When the plateau goes quiet and the driveway turns to ice, a lot of Cashiers and
Highlands homeowners head “down the mountain” to Florida. This guide is for you:
a Christmas cheat sheet for the Florida bases where plateau people tend to land—
Naples, Palm Beach & Boca, Tampa Bay, Amelia Island & Jacksonville,
Orlando, and the Emerald Coast.
Think of it as the off-mountain companion to our
Christmas in Cashiers
guide: same people, different palm trees.
1. Why Florida shows up so often on plateau mailing addresses
Read enough plateau real-estate blurbs and you see the pattern: Naples, Fort Myers,
Boca Raton, Palm Beach, Tampa, Orlando, Jacksonville/Amelia, and the 30A corridor
pop up again and again as “home base” for Highlands–Cashiers owners and agents.
Some examples:
- Realtors and clients who moved from Boca Raton, Naples,
and the Fort Myers / Sanibel area to the plateau or split time between both. - Plateau pros who now winter in Yulee / Amelia Island (north of Jacksonville),
and designers who bounce between Anna Maria Island and Cashiers–Lake Toxaway. - Magazine distribution and travel pieces connecting Naples, Tampa Bay,
and Palm Beach readership directly to Highlands–Cashiers second homes.
So for this page, we’ve focused on Florida hubs that repeatedly show up in that
Cashiers–Highlands ↔ Florida loop.
2. Southwest Florida: Naples, Fort Myers & Sanibel
If Highlands is your summer high-elevation escape, Naples and the SW Gulf Coast are
the winter mirror image: palm trees, Gulf sunsets, boat parades, and illuminated gardens.
Naples Old-Florida Christmas
Naples Lights · Parades · “Snow” on Third & Fifth
December in Naples is all about lit-up shopping streets and Gulf breezes. Third Street
South and Fifth Avenue South anchor the season with tree lightings, carolers, and
faux snowfall between palm trees.
Lights in the Garden & Boat Parades
Naples & Fort Myers Botanical lights · Boat parades
For a slower night, stroll Naples Botanical Garden’s Night Lights in the Garden
or watch decorated boats glide by at one of the Gulf Coast’s many Christmas boat parades.
- Holiday Events in Naples – Night Lights in the Garden & more
- Christmas Boat Parades – Naples, Fort Myers & Cape Coral
Best plateau move: do one high-energy night on Third/Fifth, one quiet night in the garden.
3. Palm Beach, Boca & South Florida Lights
For plateau folks who winter on Florida’s southeast coast, Christmas often means boat
parades, charity drives, and palm-lined streets lit up like a resort version of Main Street.
Palm Beach Holiday Boat Parade
Palm Beach County Boats · Toys for Tots · Fireworks
The Palm Beach Holiday Boat Parade runs along the Intracoastal from North Palm Beach
to Jupiter, with decorated boats, fireworks, and a big Toys for Tots & Little Smiles
charity component. It’s one of the cleanest “we live in Florida now” Christmas vibes.
Boca Holiday Street Parade & SoFlo Extras
Boca Raton & South Florida Street parade · Coastal Christmas
In Boca, the Holiday Street Parade takes over Federal Highway with floats,
bands, and community groups. Layer on coastal light displays, pop-up markets, and the
usual South Florida “it’s 75° and we’re in shorts” December energy.
- Boca Raton Holiday Street Parade
- Look for local guides via Boca / Palm Beach magazines for pop-up markets
and neighborhood light displays.
4. Tampa Bay & St. Pete Christmas on the Water
Tampa Bay is a natural winter base for some plateau owners—an easy flight or full-day
drive from the mountains with big-city sports, museums, and a serious boat-parade game.
Tampa Riverwalk Holiday Boat Parade
Tampa Hillsborough River · Lighted boats · Downtown crowds
Tampa’s largest lighted boat parade runs along the Hillsborough River past Sparkman
Wharf, Harbour Island, and the Tampa Convention Center—hundreds of boats, thousands
of lights, and that “everyone in town is out” feeling.
Markets, Festivals & Flamingos
Tampa Bay & St. Pete Holiday markets · Neighborhood events
Around the bay, December weekends bring pop-up markets, “shop local” events, and
neighborhood light displays—from Flamingo Festivals at Sunken Gardens to holiday
indie markets and parades in Zephyrhills, Safety Harbor, and more.
For a current list of holiday events, check local roundups from Tampa Bay visitor
bureaus and regional news sites.
5. Amelia Island, Yulee & Jacksonville’s Dickens Christmas
A surprising number of plateau folks winter along the North Florida coast—Yulee,
Amelia Island, and Jacksonville—where Christmas looks like Victorian street festivals
by the water.
Dickens on Centre – Amelia Island
Fernandina Beach Victorian market · Lantern parades
Each December, downtown Fernandina Beach transforms into a Victorian Christmas
village for Dickens on Centre—a free street festival with costumed
characters, markets, kids’ zones, and even drone shows in recent years.
Jacksonville Lights & Riverfront Events
JAX & North Florida Boat parades · Light displays
Jacksonville layers on its own riverfront boat parades, neighborhood lights, and
coastal town events. If you’re wintering in Yulee or Amelia, you can dip into JAX
for bigger events and then retreat to the quieter island vibe.
6. Orlando & Central Florida: Theme-Park Christmas Overload
For plateau families who winter in Orlando, Christmas can be as low-key (light shows
and neighborhood events) or as over-the-top (Disney/Universal/SeaWorld) as you want it.
Theme Park Holidays
Orlando Disney · Universal · SeaWorld & more
Orlando’s theme parks go all-in on Christmas: Mickey’s Very Merry Christmas Party
at Magic Kingdom, EPCOT Festival of the Holidays, Christmas at Universal (think
Grinchmas & Wizarding World decor), SeaWorld’s Christmas Celebration, and
LEGOLAND’s holiday shows.
I-Drive Lights & ICON Park Snow
International Drive Light shows · ICON Park · “Snow”
ICON Park turns into a winter wonderland with a 50-foot tree, nightly “snow”
flurries, Santa visits, and a synchronized light show on The Wheel, while the rest
of International Drive fills with light displays and holiday happenings.
7. Emerald Coast & 30A: Beach Town Christmas
Panhandle beach towns—Destin, 30A, Santa Rosa Beach—are a natural winter flip-side to
Highlands–Cashiers: smaller, laid-back, and heavy on lights, music, and Gulf sunsets.
Destin & HarborWalk Village
Destin Jolly Jubilee · Santa visits · Boat parades
Destin Commons runs its Jolly Jubilee with live music and a 50-foot
tree; HarborWalk Village hosts Santa visits and photos, plus coastal light displays
and events that stretch across November and December.
30A & Santa Rosa Beach
30A Corridor Town squares · Lights · Coastal markets
Towns along 30A (Seaside, Rosemary, Alys, WaterColor, etc.) lean into tree lightings,
caroling, artisan markets, and coastal-luxe decor—basically “plateau people at the
beach” energy all December.
Use local 30A event calendars and vacation-rental blogs to pick which town square
fits your family’s pace.
8. How to stitch this into your plateau calendar
The magic move isn’t “mountains or Florida?”—it’s using both. A lot of plateau families
end up with a rhythm that looks something like:
Late October–Thanksgiving
- Fall color + leaf season on the plateau.
- Highlands Food & Wine; last big weekends before winter.
- Head down the mountain just after Thanksgiving.
December in Florida
- Pick your base (Naples, Palm Beach/Boca, Tampa Bay, Amelia, Orlando, 30A).
- Anchor one or two “big” events (boat parade, Dickens on Centre, theme-park night,
basement-fare miles burn for Turks & Caicos). - Fill the rest with low-key nights in your own neighborhood lights.
January–February & Back Again
- Use the quietest plateau months for travel deals, warm-water trips, and
off-mountain projects. - Let Cashiers Note be your “early
warning system” when plateau listings or club news make it worth heading back up
sooner.
One inbox, two lives: plateau & Florida
This guide gives you the Florida side of the Highlands–Cashiers story. The free weekly
Cashiers Note ties it together—mountain moves, Florida
winter tips, travel deals we actually like, and one Property of the Week
that might eventually make “Christmas in Florida” just another part of your plateau life.