Orlando · WINTER ACTIVITIES

9 Winter Trips near Orlando, Priced and Compared

9 tours  ·  from $42 per person

Here are 9 winter trips that earn a slot in an Orlando week, each with its price, its traveller verdict and the one detail to check before you pay.

Winter Park Chain of Lakes Day Time Clear Kayak Paddle - Choosing a departure time and setting expectations
Orlando Kayak Tours, Tour Reviews, Tours in Orlando, Winter Activities

Winter Park Chain of Lakes Day Time Clear Kayak Paddle

1.Winter Park Chain of Lakes Day Time Clear Kayak Paddle

★★★★★★★★★★5.0 · 216 reviews · from $69Top choice

Set out from Dinky Dock Park in a clear kayak for a roughly two-hour guided paddle through Winter Park’s lakes and Venetian-style canals. You’ll pass waterfront homes and natural areas, with chances to spot local wildlife and hear about the area. Groups are capped at 10, and guides have included Cameron, Rosa, Keith, Chad, Jansen, and Ryan.

“This was a beautiful experience! This was my first time on a Kayak but not the last. The park has limited parking, restrooms and plenty of space to relax and take in the sun. We circled the parking lot a few times to catch people leaving. Read more”

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Clear Kayak Sunset Tour through The Winter Park Chain of Lakes - Sunset on the open water
Evening Experiences, Orlando Kayak Tours, Tour Reviews, Tours, Tours in Orlando, Winter Activities

Clear Kayak Sunset Tour through The Winter Park Chain of Lakes

2.Clear Kayak Sunset Tour through The Winter Park Chain of Lakes

★★★★★★★★★★5.0 · 198 reviews · 2 hours (approx.) · from $80

Set out from 410 Ollie Ave in Winter Park for an approximately two-hour clear-kayak paddle through narrow, Venetian-style canals and connected lakes. Your guide leads the way, shares local history and stories about the grand lakeside homes, and helps you look for birds and fish as the light softens toward sunset. Kayak, life jacket, and whistle are included.

“We had a wonderful time kayaking the Winter Park lakes. The weather was perfect. Chad was our guide and he was very personable and helpful on our tour. He gave us local history and guided us through all the canals. That was the best part and the sunset!!”

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Clear Kayak Glow in the Dark Tour Through Winter Park - What you can see through the kayak
Cocoa Beach Bioluminescence Tours, Orlando Kayak Tours, Tour Reviews, Tours, Tours in Orlando, Winter Activities

Clear Kayak Glow in the Dark Tour Through Winter Park

3.Clear Kayak Glow in the Dark Tour Through Winter Park

★★★★★★★★★★5.0 · 102 reviews · 1 hour 30 minutes (approx.) · from $90

Set off near Rollins College in a clear, illuminated kayak and paddle Winter Park’s connected lakes and canals with a guide. You’ll get the kayak, paddle, life jacket, and whistle, plus basic instruction if you’re new to paddling. Look for fish and plants below the boat, birds along the water, and large homes on shore. The outing lasts about 90 minutes and returns to the starting point.

“Chris was an awesome guide and so friendly! Such a peaceful and beautiful trip! Would highly recommend!”

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Flavors of Winter Park Foodie Walking Tour - What happens between 10:45 and the final tasting
Orlando Food Tours, Orlando Walking Tours, Tour Reviews, Tours, Tours in Orlando, Winter Activities

Flavors of Winter Park Foodie Walking Tour

4.Flavors of Winter Park Foodie Walking Tour

★★★★★★★★★★4.5 · 42 reviews · 2 hours 30 minutes (approx.) · from $66

Walk Winter Park with an English-speaking guide, hearing stories about Park Avenue, local history, and notable visitors while sampling food and drinks at about six stops. Tastings can include sweets, savory bites, and wine. The 2.5-hour tour starts at 10:45 am, costs $66.84 per person, and is limited to 16 people.

“Our Tour guides did a great job and we’re very informative. They worked well together. The food samples were very good but the portions as most places were quite small. We were given wrist bands that we could go back to the places we visited and would receive a 10% discount. Nice perk except the restaurant we went back to, The Bridge, would not honor that offer. Despite that, the food was delicious! We learned a lot about Winter Park, had a nice time and ate some yummy food.”

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Winter Park Paddle Board Tour - Wildlife watching, with reasonable expectations
Orlando Kayak Tours, Tour Reviews, Tours, Tours in Orlando, Winter Activities

Winter Park Paddle Board Tour

5.Winter Park Paddle Board Tour

★★★★★★★★★★5.0 · 14 reviews · 2 hours (approx.) · from $59

Paddle the Winter Park Chain of Lakes on a two-hour guided outing from Kraft Azalea Garden. Choose a day or sunset tour, follow canals beneath leafy branches, and watch for birds, turtles, otters, and more. Boards, safety gear, instruction, a dry bag, and photo and video package are included. Guides have included Rachelle and Celia.

“Amazing day! Great way to end our trip - Celia was amazing. Highly recommend to anyone who enjoys the water and nature.”

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Flavors of Winter Haven Food Tour - SmokinOX adds smoked meat and Southern flavors
Food & Drink, Orlando Food Tours, Tour Reviews, Tours, Tours in Orlando, Winter Activities

Flavors of Winter Haven Food Tour

6.Flavors of Winter Haven Food Tour

★★★★★★★★★★4.5 · 10 reviews · 3 hours (approx.)

Amada Anderson’s three-hour Winter Haven tour pairs downtown food tastings with local stories and landmarks, including Gram Parsons’ Derry Down and the original Publix site. Expect a changing mix of coffee, burgers or barbecue, Thai dishes, and gelato. It starts at 2 pm, is limited to 10 people, and includes lunch, snacks, and coffee or tea.

“Our host was very nice and knowledgeable about Winter Haven. The food was good and we learn a lot about Winter Haven”

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Winter Haven Guided Brunch Tour - Should you book the Winter Haven brunch tour?
Guided, Tour Reviews, Tours, Tours in Orlando, Winter Activities

Winter Haven Guided Brunch Tour

7.Winter Haven Guided Brunch Tour

★★★★★★★★★★4.5 · 10 reviews · 3 hours (approx.)

Join guide Amada Anderson for a small-group, three-hour walking brunch tour through downtown Winter Haven. Taste coffee, cupcakes, brunch dishes, olive oils, pizza, and bakery treats, while seeing the original Publix site, the Ritz Theater, and other local landmarks. The tour is in English, with a maximum of 10 people.

“This was a very fun and informative tour. Amada was a very informative and personable tour guide. We learned a lot about Winter Haven and found the town to be delightful. The food was very good but we did have to wait quite a while for it to be prepared at 2 different places. Possibly better coordinating food prep with arrivals at locations. The only negative was the 2 hour drive back to Orlando in traffic after the tour. I would highly recommend this brunch tour.”

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Private Winter Haven Chain Fishing Charter in Central Florida - What the four-hour trip feels like
Orlando Fishing Charters, Private, Tour Reviews, Tours in Orlando, Winter Activities

Private Winter Haven Chain Fishing Charter in Central Florida

8.Private Winter Haven Chain Fishing Charter in Central Florida

★★★★★★★★★★4.0 · 8 reviews · 4 hours (approx.)

Meet your licensed local captain at Lake Summit Boat Ramp for a private bass-fishing charter on Winter Haven’s Chain of Lakes. You’ll have rods, reels, tackle, safety equipment, ice, and bottled water provided. The four-hour option costs $475 for up to two people; longer trips, from four to 12 hours, are also offered.

“Travelled from Missouri all the way to Orlando on fiancé’s birthday. We drove an hour to get to the charter and arrived to the location 2 hours early only to find out that no one was coming. Called they said they never got the booking even though we had the confirmation number and emails. It sucked because we were super excited for the trip.”

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Ghosts of Winter Park - A Chilling Walking Tour! - What the walking route can and cannot promise
Orlando Walking Tours, Tour Reviews, Tours, Tours in Orlando, Winter Activities

Ghosts of Winter Park – A Chilling Walking Tour!

9.Ghosts of Winter Park – A Chilling Walking Tour!

★★★★★★★★★★5.0 · 4 reviews · from $42Lowest price on this list

At 7:30 pm, a guide leads you through Winter Park’s old brick streets and sites tied to ghost stories, unsolved mysteries, and the town’s founders. Hear tales of a stage actress, an artist, and German prisoners of war. The walk lasts about 90 minutes, starts and ends at 401 S Park Ave, and has a 30-person limit.

“We visited a couple weeks ago and had a great time. Luckily for us it was only me and my boyfriend on the tour so it was so private which I liked. The two tour guides were very knowledgeable and nice. We had a fun and spooky time”

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