By Kate Cohen
October 13, 2026
Orlando is the perfect place for bleisure.
This word perfectly encompasses the balance between business and leisure travel, where productivity isn’t just on the clock and free time feels like a vacation.
There’s a reason some of the country’s biggest conferences and conventions choose Orlando as a host city, especially in winter months when the weather is absolutely gorgeous.
If you’re coming to Orlando for a business trip, extending your stay by even a day or two can transform a routine work trip into a well-deserved getaway.
And, if you’re attending an event at the Orange County Convention Center (OCCC), staying at Rosen Plaza allows you to seamlessly – and conveniently – blend business and leisure.
Here is how we recommend turning your Orlando business trip into a winter getaway.
Key Takeaways
- Start with the Right Home Base
- Take Advantage of Orlando’s Ideal Winter Weather
- Add an Extra Day or Two to Your Itinerary
- Explore International Drive After Meetings End
- Experience Orlando’s Holiday and Winter Season Events
- Venture Beyond the Convention Center
- Making the Most of Every Orlando Business Trip at Rosen Plaza
Start with the Right Home Base
The right hotel can make all the difference when it comes to travel. Convenience, comfort, and location are key.
Rosen Plaza is an Orlando hotel that offers all three.
The hotel is connected to the OCCC by a covered outdoor skybridge, meaning the city’s biggest events are mere steps away from the hotel.
When you’re not working, you can spend your time lounging by the beautiful pool with a cocktail from 39 Poolside Bar & Grill. Perhaps you’d prefer to savor an incredible meal at Jack’s Place or explore nearby attractions on International Drive.
Then again, once you see our newly renovated guest rooms, you may decide that you’d rather spend your free time in peaceful solitude, unwinding in stylish comfort.
The perfect bleisure hotel is one that seamlessly balances work and play so you can transform your business trip into an Orlando vacation.
In other words, the perfect bleisure hotel is Rosen Plaza.
Take Advantage of Orlando’s Ideal Winter Weather
Orlando’s winter weather is nothing short of beautiful, offering a warmer respite from northern forecasts and a welcome relief from the heat and humidity of summer in Florida.
Average winter temps tend to peak in the low- to mid-70s, while mornings and evenings are typically chillier and drop into the 50s. A few seasonal cold snaps are to be expected, so be sure to pack plenty of layers.
Central Florida’s mild winter weather is ideal for spending time at the theme parks, exploring local attractions, and taking advantage of outdoor dining opportunities.
Add an Extra Day or Two to Your Itinerary
Bleisure is a growing trend that reimagines professional travel.
Instead of spending your entire trip in work mode, you can make time to enjoy the destination.
Adding a day before or after your business event emphasizes a better work-life balance, provides more opportunities to unwind, and offers time for sightseeing without feeling rushed.
Even an extra 24 hours can dramatically enhance your travel experience, especially in Orlando, the most visited destination in the country.
A work event in Orlando can be a great excuse for a family theme park vacation, too. While you’re enjoying your event, family members can explore Central Florida’s best attractions.
Then, add a day or two to the end of your trip to enjoy world class theme parks. Walt Disney World Resort, Universal Orlando, and SeaWorld Orlando are just minutes away from Rosen Plaza.
Explore International Drive After Meetings End
After a productive day of networking and professional development, it’s time to enjoy Orlando’s exciting entertainment district.
International Drive (I-Drive) is an area of Orlando close to the theme parks that is packed with engaging attractions, diverse dining options, and vibrant nightlife.
Across the street from Rosen Plaza is Pointe Orlando, an entertainment complex with fun restaurants and lively bars. It’s also home to a Funny Bone Comedy Club, Regal Cinemas, WonderWorks, Main Event Entertainment, and other engaging experiences.
A bit further down I-Drive is ICON Park, home to the towering Orlando Eye observation wheel and a variety of other attractions. Here, you’ll find SEA LIFE Orlando Aquarium, Madame Tussaud’s wax museum, the Museum of Illusions, and so much more.
Take a stroll along I-Drive to find other great spots ideal for after-hours fun, including Dave and Busters, Howl at the Moon, and ICEBAR Orlando.
One of the best perks to staying on I-Drive is that you won’t need a rental car to explore the walkable area. If you do need transportation, rideshares are readily available, or you can take the I-RIDE Trolley for $2 per ride.
Experience Orlando’s Holiday and Winter Season Events
Here in Orlando, we love celebrating the holidays.
If you’re in town for business during the holiday season, there are plenty of reasons to extend your stay and enjoy the festivities.
Walt Disney World, Universal Orlando, and SeaWorld Orlando all celebrate the holidays with special events and beautiful decorations. It’s a special time of year to visit the theme parks, and a great reason to turn your business trip into a winter getaway.
But a trip to the theme parks isn’t the only way to get into the holiday spirit.
Every winter, the Harry P. Leu Gardens come to life with a spectacular light show called Dazzling Nights. This popular event is one of the best ways to experience Christmas lights in Orlando.
Other winter festivals include the Dr. Phillips Center Frontyard Holiday Festival, Wekiva Island’s Winter Wonderland, and Oh What Fun! Lake Nona.
Venture Beyond the Convention Center
There is so much to enjoy in Orlando between conference events and meetings, even if you have limited free time.
Take advantage of the beautiful weather and explore Central Florida’s diverse outdoor ecosystems.
Visit Wekiva Island for a day of kayaking or canoeing along a river teeming with wildlife. Then, pull up an Adirondack chair overlooking the water and kick back with a refreshing beer or glass of wine.
Take time to explore one of Orlando’s beautiful walking trails like the Tibet-Butler nature preserve, part of the Great Florida Birding and Wildlife Trail.
Winter is also the perfect time to play golf in Orlando. Book a tee time at Shingle Creek Golf Club, a championship course surrounded by scenic hills, trees, and water features.
If you still have holiday shopping to do, check out some of Orlando’s best shopping destinations.
Close to the I-Drive District are two excellent outlet malls: Orlando International Premium Outlets and Orlando Vineland Premium Outlets. At either spot, you’ll find fabulous deals on popular brands that will help you cross every name off your shopping list.
Disney Springs is another wonderful shopping destination. This Disney-owned complex is home to name brand stores, specialty boutiques, exciting entertainment, and great dining options.
The best part? There’s no cost to visit Disney Springs – even parking is free.
Making the Most of Every Orlando Business Trip at Rosen Plaza
Your flight is already booked. Your work obligations are covered. You’re ready for your work trip to Orlando.
The city’s unique combination of business infrastructure and world-class attractions makes it one of the best destinations to combine work and play. Staying a few extra nights can create a rewarding and memorable travel experience that balances both business and leisure.
As a guest at Rosen Plaza, you can enjoy a blend of productivity, relaxation, and entertainment.
When you stay so close to the OCCC, you’ll save time on commuting that is better spent enjoying everything Orlando has to offer.
Check out our renovated accommodations, resort-style pool, onsite dining options, and convenient location to see what makes us the obvious choice for your Orlando business trip.
We look forward to seeing you this winter.