Tripadvisor Is Giving Away an 8-Night Orlando Vacation Worth $15,000

Quick Facts: Tripadvisor Common Ground Orlando Sweepstakes

• The Common Ground Orlando Sweepstakes awards one winner and one guest an 8-night Orlando vacation with an approximate retail value of $15,000, according to Visit Orlando's announcement.

• The sweepstakes opened September 1, 2026, at 12:01 a.m. ET and closes December 31, 2026, at 11:59 p.m. ET.

• Entrants must be legal residents of the United States, Washington, D.C., Canada, Mexico, or the United Kingdom and at least 21 years old at the time of entry.

• Each person may enter the sweepstakes only once, and no purchase is necessary.

• The prize covers round-trip airfare for two, eight nights at a hotel or resort of the winner's choice, and a travel planning session with a Visit Orlando vacation planner.

• Any money left from the $15,000 budget after flights and hotel are booked is issued to the winner for theme parks, attractions, and other trip expenses.

• The sweepstakes is tied to Common Ground: Orlando Edition, a three-episode Tripadvisor series on YouTube featuring Ricardo Kaká, Joey Fatone, Michael James Scott, and other Orlando-connected celebrities.

• Tripadvisor LLC is the official sponsor of the Common Ground Orlando Sweepstakes.

What the $15,000 Orlando Prize Covers

How would you spend $15,000 on an Orlando vacation? This prize gives you plenty of say. It includes round-trip flights for two, eight nights at a hotel or resort of your choice (double occupancy), and a session with a Visit Orlando vacation planner to help you put it all together.

Once your flights and hotel are paid for, you get the rest of the money. The official rules give this example: if those bookings cost $7,000, you’ll receive the remaining $8,000 to spend on theme park tickets, attractions, meals, and whatever else makes your vacation.

That leaves you with a pretty fun decision. Pick a more affordable hotel and have more money for restaurants and park days, or put more of the budget toward that resort you’ve always wanted to try.

One practical detail before you start dreaming: the winner is responsible for applicable taxes. Check the official rules for the full prize details.

Common Ground: Orlando Edition Celebrity Episodes

The sweepstakes celebrates the launch of Common Ground, a new video series that follows familiar faces as they explore Orlando together. Created by Tripadvisor’s creative studio, Wanderlab, the show pairs celebrities with Orlando ties for unscripted conversations along the way.

Visit Orlando is the series’ first destination partner, and all three episodes debuted on September 1, 2026. Here’s who you’ll see in each episode and where they stop along the way.

Episode 1: Featuring Ricardo Kaká & Rafaelle Souza

Brazilian soccer legend Ricardo Kaká, who spent three seasons with Orlando City SC, teams up with Orlando Pride defender Rafaelle Souza. They tour Inter.co Stadium in the Parramore District, visit Grand Cypress Golf Club, stop by Conrad Orlando at Evermore Orlando Resort, and finish at BOIBRAZIL Churrascaria Steakhouse.

Ricardo Kaká and Rafaelle Souza at Inter.co Stadium, home of Orlando City SC and the Orlando Pride. Image source: Tripadvisor / Visit Orlando

Episode 2: Featuring Joey Fatone & Richard Blais

Former *NSYNC member and Orlando local Joey Fatone heads out with Top Chef All Stars winner Richard Blais. Stops include Universal Orlando Resort, where Fatone got his start; Blais's MICHELIN-recommended Four Flamingos at Hyatt Regency Grand Cypress; and Crooked Can Brewing Company at Plant Street Market in Winter Garden.

Joey Fatone and Richard Blais outside Universal Studios Florida, where Fatone got his start. Image source: Tripadvisor / Visit Orlando

Episode 3: Michael James Scott & The Valentine Brothers

Broadway's Michael James Scott, an Orlando native best known as the Genie in Disney's Aladdin, joins Pat and Zach Valentine, the Valentine Brothers, whose social content raises awareness about Down syndrome. They visit the Dr. Phillips Center for the Performing Arts, Lineage Coffee Roasters in the Mills 50 District, the swan boats at Lake Eola Park, and The Monroe in Parramore.

Michael James Scott and the Valentine Brothers take a swan boat out on Lake Eola. Image source: Tripadvisor / Visit Orlando

All three episodes are streaming on Tripadvisor's YouTube channel, and Visit Orlando's episode guide includes a map of every featured stop.

How to Enter the Orlando Sweepstakes

Entry runs through a short online form on Tripadvisor's sweepstakes page.

1. Fill in your first name, last name, email address, and ZIP code.

2. Check the box confirming you're at least 21 and agree to the Official Rules.

3. Check the box accepting Visit Orlando's and Tripadvisor's privacy and terms policies.

4. Opt in to Visit Orlando's marketing emails only if you want them. That box is optional.

5. Hit Submit.

The limit is one entry per person for the entire sweepstakes, so there's no daily re-entry and no reason to submit twice. Entries close Thursday, December 31, 2026, at 11:59 p.m. ET.

Legal U.S. residents, including Washington, D.C., can enter, along with residents of Canada, Mexico, and the United Kingdom. Every entrant must be 21 or older on the day they enter, and the sweepstakes is void where prohibited. If you're already thinking about who gets the second plane ticket, read the guest terms in the official rules first.

Planning Eight Nights in Orlando Beyond the Theme Parks

With eight nights in Orlando, you don’t have to squeeze everything into back-to-back park days. Spend a few days on the rides, leave time to recover by the pool, and explore some of the places featured in the series.

For food inspiration, start with Joey Fatone and Richard Blais’s episode. Book a meal at Four Flamingos at Hyatt Regency Grand Cypress, or spend an afternoon browsing the local vendors and grabbing a craft beer at Plant Street Market in Winter Garden.

Michael James Scott’s episode offers more ideas beyond the parks. Take a swan boat out on Lake Eola, catch a show at the Dr. Phillips Center for the Performing Arts, or head to Mills 50 for coffee, street art, and something good to eat.

Iced coffees all around at Lineage Coffee Roasters in the Mills 50 District. Image source: Tripadvisor / Visit Orlando

After a few days of rides and theme park crowds, a slower day might sound pretty good. Wekiwa Springs State Park in Apopka is about 30 minutes northwest of downtown Orlando, making it an easy escape for a swim and some time outdoors.

The spring stays around 72°F year-round, which feels especially refreshing on a hot Florida afternoon. Bring a picnic, take a dip, or rent a canoe or kayak to explore the Wekiva River at your own pace. Just get there early on summer weekends, because the park fills up quickly.

Kayaks waiting at the water's edge at Wekiwa Springs State Park, about 30 minutes from downtown Orlando

Soccer fans have another reason to check the calendar before booking. Catching an Orlando City or Orlando Pride home match at Inter.co Stadium puts you right where Kaká and Rafaelle Souza filmed their episode, with a crowd cheering around you.

And you don’t have to figure out the whole trip yourself. The prize includes a free session with a Visit Orlando vacation planner, so you can get help fitting your must-dos into the eight-night stay, with a little room to relax, too.

Plenty of travel sweepstakes lock you into fixed dates and a hotel someone else chose, and this one doesn't. Letting the winner pick the hotel and pocket the difference puts the decisions in the traveler's hands, and that's exactly what makes a trip feel like yours. It's a one-time entry that takes a minute, there are still weeks left before the deadline, and the series is a fun watch even if your name never gets drawn.

Frequently Asked Questions: TripAdvisor Orlando Sweepstakes

When does the Tripadvisor Orlando sweepstakes end?

Entries close Thursday, December 31, 2026, at 11:59 p.m. ET.

How many times can I enter?

The official rules allow one entry per person for the entire sweepstakes.

Do I have to buy anything to enter?

No purchase is necessary to enter or win.

Who is eligible to enter?

Legal residents of the U.S. (including Washington, D.C.), Canada, Mexico, and the United Kingdom who are 21 or older at the time of entry.

Does the prize include theme park tickets?

Not directly, but any money left from the $15,000 budget after flights and hotel are booked goes to the winner to spend on theme parks, attractions, and other expenses.

Can the winner choose their own hotel?

Yes, the rules give the winner eight nights at a hotel or resort of their choice, double occupancy.

Where can I watch Common Ground: Orlando Edition?

All three episodes are free to stream on Tripadvisor's YouTube channel and on Visit Orlando's website.