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    1. Local experiences/
    2. Things to do in Hilton Head Island…/
    3. Water Activities/
    4. Sailing/
    5. Private Sailing Charter on Calibogue Sound, Hilton Head
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    Private Sailing Charter on Calibogue Sound, Hilton Head

    Private captained sail on Calibogue Sound with room for your snacks and drinks

    4.6 stars• 321 reviews
    From$344incl. taxes and fees

    Duration

    1.5-2 hours

    Includes

    Private charter, Captain

    Highlights

    Step aboard a private, captained charter for a relaxing sail from Hilton Head Island. Choose a calm cruise or a faster ride as the captain sails into the wind.

    • Board a private captained trimaran for your group
    • Cruise Calibogue Sound and take in the ocean air
    • Choose sightseeing or a faster, wind-powered sail
    • Look for dolphins, sea turtles, and maybe a manatee
    • Bring a cooler with drinks and snacks to enjoy onboard

    What's Included

    • Private Captained Sailing Charter

    Cancellation Policy

    Cancel 24+ hours before for a full refund. Cancel within 24 hours and you will be charged half the ticket price. No-shows: no refund. Weather is the only exception; if they cancel due to weather, they will contact you.

    FAQs

    Yes. If you are driving in from outside the gate, there is a $10 gate fee per car (cash or credit card accepted). The gate pass is good for the whole day, and there are no other parking fees inside the resort.

    No. Bicycles cannot be ridden into Sea Pines from outside of the gate.

    Check in at the reservation booth at the start of the Harbour Town Pier. Have your email confirmation available on your smartphone when possible; they can also find your reservation by your name.

    Meeting details

    Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock!

    Experience provided by H2O Sports
    Experience provided by H2O Sports

    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

    Report an issue

    Reference #3FYVE8

    Day Sail

    $344.50

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.6
    Excellent
    321 reviews•Google Maps

    This multi-activity operator consistently delivers memorable experiences across their diverse offerings, from the popular alligator and nature tours through Sea Pines Forest Preserve to parasailing adventures and Daufuskie Island transport. Louise and Frank get special mentions as standout guides who are knowledgeable, personable, and genuinely entertaining. The alligator tours are a particular hit, with guests spotting everything from baby gators to full-grown adults while learning fascinating facts about local wildlife. The hour-plus boat rides cover multiple lakes and provide excellent value. Beyond the nature tours, visitors rave about the parasailing experiences with Jack, Kemmy, and Arthur, who create a safe yet thrilling atmosphere with plenty of laughs along the way. The Daufuskie Island transport service earns praise for being efficient and more convenient than traditional ferry options, with Captain Steve and Captain Frank both noted for their helpfulness and friendliness. Bike and jet ski rentals add to their versatile lineup. One review mentioned feeling rushed and encountering condescending staff, though this appears isolated given the overwhelmingly positive feedback about the team's professionalism and warmth across all activities.

    What people are saying

    Review 1 of 4
    5/5

    We had a great experience on the dolphin sunset cruise! Captain Steve was knowledgable but also very chill and a good captain. We saw tons of dolphins and learned a lot about the area. I much preferred their smaller Whaler-like boat they use over the much larger, multi-level boat (different company) that also had a tour at that time. Ours allowed us to be close to the water and was a more personal experience.

    Photo of Christine Schuldt

    Christine Schuldt

    March 29, 2026

    Review 1 of 1
    5/5

    We had a great experience on the dolphin sunset cruise! Captain Steve was knowledgable but also very chill and a good captain. We saw tons of dolphins and learned a lot about the area. I much preferred their smaller Whaler-like boat they use over the much larger, multi-level boat (different company) that also had a tour at that time. Ours allowed us to be close to the water and was a more personal experience.

    Photo of Christine Schuldt

    Christine Schuldt

    March 29, 2026

    Great for groups

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