We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. Things to do in St. Augustine…/
    3. Water Activities/
    4. Boat Tours/
    5. St. Augustine Sunset Cruise with Live Music & Dolphins
    Why travelers choose Greetwell
    Curated by our team

    Every experience is selected and approved for quality and safety

    Personal concierge

    Real humans available to help before, during, and after your booking

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else

    Easy booking

    Reserve in minutes with flexible cancellation on most experiences

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Concierge Support

    • Help Center
    • (650) 414-7338
    • Contact our team

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Product image 8
    Product image 9
    Product image 10
    Product image 11
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    St. Augustine Sunset Cruise with Live Music & Dolphins

    Search all experiences

    Discover what we've curated for you

    Sail past St. Augustine landmarks at golden hour with live music and chances to spot dolphins

    From$62/ personincl. taxes and fees

    Duration

    2 hrs

    Includes

    Live music, Sunset cruise

    Highlights

    Set sail on a two-hour sunset cruise along St. Augustine’s waterfront as live music sets the mood. Take in historic sights, coastal wildlife, and vibrant colors while you unwind on the Black Raven pirate ship.

    1. Glide under the Bridge of Lions and past the Castillo de San Marcos
    2. Enjoy live onboard music from local entertainers
    3. Watch for feeding dolphins, bald eagles and ospreys
    4. Capture panoramic views of the downtown bayfront at dusk
    5. Request your favorite songs at the bar and sip a cocktail

    What's Included

    1. Live music
    2. Scenic sunset cruise

    Things to know

    All ages are welcome, but the operator recommends this cruise for children aged 10 and up.

    Cancellation Policy

    Full refunds or credit are available with at least 72 hours notice.

    FAQs

    This scenic sunset cruise features live music, views of historic St. Augustine landmarks like the Castillo de San Marcos and Bridge of Lions, and opportunities to spot dolphins and local wildlife.

    Yes. The cruise includes live music performances, with songs from artists like Jimmy Buffett and Kenny Chesney. Live music is not available on Sundays.

    All ages are welcome, but the cruise is recommended for children ages 10 and older due to the duration.

    Meeting details

    Please arrive 45 to 60 minutes early at 111 Avenida Menendez, St. Augustine, FL. Check in at the Black Raven Ship Store inside the marina building to receive your boarding pass before proceeding to the ship.

    Perfect for

    • Couples seeking a romantic evening with live music and historic coastal views
    • Families with kids 10+ wanting wildlife spotting and St. Augustine sightseeing
    • Friend groups looking for cocktails, sunset scenery, and local entertainment
    Experience provided by Pirates of St. Augustine
    Experience provided by Pirates of St. Augustine

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #UPKVH6

    Adult

    $62.37

    Ages 13

    0

    Child

    $56.70

    Ages 3-12

    0

    Toddler

    $26.05

    Under Age 3 (0-2 years)

    0

    Senior

    $58.97

    Ages 55+

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

    4.3 stars• 1.1K reviews

    Review summary

    4.3
    Very Good
    1.1K reviews•Google Maps

    This pirate ship experience in St. Augustine seems to hit different notes depending on which cruise you choose. Families with young kids consistently rave about the crew's energy and how well they tailor the entertainment to different age groups. The treasure hunt activity gets enthusiastic mentions, and parents appreciate that the humor works for adults while staying kid-appropriate. The adult-only Rum Runner cruise also gets strong praise for its comedy and entertainment value, with couples highlighting the affordable drinks and hilarious skits. Several reviewers mention the crew's friendliness and how they engage with passengers throughout the trip. The sunset cruises earn special mentions for their live music and overall atmosphere. The experience isn't without hiccups though. Audio can be problematic, with the boat noise making it hard to hear the pirates at times. One disappointed group on the Rum Runner cruise felt the show didn't match the website description and found too much time spent on safety briefings rather than entertainment, questioning whether it justified the ticket cost. Some jokes and dialogue might go over younger kids' heads. Parking near the marina can apparently be tricky if you're not familiar with the area, so taking an Uber might save you some hassle. Still, the overwhelming majority of visitors seem to leave happy, whether they're toddlers clutching their treasure or adults who've enjoyed a night of laughs and drinks on the water.

    What people are saying

    Review 1 of 4
    5/5

    Fun time on the pirate ship! The crew were all entertaining.

    Photo of Michael Sullivan

    Michael Sullivan

    March 21, 2026

    Review 1 of 1
    5/5

    Fun time on the pirate ship! The crew were all entertaining.

    Photo of Michael Sullivan

    Michael Sullivan

    March 21, 2026

    Nearby activities

    Thumbnail
    Boat Tours

    St. Augustine Pirate Ship Battle & Treasure Hunt

    From$51/ person
    Thumbnail
    Comedy

    St. Augustine Adult Pirate Comedy Show Cruise

    From$41/ person
    Thumbnail
    Boat Tours2 to 14

    Small-Group Dolphin Cruise with Naturalist

    From$49/ person
    Thumbnail
    Kayaking Tours

    St. Augustine Kayak Tour Through Salt Marshes

    From$49/ person
    Thumbnail
    Culinary Tours

    St. Augustine Wine, Cocktail & Food Tour

    $147.34/ person
    Thumbnail
    Heritage Walks

    90 Min Walk Through 400 Years & Candy Shops

    $83.74/ guest