Back to the ’60s Weekend 2026

25 September 2026

Peace, love, and good times are coming to Cypress Cove!

Join us for a far-out weekend celebrating the unforgettable spirit of the 1960s. We’ll be turning back the clock with poolside entertainment, trivia, dancing under the stars, live music, games, and plenty of opportunities to let loose and have fun.

Break out your tie-dye, bell-bottoms, flower crowns, and favorite retro accessories, then get ready to groove your way through an unforgettable weekend with friends. Whether you lived through the ’60s or simply love the music and colorful style of the decade, you’ll feel right at home.

Check out the complete weekend schedule below, make your plans, and join us for three days of peace, love, and good times. Stay groovy!

Fall Volleyball Bash

2 October 2026

Celebrate the season with a full weekend of fun at Cypress Cove’s Fall Volleyball Bash! Enjoy three action-packed days filled with pool parties, trivia, karaoke, live music, dancing, delicious Sunday brunch, a special presentation from the Naked Astronomer, and a poolside dive-in movie.

Whether you’re ready to join the action, hit the dance floor, or simply relax by the pool with friends, there’s something happening all weekend long. Check out the event poster for the complete schedule, and make plans to spend your fall weekend at Cypress Cove!

Legends Weekend

9 October 2026

Cypress Cove is turning up the star power for our first-ever Legends Weekend, October 9–11! This brand-new themed weekend brings together three days of poolside music, trivia, dancing, great food, and legendary entertainment.

The highlight of the weekend takes place Saturday evening when Lakeside Live presents the Legends Show—an exciting tribute to some of music’s most unforgettable performers. After the show, keep the celebration going with a late-night dance party at Cheeks.

The fun begins Friday with a pool party, bar trivia, and dancing under the stars. Saturday also features the Cypress Cove Craft Fair, an afternoon pool party, and Dave’s Super Mega Trivia 3000. On Sunday, unwind with poolside music before wrapping up the weekend with game night and Lakeside’s special Dinner & a Movie experience.

Come spend the weekend with us and be part of the very first Legends Weekend at Cypress Cove—where the music is iconic, the atmosphere is electric, and the memories are destined to be legendary!

Fall Craft Fair

10 October 2026

Discover something special at the Cypress Cove Fall Craft Fair! Browse a wonderful selection of handcrafted goods created by talented local artisans, including soaps, lip balms, crocheted pieces, handmade woodwork, nature photography, and more. Guests can also enjoy fresh sourdough bread and a tempting assortment of homemade baked goods.

The Craft Fair will be held inside the Clubhouse, with additional vendor space available outdoors under Old Cheeks if needed.

Interested in becoming a vendor? Spaces are still available! Email Vickie at Enable JavaScript to view protected content. to reserve your spot.

Dinner & A Movie

11 October 2026

For the first time ever, Cypress Cove is transforming Lakeside into an intimate, movie-inspired dining experience—and only 50 guests will have the opportunity to attend!

Join us Sunday, October 11, from 6:00 to 9:00 p.m. for an exclusive VIP evening inspired by Dirty Dancing. The experience will combine themed trivia, a surprise welcome cocktail, an elegant multi-course dinner, a special presentation of each dish by Chef Steven, and a showing of the beloved film.

From the Kellerman Garden Salad to your choice of Royal Rib Roast or Mornay Mushroom Chicken—and a decadent chiffon cake finale—each course has been thoughtfully created to bring a little of Kellerman’s magic to Lakeside. After dinner, settle in for the movie and don’t be surprised if the romance and music inspire a little dancing before the evening is over.

Tickets are $49.95 per person, including tax and gratuity. Attendance is strictly limited to 50 guests, so early reservations are strongly encouraged. Call Lakeside at 407-933-3588 to reserve your seat for this one-of-a-kind evening.

Nude-A-Palooza 2026

24 October 2026

Welcome to Nude-A-Palooza 2026!
We’re thrilled to kick off our Annual Nude-A-Palooza Charity Benefit Tribute Band Concert series here at Cypress Cove! Get ready for an unforgettable day filled with incredible live music, a welcoming, clothing-optional atmosphere, and the kind of good vibes that only Nude-A-Palooza can deliver. From the first note to the final encore, we can’t wait to celebrate with you! Don't forget to pick up your Nude-A-Palooza event gear HERE. 

Is this your first Nude-A-Palooza? Click here to check out our helpful hints!

Cheesecakes for Boobies

As part of the Nude-A-Palooza celebration, we proudly feature Baking for Boobies, a heartfelt initiative led by our beloved bartender, Herman. In the week leading up to Nude-A-Palooza, Herman transforms the Game Room into a vibrant bake sale extravaganza all to raise funds for breast cancer awareness and support.

This cause holds deep meaning for Herman, as he’s supported several family members through their cancer journeys. His passion shines through every cheesecake he bakes, each one made with love, purpose, and a sprinkle of sweetness for a great cause.

Last year, thanks to our amazing community, we completely sold out of cheesecakes and CRUSHED 2024’s record, raising an incredible donation amount of $5,870! Every penny of these proceeds goes directly to our Nude-A-Palooza charity total.

A huge thank you to Herman for his dedication and to everyone who donated, volunteered, or indulged in a slice (or two!) of his legendary cheesecakes.

Mark your calendars: Baking for Boobies will return on October 17, 2026, from 12 PM to 4 PM in the Game Room. This year, we’ll be introducing something extra special: a Whole Cheesecake Sampler Auction, featuring one slice of every flavor Herman bakes. Don’t miss it!

If you’d like to make a donation, you can still do so by picking up a virtual piece of cheesecake HERE; every bit helps make a difference.

The chosen charity for 2025 was the Florida Cancer Specialist Foundation. We presented them with a check at the end of the event for over $21,000!

Nude For Charity Challenge!

#Nude4Charity Challenge
First time baring it all? No problem! You will have a wonderful time amongst this welcoming crowd. Cypress Cove is clothing optional, meaning you can take things at your own pace. Bare as you dare... we guarantee you will have a great time at our safe, wholesome, and family-friendly resort!
Have questions about your first visit? Visit here.
 

2026 Lineup

The music starts at Noon. We'll have food and beverages available for purchase. (No outside food or beverages allowed.) Clothing is optional! Bring a chair or a towel to sit on for general admission. Come dance or just kick back and enjoy the music! And you can feel good about contributing to this great cause - proceeds go to Florida Cancer Specialists Foundation.

Want to tent camp for the weekend? We also have a combo ticket that includes tent camping! Book early; space is limited.

Staying in a Villa for the Event?

Guests who are staying in a Villa during the event for two or more nights can purchase up to two tickets at 50% off. Please visit or call the front desk to purchase your tickets.
Call 407-933-5870 for your Nude-A-Palooza tickets. 
 

RAFFLE TICKETS!

Veteran's Day Ceremony 2026

7 November 2026

Veterans Day Ceremony

Cypress Cove invites members, guests, and residents to gather by the flagpole on Saturday, November 7, at 4:00 p.m. for our annual Veterans Day Ceremony.

Together, we will honor the courageous men and women who have served in the United States Armed Forces and recognize the families who have supported them along the way. This meaningful ceremony offers our community an opportunity to reflect on their dedication, sacrifice, and commitment to our country.

Please join us as we come together in gratitude and pay tribute to all who have worn the uniform. All are welcome to attend.

Resident Organized Bus Trip to Blind Creek Beach

8 November 2026

Join a bus full of your Cove friends for a carefree day at Blind Creek Beach, Florida's newest and nicest nude beach! We'll charter a 56-passenger luxury motor coach for the ride down and back, and you'll have a full day on the beach. 

Blind Creek Beach has recently received a major upgrade from the county, and now boasts indoor restrooms, showers, and a water fountain! 

Blind Creek Beach is a gorgeous, all-natural, nearly mile-long sandy beach, and the best way to enjoy it is without the hassle of driving, tolls, parking, and traffic -- so get on the big happy fun beach bus when we leave and return to beautiful Cypress Cove on November 8th! 

Tickets are on sale now through October 31, so reserve your seat now! 

See this link for full details and to book online, or email Enable JavaScript to view protected content. for information.

(This trip is organized by a Cypress Cove resident and is not managed or endorsed by Cypress Cove Resort.)

Fall Garage Sale - Community Wide

8 November 2026

It’s time to hunt for hidden treasures at the Cypress Cove Garage Sale!

As our summer guests prepare to head home, they’re clearing out items they would rather not take with them—which means plenty of great finds are waiting for new owners. Browse a variety of gently used household goods, décor, clothing, collectibles, and unexpected treasures while enjoying a beautiful day at Cypress Cove.

The sale will take place throughout the residential community, with participating residents setting up inside their homes or on their back patios. Be sure to stop by the Front Desk when you arrive to pick up a map showing all participating locations.

Join us on Sunday, November 8, from 8:00 a.m. to 2:00 p.m. Come early for the best selection, then make a day of it and enjoy everything Cypress Cove has to offer.

Grounds fees apply for non-members.