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Private Hilton Head Sunset Sailing Tour with Dolphin Watching

Recommended by 100% of travelers
Badge of Excellence
Hilton Head Island, USA
Great choice
5+ bookings last month.
  • 2 hours (approx.)
  • Mobile ticket
  • Offered in: English

Overview

Go sailing at sunset in Hilton Head Island with this private dolphin-watching tour. Climb aboard a sailboat and cruise out into Port Royal Sound during this private tour. Keep an eye out for wildlife including dolphins, manatees, sting rays, and more. Learn about sailing if you choose or just sit back and enjoy the ride, complete with sunset views.
  • Private sailing tour in Hilton Head Island
  • Set out on a dolphin-watching tour at sunset
  • Learn about local wildlife including manatees
  • Get sailing tips if you’re interested

What's Included

  • Bottled water
  • Soda/Pop

    Meeting and Pickup

    Meeting point

    • Safe Harbor Skull Creek
      1 Waterway Ln, Hilton Head Island, SC 29926, USA

      From William Hilton Parkway head north on Squie Pope Rd, straight through the traffic circle to the back gate of Hilton Head Plantation, then take your 2nd left onto Skull Creek Dr. Turn left at stop sign into parking lot for marina, where we will meet you 15 minutes prior to your sail start time.

    End point

    This activity ends back at the meeting point.

    What To Expect

    Additional Info

    • Confirmation will be received within 48 hours of booking, subject to availability
    • Not wheelchair accessible
    • Stroller accessible
    • Service animals allowed
    • Near public transportation
    • Most travelers can participate
    • Please note - To obtain your pass into Hilton Head Plantation, let the guard know that the MARINA called in a pass for you, then show them a photo ID. The pass will be in the name of the individual who booked the sail trip
    • This is a private tour/activity. Only your group will participate

    Cancellation Policy

    You can cancel up to 24 hours in advance of the experience for a full refund.

    Traveler Photos

    Gallery picture 1 (from a traveler's review)
    Gallery picture 2 (from a traveler's review)
    Gallery picture 3 (from a traveler's review)
    Gallery picture 4 (from a traveler's review)
    Gallery picture 5 (from a traveler's review)

    Featured review

    Jeremy_L
    Excellent. I'd definitely recommend the trip. Crew were great to be with. We enjoyed the sailing, the beautiful sunset, and seeing dolphins, etc.

    Reviews

    5.0
    based on 119 reviews
    Total reviews and rating from Viator & Tripadvisor

    Best sunset sail ever

    Vanessa_T, Apr 2026
    We had the best experience with our family!! Our crew was amazing entertaining and experienced! They even let us steer! It was a beautiful sunset and we saw dolphins swimming beside us. It was magical! Thank y'all so much!

    The vessel captain and...

    Brian_R, Oct 2024
    The vessel captain and crew were very nice and safe. Our family had an amazing time. Highly recommended.

    Response from Host, Oct 2024

    Brian, thank you for the great review, we are glad you had an amazing time. We look forward to sailing again soon with you!

    Wonderful sunset tour

    Franciesca_S, Oct 2024
    Beautiful evening. Captain and his first mate were knowledgeable and very friendly. It made for a wonderful evening and the sunset was spectacular.

    Response from Host, Oct 2024

    Thank you for the great review, we are very glad you enjoyed your sunset sail with us. We look forward to sailing again soon with you!

    Sailing from Kentucky

    Elizabeth_M, Sep 2024
    Captain Andy & Dave were wonderful! So much knowledge to share. We’d been on touring boats before but this was by far the best experience. Teaching us about the sailboat, offering us to steer & feel how the sailing works, just amazing. Plus the beauty of the lowcountry & Dave giving us such cool information on it we’d never heard. Well worth it, highly recommend!

    Response from Host, Sep 2024

    Elizabeth, Thank you for the great review. We are so glad you enjoyed your sail with us and will pass this on to both Captain Andy and Dave as well. We look forward to sailing again soon with you!

    A magical evening!

    Katie_W, Jul 2024
    What a truly magical experience!! My family and I chartered a private boat for my dad and his wife’s 80th birthdays. We had such a beautiful ride out, and saw some dolphins along the way! But truly nothing prepared us for the absolute joy and splendor of being on a sailboat, watching one of the most beautiful sunsets we had while in Hilton head. If you are on the fence, I highly encourage you to book this experience. It was so relaxing and joyful, and Jude and Captain Andy made the experience so incredible for us! They both were such a joy to talk with and gave us so much information on sailing! Our entire family agreed that it was the standout experience of our trip.

    Response from Host, Jul 2024

    Katie, thank you for the wonderful review. We are so glad you enjoyed your sail with us and the company of Andy and Jude. We look forward to sailing again soon with you next time your in Hilton Head!

    Something for the whole family!

    Amy_W, Jun 2024
    This was a wonderful adventure! All 6 of us (including 4 teenagers), give it 5/5 stars! Highly recommend!

    Response from Host, Jul 2024

    Thank you Amy for the great review, we are very glad you enjoyed your sail with us and we look forward to our next sail together!

    Must do bucket list thing

    Kelsey_T, Jun 2023
    Captain Randy and shipmate Gibbs were so personable, funny, and caring! We had such a wonderful time and saw dolphins 6 different times!! It was amazing!!!

    Response from Host, Jun 2023

    Thank you Kelsey for the great review. We are thrilled that you enjoyed your sail. We love seeing the dolphins too and glad they showed up for us so many times. We look forward to sailing again soon with you!

    A spectacular evening!

    Heather_R, Sep 2022
    We had a group of 4 for a girl's weekend. We saw so many dolphins and birds!! Our crew was courteous, knowledgeable, and we loved the cozy blankets they offered as the evening grew chilly. We highly recommend!

    Response from Host, Sep 2022

    Thank you, Heather, for the great review. We are very glad you 4 enjoyed your sunset sail with us. We look forward to our next sail together - we will keep the blankets warm for you!

    Fun Evening

    Christopher_S, Aug 2022
    Very chill, relaxing sail. Winds were mild but guys did a great job finding a bit and teaching our teenage boys about sailing and letting them get in on the 'action'.

    Response from Host, Aug 2022

    Chris, thank you for the great review. I wish we could control the wind but so far we have been unsuccessful. I am glad that you enjoyed your sail and we look forward to sailing again soon with you and hopefully we can show you the exciting side of sailing with good wind!

    Awesome experience!

    JENNIFER_K, Aug 2022
    Paul and David were great captains! So nice, helpful and very informative. Lots of great stories and information about local wildlife. Sunset was beautiful. Got to see dolphins. Our kids, 7 and 8 years old, were able to help with the sails and steer too. Fantastic experience all around. Highly recommend!

    Response from Host, Aug 2022

    Jennifer, Thank you for the great review. We are very glad your family enjoyed your sunset sail with us and we look forward to sailing again soon with you and your family

    Summer Sunset

    Ed_A, May 2022
    Awesome sunset. Sorry the photos did not load. Great Captain and crew. Lot of fun for all. I will do it again on my next trip to Hilton Head.

    Response from Host, Jun 2022

    Ed, Thank you for the great review. We enjoyed having the 6 of you on the boat and we look forward to our next sail together

    Perfect Family Sail!

    Connor_M, May 2022
    We went on the Sunset Sail for my mom’s 60th birthday and we loved it! Our family of 5 fit perfectly and enjoyed every minute of cruising, chatting, and site seeing with the wonderful Paul & Kevin! They made the experience so fun & relaxing, a perfect end to a day on Hilton Head Island.

    Response from Host, May 2022

    Conor, Thank you for the great review. We loved having your family on board as you were great company. We look forward to our next sail together.

    Sail of a lifetime with friends, dolphins, and a great crew.

    Darcie_L, Mar 2022
    The crew was very knowledgeable about the local area and shared some stories along the way. It was wonderful having the boat hold only the six of us so it was a wonderful, intimate cruise with my besties.

    Response from Host, Mar 2022

    Darcie, Thank you for the great review. You were a great group to have on board. We are glad you enjoyed your sail with us and we look forward to our next sail together!

    Vacation Highlight

    Larry_V, Mar 2022
    A relaxing and enjoyable trip aboard with Capt Paul and crew! Great experience for a fair price. Highly recommend if you’re in the area.

    Response from Host, Mar 2022

    Larry, Thank you for the great review. We are very glad you enjoyed your sail with us and we look forward to sailing again soon with you!

    Amazing!

    Malaya_W, Sep 2021
    We had an amazing experience. The boat was beautiful and so were the views. Capitan Paul and Kevin made sure everyone had a great time! This is a must do activity when you come to Hilton Head.

    Response from Host, Sep 2021

    Malaya, Thank you for the great review. You guys were a lot of fun to hove on board and we look forward to sailing again soon with you!

    Relaxing, fun, beautiful ocean, clouds and sunset.

    teripur, Sep 2021
    The sailing was very relaxing and fun. The ocean views and sunset were amazing. Highly recommend! This would be a great idea for a romantic marriage proposal or wedding anniversary.

    Response from Host, Sep 2021

    Teri, Thank you for the great review. I am very glad you enjoyed your sail with us and we look forward to sailing with you soon.

    Amazing trip!!!

    Allyson_H, Jun 2021
    Lots of dolphins. Great captains!! Overall amazing experience…. Learned a lot about sailing and the local area..

    Response from Host, Jun 2021

    Allyson, Thank you for the great review. We are glad the dolphins showed up for you guys. We look forward to sailing again soon with you

    Sailing at Sunset

    Robin_W, May 2021
    Paul and Kevin were the best hosts and we had an incredible time relaxing and enjoying the sunset on the water. The sailboat was lovely and comfortable and the whole experience was worth every dime. Best thing we did on Hilton Head Island.

    Response from Host, May 2021

    Robin, Thank you for the great review. We are very glad you enjoyed your sail with us and we look forward to the next time we can sail with you!

    Perfect sunset sailing experience

    Leah, May 2021
    This was such a delightful sunset cruise! Captain Pat and Kevin were so welcoming and knowledgeable. We saw so many dolphins and had such a relaxing time sailing around. Would definitely recommend this experience!!

    Response from Host, May 2021

    Leah, Thank you for the great review. We are very glad you guys enjoyed your sail with us. We look forward to sailing again soon with you!

    SAIL WITH ANCHORS AWAY!

    Alicia_B, Oct 2020
    I wish I could give this 10/5 stars. Do not pass this by!! My sister and I sailed with Captain Paul and Kevin on the private sunset sail. The wind wasn’t cooperating with us, but they did everything they could to show us a great time, including opening the sails for the few minutes they could. They didn’t have to do that, but they insisted. Their boat is beautiful and clean. Their service is above and beyond. Their knowledge of the surrounding area was great and it was delivered conversationally, which made it feel like we were sailing with friends. I can’t recommend this company enough. The experience was worth every penny.

    Response from Host, Oct 2020

    Ally, Thank you for the great review. We are so glad you enjoyed your sail with us. We will be looking forward to sailing again with our new friends!

    Great experience

    Sandra_K, Jul 2020
    Captain Paul and Jude were fabulous! We had bad weather come in and had to cut our tour short but they did a great job of making us feel safe. The short time we had was great and I would do it again.

    Response from Host, Jul 2020

    Sandra, Thanks for the great review. Sorry we had to cut the trip short but we look forward to trying again next time your in town

    Beautiful

    William_B, Jul 2020
    Captain Paul and Kevin were great! Very hospitable and made every attempt to give us the best experience possible!

    Response from Host, Jul 2020

    William, Thank you for the great review. We enjoyed having you guys on the boat and look forward to sailing with you again soon

    Fantastic Sunset Sail

    Bonita_W, Jun 2020
    We thoroughly enjoyed our sunset cruise. Couldn’t have asked for a better Capt. And FM Jude. Great conversation, sailboat and crew. A two thumbs up from the White’s!!!

    Response from Host, Jun 2020

    Bonita, We are so glad that you enjoyed your Sunset Sail with us. We enjoyed having you on the boat as well as the great conversation. We look forward to sailing again with you soon!

    Excellent

    Jeremy_L, Jun 2020
    Excellent. I'd definitely recommend the trip. Crew were great to be with. We enjoyed the sailing, the beautiful sunset, and seeing dolphins, etc.

    Response from Host, Jun 2020

    Jeremy, Thank you for the great review. We are glad you enjoyed your sail with us and we look forward to getting everyone back out on the boat soon!

    Excellent experience

    Jule_B, Jun 2020
    Captain Paul was fantastic he met us at the parking lot, gave us options for type of sail we were expecting and answered all our ?s, took personal photos and personalized the music during our sail! Can’t wait to return next year..,

    Response from Host, Jun 2020

    Thank you Jule, it was a pleasure having your family on the boat. We look forward to our next sail together when you are back down here

    From $525.00

    per group (up to 6)

    up to 24 hours before the experience starts (local time)

    Book ahead!
    On average, this is booked 35 days in advance.

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