Jacksonville, Florida is one of the most underrated weekend destinations in the Southeast. With its sprawling riverfront, miles of Atlantic beaches, eclectic neighborhoods, vibrant food scene, and outdoor adventure opportunities, Jacksonville (or “Jax,” as locals call it) offers something for every kind of traveler. Whether you’re into arts and culture, history, food, sports, or just soaking in the sun, Jax delivers an authentic Florida experience without the heavy tourist crowds.
Whether you’re a first-time visitor or a returning explorer, this two-day itinerary curated by Joseph Ellen Properties—a premier vacation rental property management company in Northeast Florida—gives you the perfect blend of city culture, coastal charm, and natural beauty. Whether you’re staying in one of our beautifully maintained rentals or simply exploring the area, this guide will help you make the most of your Jacksonville getaway.
Day 1: Urban Adventure Meets Coastal Vibes
Morning: Riverside & Breakfast with a View Start your weekend in the charming Riverside/Avondale Historic District, one of Jacksonville’s most beloved neighborhoods. Tree-lined streets, historic homes, and trendy coffee shops make it the perfect place to ease into your day.
Kick off your morning at Cool Moose Cafe, a cozy neighborhood favorite offering hearty breakfast classics and locally roasted coffee. Alternatively, Southern Grounds has an elevated brunch menu and fresh pastries in a relaxing garden setting.
After breakfast, take a stroll along the riverfront to the Riverside Arts Market (Saturdays only). Held under the Fuller Warren Bridge, this lively market is packed with local vendors selling handmade crafts, original artwork, farm-fresh produce, and unique culinary treats. Live music and food trucks complete the scene, making it a great spot to immerse yourself in local culture.
Just a few minutes away is the Cummer Museum of Art & Gardens. Overlooking the St. Johns River, the museum features European and American art as well as beautifully maintained gardens. It’s a peaceful yet inspiring place to spend your late morning.
Midday: Downtown Jax & the St. Johns Riverwalk Next, head to Downtown Jacksonville and explore the scenic Northbank Riverwalk. This pedestrian-friendly pathway runs along the St. Johns River and is dotted with public art, benches, parks, and skyline photo opportunities. It’s a relaxing way to take in the city’s urban beauty.
Art lovers should make a stop at MOCA Jacksonville (Museum of Contemporary Art), which hosts thought-provoking exhibitions by local and international artists. It’s conveniently located near James Weldon Johnson Park, another good spot for a break or quick people-watching session.
For lunch, locals love Bellwether, a modern American eatery serving creative burgers, grain bowls, and seasonal dishes. Burrito Gallery is another popular choice offering casual Mexican fare in an artsy setting.
If you’re in the mood for adventure, consider driving 25 minutes to Kayak Amelia for a guided paddle-boarding or kayaking tour. Navigate through serene tidal creeks and salt marshes, spotting local wildlife and learning about Northeast Florida’s rich coastal ecosystems.
Afternoon: Beaches Time! No trip to Jacksonville is complete without spending time at the beach. Drive east to the barrier islands where you’ll find three neighboring beach communities: Jacksonville Beach, Neptune Beach, and Atlantic Beach. Each has its own personality, with Jacksonville Beach offering more action and nightlife, while Neptune and Atlantic Beaches provide a more laid-back, residential vibe.
Not a beach fan? Hangout at a private pool offered by many of Joseph Ellen’s Properties’ homes!
Take a surf lesson, rent a beach cruiser bike, or simply lay out a towel and enjoy the ocean breeze. Most beaches have volleyball courts, fishing piers, and clean public access points. For a refreshing snack or light bite, try Jax Beach Brunch Haus or grab a smoothie bowl from Playa Bowls. The Local, just a few blocks inland, is another great option for wraps and salads.
While at the beach, take some time to visit local boutiques or grab a coffee at Bold Bean Coffee Roasters. Jacksonville’s beaches also boast a growing arts scene, with public murals and frequent open-air concerts.
Evening: Sunset, Dinner & Drinks As the sun sets, make your way to the rooftop bar at Casa Marina Hotel. Overlooking the Atlantic Ocean, this historic hotel is a prime spot to sip a cocktail and take in panoramic views of the coastline.
For dinner, you have several outstanding choices. Eleven South Bistro is perfect for a romantic evening, offering refined American cuisine in a warm, elegant setting. North Beach Fish Camp is beloved for its fresh seafood and lively ambiance. Salt Life Food Shack is a trendier, more casual option known for its sushi, tacos, and tropical drinks.
End your night with a stop at Green Room Brewing, a local brewery with a rotating selection of craft beers. Or check out Surfer the Bar, where you can enjoy live music, DJs, and an energetic beach crowd.
Day 2: Nature, History, and Local Flavor
Morning: Nature Hike or Wildlife Encounter Start your second day with an outdoor adventure. Jacksonville offers a wealth of green space and protected nature preserves.
Option 1: Explore the Timucuan Ecological and Historic Preserve. This sprawling 46,000-acre park features scenic hiking trails, marshlands, and historic sites such as Kingsley Plantation—a well-preserved antebellum estate that provides important insight into Florida’s colonial and plantation history.
Option 2: Visit the Catty Shack Ranch Wildlife Sanctuary. This non-profit sanctuary is home to rescued lions, tigers, cougars, and leopards. It’s an ethical and educational experience for animal lovers and families. Morning tours are quieter and offer a better chance to see the animals active.
For a more relaxed nature experience, visit the Jacksonville Zoo and Gardens, which is consistently ranked among the best zoos in the country. The zoo’s award-winning River Valley Aviary, giraffe feeding station, and themed garden trails make it an ideal stop for visitors of all ages.
Midday: Lunch in San Marco After your morning adventure, head to San Marco, one of Jacksonville’s most scenic and stylish neighborhoods. Known for its Mediterranean Revival architecture, San Marco Square is a hub for boutique shopping, fine dining, and charming streetscapes.
For lunch, enjoy artisan Italian cuisine at Taverna, where everything from fresh pasta to craft cocktails is done with flair. If you’re in the mood for something more casual, The Local offers gourmet sandwiches and creative comfort food.
After lunch, browse through the neighborhood’s unique shops, including bookstores, galleries, and fashion boutiques. If time permits, stroll along the nearby Southbank Riverwalk to catch riverfront views and maybe even spot dolphins swimming by.
You could also swing by the Theatre Jacksonville building, one of the oldest continuously running community theaters in the country. Check for matinee performances or simply admire the architecture.
Afternoon: Sports or Art Excursion Depending on your interests, spend your afternoon diving deeper into Jacksonville’s vibrant sports scene or creative community.
Sports Fan? Head to TIAA Bank Field to catch a Jacksonville Jaguars game during NFL season or a concert event. If you’re visiting in the summer, you might catch a Jacksonville Jumbo Shrimp minor league baseball game—a fun and budget-friendly outing for all ages.
Art Lover? Explore the Jacksonville Arboretum & Botanical Gardens, a peaceful escape with 120 acres of trails and themed gardens. Or visit The Art Center Cooperative downtown, which showcases the work of over 30 local artists and frequently hosts workshops and events.
You might also consider a stop at the historic Springfield neighborhood for a self-guided art and architecture walk. Known for its murals, restored Victorian homes, and creative spirit, Springfield is a great off-the-beaten-path destination for a Sunday afternoon.
Evening: Wrap It Up with a Memorable Meal For your final dinner in Jacksonville, treat yourself to a memorable meal that captures the essence of the city.
Option 1: Cowford Chophouse, located in a beautifully restored historic building downtown, offers premium steaks and seafood with skyline views from its rooftop bar.
Option 2: Orsay in Avondale is a French-inspired bistro with an elegant menu featuring oysters, duck confit, and craft cocktails.
If you’re still in the mood to explore, stop by River & Post for after-dinner drinks on their rooftop, which provides breathtaking views of the river and downtown skyline.
Cap off your weekend with a nightcap at The Volstead, a 1920s-style speakeasy downtown known for its expertly crafted cocktails, jazz ambiance, and vintage decor. It’s the perfect place to toast to a weekend well spent.
Bonus Tips for the Best Weekend Experience
Getting Around: Jacksonville is the largest city by land area in the continental U.S., so plan your transportation accordingly. Renting a car is often the easiest way to explore, though rideshare services are widely available.
When to Visit: Spring (March-May) and fall (September-November) offer ideal weather. Summer is hot and humid but perfect for beach lovers and water activities.
Local Events: Jacksonville hosts a variety of annual events and festivals, including the Jacksonville Jazz Festival, One Spark Innovation Festival, Art Walks, and food truck rallies. Check local calendars to see what’s happening during your visit.
Where to Stay: Choose accommodations based on your interests. For beach access, stay at a hotel in Jacksonville Beach or Atlantic Beach. If you prefer urban energy and walkability, look into boutique stays in Riverside, San Marco, or Downtown.
Whether you’re drawn to the surf, the art, or the rich diversity of neighborhoods, Jacksonville offers a fulfilling weekend getaway with more than meets the eye. With the help of this guide from Joseph Ellen Properties, you’ll experience the best the Bold City has to offer—and maybe even find a corner of Northeast Florida you’ll want to come back to again and again.
Looking to make Jacksonville a recurring part of your travel plans or just want a seamless vacation stay? Joseph Ellen Properties specializes in managing top-tier vacation rentals throughout Northeast Florida—from cozy beach cottages to luxurious city lofts. Whether you’re an investor seeking expert property management or a guest searching for the perfect weekend retreat, we’re here to help. Contact us today to learn more about how we can make your Northeast Florida experience unforgettable.