Key West isn’t just about stunning sunsets and laid-back vibes; it’s a lively hub for live music and unique concert experiences on the water. Whether you’re into dancing under the stars, savoring tropical cocktails, or exploring the island’s musical roots, Key West offers a variety of ways to enjoy its soundscape. We’re particularly fans of the Key West Sunset Sail with Live Music for its combination of breathtaking scenery, local tunes, and all-inclusive drinks. It’s a classic way to unwind after a day exploring the island, and the reviews sing its praises—many noting the friendly crew, great music, and spectacular sunsets. For a more laid-back, cultural dive into the island’s musical soul, the 2-Hour Live Music Guided Tour is perfect for those who want to discover why Key West has such a vibrant live music scene.
If you’re looking to combine a delicious dinner with your sunset experience, the Key West Sunset Dinner Cruise with Open Bar & Live Music offers a tropical feast and panoramic views. For something more energetic and fast-paced, the Key West Sunset Sail with Full Bar, Live Music and Hors D’oeuvres is a great choice, with rave reviews about its well-organized crew, ample food, and excellent music.
Quick Overview
Our list covers a broad spectrum of concert experiences in Key West, from sailing cruises with live music (see here) to guided music tours (check this out). These tours range from 2-hour sunset sails perfect for a quick romantic evening, to full-day combo cruises that include snorkeling, dinner, and multiple live music moments. Whether you want a lively party on the water or an intimate look at Key West’s musical venues, there’s something here for you.
1. Key West Sunset Sail with Live Music, Drinks and Appetizers
This classic party cruise offers a lively two-hour sail featuring live music from some of the island’s best singers and songwriters. It’s a popular choice for those who want to combine breathtaking sunset views with a festive atmosphere. The boat departs from Fury Watersports, a well-known operator in Key West, and offers unlimited drinks and appetizers, making it a true floating celebration. The appetizers include an antipasti platter, seasonal fruit, hummus, and pinwheel sandwiches, while drinks range from wine and beer to sparkling champagne and margaritas.
What makes this tour stand out is the live music—local musicians create a soundtrack that fits perfectly with the changing sky. Many reviews highlight how fun and friendly the crew is, with one guest noting the band “Killer Dudes” as a highlight. The spacious deck and shaded lounge areas ensure everyone can enjoy the views comfortably. Best suited for travelers who want a lively atmosphere with great entertainment, plentiful drinks, and a memorable sunset.
Bottom Line: This sail combines great music, scenic views, and a party vibe, making it ideal for celebrating a special evening or just enjoying a lively cruise with friends.
2. Sunset Sip and Sail Key West with Open Bar and Live Music
For around the same price as the previous option, the Sunset Sip and Sail offers a similar 2-hour cruise with the added bonus of an open bar. This vessel is new and spacious, providing plenty of room for larger groups to enjoy the sunset without feeling crowded. It’s perfect if you want a more relaxed yet festive atmosphere, with tasty appetizers and live music as a soundtrack.
The crew is praised for being friendly and professional, creating a safe, fun environment. Many reviews emphasize the smooth ride and the fast service at the bar, which helps keep the party going. Guests also appreciate the beautiful sunset views and the opportunity to see Florida from a fresh perspective. This tour is a good choice if you want a combination of sightseeing, music, and socializing in an elegant setting.
Bottom Line: The open bar and ample space make this option perfect for travelers who want a relaxed, fun cruise with plenty of room to dance and enjoy the sunset.
3. Key West: 2-Hour Sunset Sail with Live Music
This all-inclusive sailing trip is a solid choice for those who want to experience breathtaking sunset views with unlimited drinks and live music on a comfortable catamaran. Many travelers love its spectacular scenery and the chance to hear about local points of interest while floating on the water. The tour departs from a well-equipped vessel, and the live music helps set a relaxed, festive tone.
Guests consistently mention the quality of the views and the delicious spread of appetizers. It’s a great option for travelers who want a peaceful yet lively experience, combining nature’s beauty with music and refreshments. The reviews highlight the value for money, with many noting the experience as a memorable way to end a day in Key West.
Bottom Line: With a focus on comfort, scenic views, and good entertainment, this cruise suits those looking for a beautiful, laid-back evening on the water.
4. Key West: Sunset Dinner Cruise with Open Bar & Live Music
At number 4 on our list, the Sunset Dinner Cruise combines spectacular Gulf views with a tropical buffet dinner and live music. This cruise is perfect for travelers who want an elegant evening with gourmet food and uninterrupted sunset viewing. The vessel departs from the Gulf of Mexico, offering panoramic views, while the buffet includes dishes like Caribbean Roast pork, fried fish, and grilled chicken—ideal for satisfying hungry travelers.
The live music on the upper deck adds a festive, tropical soundtrack, and the open bar ensures everyone can toast the sunset with their favorite drink. Many reviews mention the beautiful scenery and delicious food. While the trip is priced slightly higher, the quality of the experience—including the food and views—makes it a good value for special occasions or romantic evenings.
Bottom Line: If you’re after a luxurious, dinner-oriented sunset experience, this cruise provides the perfect mix of scenery, food, and live entertainment.
5. 2-Hour Live Music Guided Tour in Key West
For a taste of Key West’s local music scene, the 2-Hour Live Music Guided Tour offers a different kind of experience. Led by a local guide, you’ll visit 4 iconic venues including the Little Room jazz club and the Green Parrot bar, gaining insight into the island’s musical roots. This tour includes drink discounts, a digital guide to upcoming events, and a download of local artists’ music.
What makes this experience stand out is the personal storytelling about the venues and musicians who shaped Key West’s sound. Guests rave about how knowledgeable and friendly the guide Maxwell is, making this a more intimate, cultural experience. It’s ideal for travelers who want to enjoy the local music scene, learn the stories behind the music, and perhaps discover new favorites.
Bottom Line: Perfect for music lovers curious about local artists and venues, this tour offers a personalized glimpse into Key West’s musical heartbeat.
6. Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music
This dinner cruise stands out for its tropical buffet and live Caribbean-style music on board a modern catamaran. It departs from Sunset Bight Marina, with check-in straightforward and the cruise setting the scene for a relaxed, festive evening. The buffet features dishes like Caribbean Roast pork, fried plantains, and pasta salad, satisfying even the heartiest appetites.
The open bar includes margaritas, rum runners, wine, and beer, making sure you’re well-hydrated for the sunset spectacle. Many reviewers praise the friendly crew and the beautiful sunset views. This cruise is particularly good for travelers looking for a more casual, lively dinner experience with great music and viewing comfort.
Bottom Line: If a tropical-themed buffet and lively atmosphere are your priorities, this cruise delivers a memorable sunset with excellent food and drinks.
$99.99 per person
7. Key West Sunset Sail with Full Bar, Live Music and Hors D’oeuvres
This popular sunset sail provides a full bar, live music, and delicious hors d’oeuvres on a 70-foot catamaran. It’s one of the most reviewed tours, with over 3,000 reviews praising its organized crew, ample deck space, and quality food like peel-and-eat shrimp. Departing from the usual sunset location, it offers a two-hour cruise that is perfect for romantic couples, groups, or even solo travelers.
The music features local artists, and the full bar includes wine, champagne, and craft cocktails. Many reviews note the peaceful sailing experience and the unbeatable views of the sunset. It’s suited for travelers wanting an all-around enjoyable evening with good drinks, music, and scenery.
Bottom Line: With its great reviews and lively ambiance, this cruise is ideal for those who want a classic sunset sail with plenty of drinks and entertainment.
8. Key West Sunset Cruise: Dinner, Live Music & Drinks Included
This dinner cruise offers a tropical buffet and live music aboard a well-equipped 65-foot vessel. It departs from Sunset Watersports, with a focus on watching the iconic Key West sunset from the upper deck. The buffet includes dishes like Caribbean Roast pork, fried fish, and Cuban bread, with drinks such as margaritas and beer.
The live music enhances the festive atmosphere, and the cruise also passes by Mallory Square and the Florida Keys National Marine Sanctuary. The cruise receives high marks for beautiful scenery and friendly staff, though some mention the need for more shade during hot days. It’s perfect for travelers who want a combination of good food, scenery, and entertainment.
Bottom Line: This cruise is a solid choice for those wanting a well-rounded experience of sunset, food, and music in a comfortable setting.
$92.95 per person
9. Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
For the adventurous, this full-day combo tour includes an early morning snorkeling trip plus an evening sunset dinner cruise, all on a catamaran. It’s a longer, more comprehensive experience that covers both underwater exploration and sunset viewing. The snorkel visits sites like Sand Key Light House and Eastern Dry Rocks, with light breakfast provided beforehand.
In the evening, enjoy a buffet dinner, live music, and an open bar. While it’s the most expensive option, it suits travelers wanting an active day of exploring both above and below the water. The reviews highlight the quality of the snorkeling and the beautiful sunset at the end. This experience is best for active travelers with time to spare and a love of both music and snorkeling.
Bottom Line: If you want a full-day adventure combining snorkeling and sunset, this combo tour offers a well-rounded day in Key West.
$159.99 per person
How to Choose Your Perfect Key West Concert Experience
When selecting your ideal concert experience, consider your budget, the type of scenery you prefer (water, land, or a mix), and whether you want dining, dancing, or cultural insights. For a lively party with drinks and music on the water, the Key West Sunset Sail with Live Music or the Sunset Sail with Full Bar are excellent choices. If you’re after a more casual, local vibe, the Live Music Guided Tour provides insight into Key West’s musical roots. For a luxury dinner with panoramic views, the Sunset Dinner Cruise delivers a refined experience.
Booking early is wise, especially during peak season, and always check the latest reviews for updates on the crew and amenities. Whether you prefer a quick two-hour sail or a full-day adventure, there is something to match every traveler’s style.
Final Thoughts
From music-filled sunset sails to cultural tours through Key West’s live music venues, this list showcases the island’s rich musical offerings. For a festive, all-out party, the Sunset Sail with Full Bar is hard to beat. For those seeking a more intimate, educational experience, the Live Music Guided Tour reveals the island’s musical soul. And for lovers of fine food and scenery, the Sunset Dinner Cruise offers a luxurious, memorable evening.
Whatever your style, booking early and choosing the experience that matches your interests will help you make the most of your time in Key West. With these options, you’re all but guaranteed a memorable soundtrack to your island getaway.