Offering the Newest, Largest, and only
PRIVATE MONOHULL Sailboats on the Island!


Anchor's Away Sailing Charters is the premier boat cruise provider in Hilton Head, SC with a variety of sailboat and power boat cruises available daily. From Sunset Cruises, Sailing Tours, and Wedding Proposals at Sea, to Dolphin and Wildlife Watching Tours, our expert Captain and professional Staff will make your boating experience one to remember. Below are just a handful of positive reviews from our highly satisfied customers that have enjoyed memorable moments on our boat tours. Read more from well over 150 positive Google reviews »

Sunset Evening Cruise @ Hilton Head
This was absolutely beautiful and wonderful. Denise and I had an extremely relaxing & informative 2 hours. If it was 10 Stars, we would give it that. Captain Paul & First Mate Dave were extremely helpful and informative. Found out that Captain Paul came from the Kansas City Area, which shows just how small the world really is. We got to experience actual sailing in a smaller craft than a cruise ship. The sailboat, was extremely clean. We saw dolphins, and manta rays, and learned about the research projects on great white sharks in Hilton Head. Last but definitely not least, we saw one of the prettiest sunsets we have ever seen. All in all it was a fantastic way to finish our first trip to Hilton Head.
Maurice A

Private Sunset Sail
I absolutely encourage anyone considering a sunset sail to sign on with Anchors Away! Captain Paul and David provided us with an enjoyable and entertaining evening. Their stories of the islands and knowledge of the area and tides made for a fabulous event. The views and wildlife did not disappoint and we came away with every intention of a repeat performance next year! Don't sign on with one of those charters where you're just another passenger; register now for your private sail and make this a memorable trip!
Carrie H

Wonderful Evening Sailing on Port Royal Sound
AWESOME EXPERIENCE!! Captain Paul and First Mate Dave were great! We sailed with two other couples, all friends and had a wonderful time. Captain Paul explained many things about sailing, Hilton Head Island, Port Royal Sound and much more! The scenery was beautiful and the sailing was very peaceful. We brought some white wine and enjoyed the evening immensely. Cannot recommend Anchors Away Sailing enough. 5 plus stars. Thank you!

The perfect sunset sail
What a perfect moment in time ! Many thanks to Captain Paul and first mate Dave for a magical evening . Highly recommend !
Cat M

Sunny Days
We enjoyed the peaceful sailing around the sound. It was a beautiful, sunny day with a low wind. The Captain and crew were friendly & entertaining, regaling us with stories and the history of the area. We didn't see any dolphins on this trip, but more likely due to the approaching storm (Ian). We'll definitely return for another trip.
Bob S

Highlight of Trip!
Amazing sunset sail with Paul & Dave!
Gorgeous boat, the cleanest I've ever been on & very informational! Lots of fun facts about the local area, wildlife & sea life. We also had dolphins right next to the boat! The highlight of our girls' trip!
Best sailboat charter cruise I have taken in 30 years!

Well worth the cost!
We did the powerboat tour with Captain Paul. Everything about the experience was perfect! Booking was easy, directions were easy to follow, and the boat was clean. Captain Paul was very knowledgeable and we even went for a quick swim off of the boat. Learned about (and saw) dolphins.

Sailed Away!
Such an amazing experience. We had never been on a sailboat before but our captain and first mate were very knowledgeable and made us feel right at home on the water and explained everything in great detail. They even provided the history of the island and explained everything around us. It was such an awesome and peaceful experience to enjoy on our honeymoon and would definitely come back!

Enjoyable Sail
Friendly and knowledgeable crew, took good care of us. We all had a great time and would highly recommend it.

Amazing sailing trip
Our trip with Captain Paul and David was amazing! They were very informative about the local area. We had tons of fun on this incredible sailboat . I highly recommend this private charter, it made our special occasion very special indeed!!

We had an incredible trip. Paul was informative, fun, and safe. Our family, including two kids, all believed this was the highlight of our trip to Hilton Head.
Barbara S.

The weather didn't cooperate for our sunset/dolphin cruise but Paul got us scheduled for a daytime cruise on a different day. Kevin (the captain) was awesome! Laid back, friendly, and knows the history of the area too. The best part is he let our son "drive" the boat in his direction. By far the best experience we had while we were here on vacation. We will definitely schedule a trip next time we are in!
Dan E.

My family of 6 went out sailing with Captain Paul and Kevin on July 6th and had a great time. The boat is very clean and comfortable. It's a great way to spend a couple of hours in Hilton Head. Captain Paul and Kevin are very knowledgeable about the area and the different types of sea life in the area. We got to see many dolphins while out sailing.They shared some very funny stories with us and all around a great time by all. We definitely will do this again when we visit again
Dennis L.

Great sailing trip today! Captain Paul and crew member Don were great guides and sailors. It was excellent weather and we spotted some dolphins! It was just me and my husband on board and Paul and Don provided an excellent experience on board their sailboat! Got some drinks and donuts on the trip. It was the highlight of our trip to Hilton Head!
Emily L.

What a delightful experience. Our original schedule was impacted by Elsa. The Anchors Away crew contacted us and rebooked a time that worked with our schedule. I charter this for my wife and me as a private experience and we thoroughly enjoyed every minute. Captain Paul and Don were great! Very friendly and extremely knowledgeable about the area and sailing. We learned a lot. Didn't get to see any dolphins up close, however we absolutely intend to return with a couple of friends next time we are in the area. Captain Paul and Don, thanks for the experience!!
C G J.

This was our very first sailing experience. For me, I wanted to see dolphins. My partner wanted to actually help sail. We both got exactly what we wanted and more. Captain Paul and Kevin were great hosts. They patiently answered all of our questions and educated us about the surroundings, the great white sharks, and dolphins. We saw quite a few dolphins, which was amazing, and Captain Paul always turned down the engine and allowed us to hover nearby them to truly enjoy their beauty. Kevin kept us laughing with his one-liners and always made sure we had what we needed to enjoy the afternoon out. It was a little windier than we might have liked, but Captain Paul was very communicative about the conditions and what to expect. I would highly recommend them and plan on coming back to do it again next time we're in town
Sherin S.

Fabulous boat! Great captain and first mate (Paul & Kevin.) Our group had a wide comfort range from those who had never been on a sailboat and were nervous about heeling to those who wanted speed and heeling to the max. Paul & Kevin managed to make our nervous guests at ease and worked up to some awesome sailing for all. Kudos to them and their knowledge of the boat and water. Thanks for an excellent time!
Jill K.

We booked a sunset sail for the night of 7/23 with anchors away. Captain Paul met us at the dock and took us about his lovely sailboat. He was very cordial and professional and he had a bottle of chilled champagne waiting for my wife and me (it was our one-year wedding anniversary). Captain Paul did a great job of navigating us around and maximizing our sunset views. He let us drive the boat and answered all of our silly sailing questions. It was a great time. Would recommend it to anyone.
Rob R.

We did the powerboat tour with Captain Paul. Everything about the experience was perfect! Booking was easy, directions were easy to follow, and the boat was clean. Captain Paul was very knowledgeable and we even went for a quick swim off of the boat. Learned about (and saw) dolphins.
Diane Schaefer Fabri

This was my 1st time sailing, we went on the 2-hour sunset cruise. I am so glad we booked with this charter. Captain Paul & JT were professional, polite, knowledgeable and loads of fun.
Told us lots of HH facts and lore, knew of the flora and fauna, and answered every question we had, which was a lot.
I cannot recommend Anchors Away more, I 'd love to go on some of the other cruises they offer.
Geri Rice

Our group of four enjoyed a fabulous sail today! Crew, boat and weather were absolutely fantastic! Highly recommend! Five stars!
Suzy Carey

Excellent sunset dolphin cruise. Captain Trent was awesome, and very knowledgeable, we saw lot of dolphins, and he knew the perfect place to swim and see the sunset. Highly recommend. It was a great family adventure.
Kirk Steffes

Had a great time on the sunset sail last night with my wife and 2 kids. Capt. Paul gave us some good info on the island and area. He and the crew were very good with kids and everything. Did a lot of sailing and was very safe. It was out of their control but didn't see any dolphins perfect other than that
Mike Prego

Paul and Deb were amazing hosts to our sail last night . Highly recommend and encourage you to sail with them!
Denise Lemon

Captain Paul and his crew were phenomenal! They were professional mariners, even going so far as to call and rebook our charter when the Captain had concerns over rough seas knowing we had little ones on board. The day of the charter was great, with everyone sharing their knowledge of the water, the island, marine life and the environment, and even some pirate history. They involved the kids (ages 6, 4, and 2), all of whom had a great time. We definitely will be back for another charter!
Markus Apelis

My husband has past experience on a sailboat but for me it was my first time sailing. Knot the Office is a very clean & well-maintained boat. I felt safe and comfortable. Had a great time learning how to handle the sails. Overall, great experience for my first time on a sailboat.
Elaine Coh

Paul made this first sailing experience very memorable. He taught us some basics, told us about the area we were sailing, and made the trip not only a delightful experience but a learning experience also. The chairs on the front were a perfect way to cruise up the intercostal from the marina. We watched dolphins while sipping champagne and eating chocolate. Very professional and a joy to converse with.
john coreil

Our family had a great time with Captain Paul and his Crew. Captain Paul was extremely easy to work with in scheduling our sail and making sure our trip was a memorable one. We only wish we had more time on board and we will definitely be back again in the future!
Mike Fowler

What a Pleasure to sail with Captain Paul at Anchor's Away Sailing Charters. Paul is a wonderful captain and teacher. What a treasure to learn about the art of sailing, the Port Royal Sound and his adventures on the water. Captain Paul made our family feel comfortable on “Knot the Office”. The afternoon was spent relaxing and enjoying each other's company, as well as marveling at the amazing creation. The sailing vessel was immaculate and the wood in the berth is truly beautiful. We had a fun family day of adventure! For a low-key, joyful day sailing in the low-country set sail with Captain Paul!
Amy & Travis V.

Riding on Paul's sailboat was a wonderful experience. We were hesitant to bring our four kids but it was peaceful and relaxing the whole way. My kids were completely enthralled with the whole adventure. Paul warmly welcomed us aboard his boat and operated the boat with professionalism. It was clear he thought of every detail from the weather to drinks to music, and made sure we were enjoying ourselves. It was a beautiful evening. Nothing short of smooth sailing. Highly recommend.
Sam & Heidi

We had our first sailing experience with Captain Paul. The boat, "Not the Office" is beautiful. He is both professional and knowledgeable and we actually learned a lot from him. We enjoyed it so much that we did it again and we know that when family comes to visit, sailing with Captain Paul will be on our agenda.

We highly recommend sailing with him to anyone who wants to get out on the water and have fun.
Chuck & Patti

We enjoyed the sailing trip a lot! We liked how Paul showed us how to see the ocean depths and explained the equipment. He was very skilled and knowledgeable in not only the sailing aspect but the water as well. We enjoyed the part of the trip where we got to learn how the channel locks work for taking the boats in and out of the harbor. He made you feel like a part of the sailing experience and explained the “why” behind what he was doing as we were sailing. He was professional and made us want to book another venture.
Megan & Darren

"Sailing with Captain Paul was very fun. The boat was clean and comfortable. There is something about moving across the water without the noise of an engine that makes me smile and I don't know of a better way to watch the sunset. Captain Paul is very knowledgeable, so I enjoyed asking questions and helping with the sails. It was pretty cool to see some dolphins too."

Anchors away sailing charters gave my wife and me a great impression and experience on our very first sunset tour! Paul the captain was extremely knowledgeable about the area! His sailboat was very accommodating! We will defiantly be booking again on our next vacation!! Highly recommend!
Jonathan E.

I truly enjoyed my time sailing with Captain Paul. It was the middle of February and we still saw dolphins several times throughout the afternoon. The sailboat itself was well-maintained and worked well. I found it comfortable and easy to maneuver around on the boat. It was great to be able to have a smooth sail without a motor running the entire time, which other companies have done. I give it two thumbs up.

“My wife and me had never been sailing before and had an opportunity to experience Sailing for the first time just a few short weeks ago.
Paul, the owner, seemed to have an ease about him that made everyone in the boat feel comfortable and relaxed at all times; he even let us help with letting the lines in and out! This Charter is absolutely Top notch and we couldn't recommend Paul and Anchors Away Sailing any more highly! If you like to sail or, like us, are just curious and want to try something new while in Hilton Head/Bluffton, this should be an absolute MUST on your vacation trip! I can hardly wait until our next Charter with Anchors Away!”
Spencer and Felicia

Captain Paul is THE BEST! Very welcoming, super knowledgeable and an absolute blast to hang out and sail with. This was my first time ever on a sailboat and I loved every minute of it! Lots of laughs and lots of great memories were made (especially getting to help with the sails and maneuvering the boat). The wind / weather was perfect which made for some awesome sailing! Paul is an experienced sailor and he's even a pilot so I can assure you you're in good hands! And the boat is beautiful too! 5 STARS!!!
Thanks for a great time and I look forward to doing it again!

Captain Paul, We had a great time aboard Knot the Office. As you know, I am an experienced sailor, but only on inland lakes with a much smaller boat. Thanks for your patience in letting me have the helm for a time, and handle the lines at other times. Fun–and you are a good coach! I was also impressed with your hospitality, knowledge, good judgment and seamanship. All in all, a wonderful experience. I am recommending Anchors Away Sailing to friends and family. Blessings!

Had the experience of sailing on the "Knot the Office" sailboat with Captain Paul.
Very professional, and knowledgeable about his boat and the waters.
It is a true sailing experience, with all the action of tacking, hauling in lines, and watching the fun meter! There was never a dull moment onboard. True sailing on a great sailboat, with all the accommodations, for a great time!
I highly recommend this experience to customers that really want to sail.

My fiancé and I recently had the pleasure of going out in the water with captain Paul and Anchors away sailing charters. As it was her first time in a sailboat she was a little uneasy at first. Paul and crew did a fantastic of explaining everything they were doing and why. Halfway into the charter the only thing my fiancé was concerned with was how many more dolphins will she get to see. Paul and the crew were very professional and provided a relaxing beautiful sailing experience. For me the best part was the fact that you as a guest get to be hands-on. You learn what and when to do things and actually help sail the boat. I highly recommend Captain Paul and his crew!

Wonderful and relaxing cruise. First time sailing and we loved it!! Captain Paul was very knowledgeable and easy going which made the experience even more enjoyable. It was nice to view Hilton Head and other surrounding areas from such a beautiful sailboat. We found it to be very peaceful sitting under the sails and watching them move with the wind. Thanks to the Captain, we were able to get some photos of our first time sailing on Knot the Office. We truly enjoyed it and recommend everyone give sailing with Captain Paul a try!
J Kelley