Experience St. Augustine’s only all-inclusive sunset sail with live music, drinks, and stunning views. Perfect for families and couples. Book now!
Experience St. Augustine’s only all-inclusive sunset sail with live music, drinks, and stunning views. Perfect for families and couples. Book now!
250 Vilano Rd - Discover St. Augustine from the water on this relaxing and entertaining live music excursion. With two cruise options to choose from, this is the perfect way to enjoy coastal views, fresh air, and great music while cruising past the historic downtown waterfront.
All cruises feature live music performed onboard by talented local…
250 Vilano Rd - Discover St. Augustine from the water on this relaxing and entertaining live music excursion. With two cruise options to choose from, this is the perfect way to enjoy coastal views, fresh air, and great music while cruising past the historic downtown waterfront.
All cruises feature live music performed onboard by talented local musicians, creating a fun and laid-back atmosphere as guests glide through the Intracoastal waterways.
The two-hour Live Music Sunset Sail is ideal for guests who want extra time on the water and the best views of golden hour over St. Augustine. Departing from Vilano Beach, the sail follows the shoreline as the sun sets, casting warm colors across the water and illuminating the historic downtown skyline.
On select evenings, guests can also choose a 90-minute After Dark Live Music Cruise (sail will be down), departing after the sun has fully set. This cruise offers a relaxed and intimate way to enjoy St. Augustine from the water as the city transitions into night.
Complimentary drinks and snacks are included on either option!
Oct 31 Boo Bash - Celebrate Halloween on the water! Costumes are encouraged! Nights of Lights viewing available mid-November through mid-January only

- Sunset - Available on 2 hour sunset trip only
- Carbonated beverages
- Alcoholic beverages
- Snacks
- Sunset - Available on 2 hour sunset trip only
- Carbonated beverages
- Alcoholic beverages
- Snacks
- Gratuities
- Dinner
- Gratuities
- Dinner
Step aboard our spacious, cutting-edge catamaran and select your ideal St. Augustine adventure! Choose between a two-hour sunset sail with live music and full sails, or relax on a 90-minute After Dark Live Music Cruise (without sailing). Enjoy complimentary beer, wine, soda, water, margaritas, champagne, and snacks while listening to live performances…
Step aboard our spacious, cutting-edge catamaran and select your ideal St. Augustine adventure! Choose between a two-hour sunset sail with live music and full sails, or relax on a 90-minute After Dark Live Music Cruise (without sailing). Enjoy complimentary beer, wine, soda, water, margaritas, champagne, and snacks while listening to live performances by some of the city’s beloved musicians. Share the moment with someone special and let the music carry you away, creating unforgettable memories on the tranquil waters of this historic city. Marvel at views of the Castillo de San Marcos, the iconic Bridge of Lions, and possibly the St. Augustine Lighthouse. This tour is perfect for both families and couples!
- Guests must be 21+ to consume alcohol
- Guests 17 and younger must have an adult chaperone with them at check in to sign their waiver
- Guests 14 and younger must have an adult chaperone accompany them on the tour
- Please note : We cannot accommodate special dietary requests
- Guests 18 and up must bring a valid, government issued photo I.D.
- Infants may be held or in a carrier, no strollers allowed
- Infants are free (3yrs and under) however, they must have a ticket
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.