Celebrate the Season with Coastal Charm
As the rest of the country bundles up for winter, Northeast Florida is just starting to shine. The mild coastal weather, festive lights, and lively local traditions make this region a perfect destination for a holiday weekend getaway. Whether you’re drawn to the historic charm of St. Augustine, the riverfront energy of Jacksonville, or the laid-back beaches in between, you’ll find endless ways to celebrate the season.
Here’s how to plan a perfect three-day holiday itinerary that blends cozy relaxation, local flavor, and plenty of festive fun.
Day One: Arrive & Unwind in Coastal Comfort
Morning: Check In and Get Settled
Kick off your holiday weekend by checking into your Joseph Ellen Properties vacation home — your personal retreat in the heart of Northeast Florida. Whether you’ve booked a charming downtown cottage, a beachfront escape, or a spacious family home, you’ll be greeted with comfort and local character that instantly sets the mood for your stay.
After unpacking, take a few moments to enjoy your surroundings — perhaps a cup of coffee on the porch, or a short stroll to explore your neighborhood.
Afternoon: Explore the Historic Streets
Once you’ve settled in, head out to St. Augustine’s Historic District or Downtown Jacksonville for a laid-back afternoon of sightseeing and holiday charm.
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In St. Augustine, walk the cobblestone streets lined with centuries-old architecture and festive decor. Browse the local shops and galleries on St. George Street, and stop for a sweet treat or warm drink at a local café.
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In Jacksonville, start at the Riverside Arts Market (open Saturdays year-round) or stroll the San Marco Square boutiques for stylish, local holiday shopping.
Evening: Dinner & Lights
As the sun sets, it’s time to experience the magic that Northeast Florida is famous for — twinkling holiday lights reflecting off the water.
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In St. Augustine, take an evening walk or carriage ride through the historic streets aglow with thousands of white lights.
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In Jacksonville, enjoy a festive meal along the Riverwalk or Jacksonville Beach Pier, where many restaurants deck their patios with holiday decor.
Finish the night with a warm cocktail, glass of wine, or locally brewed beer while soaking in the relaxed, coastal holiday vibe.
Day Two: A Festive Coastal Adventure
Morning: Brunch & Beach Views
Start your day with a leisurely brunch — there’s no better way to enjoy a Florida winter morning. Jacksonville’s beachside cafés and Avondale bistros serve everything from Southern classics to fresh seafood. In St. Augustine, try one of the charming breakfast spots tucked into the historic district.
Afterward, take advantage of the comfortable weather with some outdoor exploring:
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Walk or bike along Vilano Beach, Atlantic Beach, or Ponte Vedra for a dose of sea breeze and sunshine.
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Prefer something more nature-focused? Head to Anastasia State Park or Guana River Preserve for gentle trails, birdwatching, and stunning coastal views.
Afternoon: Shop Local & Soak in the Spirit
The holidays are the perfect excuse to shop local. Wander through artisan markets and independent boutiques to find one-of-a-kind gifts and souvenirs.
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In St. Augustine, the narrow lanes of the historic district are filled with local artisans selling handcrafted jewelry, art, and décor.
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In Jacksonville, head to Riverside or Murray Hill for quirky boutiques, vintage finds, and local pop-ups.
Take a break midafternoon with a stop at a local coffee shop or brewery — the region’s craft beverage scene is thriving, and many spots serve seasonal flavors.
Evening: Coastal Dining & Live Music
As night falls, treat yourself to a festive dinner. Choose from fresh seafood restaurants with ocean views, or cozy local spots tucked into historic streets.
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In Jacksonville, try one of the riverfront restaurants downtown or along Atlantic Beach Town Center.
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In St. Augustine, enjoy dinner under the glow of café lights on Aviles Street, followed by dessert from a local bakery or gelateria.
Cap off the night with live music or local entertainment — from jazz in St. Augustine to acoustic sets in Jacksonville Beach, the area’s nightlife is lively but laid-back.
Day Three: Relax, Reflect, and Savor the Season
Morning: Slow Start & Scenic Stroll
After two days of exploring, enjoy a slow morning in your vacation home. Brew some coffee, make breakfast in your fully equipped kitchen, and maybe step outside to enjoy the crisp coastal air.
When you’re ready to venture out, take one last scenic stroll:
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Visit the Jacksonville Arboretum, Treaty Oak Park, or Castillo de San Marcos in St. Augustine for peaceful morning views.
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If you’re staying near the coast, a morning beach walk is the perfect way to soak in your final hours of sunshine.
Afternoon: Local Farewell & Farewell Lunch
Before you head home, stop for a farewell lunch at a local favorite — maybe fish tacos by the beach, or a casual downtown café where the locals gather.
If you’re leaving later in the day, consider a short side trip:
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Visit Fernandina Beach on Amelia Island for a dose of old-Florida charm.
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Or stop at one of Jacksonville’s breweries or coffee roasters for a final taste of the region to take home.
Evening: One Last Look
If you have time before heading out, return downtown to catch the lights one last time. There’s something special about watching the glow reflect on the water — a perfect way to wrap up your holiday weekend in Northeast Florida.
Holiday Highlights to Enjoy Anytime
Even if you’re not visiting during a specific event weekend, these local favorites are always worth adding to your itinerary:
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Waterfront walks along the St. Johns River or Matanzas Bay
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Local art walks and gallery nights in downtown districts
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Seasonal boat parades or dockside lights (check local listings)
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Farmers markets and open-air food vendors
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Historic tours and museums that bring the region’s story to life
Where to Stay: Cozy Holiday Retreats by Joseph Ellen Properties
Make your holiday weekend even more memorable with a stay at one of Joseph Ellen Properties’ curated vacation homes across Northeast Florida. Each home is designed for comfort and convenience — offering spacious living areas, full kitchens for your holiday meals, and ideal proximity to the region’s best attractions.
Whether you’re:
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Hosting a family holiday getaway,
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Escaping for a romantic long weekend, or
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Planning a friends’ holiday retreat,
You’ll find a space that feels like home — just with better weather and palm trees.
Explore our available homes in St. Augustine, Jacksonville, Ponte Vedra, and the surrounding areas at JosephEllenProperties.com.
Your Perfect Florida Holiday Awaits
Northeast Florida in November and December is all about balance — sunny days, cool evenings, festive lights, and peaceful moments by the water. Whether you fill your weekend with sightseeing, dining, and shopping, or simply relax in your vacation home with loved ones, you’ll experience the warmth and wonder that make this corner of Florida special.
So pack light, bring your holiday spirit, and let Joseph Ellen Properties be your home for the season.
Plan your holiday weekend getaway today — and discover why the holidays shine brighter on Florida’s First Coast.