May: Bringing That Summer Energy
May is that in-between month we secretly love. The rush of spring starts to soften, summer is still a promise on the horizon, and everything feels just a little more open—longer evenings, looser schedules, and last-minute “why not go?” decisions.
At Legacy Vacation Resorts, we don’t think May is a transition month. We think it’s the sweet spot. The calm before peak summer energy, where each destination starts showing off in its own way.
Here’s what we’re seeing across our resorts this month—and why it might be the best time to show up before everyone else does.
Orlando, Florida — The “soft launch” of summer energy
Orlando in May is a bit of a hack. The crowds haven’t fully arrived, but the sunshine absolutely has. The parks are buzzing, but not overwhelming. And the city feels like it’s quietly gearing up for its busiest season without the chaos just yet.
At our resort, May is about early pool days, relaxed mornings, and being close enough to everything without feeling like you’re in the middle of everything.
Things to do in Orlando in May
- Walt Disney World Resort – classic parks with shorter wait times than summer
- Universal Orlando Resort – rides, immersive worlds, and CityWalk nightlife
- ICON Park – skyline views, dining, and evening energy
- Lake Eola Park – walking paths, swan boats, and downtown sunsets
- International Drive – attractions, dining, and entertainment corridor
- Leu Gardens – quiet botanical escape near the city
Between park days and city outings, your stay matters just as much as your itinerary.It’s all about pool days, relaxed mornings, bbq’s, and being close enough to everything without feeling like you’re in the middle of everything. The best part, our suites have full kitchens, large living spaces, and spacious rooms to reset between sunny, high- energy days.
Start summer early—lock in your Orlando stay at Legacy before peak season hits.
Kissimmee, Florida — Where May feels like a local secret
Kissimmee has its own rhythm in May. It’s warmer, yes—but it’s also slower in the best possible way. Think evening walks, easy access to nearby attractions, and that “we planned this perfectly” feeling when you realize you’re just minutes from everything, but not stuck in the noise of it all.
Things to do in Kissimmee in May
- Walt Disney World Resort – minutes away from your stay
- SeaWorld Orlando – rides, shows, and marine life experiences
- Old Town Kissimmee – dining, entertainment, and classic Florida energy
- Gatorland – iconic wildlife attraction
- Lake Tohopekaliga – boating, sunsets, and lakeside downtime
- Shingle Creek Regional Park – trails and natural Florida scenery
After full days out, Kissimmee becomes about recovery as much as exploration. Suites give you kitchen space for easy meals instead of eating out every night, living areas to actually relax in, and resort amenities like pools where the day slows down naturally. It’s the difference between staying near everything—and feeling like you can breathe between it all.
It’s the kind of stay where May feels like a personal discovery rather than a travel destination.
Claim your May escape—Kissimmee is waiting quietly (for now).
Palm Coast — Sun-washed days, no itinerary required
Palm Coast in May doesn’t try too hard—and that’s exactly the point. It’s warm, breezy, and perfectly unhurried. While it’s not directly on the beach, it’s close enough to let you decide how “coastal” you want your day to be.
Some guests head out to nearby shorelines, others stay local and lean into golf days, quiet mornings, and long afternoons that don’t ask for much planning at all.
May here is less about checking boxes and more about loosening your schedule.
Things to do near Palm Coast in May
- Washington Oaks Gardens State Park – coastal gardens and scenic shoreline trails
- Marineland Dolphin Adventure – nearby marine experiences
- Flagler Beach – laid-back coastal town atmosphere
- A1A Scenic Coastal Drive – iconic Florida road trip route
Here, the resort experience naturally matches the destination. Your stay becomes part of the slowdown—pool time, open space, and the ability to move at your own pace without pressure to constantly be out.
Slow your May down in Palm Coast.
Steamboat Springs — Mountain air, still-calm trails, and the pre-summer glow
LVR- Steamboat Springs Hilltop
Steamboat in May feels like the mountains taking a deep breath before summer arrives. The views of Mt. Werner are still dramatic, the air is still crisp, and the town is in that peaceful in-between where locals know they’ve got something special before the summer wave rolls in.
Things to do in Steamboat Springs in May
- Steamboat Ski Resort – Mt. Werner views and gondola rides
- Fish Creek Falls – waterfall hikes and spring runoff views
- Downtown Steamboat Springs – local dining and mountain-town atmosphere
- Yampa River Core Trail – scenic walking and biking paths
It’s a great month for scenic drives, quiet mornings, and catching the last hints of spring before everything turns green and lively again.
Catch Steamboat in its calmest season—before summer shows up and changes everything.