Resort Happenings

TradeWinds offers the perfect setting for a holiday weekend getaway or special event. Check back as the holidays approach for event details.

Activities

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Halloween Weekend

Get ready for a spooktacular Halloween weekend filled with family-friendly fun, festive activities, costumes, parties, and plenty of Halloween surprises! There's something spooky for everyone.

  • Spooktacular Crafts - perfect for little ghosts and goblins.
  • Haunted Waterway - take a chiling paddleboat journey through our waterway... if you dare!
  • Monster Mash Silent Disco and Glow Party - dance the night away featuring your favorite Halloween vibes.
  • Poolside Costume Contest and Dog Costume Contest - show off your best Halloween look.
  • Trick-Or-Treat Trail - grab your treat bag and follow the trail for treats and surprises.
  • Adults-Only Boo-zy Party at Cabana Bar. Enjoy a featured Espolòn Tequila cocktail and activation, music by DJ Quest, and a festive night of Halloween fun. Sat., 6-10 pm. This is a free event. Reserve your spot today!

Halloween Activity Times

Friday, October 30
10 AM–4 PM — Spooktacular Crafts | Shelldon's Discovery Cove
3 PM — Mummy Game | Beachfront Pool
6-10 PM — Kids Night Out | Shelldon's Discovery Cove
7 PM — Mad Science Show | Garden Courtyard
7-10 PM — Haunted Waterway | Paddleboat Landing | Ages 8+
8-10 PM — Monster Mash Silent Disco | SandBox

Saturday, October 31 | Halloween
10 AM–4 PM — Spooktacular Crafts | Shelldon's Discovery Cove
3 PM — Costume Contest | Beachfront Pool
3:30 PM — Dog Costume Contest | Beachfront Pool
4 PM — Trick-Or-Treat Trail | Beachfront Pool
6-10 PM — Boo-zy Halloween Party | Adults Only | Cabana Bar | 21+
6-10 PM — Kids Night Out | Shelldon's Discovery Cove
7-10 PM — Haunted Waterway | Paddleboat Landing | Ages 8+
8-10 PM — Glow Party | SandBox

Not staying with us? Locals can join in the Halloween fun with a Day Pass!

A Group Of People In A Bar

Bucs Watch Party: Nov. 22

Game day is better at the beach! Join us on the RumFish Lawn for the ultimate watch party on Nov. 22. Catch all the action on our large outdoor screen while enjoying food and drinks at The SandBar, Cabana Bar & Bites, and Gulfside Kitchen.

Bring your team spirit—and don’t forget your bathing suit! Fans can enjoy access to the resort's pools and beach. Catch appearances by a Bucs Legend Player, Captain Fear, Bucs Cheerleaders, the Bucs Street Team, and more! Game-Day Fun Includes:

  • Raffles and Swag Giveaways
  • Quarterback Toss Inflatable
  • GIF Photo Machine
  • Cornhole and Giant Jenga
  • Drink Specials
  • Parking is included!

Save the dates: November 22
Location: RumFish Lawn, located at RumFish Beach at TradeWinds
Time: 12:00 p.m. (kickoff at 1:00 pm)

Gather your crew, wear your Bucs gear, and make game day an unforgettable beachside experience!

A Table Full Of Food

Thanksgiving on the Beach

Gather, Give Thanks & Make Memories. Spend Thanksgiving on the beach and enjoy a holiday filled with family-friendly activities, festive fun, and delicious seasonal dining. From a Turkey Trot and pumpkin pie eating contest to glow parties, crafts, and Thanksgiving favorites, there’s something for everyone to enjoy throughout the holiday weekend.

Score bigger savings with Beach Life Boutique's Black Friday Sale, Nov. 27. Enjoy limited-time discounts throughout the day: 9-10AM: 20% off, 10AM-1PM 15% off, 1PM-Close 10% off.

Thanksgiving Brunch & Dinner Specials

Experience a Thanksgiving Brunch Buffet where indulgence meets tradition. Savor an array of seasonal delicacies, from traditional roasted turkey with all the fixings to decadent desserts that capture the warmth of the season. A special Thanksgiving dinner menu will also be served at Pete's Gulf Bistro and Palm Court Italian.

Thanksgiving Brunch Thanksgiving Brunch

Thanksgiving Weekend Activities

Wednesday, November 25
10 AM–4 PM — Slime Lab | Shelldon's Discovery Cove
5 PM — Photo Scavenger Hunt | The Boardroom | Teens Only
8 PM — Dive-In Movie | Cypress Pool

Thursday, November 26 | Thanksgiving
9 AM — Turkey Trot | Beach Hut. Reserve your spot!
11 AM–3 PM — Thanksgiving Brunch | Grand Palm Colonnade. Reserve your spot!
1 PM — Pumpkin Pie Eating Contest | Beachfront Pool
5–7 PM — Beach Volleyball Round Robin | RumFish Beach
8–10 PM — Karaoke | SandBar

Friday, November 27
12 PM — Mixology Class | RumFish Sports Bar & Deck | Reservation link coming soon.
8–10 PM — Teen Bonfire | Pirate Island | Teens Only
8–10 PM — Decades Silent Disco | SandBox

Saturday, November 28
8 AM–12 PM — Breakfast With Santa | Pete's Gulf Bistro
10 AM–4 PM — Beachy Ornaments | Shelldon's Discovery Cove
11–11:30 AM — Shell-fies with Shelldon | Island Grand Lobby
8–10 PM — Glow Beach Bash | Sandbox

Sunday, November 29
1 PM — Flag Football | Beach
8–10 PM — Family Feud | RumFish Sports Bar & Deck

Two Glasses Of Liquid With Limes

Weekly Sips & Bites

Enjoy fresh flavors and featured drinks, served up every week!

• Margarita Monday @ Playa Taco: Enjoy a margarita flight featuring 4 flavors, plus chips & salsa. Available all day! $22
• Taco Tuesday @ Playa Taco: $2 off all tacos. 50% off Playarita house margarita. Available all day.
• Tequila Tasting Wednesday @ Playa Taco: Enjoy two complimentary 0.5 oz spirit tastings, followed by a classic margarita crafted with the featured spirit. 4 p.m. Space is limited. Reserve your spot!
• Wine Wednesday @ Palm Court Italian, Pete's Gulf Bistro, and RumFish Grill: 50% off select bottles of wine (priced under $110) during your dining experience.
• Whiskey Tasting Thursday @ Pete's Gulf Bistro: Enjoy two complimentary 0.5 oz spirit tastings, followed by a classic Old Fashioned crafted with the featured spirit. 4 p.m. Space is limited. Reserve your spot!
• Rum Tasting Friday @ RumFish Sports Bar: Enjoy two complimentary 0.5 oz spirit tastings, followed by a Mojito or Old Fashioned crafted with the featured spirit. 4 p.m.

A Plate Of Food

Christmas Week at TradeWinds

Stay at TradeWinds over Christmas weekend and enjoy all the Holiday Happenings that we offer our guests!

  • Breakfast & Photos with Santa | Pete's Gulf Bistro: Nov. 28, Dec. 5, 12 & 19.  8-11 a.m. Reservations recommended. 
  • Letters to Santa at Shelldon’s Discovery Cove: Dec. 23 & 24, 10 a.m.–4 p.m.
  • Holiday-Themed Activities: Holiday Slime Lab, Stocking Decorating and Candy Cane Hunt
  • Holiday Mixology Class at Santa’s Pub: Dec. 23 at 12 p.m. | 21+
  • ’Twas the Night Before Xmas PJ Party & Fireside Movie: Dec. 24, 8–10 p.m. | Family-friendly
  • Silent Night Disco: Dec. 25, 8–10 p.m.
  • Glow Beach Bash at the SandBox: Dec. 26, 8–10 p.m.
  • Teen PJ Party & Fireside Movie: Dec. 27, 8–10 p.m. | Teens only
  • Holiday Lights Canal Cruise: Dec. 23 & 24 at 5 p.m. | Reservations coming soon
  • Holiday Specialty Drinks: Enjoy festive seasonal drinks throughout the week at Santa’s Pub.

Christmas Day Brunch & Dinner

Celebrate the season with our festive Christmas Buffet, where holiday cheer meets culinary delight. Additionally, enjoy plated Christmas specials at Pete’s Gulf Bistro, Palm Court Italian, and RumFish Grill on Christmas Day, making your holiday truly unforgettable.

A Group Of Fireworks

New Year's Eve Party & Dinner Experiences

Ring in 2027 with an unforgettable New Year’s Eve celebration filled with vibrant energy, exceptional dining, and plenty of fun. Plan a truly memorable evening with special New Year’s Eve dinner offerings at Pete’s Gulf Bistro, Palm Court Italian, and RumFish Grill.

A Group Of People In A Bar

Big Game Watch Party

Catch every play, celebrate every touchdown, and soak up the ultimate game-day atmosphere! Join us for a beachfront celebration packed with football, food, and fun in the Florida sunshine!

  • Tailgate Party: Watch the big game on a giant LED screen by the beachfront pool.
  • Football-Themed Contests: Show off your skills with field goal kicks, longest throws, best touchdown dances, football trivia, and logo match challenges.
  • Super Bowl Bingo: Get in on the action with game-day bingo and football squares.
  • Salty’s Cookout: Fuel up with delicious cookout favorites from 11 a.m. to 4 p.m.
  • Game-Day Cabana Specials: Reserve a poolside cabana featuring Super Bowl-inspired food and festive décor.
  • Watch Parties: Cheer on your favorite team at RumFish Sports Bar or at the Beachfront Pool.
  • Beach Flag Football: Hit the sand for some friendly football fun.
A Group Of Lights

Valentine's Day Events

Celebrate love, friendship, and family with a beachfront Valentine’s Day getaway! Enjoy romantic experiences, festive dining offerings, relaxing spa specials, and fun for all ages.

A Little Girl Standing Next To A Beach

Easter Weekend Eggstravaganza!

Celebrate Easter weekend with a lineup of festive holiday happenings for the whole family! Delight the little ones with a surprise Easter basket delivered right to your room, enjoy exciting Easter egg hunts, and take part in a variety of seasonal activities.

Indulge in our popular Easter Brunch or savor specially curated holiday dinners, all designed to make your stay extra memorable.

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Bucs Beach Bash: May 1

Get ready for a weekend of sun, fun, and football at the 7th annual Bucs Beach Bash, May 1, 2027! Stay at the official partner of the Tampa Bay Buccaneers and set sail for the wildest beach party of the year with live beachfront music events and more!

Event Highlights:

  • Free Live Beachfront Music Events
  • Cornhole Tournament
  • Special Weekend Activities, and more!
A Person Sitting On A Table

Mother's Day Specials

Treat Mom to the Gulfside escape she deserves and enjoy a relaxing stay filled with special touches just for her.

Mother's Day Brunch &  Dinner Specials

Make it a weekend Mom will cherish with our popular Mother’s Day Brunch, plus delicious dinner specials. Celebrate the moms in your life with unforgettable flavors, beautiful views, and memories made by the shore.

A Person Holding A Flag

Memorial Day Weekend

Stars, Stripes, Sips & Bites!

Kickstart your summer with a festive weekend packed with family-friendly fun and patriotic celebrations by the beach!

  • Beachfront Cookout featuring food specials all weekend
  • Memorial Day Dinner Buffet
  • Red, White & Boozy Adults-Only Party 
  • Weekend Activities and a Dazzling Fireworks display on the beach
A Person Holding A Baby

Father's Day

Celebrate Father's Day Island-Style!

Treat Dad to a well-deserved beachside escape filled with sunshine, relaxation, and unforgettable moments. After a day of soaking up the sun, savor delicious Father’s Day dinner specials at one of our restaurants. Whether he’s enjoying a memorable meal by the Gulf, kicking back with a cocktail, or simply taking in the island views, this getaway is the perfect way to celebrate Dad.

A Person Holding A Flag

4th of July Weekend

Celebrate the 4th of July with a weekend of family-friendly events, live entertainment, festive activities, delicious dining, and spectacular fireworks—all at your beachfront escape.

Fireworks In The Sand On A Beach

Labor Day Weekend

Close the chapter on summer with a spark-tacular beach weekend filled with sand between your toes, a cocktail in your hand, and activities for everyone to enjoy. From live music and poolside games to beach parties, and dining specials, there’s no shortage of ways to make the most of summer’s final days!