Orlando isn’t just about theme parks; it’s a city with a surprising amount of water-based fun. Whether you want to enjoy a lively pub crawl on the Chain of Lakes or unwind on a private sunset sail, there are plenty of options to get on the water. Our favorites include the Pontoon Pub Crawl, which combines socializing with scenic views, and the Private 2-Hour Sunset Sailing that offers a peaceful escape. For wildlife lovers, the 90 Minute Pontoon Cruise in Florida provides a chance to spot alligators and exotic birds. Whatever your style, Orlando’s boat tours promise memorable experiences on the water.
Quick Overview
This list covers a range of boat tours and cruises, from lively pub and wildlife excursions to private sunset sails and space-themed adventures. You’ll find group pub crawls and scenic wildlife cruises that highlight Florida’s natural beauty. For those interested in space, the Kennedy Space Center with Airboat Ride combines NASA history with swamp exploration. Families, couples, and solo travelers alike will find options suited to their interests and time constraints.
1. Pontoon Pub Crawl, 5 Lakeside Pubs and Restaurants Visit by Boat
Enjoy a pub crawl like no other in Winter Haven’s Chain of Lakes region. Meet your helmsman guide at Tanners Lakeside Restaurant & Bar, and then hop aboard a small-group pontoon. Over roughly three hours, you’ll visit five popular lakeside bars and restaurants, with the chance to order drinks and bites at each stop (own expense). The guide takes care of navigation so you can focus on soaking up the scenery and wildlife, including the chance of spotting alligators. Many reviews praise Captain Dave’s engaging personality and the personalized experience he provides, with a rating of 5.0/5 from 92 reviews. This tour appeals to those wanting a fun, social outing with wildlife viewing thrown in. It’s perfect for celebrating special occasions or just enjoying a laid-back day on the water.
Bottom Line: A lively, social way to explore Winter Haven’s lakes while enjoying drinks, wildlife, and sunset views in a small-group setting.
2. Private 2-Hour Day Sailing Experience
Set amid Orlando’s lakes, this private sailing experience offers peaceful waters and a chance to learn the basics of sailing. Meet at Lake Fairview Park and hop aboard a comfortable 25-foot MacGregor sailboat with Captain Dan. During this roughly two-hour trip, you can relax and catch rays or lend a hand with rigging if you want to learn. The reviews highlight how tranquil and customizable this trip is, with guests praising Dan’s friendly, knowledgeable approach. The tour is ideal for couples or small groups seeking a quiet, scenic escape from Orlando’s busy theme parks.
Bottom Line: Perfect for a relaxing, personalized outing, especially if you’re curious about sailing or just want a peaceful day on the water.
3. 90 Minute Pontoon Cruise in Florida
This 90-minute pontoon cruise takes you into the heart of the Everglades near Kissimmee. It’s a great way to see Florida’s native wildlife, such as alligators, snakes, turtles, and a range of bird species. Captain Chris and his wife are known for their friendly, knowledgeable hosting, and you might even get lucky and see some wildlife in action. The cruise is suitable for all ages and offers a glimpse into the natural environment of Florida’s wetlands. Guests laud the wildlife sightings and the informative narration. The experience also offers the flexibility of requesting a private tour, making it adaptable for special occasions.
Bottom Line: An excellent wildlife-focused cruise for families and nature lovers wanting an intimate look at Florida’s iconic animals.
4. Private 2-Hour Sunset Sailing Tour on Lake Fairview
For those seeking romance or a peaceful wrap-up to a day, this private sunset sailing is hard to beat. Meet your guide at Lake Fairview Park and enjoy a serene two-hour cruise on a 25-foot sailboat, with all the tranquil beauty of a Florida sunset. Guests love bringing their own food and drinks, which adds a personal touch. Reviewers mention how Captain Dan’s friendly manner and the beautiful scenery make this an unforgettable experience. Ideal for couples, small groups, or families wanting an intimate way to enjoy Florida’s evening colors.
Bottom Line: A personal, romantic outing that’s perfect to enjoy a sunset or celebrate a special occasion.
5. Port Canaveral Cruise Transfer to/from Orlando Intl Airport
Travel logistics can be tricky, but this direct transfer simplifies your journey between Orlando International Airport and Port Canaveral. The private vehicle service tracks your flight, ensuring timely pickup and drop-off. The reviews reflect consistent professionalism and punctuality, making this a reliable choice for cruise travelers. It’s an affordable way to avoid the hassle of taxis or public transport, especially with luggage or tight schedules.
Bottom Line: A no-stress transfer option for cruise passengers, combining convenience with peace of mind.
6. Kennedy Space Center with Airboat Ride Swamp Boat
This day trip combines the awe of space exploration with Florida’s swampy wilderness. Explore NASA’s Kennedy Space Center, meet an astronaut, and see the Space Shuttle Atlantis up close. Then, venture into the wetlands with a 30-minute airboat ride on the St. Johns River, searching out alligators, herons, and other wildlife. The tour covers a full 10 hours, making it perfect for space enthusiasts or wildlife watchers. The reviews mention how informative and fun the space exhibits are, while the swamp ride adds an adventurous element.
Bottom Line: An educational and exciting day for families and curious travelers interested in both NASA and Florida’s wild side.
7. Orlando Sightseeing Tour with Optional Boat Cruise
This city and lake tour offers a good overview of Orlando’s downtown highlights plus a scenic boat ride through Winter Park. It’s especially suitable if you want a quick, guided introduction to the city without missing out on lakeside scenery. The tour includes a visit to Lake Eola Park and a 1-hour boat cruise, with optional extensions onto Winter Park’s canals. Reviewers appreciate the mix of cultural sights and natural beauty, with the guide bringing the city’s stories to life.
Bottom Line: A practical tour to see Orlando’s key sights, with the option to add a scenic boat cruise for extra charm.
8. Orlando: Private Sunset Sailing Trip on Lake Fairview
This private sunset sailing offers a peaceful escape on Lake Fairview. It’s similar to the earlier sunset cruise but emphasizes privacy and personalized service. Guests mention how relaxing it is to enjoy the golden skies, and many appreciate the Captain’s engaging conversation. Perfect for a romantic date or a quiet family outing, this tour allows you to bring your own food and beverages for a custom experience.
Bottom Line: Ideal for those seeking an intimate, scenic, and flexible sailing experience to unwind at sunset.
9. Sea Screamer Boat Cruise in Clearwater Beach with Transport
Escape Orlando for a day at Clearwater Beach with this full-day trip. The highlight is the Sea Screamer, the largest speedboat on the East Coast, which roars out into the Gulf of Mexico for about an hour. You’ll look out for dolphins and marine wildlife amid the waves. Plus, you get free time on the sandy shores to relax, swim, or enjoy lunch (if you select the package). The trip includes hotel pickup and drop-off, making it easy to plan. Reviewers mention the thrill of the speedboat ride and dolphin sightings.
Bottom Line: A high-energy, family-friendly cruise combining marine wildlife viewing with beach relaxation.
10. Orlando: Sailing Tour with Certified Sailing Instructor
Learn to sail with an experienced instructor. This 2-hour tour provides hands-on experience aboard a 25-foot MacGregor sailboat. The guide shares sailing basics and helps you get involved, making it perfect for beginners or anyone eager to learn. Reviewers describe it as a fun, engaging way to experience Florida’s waters without needing prior sailing skills. It’s best suited for small groups or couples, aiming for a more interactive outing.
Bottom Line: Great for novices or those wanting to get involved in sailing, blending education with relaxation.
11. Brightline Orlando Train Station to Port Canaveral Cruise Ships
This train transfer provides a smooth, modern way to get from Orlando to Port Canaveral. It’s a quick 1.5-hour ride with comfortable seating and reliable service. Travelers praise it for its efficiency and ease, especially if you want a hassle-free start or end to your cruise. The train trip is perfect for those avoiding traffic or looking for a scenic ride.
Bottom Line: A quick, comfortable, and dependable transfer option for cruise travelers heading to or from Port Canaveral.
12. Oneway/Roundtrip: Port Canaveral Cruise to Orlando Intl Airport
Book a private transfer to ensure smooth travel from your cruise to Orlando International Airport. This service guarantees timely pickups, with reviews confirming punctuality and professionalism. It’s a great way to avoid the stress of taxis or rideshare apps, especially if you have luggage or a tight schedule.
Bottom Line: Reliable, private transportation tailored to cruise travelers needing a stress-free route to the airport.
13. Hello Neighbor! The Mister Rogers Walking Tour + Boat Tour
Celebrate the life of Mister Fred Rogers with this walking and boat tour. It explores Winter Park through the eyes of the beloved TV icon, visiting his college, childhood homes, and local sites. The boat tour adds a scenic touch, cruising past homes and landmarks linked to Rogers. Reviewers find it heartfelt, informative, and charming, ideal for fans of his gentle kindness or those interested in local culture.
Bottom Line: A moving tribute that combines history, scenic views, and personal stories, suitable for all ages.
14. St. Johns River High-Tea Cruise Tour in Sanford
Enjoy a refined afternoon on the High-Tea Cruise. The paddle-wheeler “Barbara-Lee” hosts a full table service, serving savory finger sandwiches, scones, sweets, and endless tea. Glide across Lake Monroe and the St. Johns River, enjoying live entertainment. The full-service experience makes it perfect for celebrating a special day or enjoying a leisurely afternoon in style.
Bottom Line: An elegant and relaxing way to experience Central Florida’s waterways with a touch of luxury.
$48.00 per person
15. Rainbow River: 8AM & 3PM Snorkel or Scenic Wildlife Cruise
Explore the crystal-clear waters of Rainbow River on a small-group cruise that combines snorkeling and wildlife viewing. Departing at 8AM or 3PM, the tour allows you to either snorkel among fish, turtles, and aquatic plants, or simply relax on deck. With a maximum of 6 guests, it’s an intimate experience. The river’s visibility and lush scenery make it a favorite for eco-minded travelers.
Bottom Line: An excellent, personal way to experience Florida’s spring-fed rivers, with options for snorkelers and nature lovers alike.
$95.00 per person
16. 1 Hour Scenic Pontoon Day Cruise
Most Florida boat rides pack in too many people, but this private pontoon offers a quiet, personal experience on Lake Eloise. You can enjoy unobstructed views of LEGOLAND® from the water, spot alligators, and relax in comfort under a Bimini sun top. Perfect for travelers who are short on time but want a taste of Florida’s lakeside scenery, this cruise offers flexibility with multiple times available.
Bottom Line: A quick, private, and flexible cruise for wildlife viewing and lake scenery, ideal for a short visit.
How to Choose Your Perfect Orlando Boat Tour
When deciding between these options, consider your budget, time, and interests. Want a lively social experience? The Pontoon Pub Crawl offers fun and wildlife in one package. Looking for a peaceful escape? The Sunset Sailing or Private Lake Fairview trip are excellent choices. For wildlife lovers, the 90-minute Florida cruise provides a glimpse of alligators and exotic birds. Families will enjoy the Clearwater speedboat trip, while space enthusiasts might prefer the Kennedy Space Center. Booking early is recommended, especially for private tours or popular dates.
Orlando’s boating options give you a chance to explore the city’s lakes, wetlands, and coastlines in ways that suit almost every taste. Whether you’re after a loud pub crawl, a tranquil sunset sail, or a wildlife adventure, there’s a boat tour waiting to make your trip memorable. Take your pick, plan ahead, and enjoy the waters of Central Florida—you’ll find it’s just another way Orlando shows its best side.