St Augustine: Live Music Sunset Sail & After Dark Cruise

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Free cancellationTravelers' pick

1/22

Duration1h 45m

GroupUp to 120

Mobile ticketAccepted

The Catamaran Leaves in Twenty Minutes—and You're Still Deciding Between Sunset and Night

You board a catamaran at Vilano Beach and choose between a two-hour sunset sail with sails raised or a 90-minute evening cruise after dark. Either way, you get live local musicians, complimentary drinks (beer, wine, champagne, margaritas), snacks, and views of the Castillo de San Marcos and Bridge of Lions. The sunset option catches the city's golden hour; the After Dark cruise trades that for a more intimate, quieter evening on the water.

1h 45m

Step-by-step itinerary

Live music sail with drinks and views

Board catamaran at Vilano Beach
Choose sunset sail or after dark cruise
Enjoy live music onboard
Drink complimentary beer, wine, and cocktails
Snack while cruising the Intracoastal waterways
View Castillo de San Marcos and Bridge of Lions
Possibly see St. Augustine Lighthouse
Relax and enjoy coastal views

The Experience

The choice hits you the moment you arrive at Vilano Beach: do you want the two-hour live music sunset sail with all sails raised, or the 90-minute After Dark cruise once the sun's already gone? It's the kind of decision that shouldn't stress you, but somehow it does. Both are on the same state-of-the-art catamaran. Both have live musicians from St Augustine playing as you move through the water. Both come with complimentary beer, wine, champagne, margaritas, soda, and bagged snacks. The difference is the light—and what you're chasing.

The sunset sail is the obvious pull. You're on the water as the sky turns gold and then pink, watching the Castillo de San Marcos and the Bridge of Lions catch that last warm glow. The sails go up, which means you're actually sailing, not just motoring, and there's something about that feeling—the boat moving because of the wind, not an engine—that changes the whole thing. Two hours is long enough to settle in, get a drink in hand, and let the live music and the view do their work. If you're there mid-November through mid-January, you'll also see the Nights of Lights reflecting off the water, which adds another layer.

The After Dark cruise trades that golden hour for something quieter. Ninety minutes, sails down, the city already lit up and the water dark. It's more intimate, less about the show and more about the sound—the musicians, the conversation, the fact that you're floating on water in a historic city and nobody's rushing you. Both cruises work for families and couples, though kids under 14 need an adult with them, and anyone drinking needs to be 21 or older with a valid ID. Infants ride free if they're three or under, but they need a ticket and can't bring a stroller—they sit on a lap or in a carrier.

The boat's spacious enough that you don't feel cramped, and the drinks and snacks keep coming. If you're torn between the two, think about what you actually want from the evening: the visual spectacle of sunset over historic water, or the quieter pleasure of live music and city lights reflected in the dark. Either way, you're getting the same musicians, the same boat, the same complimentary spread. The only thing that changes is when you go and what the sky looks like when you do.

What’s included

Your cruise includes complimentary beer, wine, champagne, margaritas, soda, water, and bagged snacks.
Live music performed by local St Augustine musicians plays throughout.
You'll see the Castillo de San Marcos, Bridge of Lions, and possibly the St.
Augustine Lighthouse.
The sunset sail option includes all sails raised and runs two hours; the After Dark cruise runs 90 minutes with sails down.
Nights of Lights viewing is available mid-November through mid-January on the sunset sail.

Good to know

Easy physical levelPublic transport nearbyInfants must sit on laps

Operated by Fury Water Adventures St. Augustine

Is this one for you?Pick this if you want live music and drinks on the water without arranging a separate dinner or entertainment—the catamaran and the musicians handle both, and you just choose whether you want to chase the sunset or the quiet of night.