St Augustine, Florida, isn’t just about historic streets and charming architecture; it’s also a wonderful place to enjoy music and maritime scenery. The city’s warm coastal vibe makes for memorable concert experiences, especially when combined with breathtaking sunsets or seasonal celebrations. We particularly like the Sunset Cruise with Live Music and Drinks because it offers a relaxed, scenic way to enjoy local musicians over the calm waters, with drinks and snacks included. It’s a great way to unwind after a day of sightseeing and soak in the natural beauty of St Augustine.
For those looking to experience the city’s famous Nights of Lights spectacle, the Nights of Lights Sunset Sail with Live Music combines the magic of holiday lighting with a lively cruise, making it perfect for romantic evenings or festive gatherings. And if you’re visiting during Halloween, the Halloween Boo Bash Sunset Sail offers a fun, spooky twist on the usual boat trip, complete with costume contests and themed bites. Each of these options showcases how St Augustine blends music, scenery, and seasonal fun into memorable experiences.
1. St. Augustine: Sunset Cruise with Live Music and Drinks
At number one, the Sunset Cruise with Live Music and Drinks provides a relaxed but lively way to experience St Augustine from the water. This 2-hour cruise on a modern catamaran takes you through the serene waters as the day transitions into evening. You can expect live performances by local musicians, creating a festive atmosphere against the backdrop of a stunning sunset. The cruise includes complimentary beer, wine, margaritas, champagne, soda, and water, making it perfect for unwinding with a drink in hand.
What makes this tour stand out is its combination of natural beauty and entertainment. As you sail, you’ll feel the gentle breeze and watch the skyline change colors—it’s particularly breathtaking during golden hour. The light snacks add to the experience without making it overly filling, so you stay eager for the next musical number or sunset view. With a 4.8-star rating from 104 reviews, this cruise is praised for its excellent value and friendly crew. It’s best suited for those who want a laid-back, scenic evening with good music and drinks without any fuss.
Bottom Line: If you love combining coastlines, cocktails, and live music, this cruise offers a relaxed, enjoyable evening with a friendly crowd and beautiful views.
2. St Augustine: Nights of Lights Sunset Sail with Live Music
Second on our list, the Nights of Lights Sunset Sail elevates the experience during one of St Augustine’s most dazzling times of year. This 2-hour cruise not only offers a chance to enjoy live music and drinks but also to witness the city illuminated with the famous Nights of Lights display. The deck of the spacious, state-of-the-art catamaran is perfect for viewing the sparkling lights while the sun dips below the horizon.
What sets this tour apart is its timing during the holiday light season. The glow of thousands of tiny bulbs reflecting on the water creates an ambiance that’s almost otherworldly. The cruise includes complimentary margaritas, champagne, beer, wine, and sodas—so you can toast to the holiday season. The tour has an impressive 4.9-star rating from 50 reviews, with many travelers commenting on how magical the experience feels. It’s ideal for couples, families, or anyone eager to combine their love of music, scenic vistas, and holiday cheer.
Bottom Line: If you want to see St Augustine sparkle and enjoy a lively, festive atmosphere on the water, this sunset sail during Nights of Lights is a top pick.
3. St. Augustine: Halloween Boo Bash Sunset Sail with Live Music
For a one-night-only experience, the Halloween Boo Bash Sunset Sail offers a fun, spooky celebration along the coast. This 2-hour cruise features upbeat live music, a costume contest with prizes, and a curated selection of refreshments including beer, wine, and champagne. It’s perfect for those looking to combine festive Halloween fun with scenic sailing.
The event’s highlight is its lively, party-like atmosphere with decorations, costumes, and a bit of friendly competition. As you drift along the coast, keep your eyes peeled for dolphins and seabirds that often appear in the late afternoon. While reviews aren’t available yet, the concept of a themed sunset sail with entertainment makes it a unique experience for Halloween lovers or anyone wanting a different way to celebrate the season. Light bites are included to keep your energy up for dancing and costume contests.
Bottom Line: If you enjoy celebrating holidays with a maritime twist, this Halloween cruise offers a spirited, festive evening with live music and the chance to meet fellow costumed boaters.
$69 per person
How to Choose the Right Concert Experience
When deciding between these options, consider your interests and timing. The Sunset Cruise with Live Music and Drinks is ideal if you want a relaxed, less themed experience perfect for unwinding. The Nights of Lights Sunset Sail is best during the holiday season if you want to see the city’s beautiful lights. For a festive, holiday-themed celebration, the Halloween Boo Bash Sunset Sail offers a fun, spooky twist.
Think about your budget, the time of year, and whether you prefer a more casual or lively atmosphere. Booking early is recommended, especially during popular seasons like Nights of Lights, to ensure your spot.
Final Thoughts
St Augustine’s concert experiences on the water showcase the city’s vibrant spirit and scenic charm. Whether you opt for the serene beauty of a sunset cruise, the illuminated spectacle during Lights season, or a Halloween-themed party, each tour offers something special. For travelers seeking a relaxing way to enjoy local music and coastal views, the Sunset Cruise with Live Music is a top choice. Those looking for a festive, holiday-themed event will find the Nights of Lights Sunset Sail perfect, while Halloween fans shouldn’t miss the Boo Bash.
No matter your preference, booking these experiences early will ensure you get to enjoy the best of what St Augustine offers—combining music, scenery, and seasonal festivities in unforgettable style.