Refresh, Reset, Reboot!
Listen, Sing, Laugh, & Be Entertained!
We have terrific music, comedy, and dancing in store for you to add to your vacation relaxation experience. In the “laughter IS the best medicine” category we have Karen Williams, Dana Goldberg, Jen Kober, and (new to Olivia!) Kristin Key. You’ll have the chance to enjoy music by Be Steadwell and Gina Chavez – two fabulous singer-songwriters who will lift you up and make you want to sing too. And of course, theme parties, pool parties, and Club O’s featuring the beats of DJ Rockaway and DJ Olga T.
Prepare to be energized and uplifted by self-love and motivational powerhouse Amber Whittington (aka AmbersCloset), insightful influencer and Under the Desk journalist V Spehar, and empowering and award-winning sex edutainer Dirty Lola.
We’re also thrilled to welcome back the world’s #1 Female Senior Pro Pickleball Player, Lee Whitwell and Pickleball Pro Domenika Turkovic. They’ll lead a special, limited 4-court Pickleball program.
Karen Williams
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Karen Williams
Karen Williams is a force, a buzzsaw joke machine. She is proactively provocative, and fearless in confronting cliches, and investigating stereotypes through hyperbole. Her comedy stands out as a distinct, cantankerous voice in the lesbian community and a unique perspective on the world at large. “Human Beings: What A Concept,” Karen Williams’ debut comedy album, is a glimpse into the inner politics of a marginalized group that, by necessity, became curators and creators of their own culture. Karen addresses conformity in kindness, love, and relationships. She shares misgivings about aging, codependency, motherhood, and sexuality, especially regarding intersections with race and libertine living. Karen tells it like it is, as she sees it, cutting through the pleasantries with nuance, texture, ambiance, ambivalence, and gusto. She has lingo for those in the know and expertly crafted elaborations for those who aren’t. Throughout, Karen displays an unmatched genius for sarcasm, irony, and rhetoric. If something doesn’t make sense, she’ll knock some sense into it, but gracefully. Her technique is impressive. Rather than beat her opponent over the head, she’ll take the egregiously erroneous or misinformed stance as her own, stretch the faulty logic until it’s paper thin, and wrap the whole farce up into a bow. Karen Williams is special. For more about Karen's humor and healing work, visit www.hahainstitute.com
Dana Goldberg
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Dana Goldberg
Writer, comedian, and activist, Dana Goldberg has been seen on ABC, TBS, and Last Comic Standing. She is a force of nature on stage and was named to CURVE Magazine’s Power List of 2024 and GO Magazine’s 100 Women We Love. With performances at the San Francisco International Comedy Competition, The Comedy Festival produced by TBS and HBO, and the Fringe Festival in Edinburgh, Scotland; her quick wit and playful stage presence have her earning loyal fans across the world.
In addition to headlining theaters and festivals, Goldberg has performed at and emceed hundreds of high-profile events, sharing the national stage with luminaries like President Barack Obama, President Joe Biden, Vice President Kamala Harris, Kristin Chenoweth, Meryl Streep, Carol Burnett, Sir Elton John and countless others.
Combining her gift of humor with humanitarian efforts, Goldberg has raised over $50M for non-profits around the country in the fight for LGBTQ rights, women's health, and HIV/AIDS education and prevention. Goldberg is the co-host of The Daily Beans and is currently developing her first TV pilot with SOTO Productions.
Jen Kober
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Jen Kober
Originally from Lake Charles, Louisiana, Jen Kober has energetically bounded onto the national stage bringing crowds to their feet with her original blend of stand-up, storytelling, and improvised rock-n-roll comedy. Her hard-hitting hour is phenomenally funny—Kober commands the stage and dares you not to laugh. Jen was the 2017 Winner of NPR's Snap Judgement Comedic Performance of the Year for her Girl Scout Cookie Caper story, which went viral upon its release earlier that year. Kober received the 2018 Comedic Performance of the Year for her story titled Nana Vs. OJ.
Jen appeared on Netflix in 2019 as she joined the cast of two of its original shows. Including RuPaul’s sitcom, AJ & The Queen and Dead to Me. Jen had audiences rolling in the aisles on The Righteous Gemstones on HBO, played a no-nonsense detective in The Purge on USA Network, and was a wacky science teacher in Diary Of A Future President, on Disney+.
In 2021, Jen 's momentum continued with a recurring role on American Horror Story, a guest star on Showtime's Black Monday with Regina Hall and Don Cheadle, and a Season 2 regular on Apple TV's new queer sitcom, The Browns.
Recently Jen joined the cast of the Cirque du Soleil show MAD APPLE at the New York, New York Casino and Resort in Las Vegas, NV, and is a featured Comedian in NETFLIX is A Joke, with her own sold out show coming this May! A new comedy special No Flies On Me is set to be released this spring on streaming platforms, and Jen’s new podcast, Bitchin’ Over Biscuits just launched to rave reviews.
Kristin Key
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Kristin Key
Kristin Key is a nationally headlining, queer, musical comedian with sold-out shows nationwide. Her hilarious viral videos—including the iconic LESBIAN NATIONAL ANTHEM—have garnered over 92.2 million views from more than 590,000+ dedicated followers across social media. Using comedy as a way to uplift her community and create safe spaces for comedy fans from all walks of life, Kristin also donates to local nonprofits with every date on her 2024 Lesbian Army Tour.
Kristin Key grew up a minister’s daughter in the conservative West Texas town of Amarillo. Unsurprisingly, when Kristin came out of the closet at 16, it did not go well. So, she said, “Just kidding!” and went back in the closet. At 19, while in college to become a paramedic, Kristin signed up for a local open mic that would change her life forever. After searching for connection and self-expression, she felt at home the moment she took the stage. Though her outrageous observations and quick wit made her a local favorite, she still remained in the closet, fearful of how her new fans would react. Small shows in the Texas panhandle turned into touring the country where audiences fell in love with Kristin’s original comedy songs and rapid-fire humor coming from the “Preacher’s Kid." After reaching a national audience as a finalist on NBC's Last Coming Standing, Kristin moved to LA.
While performing at an anti-bullying fundraiser in 2015, Kristin felt inspired to come out (again). For the first time ever, she publicly shared her journey of coming out, taking it back, living in the closet, and meeting her wife. Now, 20 years after that first open mic—sober, and happily married—Kristin Key is a national headline comedian and viral sensation, With hilarious material about everything from queer culture and relationship dynamics to cats and crocheting, Kristin is proud to use her platform to live her truth and inspire others to do the same. With every show or viral video, she's building a powerful and inclusive community of comedy fans from all walks of life.
To date, Kristin has recorded 6 full-length comedy albums & 1 DryBar comedy special and has appeared on NBC'S Bring the Funny & Last Comic Standing, VH-1, SiriusXM, and more. Her social media videos have over 92.2 million views and Kristin has over 590,000 followers. She currently hosts Kristin Knows Blank, a popular comedy podcast available on all major streaming platforms. Kristin's additional credits include Comics Unleashed, VH-1’s 100 Greatest Series, The Bob and Tom show, and SiriusXM Satellite Radio.
Be Steadwell
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Be Steadwell
Be Steadwell (They, She, He, Be) is a queer pop composer and storyteller from Washington DC. Be composes songs on stage using looping, vocal layering and beat boxing. Be's original music features earnest lyricism and affirming queer content. Be's goal as a musician is to make other black girlies, introverts and weirdos feel seen and loved.
Be earned a BA in Black Studies from Oberlin College and an MFA in film from Howard University in 2014. Be's thesis film Vow of Silence screened in film festivals around the world, including Black Star, HBO's OutFest, The Schomburg Center, and Inside Out Toronto.
In 2019, Be composed the music for The Alvin Ailey Dance Company's production of "the gone". Later that year, Be wrote and directed A Letter to My Ex, the musical. A Letter to My Ex imagines a queer black woman's experience of healing after a breakup. In 2021 Be released their latest album, Succulent.
In 2023, Be joined the cast of Parable of the Sower, the Opera by Toshi Reagon and Dr Bernice Johnson Reagon.
Gina Chavez
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Gina Chavez
Gina Chavez (she/they) is a Latin Grammy nominee, internationally acclaimed recording artist, wife and philanthropist. Born in Austin, she is a 16-time Austin Music Award winner. Gina's first all-Spanish language album, La Que Manda, was nominated for a 2020 Latin Grammy in Best Pop/Rock, making them the third Latine born in the continental U.S. to ever be nominated in history of the category (and the first queer Texan). Gina’s NPR Tiny Desk concert has more than 1.3 million views and she is featured on Brené Brown's hit podcast, Unlocking Us, for which she co-wrote the theme music. Gina tours internationally as a cultural ambassador with the U.S. State Department and runs Niñas Arriba, a college fund Gina and their wife founded for young women in gang-dominated El Salvador. Her official TED Talk is out now.
DJ Rockaway
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DJ Rockaway
Born and raised in Queens, DJ Rockaway has been bringing her passion and love for music to US and international dance floors for nearly two decades. Although she is true New Yorker (just listen to her talk!), she is a regular on both the East and West coasts. You’ll find her spinning at nightclubs, weddings and other private events, and galas for national nonprofits, such as NCLR, HRC, and Equality California, to name a few—and she is also a regular DJ on Olivia cruise and resort vacations.
The executive producer of the San Francisco Women’s Stage and the founder of PLAY San Francisco and PLAY San Jose, monthly events for women who love to dance, DJ Rockaway has created a unique mix of music styles—dance, hip-hop, R&B, house, club, retro—that allows her to play for all who love to dance and feel the music. In her spare time, you can find her behind a camera lens, playing with her drone, or filming and editing music videos. For DJ Rockaway, music is more than a blend of sounds, music is an experience… she wants you to feel it, live it, escape into it.
DJ Olga T
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DJ Olga T
A Puerto Rican lover of all things music, dogs, community and human connection through the language of rhythm and beats, born in NYC and raised in San Francisco, Olga T has an exceptional style of DJing that never fails to grab your attention on the dance floor. This northern California legend is known for masterfully transitioning through nearly every genre of music and always being committed to working with the original Technics 1200 turntables while making creative use of ever evolving digital accessories.  DJing for the past 20 years while producing legendary Bay Area events (Mango SF, Good Times Oakland), spinning at major corporate gigs (Salesforce, Oracle, etc.), previous Olivia trips and events as well as queer festivals (SF Pride, Folsom SF) year-round in addition to teaching DJ classes, creating exclusive remixes, edits and mixtapes is Olga T's fulltime passion.
To listen and download various music genres mixtapes created by DJ Olga T, go to https://soundcloud.com/djolgat)
Amber Whittington
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Amber Whittington
Amber Whittington, also known as AmbersCloset, is an Activist, Social Influencer, and Host, whose videos range from self love/motivational, LGBTQ+, food, fashion, politics and more. She started her channel to help others that might be struggling with their identity and to break stereotypes. She believes in changing the world by changing within. Her goal is to Empower everyone through positivity, self love, and self confidence; so they feel inspired to show their true authentic self to the world and to show up as the best versions of themselves.
Vitus "V" Spehar
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Vitus "V" Spehar
V has quickly become a go-to source for news, building a loyal following of over 3 million subscribers who turn in daily for content that informs and educates while centering the emotional safety of viewers. V Spehar was a nominee for the 2023 GLAAD media award for Outstanding Podcast (V Interesting) and winner of the 2023 Webby's Special Achievement Award. V has been a decades long champion for LGBTQ+ leadership in the policy and culinary space and is a board member of Rainbow Families. Their pronouns are They/Them and they will be joining us on the trip with their wife, Natalie V Spehar, a prominent cellist most recently seen in the Broadway touring cast of Hadestown and The Last Match.
Dirty Lola
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Dirty Lola
Dirty Lola is an award-winning sex edutainer, speaker, and self-proclaimed dildo slinger. Known for her live sex ed, Q&A show Sex Ed A Go-Go, and as a Sexpert on the Emmy-nominated Netflix docuseries The Principles of Pleasure, Lola has spent over a decade working to end the stigma and shame surrounding sex and sexuality while sharing her personal discoveries with polyamory and kink online.
Lola uses her knowledge, warm candor, and public platforms to teach the masses in person and rapt Internet and television audiences. In addition to her educational projects, Lola is on the advisory board for the Youth Sexpert Program and has brought her unique brand of sex-positive sex education to brands such as Shag Brooklyn, B-Vibe, Blush, Freya, Womanizer, and Spencers Gifts, and media outlets such as New York Magazine, HBO, and Vice.
Lee Whitwell
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Lee Whitwell
Number One Ranked Female Senior Pro, International Professional Pickleball Player, Coach, Consultant, and Business Owner
Lee Whitwell is not only the number one ranked female senior pro in the world but also a top-ranked international professional pickleball player, respected coach, and pickleball club consultant. Voted MVP of Major League Pickleball (MLP) in both 2021 and 2022, she continues to inspire both on and off the court.
Born in Gibraltar, a British overseas territory, Lee ventured to America for college and made her mark in professional tennis before transitioning to pickleball. Known for her fierce competitiveness, she captivates audiences with her humor and crowd engagement skills. Lee’s journey through the sport is not just about individual success but also about giving back.
In addition to her competitive career, Lee is the Next Gen National Team Coach, where she helps mentor and develop the future stars of pickleball. She is also the co-founder, alongside her business partner Angela Farmer, of Game ChangeHer Events—a grassroots pickleball events company dedicated to empowering women, particularly focusing on the senior pro division. Together, they advocate for the growth of women's pickleball at both national and international levels, especially among women over 50. Lee embodies sportsmanship, consistently demonstrating compassion, kindness, and a genuine passion for the sport.
Domenika Turkovic
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Domenika Turkovic
Touring Pickleball Pro and Former Division 1 Tennis Standout
Domi started her pickleball adventure after she finished competing in tennis for the Arizona State Sun Devils, a division 1 school competing in the PAC-12. She was ranked as high as number 7 in the country in doubles and 69 in singles. Domi was a top player in Croatia in juniors and played a few professional tournaments before continuing her education in the US. After a successful tennis career, she decided to turn her attention to pickleball. She has been coaching for the past two years and started playing tournaments at the beginning of the year. Domi is currently a full time professional player looking to share her knowledge and experience with the world. Her teaching motto is to have fun, keep moving, and to improve your physical and mental abilities on and off the court.