
Private Hilton Head Sunset Sailing Tour with Dolphin Watching
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 127 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Hilton Head Sunset Sailing Tour with Dolphin Watching worth booking?
Private Hilton Head Sunset Sailing Tour with Dolphin Watching is a 2-hour experience in Hilton Head Island, United States, from $525 per person. It scores 73 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 5/5 rating across 127 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 73 / 100
- Rating
- 5/5 (127)
- Duration
- 2 hours
- From
- $525 per person
This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy wit
What you get
About this experience
This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some good sailing. Perfect way to wind down and enjoy the ending of a great day. We will take the sails down to peacefully enjoy the beautiful show of an amazing Hilton Head Sunset. After the sun sets, we motor back to the marina and usually dock right around last light for the day. Sunset tours are usually full of wildlife such as dolphins, birds, sting ray and manatee which are some of the great wildlife that are often very prevalent in the evening. You will also have some great scenic views of Hilton Head, Pickney island and Parris island to mention a few. All of our sail trips we encourage our guests to be as involved in the sailing process as they would like. If you would instead like a relaxing trip, we then encourage you to relax and let the crew do the work.
What's included
Included
- Carbonated beverages
- Bottled water
Where it starts and ends
Meeting point
Hilton Head Island
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.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
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.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Mon, Tue, Wed, Thu, Fri, Sat
- Group size
- Up to 15 travelers per booking
- Operated by
- Anchors Away Sailing Charters
Know before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- 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
Photos






What travelers are saying
Outty’s summary of the themes that recur across 126 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
6 mentionsReviewers describe the commentary as informative rather than scripted.
Good for families
6 mentionsReviewers traveling with kids report it landed well with their group.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Traveler reviews
126 verified traveler reviews for Private Hilton Head Sunset Sailing Tour with Dolphin Watching. Ratings and reviews provided by Viator and Tripadvisor.
Amazing Experience, Amazing Hosts
We took the trip for a sunset sailing adventure. Captain Paul and first mate Grayson were stellar hosts. Paul is extremely knowledgeable and told great stories about his experiences with sailing, family, friends, and taught us a great deal about the wildlife. We have already booked another tour with him for Labor Say Weekend to take some friends from out of town. If you haven’t been, it’s a must do. Should be on everyone’s bucket list.
Response from the operator: Thank you Mike for the amazing review. We are so glad you enjoyed your sail with us and we look forward to sailing with you and friends on Labor Day weekend!!!
via Tripadvisor
Mother’s 80th birthday family cruise. Couldn’t be happier!
Paul and Dave were amazing. The boat exceeded expectations and the crew did too. Would 100% recommend and will be doing again.
Response from the operator: Michael, Thank you for that amazing review. We are thrilled that you had an amazing time, and we look forward to sailing again soon with you - Happy Birthday again to your Mom!
via Tripadvisor
Family Sunset Sail
The sunset sailing cruise was amazing. Our hosts were outstanding, knowledgeable, friendly, and entertaining. We saw dolphins, and even though there were a few lower clouds, we still got great pictures of the sunset. Well worth every penny.
Response from the operator: Thank you for the great review. We are so glad you enjoyed your sunset sail with us and we look forward to sailing again soon with you!
via Tripadvisor
Geri, John and Family
Our sunset sailing tour with Captain Paul and first mate Dave on “Seas the Moment” was the highlight of our annual family reunion! The sailboat was absolutely stunning, as was the orange sunset. The children enjoyed taking the wheel and our son helped Dave with the sails! Communication before the trip was excellent. The entire experience was carried out in a knowledgeable and professional way. We highly recommend this phenomenal experience! Thanks Paul!
Response from the operator: Geri, John, and Family - Thank you for the amazing review. We are thrilled that you all enjoyed your sunset sail with us, and we look forward to sailing again soon with you all!
via Tripadvisor
The perfect way to celebrate our anniversary 🌅
My husband and I celebrated our first anniversary here! Our captain and crew were incredible and made this a memorable experience for the both of us. We hope to come back and do it again!
Response from the operator: Kate, Thank you for the amazing review. Happy Anniversary! We are so glad you enjoyed your sunset sail with us, and we look forward to sailing again soon with you!
via Tripadvisor
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Mon, Tue, Wed, Thu, Fri, Sat
- Price range
- $525 to $565
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 44
- Verdict
- Strongly Recommended
Why this scores 73
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Hilton Head Sunset Sailing Tour with Dolphin Watching: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Hilton Head Island.
How much does Private Hilton Head Sunset Sailing Tour with Dolphin Watching cost?
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Prices start at $525 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Hilton Head Island usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Hilton Head Sunset Sailing Tour with Dolphin Watching take?
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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Hilton Head Island is not rushed.
Is Private Hilton Head Sunset Sailing Tour with Dolphin Watching worth it?
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It holds an Outty Ranking of 73 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (5/5 across 127 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Hilton Head Island, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Hilton Head Sunset Sailing Tour with Dolphin Watching?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Hilton Head Sunset Sailing Tour with Dolphin Watching suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Hilton Head Sunset Sailing Tour with Dolphin Watching?
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Around 44 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Hilton Head Island can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Hilton Head Island and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does Private Hilton Head Sunset Sailing Tour with Dolphin Watching start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Hilton Head Island within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Hilton Head Island?
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Hilton Head sells dolphin and sunset cruises out of Broad Creek, kayak and boat trips through Lowcountry salt marsh, bike rentals for the island trail network and shrimping demonstrations. On Outty we rank every Hilton Head Island experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include 2-Hour Hilton Head Guided Kayak Nature Tour, Hilton Head Island Dolphin Boat Cruise, Daufuskie Island Guided History Tour from Hilton Head. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Hilton Head Island?
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March to May and September to November, warm without peak summer crowds. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Hilton Head Island?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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