The Cheeky Butlers
we make it impossible for boring parties to happen
Welcome to Key west, fl
Welcome to Key West, the southernmost point of the USA and the ultimate destination for any bachelorette party or milestone birthday celebration. Famous for its relaxed island vibe and legendary party entertainment, Key West offers a perfect blend of boisterous nightlife on Duval Street and serene, turquoise waters ideal for lounging.Planning a private party in the Florida Keys requires local knowledge.
To ensure your event is a hit, you need access to the best clubs, dining, and, most importantly, the right kind of fun. That’s where The Cheeky Butlers comes in. From sophisticated pool parties to wild girls' nights out, we provide the perfect party entertainment to elevate your event. Our services include professional, charismatic shirtless waiters and cabana boys who are experts in hosting naughty games and serving up body shots.
Clubs & unique dining experiences
An iconic, no-frills local favorite known nationally for showcasing some of the best live music bands in Florida.
A three-story entertainment complex featuring a casual bar (The Bull), a lively game bar (The Whistle), and a clothing-optional rooftop lounge (Garden of Eden).
A high-end, award-winning restaurant and bar located on the pier at the Ocean Key Resort, offering a prime view of the famous sunset celebration.
A large complex with eight bars in one location, featuring everything from a dance club and live music to a sports bar, perfect for a long pub crawl.
A popular and welcoming gay nightspot known for its hilarious and highly professional nightly drag cabaret and high-energy dance floor.
Home to the famous Aquanettes drag performers, this bar offers a lively schedule of drag bingo, karaoke, and nightly cabaret shows.
A casual, classic Key West harbor-side bar offering breakfast, lunch, dinner, and live music with views of the historic port.
A world-famous chain known for its massive selection of frozen daiquiris and a vibrant, DJ-fueled dance floor on Duval Street.
A lively waterfront spot at the end of Duval Street that offers cocktails and live music right on the water, ideal for enjoying the nightly Sunset Celebration.
cool things to do
Book the best shirtless waiters, cabana boys, and exotic dancers for in-house party entertainment including body shots and naughty games.
Offers a variety of thrilling group excursions, including the Commotion on the Ocean sunset sail with live music and open bar, perfect for a bachelorette.
Specializes in custom, creative menus focused on Key West-Cuban-Bahamian cuisine, bringing the full fine dining experience to your rental.
Food Fire + Knives
A service that connects you with vetted, local private chefs who handle all the shopping, cooking, and cleanup for an effortless, gourmet private party.
Chef Callie Morehouse offers custom menu planning and provisioning services to fully stock your vacation home or yacht before you arrive.
Provides various snorkeling tours, sunset sails, and catamaran cruises that include complimentary drinks and light food.
Key West First Legal Rum Distillery
Offers free rum tasting tours and a popular Mojito Making Class for groups, a great interactive activity for a birthday event.
Offers private, all-inclusive party boat rentals and charters with captains, specializing in sandbar trips and customized bachelorette experiences.
A lively, massive pool bar and restaurant with live music, making it an ideal spot for a mid-day pool partyand socializing.
Renting a six-seater golf cart is the most fun and convenient way for your group to zip around the compact island between venues.
The Old Town Trolley offers narrated tours that are a fun, casual way for your group to see the major historical sites and landmarks.
Offers serene spa services like massages, facials, and group manicures, providing a necessary recovery day from Duval Street partying.
Famous for its Key lime pie on a stick (dipped in chocolate), this is a must-visit for a casual group treat or birthday dessert.
A quirky, open-air train tour that provides an entertaining and comprehensive overview of the island's history and attractions.
A boutique shop on Greene Street specializing in coastal-chic apparel, accessories, and gifts perfect for group shopping excursions.
A popular stop for craft beer enthusiasts, offering local brews and a chill tasting room atmosphere for a relaxed group outing.
Offers drop-in group classes or can arrange a private yoga session at your location for a relaxing morning activity.
Local experts who can assist with full bachelorette partylogistics, including reservations, transport, and custom decor setups.
Booking a private boat for snorkeling allows your group to customize the itinerary to visit pristine reefs or secluded sandbars.
Hire a photographer to take your group on a customized walking tour, capturing stunning, high-quality photos at the island's best backdrops.
Our Cheeky Butlers and professional event staff provide premium service across every major hotspot and hidden gem in the Southernmost City, including:
Duval Street, Mallory Square, The Historic Seaport, Sunset Key, Smathers Beach, Fort Zachary Taylor, Bahama Village, Casa Marina, Southernmost Point, The Truman Annex, Key West Bight, Stock Island, The Reach Resort, Pier House Resort, Ocean Key Resort & Spa, Sloppy Joe’s, Green Parrot Bar, Irish Kevin’s, Hog’s Breath Saloon, The Garden Café, First Flight Island Restaurant, The Perry Hotel, Latitudes, Dante’s Pool Bar, Rick’s Complex, The Bull & Whistle, Southernmost Beach Cafe, Smokin' Tuna Saloon, Bagatelle, Margaritaville.
We provide bespoke support for any high-end gathering. Bachelorette parties. Bachelor weekends. Birthday bashes. Milestone celebrations. Anniversaries. Product launches. Brand activations. Corporate events. Executive retreats. Company mixers. Networking galas. In-home private dinners. Pool parties. Beach bonfire service. Holiday parties. Wedding welcome drinks. Rehearsal dinners. Bridal showers. Engagement parties. VIP hospitality suites. Charity fundraisers. Grand openings. Art gallery showings. Luxury yacht charters. Vacation rental takeovers.