Many years ago, I met a couple who had already decided to retire to southern Florida. They loved being near the ocean, had plans to get involved in the local community, and after visiting several times before the move, they were sure they’d found their paradise. What they hadn’t done yet was build a full budget or think through what daily life there would look like once the vacations turned into an everyday routine.
A few years later, they moved to the west coast instead.
The South Florida they’d fallen for on vacation didn’t hold up once it became their everyday life. Instead of a getaway, it was suddenly just Tuesday, and everything about it felt busier and pricier than they’d expected.
I don’t share that story to talk anyone out of moving here (there’s a reason Florida is a famous destination for vacations and retirees). I share it because visiting a place and living in it are two different experiences.
Spending a week here and retiring here call for two different budgets, calendars, and conversations. That’s the planning work we do with couples before they trade the vacation for the address, so the decision holds up long after the moving truck pulls away.
3 Essential Conversations Every Couple Should Have Before Retiring to South Florida
Before you sign any paperwork, we ask you and your spouse to sit down with us and talk through three things.
1. Budget
South Florida comes with a high cost of living, particularly when it comes to housing. When we’re projecting your budget and lifestyle costs, there are several factors we’re taking into consideration that might not have been relevant in your previous home state.
High housing costs lead the list here, and it tends to bring a few uninvited guests with it:
- Home insurance runs higher in Florida than in most states.
- If you’re in a flood zone or carrying a mortgage, flood and wind coverage might not be optional.
- Utility bills have a way of surprising new residents.
If a condo is in the picture, we help you dig a little deeper. How old is the building? Does the association have appropriate reserves set aside for the big stuff, like a new roof someday? Are there assessments already on the horizon that nobody’s mentioned yet? These are the kinds of questions that feel tedious now and can potentially save money later, and they’re a lot easier to ask with someone in your corner who knows what to look for.
Related: Click here to read “The Sunshine Shift: 3 Financial Complexities Unique to Boca Raton, Florida”
Also, South Florida doesn’t skimp on restaurants, and neither will your monthly spending once you start enjoying them. We make sure to work those seemingly small everyday costs into your budget projections, because they add up over time.
And none of this changes what draws people here in the first place. Warm winters, no state income tax, a slower pace, and a built-in community of people who’ve made the same leap all make South Florida an appealing place to spend this next chapter.
2. Timing your retirements
This one seems simple until you dig in. Some couples retire on the same day and never look back. Plenty of others don’t, and there’s nothing wrong with that.
One of you might get pulled into finishing a project or training a replacement. One of you might love the work too much to walk away yet. Age differences are common here in South Florida, and sometimes one spouse keeps working a while longer purely to hold onto the health insurance, which is about as reasonable a reason as I’ve heard. We help you figure out what your version of “timing” looks like, together, instead of assuming you’re already on the same page.
3. Purpose and day-to-day
What does a normal Tuesday look like for you once the calendar is yours, and does that answer hold up whether it’s 65 degrees or 95?
This is the conversation people skip most often, and it’s the one that tends to matter the most a year in. What will you do with all that time, and does it look the same in July as it does in January? South Florida has a rhythm to it: snowbird season brings the crowds and the energy, and by summer, a lot of that same social circle heads north to escape the heat.
It’s common for one spouse to want to move immediately while the other hesitates to leave family or grandkids. We help couples model out phased transitions—like spending 3–4 months in Florida initially—so both partners feel confident.
Vacationing vs. Living Year-Round: Where’s the Disconnect?
When you visit South Florida on vacation, you see the highlights. When you move there full-time, everyday realities take over. Living in any location is always much different than vacationing, but Florida has a few unique factors I hear again and again in these conversations:
- The Weather Cycle: Winter here might be some of the best weather most retirees will ever get to live in full time, and it’s also shorter than the brochures let on, and worth planning your calendar around rather than being surprised by. Spring and fall are hot, while summers bring intense heat and humidity.
- Proximity to the Water: Vacationers usually stay right on the beach, and living oceanfront is out of budget for many people. Many South Florida communities sit 30 to 45 minutes inland. You have to ask yourselves if that drive still fits your daily beach vision.
- Building a Social Network: Moving to a new state means starting fresh socially. Building a meaningful local community takes deliberate time and effort, especially for couples that just made the move.
Legal Domicile & Estate Planning Considerations
Florida is generous to the people who live here, with strong homestead protections and better shielding from creditors than most states offer. But none of that helps if your estate plan was written for somewhere else and never got the memo.
We help you work with an estate attorney to take a fresh look and flag what needs updating. We also help you check how your accounts are registered, since Florida allows tenants by the entirety on bank and investment accounts, which gives married couples a layer of creditor protection a standard joint account doesn’t offer.
A Dedicated Team for Your Florida Transition
Some of the couples we meet in our Boca Raton office—or across the greater Miami area— have already made the move to Florida by the time they find us, usually with a list of questions about residency, updated estate documents, how their accounts are titled, and what leaving a high-tax state means for what they owe now.
Wherever you are in the process, we help you bring it all under one roof, with investment management, tax strategy, estate planning, and cash flow working together instead of four separate people telling you four separate things.
And you won’t be working with just one advisor. You get a team, which means more than one set of eyes on your plan and someone who’s still around when your circumstances change.
If we already work together and you’re considering a retirement in Southern Florida, reach out to your Team Hewins advisors. We’ll build the move into your plan, from the budget through the domicile checklist. If you’ve already relocated and haven’t revisited your documents or account registrations since, that’s a great place for us to start.
And if this decision is on your mind and you aren’t yet working with Team Hewins, we’d be glad to hear what you’re planning. Book a complimentary Big Decision Clarity Meeting to get started.
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Team Hewins, LLC (“Team Hewins”) is an SEC-registered investment adviser; however, such registration does not imply a certain level of skill or training, and no inference to the contrary should be made. We provide this information with the understanding that we are not engaged in rendering legal, accounting, or tax services. We recommend that all investors seek out the services of competent professionals in any of the aforementioned areas. Certain information provided herein is based on third-party sources, which information, although believed to be accurate, has not been independently verified by Team Hewins. Team Hewins assumes no liability for errors and omissions in the information contained herein.