snow, the southernmost point in the continental U.S. is heading into its best season. In Key West (a.k.a. “The Conch Republic”), December through March brings dry, sunny days, mid-70s temperatures, and an easy island pace. I have a lot of friends who head to Florida for the winter—many have been going for a decade or more—yet they have never stepped outside their “easy-living” comfort zone and made their way to Key West. What a shame. There’s no denying that it is a bit of a tourist trap, but at the same time, it has a vibe unlike anything you’ll find elsewhere.

Drive it if you can.
The Overseas Highway (U.S. 1) runs about 160 miles from Miami, roughly four hours without stops. It's the only road in, and it crosses 42 bridges with turquoise water on both sides. You’ll see folks fishing from the old railroad viaducts and ask yourself, “How did this get here?” Good stops include Key Largo for key lime pie, Islamorada for lunch on the water, the Seven Mile Bridge, and Bahia Honda State Park. Start early, since traffic can back up.

Or come by air or sea.
Key West's small airport is two miles from downtown, and several airlines have nonstop winter service, so book early. If you're coming from Tampa or anywhere on Florida's Gulf coast, there's a third option: the Key West Express, a passenger ferry from Fort Myers Beach. It's a jet-powered catamaran with a bar and snacks on board, and the crossing takes about 3½ hours. It departs in the morning and returns in the evening, so you can make a day of it or stay a few nights. One caveat: on the day my wife and I booked this, the water level was too low for the boat to get to where we were supposed to board, so they bussed us to a different location. Not a big deal, but it did take a chunk out of our time in Key West. There’s no direct ferry from Tampa, so you'll drive to Fort Myers Beach first, and the ferry carries passengers only, not cars. You won't need one in Old Town, where it's easy to get around on foot or by bike.

What to do:
If you're already dreaming about warm sand, consider this your itch to start planning.

To everything there is a season.
For many, the season to travel is later in life, when time is more flexible and the passion to explore is greatest. While there are hundreds of podcasts and newsletters that focus on traveling, we’re hoping “Still Got The Itch", strikes a chord with those of you who have been dreaming of going somewhere special, but have let life put it off. If you like what we’re doing, please hit subscribe. It doesn’t cost anything. If you have a story to share, we would love to hear it - email [email protected].