Key West’s best concert experiences happen on the water, where music meets maritime charm.
Three standout options offer different ways to enjoy live entertainment while cruising:
The 60-foot catamaran sunset sail is our favorite, combining live music with an all-inclusive package of drinks and substantial appetizers – perfect for music lovers who want a refined experience.
For those seeking dinner and a show, the 2-hour sunset dinner cruise delivers with its tropical buffet and entertainment, though it can get crowded during peak season.
The Sunset Sip and Sail provides a more intimate setting, with unlimited beverages and light bites – ideal for couples or small groups who prefer a cozier atmosphere.
Let’s explore these top-rated musical cruises in detail.
Key Points
- Key West is known for its vibrant live music scene, with various venues hosting concerts and performances throughout the year.
- The Green Parrot Bar and Sloppy Joe’s Bar are popular spots for catching local and regional acts performing a range of musical genres.
- The annual Songwriters Festival in Key West features intimate performances by acclaimed songwriters from across the country.
- The Key West Amphitheater hosts larger-scale concerts, with past performers including national touring acts and popular music festivals.
- Many sunset sails and dinner cruises in Key West incorporate live music, providing a unique concert experience while enjoying the scenic water views.
Key West Sunset Sail With Full Bar, Live Music and Hors Doeuvres
Witness the captivating allure of a Key West sunset as you embark on a leisurely cruise aboard a 60-foot catamaran.
With a maximum capacity of 80 travelers, this Key West Sunset Sail offers an intimate and unforgettable experience. Indulge in a selection of chef’s choice hors d’oeuvres, including shrimp cocktail, while sipping on an all-inclusive full bar of beer, wine, champagne, sangria, and soft drinks.
The soothing sounds of live Key West musicians provide the perfect soundtrack as you take in the scenic views of the seaport, Mallory Square, and Fort Zachary Taylor Historic State Park.
As the sun dips below the horizon, you’ll have ample opportunities to capture the breathtaking moments through photography.
With a 92% recommendation rate and a Badge of Excellence, this sunset sail is a must-do activity for your Key West visit, priced at $79 per person.
Read our full review: Key West Sunset Sail With Full Bar, Live Music and Hors Doeuvres Review
Book now: Check availability
Key West: Sunset Dinner Cruise With Open Bar & Live Music
Set out on a captivating Sunset Dinner Cruise in Key West, where you’ll witness the captivating allure of the Gulf of Mexico‘s horizon as the sun dips below. Priced from $89.95 per person, this 2-hour experience offers an open bar, a tropical buffet, and live music on the upper deck.
Savor roast pulled pork, fried fish, and other local delicacies as you sip on margaritas and rum runners while enjoying panoramic views.
With an overall rating of 4.3 out of 5 from 154 reviews, guests praise the food quality, service, and atmosphere. Notable reviews highlight an “amazing time” and “surprisingly good food.”
The cruise also includes hotel pickup and drop-off, and offers free cancellation up to 24 hours in advance. Bring your passport or ID card and check availability for the best start time to embark on this unforgettable sunset adventure in Key West.
Read our full review: Key West: Sunset Dinner Cruise With Open Bar & Live Music Review
Book now: Check availability
Sunset Sip and Sail Key West With Open Bar and Live Music
Basking in the golden glow of the setting sun, you’ll set sail on Key West’s premier Sunset Sip and Sail experience.
With a maximum of 75 travelers, this top-rated cruise offers an intimate and exclusive atmosphere. You’ll indulge in an unlimited open bar, savoring draft beer, wine, champagne, and a variety of mixed drinks as you sway to the live music of one of Key West’s best musicians.
The menu features a tempting selection of appetizers, including Jamaican jerk chicken sliders, BBQ meatballs, and pita with hummus, allowing you to savor a taste of the island’s flavors.
Though some reviews note the music isn’t for dancing, the lively atmosphere and stunning sunset views make this a highlight of any visit to Key West.
With a convenient meeting point, easy accessibility, and free cancellation, the Sunset Sip and Sail is a must-do for anyone seeking a memorable and relaxing evening on the water.
Read our full review: Sunset Sip and Sail Key West With Open Bar and Live Music Review
Book now: Check availability
Key West: 2-Hour Sunset Sail With Live Music
As the sun begins to dip below the horizon, you’ll set sail on an enchanting 2-hour sunset cruise around the vibrant waters of Key West. Priced from $79.95 per person, this experience offers unlimited drinks, appetizers, and live music, along with breathtaking views of landmarks like the Historic Seaport and Fort Zachary Taylor.
The cruise departs from the local partner’s office on Lazy Way Lane, and you’ll want to arrive 30 minutes early. Once on board, you can sit back, relax, and enjoy the sights and sounds of the evening. The crew provides a welcoming atmosphere, and many guests have reported seeing dolphins during their sail.
While the majority of reviews praise the beautiful sunsets and overall experience, some feedback mentions limited seating and occasional crowding.
Nonetheless, this sunset sail caters to a variety of guests, from couples to families and solo travelers, making it a popular choice for those seeking a memorable evening in Key West.
Read our full review: Key West: 2-Hour Sunset Sail With Live Music Review
Book now: Check availability
Key West Sunset Buffet Dinner Cruise With Open Bar and Live Music
For those seeking an unforgettable evening on the water, the Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music offers a captivating experience.
This 2-hour cruise features a delectable dinner buffet with vegetarian options, an open bar serving tropical-inspired drinks, and live music to set the mood as you witness the stunning Key West sunset.
Operated by Attractions4us LLC, the cruise can accommodate a maximum of 56 travelers and departs from the Historic Seaport Pier.
While not wheelchair accessible, the cruise provides complimentary hotel pick-up and drop-off for those interested in the wine tour option.
Despite having only 2 reviews, the overall rating of 2.5 out of 5 stars suggests a mixed reception, with no 4-star or 5-star ratings.
However, one reviewer positively described the experience as “watching the Key West sunset with my mom and listening to the DJ” and noted the “good food and drinks.”
Read our full review: Key West Sunset Buffet Dinner Cruise With Open Bar and Live Music Review
Book now: Check availability
Recap
You’ll find a wide range of live music experiences to enjoy during your sunset cruise in Key West. Whether it’s a sunset sail with an open bar and hors d’oeuvres, or a dinner cruise with a buffet and open bar, you can’t go wrong. The live music will set the perfect mood as you take in the stunning views of the Florida Keys.