2-Hour Private Hilton Head Afternoon Dolphin Watching Sail in Hilton Head Island
Hilton Head Island, United States

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail

Outty Ranking 73 5.0 · 125 traveler reviews2 hoursFrom $485

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September 2026

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Adults

Age 13 and over

2

Children

Age 12 and under

0

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From, per person$485
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Outty Ranking

73/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 125 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail worth booking?

2-Hour Private Hilton Head Afternoon Dolphin Watching Sail is a 2-hour experience in Hilton Head Island, United States, from $485 per person. It scores 73 out of 100 on the Outty Ranking, which we label “Strongly Recommended, based on a 5/5 rating across 125 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 (125)
Duration
2 hours
From
$485 per person

This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting win

What you get

    About this experience

    This 2 hour Private Afternoon Sailing tour will take us to Port Royal Sound (generally the best wind for sailing on Hilton Head) on the North side of the island. During the day, this is generally filled with exciting winds for great sailing along with the beautiful scenery and wildlife such as dolphins, birds, sting ray and Manatee are some of the great things we get to see on a very regular basis. This is a Monohull Sailboat which means it will heal over (completely normal but very exciting - designed not to tip over!). All this without the noise of the motor in the back ground - we like to sail not motor sail!!! We want our guest to be very comfortable on board our vessel known as "Knot the Office" and therefore if anyone is uncomfortable with the healing we can significantly reduce the healing to ensure everyone is comfortable. This is a fun and exciting activity but yet very relaxing and rewarding at the same time. Please call us directly to discuss other sail trip options

    What's included

    Included

    • Carbonated beverages
    • Bottled water

    Not included

    • Gratuity for Captain and Crew Member

    Where it starts and ends

    Meeting point

    Hilton Head Island

    We are located at Skull Creek Marina located inside of Hilton Head Plantation. Please come to the back gate of Hilton Head Plantation located off Squire Pope Road. Let the guard know that the Marina has called in a pass for your group and provide a drivers license (from the person who booked this)

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    We are located at Skull Creek Marina located inside of Hilton Head Plantation. Please come to the back gate of Hilton Head Plantation located off Squire Pope Road. Let the guard know that the Marina has called in a pass for your group and provide a drivers license (from the person who booked this)

    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

    Photos

    2-Hour Private Hilton Head Afternoon Dolphin Watching Sail in Hilton Head Island, photo 22-Hour Private Hilton Head Afternoon Dolphin Watching Sail in Hilton Head Island, photo 32-Hour Private Hilton Head Afternoon Dolphin Watching Sail in Hilton Head Island, photo 42-Hour Private Hilton Head Afternoon Dolphin Watching Sail in Hilton Head Island, photo 52-Hour Private Hilton Head Afternoon Dolphin Watching Sail in Hilton Head Island, photo 62-Hour Private Hilton Head Afternoon Dolphin Watching Sail in Hilton Head Island, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 125 traveler reviews. Written by us, not quoted from reviewers.

    Knowledge and storytelling

    5 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Good for families

    5 mentions

    Reviewers traveling with kids report it landed well with their group.

    Photo opportunities

    2 mentions

    The views and photo stops come up again and again.

    Traveler reviews

    125 verified traveler reviews for 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    122
    4 star
    1
    3 star
    1
    2 star
    1
    1 star
    0
    Sort
    barbb213 · July 2026

    Great experience

    This is a fabulous tour and well worth the money! The boats are well kept and comfortable and Captain Paul is knowledgeable and accommodating. Highly recommend.

    via Tripadvisor

    jonathanearlw · July 2026

    Wonderful family sailing experience!

    Captain Andy and Mikala were friendly, knowledgeable, a fun to be with. We had a great time! The boat was clean and well kept. We highly recommend them!

    Response from the operator: Thank you, Jonathan, for the wonderful review. We are glad you had a great time, and we look forward to sailing again soon with you!

    via Tripadvisor

    nennigoat · May 2026

    Great, relaxing sail trip!

    This was our second time with Anchors Away. We had a fantastic, relaxing time on the sail boat! Captain Paul, Dave, and Mikaela took great care of us and made sure we had a great experience! Good conversation and stories with the crew. We also saw a Manta Ray jumping out of the water. Thank you for a wonderful trip! We will definitely do it again the next time we're in town.

    Response from the operator: Thank you for this great review, we are very glad you enjoyed both sails with us and we look forward to our third sail together!

    via Tripadvisor

    WelshHillsInn · February 2026

    Making Memories Together

    Master Captain Paul and David provided just an OUTSTANDING and fun-filled afternoon of sailing on Seas the Moment in Port Royal Sound for the three of us - plus the added bonus of learning first-hand about the local sea life around Hilton Head Island. The boat was immaculate and you can tell immediately that Paul takes great care and pride in it. We can't express what a wonderful and relaxing time that we had - especially enjoying the dolphin swimming playfully alongside the boat. This was our first experience using Anchors Aweigh Sailing Charters but can guarantee that it won't be our last! Thank you Paul and David for making it such a special day for our family.

    Response from the operator: Thank you for this wonderful review! We loved having you guys on board, and we look forward to sailing together again next time you're in Hilton Head! You guys certainly got a great dolphin show as we were coming in!

    via Tripadvisor

    adarion · September 2025

    Good times on the Port Royal Sound with Anchors Away

    This was supposed to be a sunset cruise, but the weather did not cooperate., Fortunately, Anchors Away got use a delightful sail in Port Royal Sound ahead of the weather.

    Response from the operator: Thank you for the great review. We were glad we were able to get you out on the water ahead of the weather. 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
    $485 to $525
    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.

    Traveler sentiment (30% weight)98
    Review evidence (18% weight)67
    Booking momentum (14% weight)61
    Value for money (12% weight)0
    Listing quality (10% weight)85
    Local standing (8% weight)76
    Booking flexibility (8% weight)100

    2-Hour Private Hilton Head Afternoon Dolphin Watching Sail: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Hilton Head Island.

    How much does 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail cost?

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    Prices start at $485 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 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail 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 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail worth it?

    +

    It holds an Outty Ranking of 73 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (5/5 across 125 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 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail?

    +

    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 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail suitable for kids and families?

    +

    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 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail?

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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?

    +

    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 2-Hour Private Hilton Head Afternoon Dolphin Watching Sail 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?

    +

    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?

    +

    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?

    +

    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?

    +

    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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