Memorial Day Weekend has always been considered the unofficial kickoff to summer, and getting away for the long weekend is a tradition that may have you considering a vacation in Kissimmee! Offering a plethora of exciting Memorial Day activities while still maintaining a quiet hometown feel, the only thing better than spending the holiday in Kissimmee would be spending the holiday in one of our Memorial Day escapes at Tropical Escape Vacation Homes! Come explore the magic of the “theme park capital of the world” while exploring the softer side at home with us and discover what could be a new holiday tradition for your family. This guide to spending Florida Memorial Day in Kissimmee will give you the tools to enjoy a vacation filled with excitement, relaxation, and dreams that come true!

Orlando Carnival Downtown, May 26 through May 29

America is a melting pot of people and traditions from all over the world, and this Caribbean-themed festival is the perfect example for those who expected to spend this holiday exploring more all-American options. Offering the food of the islands, live music, handmade gifts, and a party that you would kick yourself for missing, you don’t have to spend every day of your getaway exploring the treats and fun found at Orlando’s best three-day party, but you may want to!

Memorial Day 4-Day Weekend, May 27 through May 30, Margaritaville Boulevard, Kissimmee

Because Orlando and Kissimmee are so close, we tend to appropriate their events as our own, but this extended celebration is all Kissimmee. Lasting four beautiful days, each more fun-filled than the one before it, guests can expect this party to rock their socks off! Gorge yourself on delicious food, sing along to the songs that are constantly playing, (This event offers non-stop music!) and find your newest obsessions in the Car Show and Craft Markets that line the streets. The highlight of this fantastic street party, however, will be the Sunset Promenade, taking place every night at sunset, in which they pay homage to the men and women of our military who have sacrificed everything so we can enjoy the freedoms they protected.

All That Disney Has to Offer

You’re going to be in the area for a few days at least, and chances are you will want to spend at least one day exploring the house the mouse built, and surprisingly, Memorial Day Weekend isn’t one of the busiest days of the year! The crowds are smaller, making the park more manageable, but the fun is not lessened. Ride the rides, eat the food, and enjoy the magic of Disney as you participate in an all-American activity that stays American, even as the magic spreads to other parts of the world. The parade that runs down Main Street every evening may even offer some red, white, and blue thrills that will make this day even more special.

Make It Personal

We are all linked to the fallen heroes to which this day is meant to pay homage, and you may be wanting a more personal, more meaningful way to do so. If this is the case, a visit to Orlando Veteran’s Memorial Park at 2380 Lake Baldwin Lane should be moved to the top of your Memorial Day bucket list. Open every day from 5 AM until sunset, this worthy park offers a paved walking path, lake views, a gazebo, and a memorial that honors all those who have sacrificed their lives for our country. Shaded by mature trees, there is no cooler way to pay homage to the heroes.

An All-American Barbecue

We all know the traditional celebration for all of the summer holidays begins with an all-American barbecue, and that is a tradition you won’t have to skip just because you chose to travel over this holiday! Our Tropical Escape Vacation Homes holiday havens provide the perfect backyards for the most beautiful barbecue ever, featuring private and resort pools, barbecue grills, and lounge chairs on which you can devour the burgers you grilled while relaxing in the Florida sun. Whip up mojitos in the fully equipped kitchens, watch the Indianapolis 500 in air-conditioned coolness on state-of-the-art televisions, and gather with the family around large dining room tables, constructing puzzles, playing boardgames, and tightening the bonds that draw you and your family closer together.

When the sun sets and the kids are deeply asleep in themed bedrooms, head outside for one more mojito and some quiet moments enjoyed with the human you call yours and discover why there is no place else on earth you would rather be! As the night grows later and your eyes grow heavier, the premium beds inside your home sweet vacation home will call to you, promising a night filled with deep sleep and happy dreams. Be sure to answer the call, because tomorrow brings another day of exciting adventures, and you want to be refreshed and ready for them. Reserve your favorite Florida Memorial Day escape and contact us today!

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