Want to Spend Part of the Winter Somewhere Warmer? Here’s Where to Begin
Maybe you've thought about spending January and February somewhere warmer. Or maybe after another long winter, you've caught yourself wondering what it would be like to spend the winter in Florida or somewhere else in the Southeast for a month or two.
It sounds appealing, but then the questions start. Where would you go? How long would you stay? What would it cost? How do you find a rental? What do you do about your house while you’re gone? Do you drive or fly? And how far ahead do you need to start planning?
You may not even think of yourself as a future “snowbird.” You just know you’d like to spend part of the winter somewhere warmer and you’re wondering where to begin.
You don’t have to figure everything out at once. Start with a few basic decisions and see where they take you.
Think About What You Want From the Destination
Warm weather may be the reason you're thinking about getting away, but temperature is only one part of choosing where to spend the winter. Think about what you would actually like your days to look like once you're there.
Do you want to be near the beach or spend your time boating or fishing? Are golf, pickleball, biking or walking trails important to you? Would you rather have restaurants, shopping and entertainment close by? Think about whether you’d enjoy a busy seasonal community with plenty going on or somewhere quieter where you can settle into a slower pace.
Also think about how far you're willing to travel from home and whether you'd like family or friends to be able to visit. You don't need to choose a specific city yet. At this stage, you're simply narrowing down the kind of place that would make spending part of the winter away enjoyable for you.
Decide How Long You’d Like to Be Away
You don’t have to leave home for the entire winter to try this.
For some people, a month away sounds just right. Others want to miss January and February, while experienced snowbirds may head south for three or four months.
If this would be your first extended winter stay, think about what feels realistic. Work, family, pets and other responsibilities may influence the decision. You may also discover that the length of your stay changes as you become more comfortable with being away.
The important thing is that there isn’t one correct way to do it.
Get a Rough Idea of What You Can Spend
Before you fall in love with a particular destination or rental, get a general idea of what you're comfortable spending.
Housing will probably be the biggest expense, but it isn't the only one. You'll also need to think about transportation, groceries and dining, activities, utilities that aren't included with the rental, pet expenses if you're bringing one, and the expenses that continue at your home while you're gone.
The numbers don't have to be exact at this stage. Your first winter away is partly about figuring out what works for you.
A rough budget simply helps you narrow your choices and avoid spending time looking at options that aren't realistic for you.
Start Exploring Rentals Before You’re Ready to Book
Looking at winter or snowbird rentals is one of the easiest ways to begin understanding what your winter away might actually look like. The earlier you start looking, the more choices you're likely to have, especially in popular areas. But don't assume you've missed your chance if you're starting later. Rentals sometimes become available because of cancellations, and newly renovated or recently listed properties can come onto the market throughout the season.
Browse rentals in several areas. Look at prices, locations, amenities and what's included. Notice how much availability changes depending on the month and length of stay.
If you have a pet, pay attention to pet policies as you browse. Pet-friendly rentals can narrow your choices, and some communities or associations have additional restrictions that aren't always obvious from the rental listing.
You don't have to book anything yet. At this stage, you're simply trying to get a sense of what's available and the range of costs.
Picture What Everyday Life Might Look Like
Spending a month or more somewhere is different from taking a vacation. You probably won't be sightseeing or eating out every day. Think about what an ordinary Tuesday might look like. Maybe you'd walk the dog, play pickleball, go fishing, meet someone for lunch, spend a few hours at the beach or simply read outside in the sunshine.
You don't need to fill every day with activities. Part of the appeal can simply be doing many of the things you normally do at home, only somewhere warmer.
Think About the Home You’re Leaving Behind
It's easy to spend all your time thinking about where you're going and forget about the house you're leaving.
If you're away for several weeks or months, you'll need to think about mail, packages, heating, security, snow removal, plants and who could check the house if something goes wrong.
None of these things is particularly difficult, but they're much easier to handle when you think about them ahead of time rather than a few days before you leave.
Consider How You’ll Get There
Driving may seem like the obvious choice because you can bring more with you and have your own vehicle when you arrive. But it isn't your only option.
Some people fly and rent a car. Others fly and have their own car shipped. Train travel and combinations of different transportation options may also work depending on where you're going.
Think about more than the cost. Consider the distance, how comfortable you are with a long drive, how much you want to bring and whether you'll need a car regularly once you arrive.
You Don't Have to Decide Everything Now
If you're considering spending part of the winter somewhere warmer for the first time, you don't need to have everything figured out before you begin.
Start looking at destinations. Browse some rentals. Estimate what a month or two might cost. Talk to someone who has done it. Pay attention to what appeals to you and what doesn't.
You may decide you'd love to spend several months away every winter. You may decide one month is plenty. Or you may decide you'd rather take shorter winter vacations instead.
The point isn't to become a snowbird. It's to find out whether spending part of the winter somewhere warmer could be something you'd enjoy.
Ready to Learn More?
I spent more than 25 years watching my parents make the trip south each winter before eventually spending part of my own winters in Florida. Along the way, I learned that there are plenty of things you don't think about until you actually start doing it yourself.
I wrote Snowbird Like a Pro for people who are at exactly this stage: curious about spending part of the winter somewhere warmer but not quite sure where to begin.
The book takes you through the complete process, from what a day in the life of a snowbird can actually be like and some of the unexpected benefits of the lifestyle to comparing destinations, understanding costs, finding seasonal rentals, preparing your home, choosing how to travel, packing, settling in, and eventually preparing for the trip home. It also includes worksheets and checklists to help you organize your own plans.