One of our tricks to surviving cruel winter months in the northeast is to have a vacation planned mid-season to somewhere warm. It was a tradition when we were both working (and had more disposable income) to go away in November for our ‘meetaversary’ and again in February to celebrate my husband’s birthday and Valentines day. This annual February trip also became our salvation, as this is without question the worst time of year weather-wise in our region.

These trips I’m listing met all of our winter getaway criteria:

• Warm!!
• Near water (beaches and pools)
• Hotel amenities (hot tubs, saunas, bikes, spas)
• Have a lot to do in terms of restaurants and nightlife
• Allow for a balanced vacation (rest and activity)

These are winter trips we have taken in the past ten years. I’ll give you the highlights and positives and negatives. See my post on travel tips for older travelers for some ideas to make traveling easier, in general, as we age!

Florida

If you live in the cold northeast, Florida is a great bet for a getaway. There are decent flights (money and time-wise), it’s not too terribly far, and the weather is usually perfect in the dead of winter. It’s honestly our go-to more than anywhere, because you can mix it up and go to so many different spots. We have no interest in living there full time, but it’s an amazing place to visit to get warmed up and refreshed. These are our favorites.

Lauderdale by the Sea. This was our most recent trip in 2025. I loved it. We did an airboat ride to see alligators- that was something different that I highly recommend.

We had a great time hanging by the pool, but the town and beach were only about a block away, and there was the coolest restaurant right on the beach, the Aruba Beach Cafe, where I could have easily hung out the entire time. My perfect combination of live music, cold martinis and incredible seafood. OMG.

I still get emails from them, and they make me want to go back today!

Cape Coral. This trip was so balanced. We stayed at a hotel with a pool, hot tub, tennis courts, and bike rentals. I’m the introvert who’s fine hanging by the pool, or on the balcony all day with some cocktails and appetizers.

But my husband likes to be DOING something. On this trip we finally learned how to marry our traveling styles, and took a look at the surrounding area for some things to do. Some of those things were a boat ride across the bay to Fort Myers (an awesome beach with great restaurants), a bike ride to some tennis courts for a few games of tennis, dinner and a play at the Broadway Palm Theater, and of course plenty of time at the pool and hot tub.

Ocala/Daytona/Disney. This was a great example of another balanced trip. We stayed with friends in Ocala, then drove to the Orlando area where we went to Epcot (an introvert/extrovert compromise for sure). We stayed in an amazing condo, ordered in some pizza, and had a low key swim at night.

We stopped in Daytona, where my husband could ride around the racing track, and we drove our car on the beach! My fave place there was a bar with an outside porch, live music and great cocktails. We got such a good crab boil there!

Mexico

Mexico is another great option if you’re looking to flee the cold weather. In addition to the heat and sun, I think the culture is fun to experience there- where you can practice your Spanish and have some incredible food!

All-Inclusive Resort. We flew to Cancun and stayed full time at the Pyramid at Grand Oasis resort. It’s the kind of place where you get a wristband and can access pretty much everything. I think you have to try this at least once, but I wasn’t a huge fan.

The positives of this situation are that you don’t need to carry cash, which is super convenient. There is a decent variety of upscale dining choices. But it’s sometimes hard to get into popular restaurants because they fill up fast. One restaurant we are able to book was the coolest ever though. The Black Hole. It’s a “blind dining experience” with 27 amuse bouche (small bites) served in complete darkness and designed to heighten your senses of smell and taste. You don’t experience this every day!!

We booked one excursion, swimming with dolphins, and the van never picked us up at the resort! There were like ten vans out front that looked exactly the same and had no markings. We waited such a long time and ended up canceling. I hope my husband got his money back, but I’m feeling we took a loss on that. We were disappointed to say the least.

So these all inclusives are great in theory but have some hiccups in terms of being overly crowded. Even when you go out to the pool(s) early, the lounge chairs were often taken.

Mexican Cruise- Miami, Cozumel.

This was my first time ever on a cruise, and if you’re also an introvert you may understand why. My husband had been wanting me to go forever, yet it just had no appeal for me. My head was saying- kids, crowds, a bunch of people stuffing their faces like they’ll never get a bite of food ever again. Sorry, I am a bit of a snot and would love to say I was wrong. I wasn’t.

Crowds (lots of hot tubs but too many people in them- gross), people stuffing their faces. There was a decent variety of food, but things I wanted, like a crab and oyster bar, were only open for limited times, as well as the dining room- where there was a dress code! What? The entertainment was cheesy- I guess it’s supposed to be, but is not my style.

What did I like? There was a gym with a sauna and steam room. Naturally barely anyone was in there, so I really enjoyed that (you don’t get a steam room every day unfortunately). They did offer spa services and we got a couples massage- yes to that too. Drinks were plentiful and included, and we opted for a room with a balcony, which was about the coolest thing about this cruise.

The rooms are SO small on cruises, so I highly suggest spending the extra money for a balcony, especially if you’re claustrophobic yet completely unafraid of deep water, like me. I loved sitting out there with a book and a drink and just watching the waves and movement of this huge ship. It was incredibly relaxing!

My favorite part of this trip was the times OFF the cruise. We tried parasailing for the first time, and (finally) did a ‘swim with the dolphins’ excursion. So much fun! 🤩

Arizona

Check out my post on this if you’re interested in more detail. This is a wonderful winter trip because the desert is just so different from the east coast. You feel like you’re in another country, and I like that.

We rented a pick up truck, and right away I would advise not doing that. You can only fit your luggage in the bed of the truck- so every time you’re stopping and getting out, your stuff is going un-watched, which we were a bit paranoid about. Also if it rains- not so good. Although it barely ever does there, it still does sometimes. So that to me was a ‘live and learn’.

Some things we definitely wanted to see were the Grand Canyon, Antelope Canyon and Sedona. A big reason I even had Arizona on my short list is because a colleague went to Antelope Canyon and the pictures were truly unreal. So that was an amazing day. At the Grand Canyon, I took my first helicopter ride (so cool), and we also went on a boat ride down the Colorado River.

Southern States

My husband decided he wanted to visit some southern states he’d never been to before for his birthday one year. Did I want to go to Alabama? Not really. So he drove south on his own little road trip, then I flew down to meet him in Kentucky (my mother was born there) and he drove us back home. I really suggest doing a vacation this way with your partner or friend, it was the ultimate compromise and saved airfare!

We did some fun things in Lexington, and decided we were going to drive up the Blue Ridge mountain trail later that day- and it started snowing! FYI, there are some warmer or southern places that still get snow storms or are colder this time of year (especially this year!).

It actually turned into a huge storm, and we had to pull over at a random hotel unexpectedly. This weirdly turned into a great night. The room had a hot tub, I had some wine (from a winery we visited that day), and proceeded to go on a long drunken rant about what a great driver my husband is- something we still joke about today 😂

Just a note about some other awesome warm-weather trips. California and Hawaii are worth it 100%. (I am going to write about Hawaii soon!) But they take more planning, more money and more time. Flying for that long, the time differences, etc. So I would save these for extra special anniversaries or birthdays (see my Trips with Teenage Girls post).

I hope you have the chance to take a winter getaway one of these days! Let me know some of your favorite places- I’m aways looking for new ideas!