Tampa Bay
Jim Harden

Jim Harden

Nov 3, 2026

25 Comments
Pirates, Parrots & Paradise Brings a Free Tropical Festival to Coachman Park
The Nov. 7-8 Clearwater event mixes pirate costumes, tiki carving, live entertainment, karaoke, vendors and family fun
Illustrative pirate entertainer at a family event — Photo by Nano Erdozain on Pexels

Coachman Park is trading its usual waterfront look for pirate garb, tropical decorations and island-themed entertainment this weekend.

 

Pirates, Parrots & Paradise runs Saturday, November 7, from 11 a.m. to 7 p.m. and Sunday, November 8, from 11 a.m. to 3 p.m. at Coachman Park in downtown Clearwater.

 

Admission is free, and the event is designed for all ages.

 

The festival combines pirate-themed fun with a tropical marketplace rather than trying to recreate a historical pirate encampment.

 

Visitors can expect live entertainment, vendors, food, pirate karaoke, a pirate garb contest and a mix of tropical and nautical activities.

 

Clearwater waterfront atmosphere — Photo by Abdullah Almutairi on Pexels

One of the advertised attractions is Captain Jack Sparrow impersonator Jay Smith.

 

The schedule also includes live tiki carving by Joe Tiki, which gives people a chance to watch a large carving take shape during the festival instead of only seeing finished pieces for sale.

 

That combination makes this weekend feel more like a themed community festival than a conventional craft fair.

 

Families can come in costume, browse vendors and stay for the entertainment without having to buy a ticket just to enter the park.

 

The free admission is especially useful for families who are not sure how long younger kids will want to stay.

 

Saturday has the longer schedule, running until 7 p.m., while Sunday wraps up at 3 p.m.

 

That makes Saturday the better choice for visitors who want the fullest festival day, while Sunday may appeal to people who prefer a shorter outing.

 

The organizer describes Pirates, Parrots & Paradise as a rain-or-shine outdoor festival.

 

Because Coachman Park is fully outdoors, checking the forecast before leaving home is still a smart move even though the event is scheduled to continue through light rain.

 

Coachman Park is at 300 Cleveland Street in downtown Clearwater.

 

The park includes paved walking areas, open lawn space, restrooms, a playground and a splash pad, although some areas can be restricted during special events.

 

Downtown Clearwater can get busy during waterfront events, so arriving earlier in the day can make parking and walking into the festival easier.

 

Anyone planning an elaborate pirate costume should also keep Florida weather in mind.

 

Heavy layers, boots and hats may look great in photos but can feel very different after a few hours in the sun.

 

The event is being produced as part of a new tropical lifestyle festival series, and Clearwater is one stop on that larger schedule.

 

For local families, though, the appeal is simpler: a free weekend event with enough visual spectacle to keep kids interested and enough vendors, food and live entertainment to give adults something to browse.

 

If you want something playful and easygoing this weekend, Pirates, Parrots & Paradise is one of the more unusual free events on the Clearwater calendar.

 

Official information: festival organizer page, Visit St. Pete-Clearwater event listing, and Coachman Park.

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25 Comments

Join the conversation

  • NP
    Norm Perez· Nov 6, 11:33 PM

    What about dogs? Want to bring ours if it’s dog-friendly.

  • JS
    Janelle S.· Nov 6, 12:57 AM

    Tropical theme plus pirates is kind of a wild combo, but sounds fun. My friends and I are in!

  • L
    Lucas_M· Nov 5, 6:51 PM

    Will there be a map of vendors? Sometimes it’s hard to find the good stuff if you show up late.

  • MK
    Maya K.· Nov 5, 5:57 PM

    Saw this on Facebook too. Clearwater stepping up their festival game!

  • SD
    Scott D.· Nov 5, 5:08 PM

    Coachman Park events always have the best people watching. I’ll be there camping out with my camera.

  • SL
    Sandra Lim· Nov 5, 4:21 PM

    Do we have to sign up for the karaoke or is it just show up and sing?

  • GP
    Gary P.· Nov 5, 2:42 AM

    Fun idea! I’ll probably dress up, but the wife says no way unless I win her a prize.

  • ER
    Elisa Romero· Nov 5, 1:56 AM

    Last time at Coachman Park the food lines were long. Fingers crossed for more food trucks this weekend!

  • VA
    Victor A.· Nov 4, 10:58 PM

    Hope the pirates aren’t too scary for the little ones. My daughter’s 4 and gets spooked easy!

  • PD
    Pat D.· Nov 4, 9:48 PM

    Not really into pirates but might go just for the market part. Always like seeing local crafts.

  • LO
    Leah O.· Nov 4, 7:16 PM

    I’m new to Clearwater, love getting these weekend tips. This one’s perfect.

  • MR
    Mick Russo· Nov 4, 6:54 PM

    Will the vendors take cash or just cards? Had that problem at Blues Fest last month.

  • KS
    Kayla S.· Nov 4, 6:18 PM

    I wish they had these kinds of events back when my kids were little. Looks like fun for families.

  • D
    Dan74· Nov 4, 5:54 PM

    Glad admission is free. We need more stuff like this that doesn’t cost an arm and a leg.

  • SC
    Samantha Chen· Nov 3, 11:46 PM

    Anyone know if the parrot part means real parrots? My kid is obsessed with birds.

  • JE
    Juan E.· Nov 3, 9:31 PM

    Coachman Park is great for festivals because of the breeze. Hope the weather holds up for this one.

  • MJ
    Maddie J.· Nov 3, 9:19 PM

    Honestly wish events for adults lasted later in Clearwater, but happy to have anything with live music!

  • DP
    Derek P.· Nov 3, 9:03 PM

    Happy to see something nonhistorical. The market and entertainment combo sounds better than the old pirate fests.

  • AL
    Ava L.· Nov 3, 8:13 PM

    I’m mostly here for the tropical food. Hope there’s good seafood.

  • CG
    Chris G.· Nov 3, 7:54 PM

    “Pirate garb contest” might be where I finally wear my Jack Sparrow getup from Halloween.

  • RJ
    Renee Jameson· Nov 3, 7:17 PM

    Wish it went later on Sunday but glad it fits around the Bucs game.

  • M
    Mike_727· Nov 3, 5:30 PM

    Is there parking nearby or should we plan to walk from the library?

  • TC
    Tina Costello· Nov 3, 3:05 PM

    Didn’t know Coachman Park did events like this. I’ll check it out after the farmers market.

  • BH
    Brian H.· Nov 3, 2:18 PM

    Pirate karaoke sounds hilarious. I might be too shy to try but I want to watch!

  • SL
    Sherri L.· Nov 3, 2:14 PM

    Free admission and fun for all ages? Can’t beat that. Definitely bringing my kids!

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