Hawaii Blue Water Sailing

Best Private and Shared Sail Tours on Oahu

Discover unforgettable adventures in Oahu with HBWS Premium Boat Charters. Experience the ultimate blend of relaxation, adventure, and romance with Hawaii Blue Water Sailing.

Our exclusive boat rentals offer Best Private and Shared Sail Tours in Oahu, designed to immerse you in the breath-taking beauty of Oahu’s waters.

Save 10%! Call NOW! Book direct.

Discover Our Sail Tours

Elopements, Proposals & Vow Renewals

Set sail into your next chapter surrounded by the beauty of the ocean. From surprise proposals to intimate elopements and heartfelt vow renewals, our curated sea experiences are romantic, stress-free, and unforgettable. Let the waves witness your love story.

Elopement

Vow Renewal

Proposal

Swap the crowded clubs for sunsets and sea breezes. Our yacht and catamaran parties are made for unforgettable last sails before the veil — complete with music, bites, and bubbly.

Because the best memories are made offshore.

We photograph your experience!

We capture every moment of your charter. Our team, also serving as your personal photographers, will ensure your adventure is documented with stunning photos. Set sail and leave your worries behind. Immerse yourself in the experience while our crew captures every magical moment.

See what our clients have to say

       All reviews
 5.0 
   Google
 5.0 
   Facebook
 5.0 
   Yelp
 5.0 
 
  
 
 
 
  Top Rated Service 2026 
 5.0
 5.0
 verified by Trustindex 
 Trustindex verifies that the company has a review score above 4.5, based on reviews collected on Facebook, Google, Yelp over the past 12 months, qualifying it to receive the Top Rated Certificate.
  Write a review     Google    Facebook    Yelp  
 
 
 
  Top Rated Service 2026 
   
 5.0
 5.0
 verified by Trustindex 
 Trustindex verifies that the company has a review score above 4.5, based on reviews collected on Google over the past 12 months, qualifying it to receive the Top Rated Certificate.
  Write a review 
 
  Top Rated Service 2026 
   
 5.0
 5.0
 verified by Trustindex 
 Trustindex verifies that the company has a review score above 4.5, based on reviews collected on Facebook over the past 12 months, qualifying it to receive the Top Rated Certificate.
  Write a review 
 
  Top Rated Service 2026 
   
 5.0
 5.0
 verified by Trustindex 
 Trustindex verifies that the company has a review score above 4.5, based on reviews collected on Yelp over the past 12 months, qualifying it to receive the Top Rated Certificate.
  Write a review 
 
 
 
   
 
 
      Posted on Google  
   
   Derek Stuart 
 21 October 2025
 
 
 Trustindex verifies that the original source of the review is Google. It was a magical evening aboard Hawaii Blue water sailing boat! What a vessel!! Capt.Matt and crew were so calm, collected, friendly and professional. Real sailing!! An unexpected delight to actually experience such beautiful sailing and conditions with the most magnificent backdrop of Waikiki, some fireworks on return, but for us the Diamond Head and Kaloko craters, the other yachts colorful spinnakers and the exclusive feel of low numbers aboard made it feel like a private tour with a few like minded folk. Will be back from our Big Island home and definitely come adventuring again with Capt Matt and crew! A really comfortable and authentic experience!
  
 
     Posted on Google  
   
   Ofure Eromosele 
 17 September 2025
 
 
 Trustindex verifies that the original source of the review is Google. Had the most beautiful morning sail!! You won’t regret it
  
 
     Posted on Google  
   
   Navy 
 14 August 2025
 
 
 Trustindex verifies that the original source of the review is Google. Matt was wonderful and ensured we all had a great time. I do recommend going with this charter service as they take a personal interest in making it the best
  
 
     Posted on Yelp  
   
   Sara R. 
 4 August 2025
 
 
 Verified Fun, safe, clean, beautiful. Fully enjoyed my time on this boat. Matt and crew were great - explained things well, friendly, knowledgeable. It was lovely.
  
 
     Posted on Yelp  
   
   Nisha P. 
 26 July 2025
 
 
 Verified Had the most magical and amazing sail boat ride with Hawaii Blue Water Sailing this evening. Captain Matt was very communicative and accommodating from the time I called to inquire about booking with him through our trip. He answered all my questions, worked with us to set up a booking that worked for our party of three, even helped us sort out parking, which I found to be very generous of him to do. He's also just a genuinely nice guy. His crew was also great -- really nice people and very knowledgeable. The boat is gorgeous and clean. We used the motor to get out of the harbor but once we made it to sea, the sails went up and we traveled with only the wind. We went from the harbor in Waikiki southeast around Diamond Head and then turned back in time for a gorgeous sunset and Friday night fireworks. Another couple joined us but it was only us 5 plus the crew of 3 on a gorgeous 65 foot sailboat. If you're thinking of booking, do it. You will be so glad you did.
  
 
     Posted on Google  
   
   Liliia Prystupa 
 23 June 2025
 
 
 Trustindex verifies that the original source of the review is Google. Absolutely the best ! My first time sailing and I loved it so much! Both captains, Clint and Matt were a blast! Had a super fun and chill time with them, will definitely go again!
  
 
     Posted on Google  
   
   Ryley Hewison 
 21 June 2025
 
 
 Trustindex verifies that the original source of the review is Google. Clint and Matt are the best crew ever!! Made the experience so enjoyable and exciting! First time sailing and couldn’t ask for a better time! A must do if you are looking for both an exhilarating and breathtaking experience on the water!
  
 
     Posted on Google  
   
   David Fowler 
 16 June 2025
 
 
 Trustindex verifies that the original source of the review is Google. Had the best sailing experience with Captain Matt and his crew.  The boat is beautiful and the view and experience is unparalleled.
  
 
     Posted on Facebook  
   
   David Fowler 
 9 June 2025
 
 
 recommendsTrustindex verifies that the original source of the review is Facebook. Beautiful boat. Had a great time sailing with Captain Matt and the crew!
  
 
     Posted on Google  
   
   Chi Nguyen 
 18 April 2025
 
 
 Trustindex verifies that the original source of the review is Google. Amazing sailing trip with captain Matt, Clint, & Mike!!! Such a beautiful yacht 👍 Everyone from the crew was kind and attentive, made sure our safety, even took very nice photos for us.  My lil sister and I had a blast!!! I’ll definitely want to go sailing with captain Matt & his crew again next time I visit Honolulu.  Thanks again to Matt, Mike, & Clint, you guys were awesome 🫶
  
 
     Posted on Yelp  
   
   Chi N. 
 18 April 2025
 
 
 Verified Amazing sailing trip with captain Matt and his crew!!! Everyone was so kind and attentive, made sure our safety and also took super nice photos for us.  My lil sister and I had a blast . We are from California and so grateful that we found captain Matt online.  Oh and we loved the color of the boat, very nice luxury sailing boat .  We will definitely want to sail with captain Matt again next time we are in Honolulu
  
 
     Posted on Google  
   
   Beau Oyler 
 6 April 2025
 
 
 Trustindex verifies that the original source of the review is Google. Captain Matt and Clint were awesome! The boat is pristine. I wanted to book a sailboat and not just another booz cruise catamaran, and this was it! The evening we went out, the wind completely died, so it wasn’t “thrilling” but it was relaxing, beautiful, and good memories.
  
 
     Posted on Google  
   
   John Gerwig 
 19 March 2025
 
 
 Trustindex verifies that the original source of the review is Google. Matt and Clint did an AWESOME job with our sunset sail. We saw fireworks and the sailing was spectacular! We have already recommended to our friends who are coming in April.
  
 
     Posted on Google  
   
   Amelie Amann 
 16 March 2025
 
 
 Trustindex verifies that the original source of the review is Google. We booked the sunset sailing tour, and it was an amazing experience! Taking the tour on a Friday made it even more special, as we got to watch the fireworks from the water—a truly unforgettable sight. The crew was incredibly friendly and welcoming, and there was plenty of space on the boat for everyone to enjoy the stunning views comfortably. Highly recommend!
  
 
     Posted on Yelp  
   
   Gary S. 
 8 February 2025
 
 
 Verified I've been on board this boat a number of times and keep coming back. Always a great experience and I've brought friends who say the same thing. Great for out of towners who call it one of their greatest memories of visiting the islands. I'll keep coming back and bringing my friends and family.
  
 
     Posted on Facebook  
   
   Jennifer Eden 
 4 February 2025
 
 
 recommendsTrustindex verifies that the original source of the review is Facebook. If you have a trip to Honolulu planned and fancy a sailing trip, check these guys out.  I was lucky enough to go out for an afternoon with all of my family, and the trip was amazing!  Captain Matt and crew were great and the boat is beautiful. Sunshine and the view of shore didn’t hurt, either!  We saw dolphins and whales in the distance, too. Very highly recommended!
  
 
     Posted on Facebook  
   
   Alex Bein 
 12 December 2024
 
 
 recommendsTrustindex verifies that the original source of the review is Facebook. We Sailed with Hawaii Blue Water Sailing and had an amazing experience!  With only the subtle sound of the wind rushing through the sails we enjoyed the blue waters with a backdrop of Waikiki and the beautiful Hawaiian mountains.  A truly unforgettable experience!
  
 
     Posted on Yelp  
   
   Brigitte H. 
 4 December 2024
 
 
 Verified Amazing time and crew. Beautiful boat.  Highly recommended for locals or visitors to the island.  Very safe.  Would love to do it again soon.
  
 
     Posted on Facebook  
   
   Danny Shereen Bickham 
 9 November 2024
 
 
 recommendsTrustindex verifies that the original source of the review is Facebook. A group of us wanted to experience sailing in Hawaii and this was a FABULOUS experience!!! This Captain had everything for safety,  all we had to do was show up! There was even free (and available) parking on this Sunday afternoon - which is rare!!!  I have done several things on Oahu but this was the best thing!!! The Captain was friendly,  talked to us,  gave us history, showed interest in us, asked questions - you could tell he and his crew really enjoyed doing this.  Definitely cared about what they did,  genuine smiles and conversation. The scenery, weather, water was great,  10/10 but I will be back and will refer all because of how it was run,  the crew and how the Captain was, that is why I would go again!!!
  
 
     Posted on Yelp  
   
   Ellen O. 
 8 September 2024
 
 
 Verified Oh my goddesses! We had a magnificent time celebrating multiple Virgo birthdays on Celestaes! Captain Matt and his crew were amazing! Thank you thank you THANK YOU to all for the incredible time together at sea.
  
 
     Posted on Yelp  
   
   S A. 
 30 July 2024
 
 
 Verified We had a wonderful experience with Captain Matt & crew!  Very nice, friendly and accommodating.  The wind was great and you could feel the sailboat gliding through the water. We even had a chance to hang our feet over the bow and certainly got some refreshing salt water.  They set up anchor on a sandbar and we were able to jump on and off the boat for some swimming.  Its so nice to look back at the waikiki skyline as its certainly a one of a kind view from off shore. Highly recommended!  If you tend to get sea sick, I would suggest taking some Dramamine.  Matt does supply ample ginger chews which help as well.  We did also bring our own "buffet" of foods and drinks as well to enjoy. ~A L O H A S
  
 
     Posted on Yelp  
   
   Yvonne J. 
 29 July 2024
 
 
 Verified Thanks Captain Matt and crew! My friends and I had an absolutely incredible experience on your luxury yacht. The beautiful, well-appointed yacht was spotless and clearly very well-maintained. The crew was friendly and attentive to ensure our comfort and enjoyment throughout the day. The highlights included sailing with stunning views of Diamond Head in the distance, as well as having the opportunity to jump in the crystal clear water for a refreshing swim. I left feeling relaxed, rejuvenated, and grateful to have spent the day on such a wonderful yacht with such a hospitable crew and my friends. I would enthusiastically recommend this charter to anyone looking for an unforgettable day on the water in Hawaii. Mahalo!
  
 
     Posted on Yelp  
   
   RaeAnne N. 
 29 July 2024
 
 
 Verified Our group had an enjoyable sail! After sailing the captain anchored the boat for a swim. The captain and crew are professional and amicable.
  
 
     Posted on Yelp  
   
   Brian M. 
 29 July 2024
 
 
 Verified Fantastic sailing outing! Massive luxury sailboat and friendly attentive captain and crew. We all had a blast!

Best Private and Shared Sail Tours on Oahu

Sail Tour Details

Step aboard Caelestis, your luxury 65’ yacht

designed for ultimate comfort and adventure. Whether you’re seeking a midday escape to unwind in the serene waters of Waikiki or a romantic sunset sail to witness the breath-taking Hawaiian sunset.

Join us for Best Private and Shared Sail Tours in Oahu!

Departure and Arrival

Tours depart from the Ala Wai Boat Harbor (slip 641). Your Day Sail excursion consists of 1.5 hours of sailing and 1.5 hours of anchoring.

Onboard Amenities

For your excursion, we provide x-large cooler with ice for your beverages brought onboard. Bottled water is provided. Enhance your excursion with custom dining to order. Guests are welcome to bring their own food and drinks.