Top 4 Must-Do August 2025 Events in the Florida Keys: Paddle & Pint, Key West Rum Fest, Dolphin Sunset Sail & Just A Few Friends

Whether you’re a first-time visitor or a seasoned traveler, August brings exciting activities that cater to every interest—from sailing with dolphins to enjoying craft cocktails at the Key West Rum Fest. Plus, with fewer crowds and endless sunshine, it’s an ideal time to relax and make lasting memories with loved ones. If you're looking to make the most of your summer getaway, these four must-do events in the Florida Keys will ensure your August visit is nothing short of spectacular.

Paddle & Pint: A Perfect Evening at The Lagoon on Grassy Key

If you're looking for the perfect way to unwind while visiting the Florida Keys this August, look no further than the "Paddle & Pint" events, held weekly at The Lagoon on Grassy Key. Every Thursday at 5:00 PM, this fun-filled gathering combines the fun of paddleboarding with the relaxation of a cold pint, making it the ideal evening for friends, families, and solo adventurers alike. Whether you're a seasoned paddler or a first-timer, the calm, clear waters offer an ideal setting to enjoy the natural beauty of the area.

Once you've worked up a thirst, head over to Bongo's Botanical Beer Garden, located on property next to the Lagoon. Here, you’ll be treated to a wide selection of craft beers on tap. They also offer delicious cocktails that perfectly complement the laid-back vibe. The beer garden’s atmosphere, surrounded by lush greenery and local fauna, makes it the perfect spot to relax and mingle after your paddle. Live music often fills the air, adding to the vibrant energy of the place.

The Lagoon offers a variety of activities for everyone. From wakeboarding at Keys Cable Park to exploring the Rhum Runner floating obstacle course, there's no shortage of fun ways to make the most of your day. After your paddleboarding adventure, you can also visit the Lagoon Saloon Surf Shoppe to gear up for more aquatic fun or simply enjoy the scenery while sipping your drink. So, grab your paddle, enjoy the view, and raise a glass at Bongo's—this is one Florida Keys tradition you won’t want to miss.

Key West Rum Fest: Sip, Savor & Support

From August 11 to 17, 2025, Key West transforms into a rum lover's paradise. The festival features over 30 rum vendors, offering tastings, masterclasses, and unique experiences across various venues in Key West and Stock Island. Highlights include sunset sails, rum cake competitions, and themed events like the Ti Punch Brunch at Hot Tin Roof and the Going Away Party at Southernmost Beach Resort.

What sets the Key West Rum Fest apart is its dedication to giving back. 100% of ticket sales benefit MARC House, a 501(c)(3) nonprofit organization that provides life services to adults with developmental and intellectual disabilities throughout Monroe County, Florida. By attending the festival, you're directly contributing to programs that enhance the quality of life for these individuals, fostering independence and community integration.

The festival's schedule is packed with events that cater to a variety of interests:

• Sunset Sails & Sandbar Parties: Set sail with rum in hand and enjoy live music on the water.

• Masterclasses & Tastings: Learn about rum's rich history and distillation process from industry experts.

• Live Music & Pool Parties: Dance the night away at venues like The Marker Resort and Southernmost Beach Resort.

• Rum Cake Competition: Taste and vote for the best rum-infused desserts.

• Grand Tasting Event: Sample a wide array of rums and meet the makers at the Key West Theater.

Whether you're a seasoned rum connoisseur or a casual enthusiast, there's something for everyone at the Key West Rum Fest.

Dolphin Sunset Sail: An Evening to Remember

Offered just once a month, the Dolphin Sunset Sail is a special after-hours event at the Dolphin Research Center. In August, the event will be held on August 27. As the sun sets over the Gulf of Mexico, guests embark on a peaceful sail, enjoying the natural beauty of the Florida Keys. Onboard, you'll have the chance to observe the dolphins' natural behaviors, learn about their unique personalities, and even participate in enrichment activities like feeding them specially prepared treats. The evening concludes with a champagne toast, celebrating the connection between humans and marine life. This intimate experience provides a deeper understanding of these intelligent creatures and supports the center's mission.

Located on Grassy Key, the Dolphin Research Center is a nonprofit education and research facility dedicated to promoting peaceful coexistence, cooperation, and communication between marine mammals, humans, and the environment. Founded in 1984 by Armando “Mandy” and Jayne Rodriguez, the center provides sanctuary to dolphins and sea lions, many of whom were born at the facility or rescued and deemed unreleasable back into the wild. The center is also licensed by the federal government to assist manatees in distress, making it a critical part of marine mammal rescue efforts in the Florida Keys.

Research at the center focuses on dolphin cognition, behavior, and husbandry, aiming to better understand these animals and improve their care both in human care and in the wild. Educational programs at the center allow visitors to learn firsthand about dolphins through narrated behavior sessions, interactive encounters, and behind-the-scenes experiences. These programs not only provide valuable insights into dolphin behavior but also foster a deeper appreciation for marine life and the importance of conservation.

"Just A Few Friends" - A Celebration of Jimmy Buffett's Legacy 

If you're planning a visit to the Florida Keys this August, be sure to check out the Just A Few Friends festival in Key West. This annual event, held from August 29 to September 1, 2025, celebrates the life and legacy of the late Jimmy Buffett, bringing together fans and locals for a weekend of music, camaraderie, and giving back.

The festival is a heartfelt tribute to Jimmy Buffett, the iconic musician whose "trop-rock" sound and laid-back lifestyle resonated with fans worldwide. Buffett's connection to Key West dates back to 1971 when he first visited the island. Upon arriving, Buffett was welcomed with a complimentary beer at the Chart Room Bar at the Pier House Motel, marking the beginning of his deep bond with the island.

Key West became Buffett's home in the early 1970s, and the island's vibrant atmosphere and unique characters significantly influenced his music. Songs like "Margaritaville" and "A Pirate Looks at Forty" reflect his experiences and love for the island. Buffett's time in Key West was not just about music; it was about embracing the island's spirit, which he often described as a place where he found his true self.

The festival promises a weekend filled with events that capture the essence of Jimmy Buffett's life and music. Attendees can look forward to:

• Live Performances: Enjoy tribute bands and musicians playing Buffett's classic hits.

• Second Line Parade: Join the spirited procession down Duval Street, a nod to New Orleans' tradition and a celebration of Buffett's influence.

• Party in the Park: Experience an evening of music and festivities at the park, featuring performances by artists like Nadirah Shakoor, a longtime vocalist with Buffett's Coral Reefer Band.

• Special Events: Participate in various activities and gatherings that highlight Buffett's connection to the island.

The festival not only honors Buffett's legacy but also supports local causes. Proceeds from the event benefit organizations like the Bahama Village Music Program and Reef Relief, which focus on music education and marine conservation in the Florida Keys.

We Invite You To Stay With Us

After a day filled with adventure and fun in the Florida Keys, there's no better place to relax and unwind than Casa Feliz. Nestled in the heart of the Keys, our beachside oasis offers the perfect blend of luxury and laid-back vibes, making it the ideal home base for your August getaway.

With top-tier amenities, personalized concierge services, and a location just minutes from all the action, it’s the perfect home base for your Florida Keys getaway. Whether you're looking to enjoy stunning sunsets, relax on the private beach, or explore all the exciting events happening around the islands, Casa Feliz provides a welcoming and comfortable space for families to create lasting memories.

We’d love to welcome you to our slice of paradise—looking forward to having you with us soon!