Go Sailing in Hawaii

Snorkel with Turtles, Swim with Dolphins in Secluded Beaches and Paradise like Bays.

Sailing Adventures

There’s no better way to explore Maui, Lanai or Molokai than by private sailing charter!

#svnaia #gosailinghawaii #naiadacat

20% Kamaiiana Discount

Current Special: 20% OFF for Returning Guests

Let’s go sailing in Hawaii:)


We will be back for another amazing sail!

Our sunset sail on the Naia was the highlight of my families visit to Oahu. We had the special treat of seeing sea turtles, monk seals and a mama and baby humpback whale! Captain Yara took great care of us and we will be back for another amazing sail!

Marcie M.


Wow, what a great sailing experience, such a stable boat and the crew was over the top….best way to wrap up our family oahu experience.

Gd S.

Don’t hesitate to book!

WOW! I can not say enough about sailing with the Go Sailing Hawaii crew! The boat is French made and 38ft. The spacious layout makes you feel like you are on a 60ft yacht. There is tons of room to lounge around in the cockpit or up on the nets across the bow. The boat was extremely clean and comfortable. We felt like it was our own personal yacht for the day and felt right at home. The Captian and crew were excellent hosts. She served delicious meats and cheeses along with pate’ and crackers. We sailed all over Waikiki, up to Diamond head and then down towards Ko’olina. The views were spectacular! I would highly recommend this charter. It was relaxing and exactly what I needed after a long week! Don’t hesitate to book!

Ashley B.

Absolutely breathtaking!!

I had an amazing time with Yara on the beautiful catamaran, Naia. This was my time exploring Kaneohe, we went out to an area called the sandbar where the water only about 2-3feet deep. Absolutely breathtaking!! I would definitely recommend GOSAILINGHAWAII to all my friends and anyone that wants a personalized catamaran experience.

Alexius D.

My son and I had the best time sailing.

It was a windy day so lots of waves which makes it exciting. Saw dolphins and stopped at turtle canyon for snorkeling, tons of fish and about ten sea turtles just hanging out. A great day on the water. I would totally recommend it.

Jay C.

Had a beautiful afternoon sail and snorkel with Captain Yara and Wes!

Quick response time to our request and easy to book. They both made the snorkeling very exciting by helping our girls get up close and personal with the sea turtles, fish and octopus. Yara was even equipped with a few remedies for one of our seasick passengers! It couldn’t have been better and would totally recommend their experience to everyone.

Lois H.

It really doesn’t get better than this!

If you are on the island of Oahu, please make a point to book a cruise with Go Sailing Hawaii. Yara was so helpful and kind in getting our sail booked – providing different options until we found one that fit our plan and budget perfectly. The crew- Captain Ryan & Wes were brilliant throughout the sail, ensuring we got to see whales, swim with turtles, have front row seats for the Friday fireworks and even to see a TRIPLE sunset- that’s right! I had a lot of fun on the island but even more fun on the water on the catamaran. It really was the highlight of my trip.

Brittany Y.

Best day EVER!

We had such a perfect sunset cruise off Diamond Head and Waikiki. We had the opportunity to snorkel and chill on rafts while enjoying the water, sun, scenery and rainbows! Yara and her crew are attentive and professional. Naia is a beautiful cat that was roomy and comfortable for everyone. We booked this cruise the day before I was departing from Hawaii after 15 years. What a great way to say Aloha… we will be booking again upon my return! Hana hou!

Victoria N.


If i could give 1000 stars I would. We had a flawless and SUPER fun experience on Naia. 5 of us in town from NY area.

Yara was easy to work with, quick to respond, and very conforming to our groups inquiries. The payment process was quick and easy. Naia was a beautiful 38ft catamaran (3 bedrooms, bathroom and a kitchen!). If you need some shade there is a super spacious couch on the boat as well.

Captain Ryan and Wes were very accomodating and made sure we found the best snorkel spot, we saw whales, turtles, fishies, a triple sunset and fireworks. They were very friendly and educational and let us have our fun. Wes even served us our drinks 🙂

I’d recommend the Friday evening cruise, 4-8pm, so you can watch the Waikiki fireworks with other sailboats.

All in all, 5 star review. Wish we would have rented it the entire day.

Thanks Yara, Ryan, Wes & Naia.

Meghan R.

Sailing Adventure

We had a wonderful day with our kids learning how to sail on this wonderful boat. It was an early fathers days gift because my husband wants to learn to sail.
Thank you Yara and James for giving us all hands on experience.
We learned a ton and had a blast.

The Stephenson Family

Kristy Stephenson

Incredible experience throughout

Incredible experience throughout! Our family did a half day trip on the beautiful Fountaine 35, and I would highly recommend the experience as a unique way to appreciate Oahu. Our time together was calming and engaging, guided capably by our crew, Yara and James, who provided us the opportunity to snorkel off the coast of Waikiki and enjoy the spectacular coastline view from south of the island (while lying comfortably on the netting in front of the catamaran). Thank you Yara and James for going out of your way to make sure we were comfortable. We will definitely be calling you on our next trip to Hawaii.

Dan and friends

We loved the day and the memories will be cherished

Thank you so much! We loved the day and the memories will be cherished. We hope to do it again some day.

The Ferrier's family

Truly grateful for the amazing sailing experience

Our family had the opportunity to do a half day sail with Yara and Captain James, aboard the Naia out of Honolulu. Everyone had an absolutely fabulous time. We got beautiful weather and some nice wind that made for a dreamy sailing experience. The catamaran was wonderful – everything was clean and in good working order. Yara and James are both skilled sailors and shared lots of great stories and information with us. Yara was a fantastic host –
offering snacks and drinks and making sure that we were all comfortable. She also took lots of pictures and videos of the excursion and put together a lovely collection of photos and a video edit for us to remember the trip. Truly grateful for the amazing sailing experience and wonderful hospitality. I would highly recommend booking a trip with GoSailingHawaii!

Joyce's family

This sailing charter rocks!

Fun, relaxing, adventurous, and breathtaking. This sailing charter rocks!

Gary and friends

Highly recommend the trip to any adventurous couple or family!

From beginning to end, this was the trip my Husband and I always dreamed about… sailing on beautiful blue waters, waking up to a sunrise over the coastal mountains, snorkeling sunken volcanoes, visiting untouched beaches, cruising and relaxing in style… our trip could not have been more perfect. Captain James was an outstanding host, guide and travel companion – making the trip even more of an enjoyment. The experience was certainly a once-in-a-lifetime adventure and we would highly recommend the trip to any adventurous couple or family!