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Last-Minute Labor Day Fun: Your Ultimate Kissimmee Trip Itinerary

Can you believe August is almost over? If you’re like me, you might be tempted to squeeze in one last family adventure before the school craziness fully takes over in September. Well, I’ve got the perfect solution—how about a quick Labor Day weekend getaway to Kissimmee near Orlando, FL? Trust me, this place has something for everyone, and it’s just a hop, skip, and a car ride away from Boca Raton! So, let’s dive into our ultimate Kissimmee trip itinerary, shall we?

 

Your Ultimate Kissimmee Trip Itinerary

Kissimmee Trip Itinerary Labor Day Travel Idea

Friday, August 30th: Sunset Walk Vibes

Start your weekend off right with the Labor Day Weekend Celebration at Promenade Sunset Walk in Margaritaville. Picture this: live music filling the air, mesmerizing street performers captivating your kids, and an artisan market offering all sorts of goodies. It’s the perfect way to ease into the holiday weekend spirit and let the summer vibes roll!

Saturday, August 31st: Adventure Galore

Saturday is your designated day for adrenaline and adventure! Head over to Revolution Adventures for some morning excitement. Whether it’s off-roading, clay shooting, or simply soaking in the outdoors, there’s something for everyone—even the little daredevils in your family.

Kissimmee Trip Itinerary Labor Day Travel Idea

Kissimmee Trip Itinerary Labor Day Travel Idea

Kissimmee Trip Itinerary Labor Day Travel Idea

After a morning of thrills, take a trip to Old Town Kissimmee and Fun Spot America. This place is a nostalgic wonderland with classic rides that will make you feel like a kid again. And for a little spooky fun, don’t miss Mortem Manor, a year-round haunted house that’s just the right amount of scary.

Kissimmee Trip Itinerary Labor Day Travel Idea

Kissimmee Trip Itinerary Labor Day Travel Idea

Cap off your adventurous day with a royal feast at Medieval Times Dinner & Tournament, one of my all-time favorites as a child. Your kids will be wide-eyed with wonder as knights battle it out right before their eyes, and you’ll be digging into a meal fit for royalty (with your hands).

 

Sunday, September 1st: Gatorland Thrills

Sunday morning, get ready for an unforgettable animal adventure at Gatorland. From thrilling animal encounters to zip lining over a gator breeding pond, this place is a wild ride! It’s the perfect blend of education and excitement, making it a hit with both kids and adults.

Kissimmee Trip Itinerary Labor Day Travel Idea

After your gator-filled morning, head back to Promenade Sunset Walk for more Labor Day festivities. There’s always something happening, and it’s a great spot to relax and soak in the holiday atmosphere.

 

Monday, September 2nd: Leisurely Farewell

As your Kissimmee adventure winds down, start your Monday with a leisurely breakfast or a final stroll through Celebration Town Center. It’s the perfect way to wrap up your trip—relaxed, refreshed, and ready to head back home with a treasure trove of family memories.

So there you have it, Boca Moms—your ultimate Kissimmee trip itinerary! Packed with fun, adventure, and a little bit of relaxation, this Labor Day weekend getaway is just what you need to bid summer a fond farewell. Ready to pack your bags?

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Michelle Olson-Rogers, Modern Boca Mom Headshot

Michelle Olson-Rogers is the founder of Modern Boca Mom, a leading lifestyle site for the stylish & modern South Florida mommy. ModernBocaMom.com features local businesses, events, lifestyle and family travel options and was the proud winner of the 2019 Florida Blog Con Sunshine Award in the “Favorite Events/Neighborhood Blogger” category. Michelle is also a regular contributor to Boca Raton magazine.

 

In addition to blogging, Michelle also serves as a Community Consultant for Grandview Preparatory School, a private PK3-Grade 12 independent school in east Boca Raton. Her successful “Modern Boca Mommy & Me” program has been running there year-round since 2014.

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