Let’s Go Sailing

 Sail Blue Hawaii                        (808) 347-0235   

 Sign up today for your sailing adventure with Hawaii’s premiere sailing charter company. capt.gaelyn@sailbluehawaii.com


Our US Coast Guard approved vessels are perfect for any kind of Hawaii sailing. Whether it’s an intimate sunset sail for two, a sailing afternoon with family and friends, whale watching, entertaining business colleagues, saying “I do”, or an overnight/inter island adventure; the experience will most probably be the highlight of your Hawaii vacation.

  • Delight in pure trade wind sailing any time of day for as many hours as you want. Sail Blue Hawaii offers the best of any private day-sailing charter. A Hawaii trade wind day-sail is an exciting sailing adventure taking advantage of the consistent and refreshing trade winds that sweep across the Hawaiian Islands. Whether you’re a seasoned sailor or someone who wants to experience the thrill of sailing for the first time, a Hawaii trade wind day-sail is an excellent way to connect with the ocean, embrace the trade winds, and create lasting memories of your time in paradise. With Sail Blue Hawaii, unlike other companies, we HOIST SAIL at the BEGINNING of your charter; the engine is turned off until we need it again at the end of your charter.  !!YES, WE SAIL THE ENTIRE CHARTER!!
  • Perhaps you’ve just flown in from the East Coast and Waikiki doesn’t wake up early enough for you. Let’s catch sunrise over Diamond Head. Maybe we’ll see dolphins in the beautiful morning light. A sunrise sail in Hawaii is a magical and serene experience. The Hawaiian islands are renowned for their breathtaking sunrises, and a sunrise sail offers an unforgettable opportunity to embrace the beginning of a new day in paradise.
  • Birthday parties
  • Corporate fun(ctions)
  • For romantics: sunset cruise: a beautiful time of day to be on the water. Treat yourselves! Whether you’re with family, friends, or that special someone, a Hawaii sunset cruise promises an unforgettable and magical evening that embodies the spirit of aloha and the beauty of the Hawaiian islands.
  • Very popular: summer only; Friday night pau hana fireworks cruise. Combine this with sunset and you have the perfect cruise.
  • Choose the one night of the month (or, the “blue moon” second night of the month) to sail from sunset to full moon. It is truly magical to see the full moon rise over Diamond Head after sailing into the sunset. Click moon phases to see full moon calendar. Sailing under the full moon you are in a magical and ethereal ambiance. The moonlight reflects off the water, illuminating the surroundings in a soft, silvery glow. It is definitely a romantic outing with a loved one. The tranquil atmosphere, the gentle rocking of the boat, and the mesmerizing moonlit scenery set the stage for an intimate and unforgettable experience.
  • When the moon is close to its new phase, we have fabulous star-gazing. Set sail for sunset and a night sail. The night sky during a new moon cruise is often clear, offering an excellent opportunity for stargazing. Away from city lights, you can see countless stars, creating a breathtaking celestial display. In winter months, the iconic Southern Cross can be seen. Your captain may be knowledgable enough to point out certain constellations. Or, you may be able to share your knowledge and show all on board 😉 A new moon cruise is a perfect opportunity to celebrate special moments, create cherished memories, and embrace the allure of the Hawaiian night sky.
  • Proposal:  how more romantic can you be when you propose to your loved one while sailing into the sunset? A Hawaii proposal at sea is a romantic and unforgettable way to pop the question in one of the most beautiful and picturesque settings in the world. 
  • Weddings for romantics:  there’s nothing more special than saying “I do” under a tropical sky  while sailing into the sunset.  Your captain will marry you with a personalized service on your own private yacht. A Hawaii wedding at sea is a dreamy and unique way to exchange vows and begin your married life, surrounded by the natural beauty of the Hawaiian islands and the vastness of the Pacific Ocean. 
  • Renewal of vows:  what a “wow” it is to exchange those vows again, to remember and re-ignite!, especially here in romantic Hawaii!  Whether you’re celebrating a milestone anniversary or simply wanting to rekindle your love, we will tailor to your preferences and desires. You can exchange personalized vows, just like you did on your wedding day, or add new vows that reflect the journey you’ve taken as a couple.
  • Sailing lessonsHelp set the sails and take the helm if you like as you learn the “ropes” of sailing.  The first thing you learn: they are not ropes. They are “lines.” Captain Gaelyn will assist you to build your skills and confidence. Learning to sail in Hawaii can be an incredible experience, allowing you to connect with the ocean and enjoy the natural beauty of the islands from a unique perspective. Whether you’re interested in cruising, racing, or just understanding the art of sailing, Hawaii offers an ideal setting to embark on your sailing journey. Sail Blue Hawaii caters to all levels of sailing experience. 
  • Memorials, ash scatterings and life celebrations: An ash scattering/ life celebration at sea in Hawaii provides a unique and heartfelt way to bid farewell to a loved one while embracing the beauty and serenity of the ocean. Family and friends can find closure and solace in the midst of nature’s splendor, creating lasting memories in a place cherished. In this private setting, on your private yacht, in Hawaii, you are given the opportunity for personal reflections, prayers, or words of remembrance to be shared in honor of your dearly departed.
  • Whale sail. In winter, humpbacks are Hawaii’s most famous tourists, making their annual 3,500 mile trip from Alaska to the islands each December through April. We’ll set sail and hope to find these gentle leviathans.
  • For the adventurous: a sailing vacation on Kaikiwimaximum: 4 adults. Charter an inter-island or around-Oahu cruise.  Get the taste of real trade wind sailing and experiences that will be a lifetime highlight.

Why go sailing in Hawaii? Just because!… 😎Let’s go sailing😎

Feel free to create your own custom cruise.  We will cater to your every whim.  Call us for your special occasion and we will design the sailing adventure of your dreams.

Do you have someone special in your life and just can’t find the right way to say “thank you” or “happy birthday/anniversary”?  Stun them with a GIFT CERTIFICATE.  It could well be the best gift they have ever received. 

The horizon is no limit.

Contact us for rates and schedules

(808) 347-0235

“On the water, life is different. Time doesn’t move hour to hour but mood to moment. We live by currents, plan by the tides and follow the sun.” – unknown