Direct from the heart of Key West’s music scene, the best concert experiences combine sailing and sound. The nightly Sunset Sip and Sail cruise packs real value – you get two hours of live music, steady drinks, and those famous Florida sunsets all for one price. Local musicians on board keep things authentically Keys.
Another standout is the Duval Street Music Tour, a 2-hour walking exploration hitting the island’s top venues. It’s perfect for understanding Key West’s musical roots, from conch shell blowers to modern-day troubadours.
Both tours earn high marks for their mix of entertainment and local culture. They’re well-organized, never feel rushed, and feature talented performers who know their craft.
Check our recommended concert tours below for full details and booking information.
Key Points
- The 2-Hour Sunset Sail with Live Music offers a scenic sunset cruise with unlimited drinks, appetizers, and live musical entertainment.
- The Sunset Sip and Sail Key West provides an evening of scenic views, live music, and unlimited drinks and appetizers aboard the newest catamaran in Key West.
- The 2-Hour Live Music Guided Tour takes visitors on an exploration of Key West’s vibrant music scene, featuring drink discounts and a personalized experience.
- The Afternoon Reef Snorkel Tour combines the opportunity to explore the coral reef with a sun deck, open bar, and potential dolphin sightings.
- The Key West Sunset Sail Experience offers breathtaking views from a large catamaran, complimentary beverages, and hearty appetizers during the sail.
Key West Sunset Sail With Full Bar, Live Music and Hors Doeuvres
The Key West Sunset Sail with Full Bar, Live Music, and Hors D’oeuvres provides travelers with a breathtaking evening experience on the water.
Guests can enjoy stunning views of the sunset and moonrise aboard a 70-foot catamaran, featuring over 1,500 feet of deck space. The tour sails to the best sunset spot, showcasing landmarks like the Key West seaport, Mallory Square, and Fort Zachary Taylor Historic State Park.
Complimentary beverages, including beer, wine, and champagne, as well as hearty appetizers, enhance the experience. Live music from local musicians creates a lively atmosphere.
With a 92% traveler recommendation and a Badge of Excellence, this sunset sail is a must-do activity in Key West.
Read our full review: Key West Sunset Sail With Full Bar, Live Music and Hors Doeuvres Review
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Key West: Afternoon Reef Snorkel Tour With Live Music & Bar
Travelers can embark on an unforgettable afternoon reef snorkeling adventure in Key West, complete with live music and an open bar.
For $59.95 per person, the 3-hour tour allows visitors to marvel at the vibrant marine life of the only living coral barrier reef in North America.
With experienced instructors providing snorkeling guidance, guests can explore the warm, tropical waters.
The catamaran also offers a sun deck for relaxation, where they can enjoy cocktails, beer, wine, and soda from the open bar.
Along the way, the crew keeps an eye out for dolphins.
Reviews praise the friendly guides and excellent value for money.
Read our full review: Key West: Afternoon Reef Snorkel Tour With Live Music & Bar Review
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Sunset Sip and Sail Key West With Open Bar and Live Music
Sunset Sip and Sail Key West offers an unforgettable experience, combining the beauty of Key West’s celebrated sunset with an open bar and live musical entertainment.
Aboard the newest catamaran, The Sandie Cat, guests can enjoy unlimited drinks and a selection of appetizers while taking in the stunning views.
With a maximum capacity of 75 travelers, the cruise ensures a comfortable and intimate setting.
While the crew and food quality receive high praise, some guests have expressed a desire for more diverse menu options and livelier musical performances.
Priced from $79.95 per person, Sunset Sip and Sail is a popular choice for a night out in Key West.
Read our full review: Sunset Sip and Sail Key West With Open Bar and Live Music Review
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Key West: 2-Hour Sunset Sail With Live Music
For an unforgettable sunset experience in Key West, the 2-Hour Sunset Sail with Live Music is a must.
This popular activity offers breathtaking views of the sunset from the water, accompanied by unlimited drinks, appetizers, and live music entertainment aboard a catamaran.
Passengers can expect to pass by local landmarks like the Historic Seaport and Mallory Square Sunset Celebration.
With an overall rating of 4.8/5 based on 100 reviews, this excursion is renowned for its great service, food quality, and scenic sunsets.
Priced at $79.95 per person and with free cancellation up to 24 hours in advance, it’s a fantastic value.
Dolphin sightings and a friendly atmosphere add to the overall experience.
Read our full review: Key West: 2-Hour Sunset Sail With Live Music Review
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2-Hour Live Music Guided Tour in Key West
Alongside the popular sunset sail, Key West offers another immersive musical experience for visitors – the 2-Hour Live Music Guided Tour.
Led by a local guide, this tour provides an insider’s look at the island’s legendary music venues and upcoming live performances. Participants can enjoy drink discounts and sip on beverages as they explore the vibrant Duval Street district.
The tour starts at the Little Room Jazz Club and ends at the iconic Green Parrot Bar, allowing travelers to fully experience Key West’s lively music scene.
With a maximum of 12 participants, this tour offers a personalized and intimate experience for those seeking an authentic taste of the island’s captivating musical heritage.
Read our full review: 2-Hour Live Music Guided Tour in Key West Review
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Key West: Sunset Dinner Cruise With Open Bar & Live Music
Travelers seeking an enchanting evening in Key West can indulge in the Key West Sunset Dinner Cruise, a 2-hour excursion that offers a delightful blend of scenic views, delectable cuisine, and captivating live music.
Priced from $89.95 per person, the cruise includes a tropical buffet, an open bar, and hotel pickup and drop-off. Guests can savor panoramic vistas of the sunset over the Gulf of Mexico while enjoying roast pulled pork, fried fish, and other Caribbean-inspired dishes.
The upper deck features live music, setting the perfect mood for a memorable experience. With a 4.3/5 rating based on 154 reviews, this cruise is a must-try for those looking to enjoy Key West’s vibrant atmosphere.
Read our full review: Key West: Sunset Dinner Cruise With Open Bar & Live Music Review
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Sum Up
Key West offers a variety of concert experiences that allow visitors to enjoy live music while taking in the stunning natural beauty of the island. From sunset sails with an open bar to afternoon reef snorkel tours, there’s something for all who wants to combine music and adventure. Whether you’re looking for a relaxing evening or an action-packed day, Key West has the perfect concert experience to suit your interests.