Monkey Island Paddleboard Pub Crawl

Schedule

Sat May 23 2026 at 10:30 am to 04:30 pm

UTC-04:00

Location

Florida Cracker Riverside Resort | Homosassa, FL

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It's a party paddling around real monkeys on Monkey Island and bar hopping down the river, enjoying cold drinks, food & music...cheers!
About this Event

Paddle around real monkeys at Monkey Island and cruise to the best riverfront bars and restaurants! Quench your thirst with cold adult bevis, and enjoy lunch with live music!

Our tours are longer than most to give ample time to connect with wildlife and nature. We include photos, guided eco-tour, instruction, and all the gear you need (quality and fitted to your size/experience level) or bring your own for a discount! Our guides and instructors are friendly, experienced, and certified. We foster an inclusive and empowering environment, and activities with intention that enhance your well-being!

Located just 1.5 hours west of Orlando, we’ll launch on the beautiful Homosassa River, abundant with manatees, birds, fish, turtles, and bordered by palm, cypress and oak trees. You'll be greeted by your friendly guides, given paddleboard instruction if needed, and outfitted with quality paddleboard gear. The site has nice restrooms and a dock/ramp launch.
First, we'll launch our boards and paddle around historic Monkey Island, with an upclose view of three spider monkey residents! It's a real sight watching them swing around their playground and lighthouse, or lay lazily on the front porch of their air conditioned cottage. And a great photo op too!

Paddling upriver taking in the scenic surroundings and seeking wildlife, our second stop is nestled back through a narrow, wooded canal. It's dotted with unique small homes and houseboats with lots of river character. At the end is Manatee Pub - the perfect divey spot with dollar bills decorating the walls, ice cold beers, a pool table, and cash only service.

Next, we'll cross to the opposite shoreline and head downriver to dock at Krump's Landing. This sprawling establishment has a sandy beach with adirondack chairs, 2 huge shaded tiki bars, and live music! Here we can enjoy full liquor and lunch service to satisfy our paddle-induced appetites.

Looping back we'll take out at Florida Cracker, with an upper deck overlooking Monkey Island and more tasty bevis. You can choose to hang as long as you want to enjoy the scenery and good vibes, as this is the last stop on our tour. It's also conveniently located at Florida Cracker Resort where you can responsibly stay the night, enjoying the pool and two restaurants for just $150/night (book in advance as they fill up fast).

What's Included:

  • All Stand Up Paddleboard Gear (quality and fitted to you)
  • 6 hour Guided Paddle Tour with experienced and certified guides/instructors (about 90-120 minutes paddle time and 3 hours bar/restaurant time)
  • Launch fees ($10 value)
  • SUP Instruction
  • Premium Photo Package
  • Paddle Tribe

Other Ticket Options Include:

  • BYOBoard/Paddle Craft for a discount. All paddlecraft are welcome.

Paddle Skill Level: All Levels. Instruction provided for beginners. Must know how to swim.

Age: 21+

Bring: Water, towel, dry bag, cash (one pub is cash only)/CC/ID, dry change of clothes. If you're bringing your own paddle craft, a life vest and whistle are required by law.

Wear: sunscreen, hat, sunglasses (with straps), apparel that is easy to move in and can get wet (like dry wicking workout clothes or swimwear), sandals/shoes that can get wet wet and a cover up to wear inside establishments.

Parking/Meet: Turn into Florida Cracker and make a right toward the dirt parking lot. Go left and follow signs for the Kayak Launch, parking as close as you can to it. You'll find us at the picnic table near the ramp and docks. If you're bringing your own board, you can unload next to the docks before parking. *IMPORTANT: Sometimes they have a parking attendant collecting money to park - tell them you are paying to launch a kayak and parking is included.

Guide: Jessica Cichra is a SUP enthusiast that has been actively paddle touring, racing, surfing, and instructing since 2009. She is the founder of Wave of Wellness, a company with a mission to empower clients through adventurous activities that enhance all areas of well-being with a focus on travel, SUP, yoga, and community. Jessica guides paddle tours in the greater Orlando area and internationally on adventure travel retreats.

Tips are highly appreciated if you believe your instruction, service, and experience to be exceptional!

IMPORTANT: In the event of inclement weather, you will be notified via Eventbrite email at least 3 hours prior to start time of a reschedule. We only reschedule so your experience will be safe and enjoyable.

*Our route and bars visited are subject to change according to weather conditions.


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Where is it happening?

Florida Cracker Riverside Resort, 5297 South Cherokee Way, Homosassa, United States

Event Location & Nearby Stays:

Tickets

USD 49.87 to USD 65.87

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