2022 Olde Cypress Preview

What if we told you there was a place where you could play golf on a completely remastered P.B. Dye-designed golf course, attend a live concert series featuring the area's best tribute bands, partake of fine and casual dining as the mood strikes you, and enjoy a seemingly endless array of social events?

Oh, and did we mention you don't even have to get in a vehicle (other than a golf cart) to enjoy all these amenities and activities? Current members might see where we are going with this. This "place" is The Club at Olde Cypress, and 2022 is shaping up to be one of the most exciting years in the club's 20-year history.

Here's a little preview of what to expect over the next four months (no, really, this is just the next four months).

New Member Events

Greetings new members, welcome to Olde Cypress. Some of you may have a clear idea of exactly how you're going to take advantage of everything we offer. Others may be asking themselves, "ok, so now what?" Either way, we've got you covered.

The club offers a "Newcomers Program" with three expertly curated new member events to start the year. On Jan. 12 we hosted a charcuterie board class. Participants learned how to build visually stunning, gourmet charcuterie boards featuring a bounty of fresh, high-quality ingredients and a variety of textures and flavor profiles.


Charcuterie Board Class 

Coming up on Feb. 11 it's all about creating new connections at our "National Make a Friend Day" Cocktail Mixer and Dinner. Enjoy cocktails with other new members while sampling light hors d'oeuvres. For dinner, we take the liberty of seating like-minded members together in the name of creating fast friends.

And on March 31, new members can join us for a "Meet our Staff Welcome Lunch." Interacting with our team is often a daily occurrence during the season for our members, and we want to ensure everyone knows exactly who their "go-to" is in each department. And besides, who doesn't love lunch?


The men's and women's member-member tournaments at Olde Cypress are two of the true highlights of the winter and spring seasons here in Naples. The "Men's Tradition" is a two-day, 36-hole event held Feb. 18-19 with an always raucous Thursday night reception. The format is an entertaining blend of a scramble, better ball and alternate shot. Identical outfits between partners are a must, traditional knickers and sox are encouraged.


Men's Member-Member: The Tradition

The women's member-member features both nine- and 18-hole editions. The nine-holer this year, held Feb. 1-2 and dubbed "Tee Times at Tiffany's," is renowned for its decorated golf carts and costumed lady participants. The 18-holer, "Stayin' Alive," pays homage to the Bee Gees and Norman Wexler's Saturday Night Fever and will take place Feb. 7-8. There's a cocktail party with games the night of the first round, and lunch and awards following the second round.


For many private golf clubs in Southwest Florida (and throughout the world), the member-guest is the Super Bowl of the annual club calendar. Olde Cypress is no exception. Our men's Cypress Cup is the stuff of legend, and this year it will be an exciting, three-day tournament held March 10-12.

The entry fee is $980 per team which includes tee gifts, all food and beverage for participants throughout the tournament and spouses on Thursday and Saturday evenings. The entry fee also includes the practice round event, special contest and cart fees. In addition, a mandatory $100 bet per team will be collected at registration for a flight pool. 


Women's Member-Guest

The format? Well, it's about as much golf as you can handle over three days. There's a practice round on Thursday, 27 holes on Friday and 18 holes on Saturday followed by a shootout. The field will be limited to a maximum of 60 two-man teams. And at Olde Cypress, it's "all about the hang," so there will be plenty of eating, drinking and good times mixed in.

The women's member-guest has rapidly risen to rival the men's in popularity. This year's tournament is held Feb. 28 – March 1 and features a "Girl Scout" theme for costumes and golf cart decorations. It gets underway on Monday with an exciting par-3 shotgun event followed by a cocktail party. Tuesday's format is a shotgun start with 18-holes of best ball followed by lunch and awards.

Concert Series

Imagine dancing outdoors under the stars at the club's alfresco Greenside Café surrounded by a delicious dinner buffet, cold drinks and your friends and family from the club. Welcome to our wildly popular tribute band Concert Series.


A Greenside Concert

The 2022 series kicks off Jan. 19 with ABBA followed by the Bee Gees on Feb. 16. Motown takes the stage on Feb. 24, and then we host back-to-back shows by the Beatles on March 23 and 24. The series is capped by two Elton John concerts on April 20-21. Rock on, Olde Cypress, Rock on.

For more information on other upcoming events, members can log into the website and check the club calendar. For prospective members, Director of Membership and Marketing Melissa Hansen is standing by to answer any questions you might have.