Top Orlando Holidays in 2026

Enjoy a pub crawl like no other in Winter Haven’s Chain of Lakes region. Meet your helmsman guide at the first stop, and order your first round of drinks. Then, hop aboard your pontoon with just a small group for company, and hit the water. You’ll travel by boat to four other popular bars and restaurants, and will have the chance to order drinks and bites at every stop (own expense).

The Moonshine Mixology Class is an island-themed experience where you'll learn to craft 2 tropical cocktails using signature Moonshine. The class includes: A hands-on lesson to make 2 signature cocktails A tasting flight of 6 craft island rums Led by expert mixologists, you'll discover the techniques and secrets behind making perfect island-inspired drinks.

Add a coastal Christmas night to your Orlando vacation. Depart Florida Mall at 6 p.m. for a shared minibus outing to Florida’s Space Coast, with round-trip transportation, a local driver-host, hot cocoa and cookies included. Enjoy seasonal neighborhood lights around Cocoa Beach and Satellite Beach, from decorated homes to palm-lined streets dressed for the holidays. The driver chooses the evening’s route, with short photo stops where safe and permitted. Relax on the ride back to the same Florida Mall boarding point; allow approximately five hours in total. Travel with up to 14 guests. Shared service may include coastal boarding stops. Tell CBT about child-seat needs and food allergies in advance so suitable arrangements can be confirmed. Individual homes, displays and stops vary by date, weather and local access. Holiday attire suggested.

If you want to spice up your work week or vacation with some spooky spirited fun, join us for our Haunted Pub Crawl! Experience up to two hours of haunting, history, and spirits of both kinds as you hop from one of Orlando's four favorite neighborhood bars to a number of haunted locations. On this excursion, you will stop at four bars in Orlando, some of which may be neighborhood bars and boutique distilleries. Between these well-known clubs and pubs, there will be additional creepy stops! Each stop will take between 15-20 minutes to an hour. Season and day of the week have an impact on the exact lineup.

Explore the spooky side of Downtown Orlando on this haunted pub crawl. Join a Ghost Ambassador to uncover chilling tales as you visit lively bars and enjoy the vibrant atmosphere. This social adventure allows you to mingle with fellow ghost enthusiasts while using K2 meters to sense the spirit world. Enjoy drink specials and grab quick appetizers at select stops while keeping the night moving. This ghostly experience lasts 2–3 hours, making it a perfect outing for those aged 21 and over looking for a unique night out. - Engage in storytelling and socializing at haunted bars - Use K2 meters for a touch of ghostly interaction - Enjoy drink specials and quick appetizers at select stops - Perfect for groups of 6 or more with private tour options available - Pictures of your outing are included FREE of charge

Consistently voted as one of the best holiday lighting displays in the world, St. Augustine's Nights of Lights celebration is sure to put even the biggest scrooge in the holiday spirit. Tour the millions of lights on the Jolly Holiday Trolley, and enjoy warm winter treats such as apple cider and homemade cookies on this day tour from Orlando.

Enjoy the haunted tales of ghostly experiences in Historic Downtown Sanford while sipping some delicious craft beer from three popular craft beer establishments. This tasting tour starting at 8:30 PM is led by our BJCP Certified Beer Judge, Gary Holmes. Learn historical stories gathered from the people who live in Sanford themselves while getting intimate with our local brewers and Sanford craft beer. Please keep in mind that we are NOT ghost-hunting! *Beer samples are included as part of this tour. All participants on tour must be 21 years of age and fill out a digital waiver.

Dive into adventure, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, this Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! Every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!

Our ship, the "Barbara-Lee", is an authentic paddle-wheeler which travels across Lake Monroe and up the beautiful St. Johns River. Live entertainment is a part of every cruise. For our Friday night Rocking on the River cruises, we host a variety of local bands, DJs, Musical Bingo nights, and more! All meals are prepared fresh in the galley. For this cruise, we will have our a la carte menu available for purchase. This menu includes nachos, wings, sandwiches, and more! A full cash bar is also provided onboard. With three dining levels and the flexibility of table setting, it is the perfect setting for anniversary and birthday celebrations. **Boarding for this cruise begins 1 hour prior to the cruise time

"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure! "

Orlando may not be known for its snowy winters, but thanks to a little Disney magic, visitors can still get into the holiday spirit during this tour. From life-sized gingerbread houses at the Walt Disney World Resort to slides crafted out of ice at Gaylord Palms Resort, this kid-friendly tour takes you to the most enchanting holiday attractions in Orlando. Plus it includes all transportation via bus with pickup and drop-off from select Orlando hotels and a parka rental for the ice attractions.

Sanford sits just north of Orlando and is a favorite watering hole for locals who love a bit of history with their craft beer. This Sanford craft beer and history tour showcases the best of both. Stroll through this small city’s streets, uncovering facts about its history with prohibition. As you walk, you’ll pop into three local breweries for sips of their best beers.

Your tour guide is a gifted storyteller and certified tour guide who has been giving ghost tours for over a decade. On this tour we will learn the rich history of Winter Haven including it's spooky hauntings and ghost stories.

Spend the morning birding in central Florida on this private half-day tour. Enjoy hotel pickup around the Orlando area or meet in Whittier. Hike and bird the Three Lakes WMA and Joe Overstreet Landing with a certified master naturalist, spotting species like Bald eagles, raptors, Painted Bunting, and Florida Scrub-jay.