5 BEST private HAWAII sailing charter ideas

  1. Sign up for a brilliant tradewind full-sail private sailing charter. You’re on your own yacht with just you and your’s in your bubble. How more perfect can it be?
  2. A private sailing charter sails past beautiful coastline in the cobalt blue blue waters of our Pacific.  Wildlife such as green sea turtles, “honu”, dolphins, “nai’a”, humpback whales, “kohola” (in winter season only), and flying fish, “malolo” are some of the critters we may see as we sail. Beautiful views of Oahu, Diamond Head and, on clear days, far in the distance, Molokai and Lanai can sometimes be seen. This is not “destination” sailing.  “Destination” is sailing. Last week as we sailed, we saw an endangered monk seal. This week a monk seal has given birth and she and her pup are hanging out at Kaimana Beach!

Looking towards the Island of Oahu

3. As we sail, especially in winter months, there is a huge chance we will see rainbows which thrill as they follow us as we sail up the coast.

This image has an empty alt attribute; its file name is IMG_1233-1024x768.jpg

4. If conditions are light, we’ll sail outside the shelter of Diamond Head where wind and waves are bigger, perhaps spraying you with delight. It is a rare day we get outside the shipping lanes!

This image has an empty alt attribute; its file name is fullsizeoutput_7a2-1024x264.jpeg

5. I was asked the other day: “don’t you ever get bored sailing every day, doing the same thing every day?”. I was speechless. Every day the ocean is different, the weather is different, and YOU, the client, are different. Such variety! Such entertainment for me! Welcome to my OFFICE!!

So, come on sailor and non-sailor alike: Let’s throw off the dock lines and explore my office by signing up for your very own Honolulu Hawaii private sailing charter. It doesn’t get any better than this!

Oahu’s best sunset cruise

Honolulu Oahu sunset cruise
Honolulu Oahu sunset cruise

Relieve your guilt by getting your work done early and grabbing your loved ones for a spectacular Honolulu sunset cruise on a private sailing charter at the end of your day. Hawaii is fast becoming the most popular post-pandemic place to be whether you are choosing to spend a month or two here to tele-work or bringing the family for a much-needed breather. While you are here there are so many reasons to get out on the water. Go ahead and treat yourself: de-stress and take some healing time that only “being out there“ can offer.


“It’s too windy,” you say.  Captain says, “no wind, no sail”:-) Hawaii is typically a windy place, and this week has been no exception.  That being said, Captain has many hidden talents, including an easy way of trimming the sails and changing the sail plan to keep you comfortable and having fun. Overall, your private sailing experience on our Honolulu sunset cruise is of the most importance to us!

CALL Sail Blue Hawaii for your private Oahu sunset cruise

Private Hawaii Sailing Charter

While sailing off the Oahu coastline, we often see Hawaiian green sea turtles lazing in the sun, dolphins jumping the bow, whales (winter only) spouting off to starboard, and the stunning shine of Venus at sunset. Leave Waikiki and the crowds behind. Step onto your own private yacht and enjoy the ride of your life. The wind is our engine as we sail the beautiful azure blue Pacific waters. The sound of the ocean will thrill. You can choose a magical sunrise cruise, an adventurous tradewind day-sail, a romantic sunset cruise; depending on your preferences and schedules…anything is available for any occasion. 

Why a private sailing charter?

Your private sailing charter in Hawaii is perfect for intimate gatherings, family vacations, or romantic getaways. It comes with an exceptionally experienced captain and crew who are knowledgeable about the islands’ marine life, culture, and history. You will enjoy tradewind sailing as only Hawaii can offer. 

What will we see?

The stunning coastal landscapes, crystal-clear waters, and the chance to see marine wildlife up close makes your private sailing charter an unforgettable experience. However, it’s essential to book in advance, especially during peak tourist seasons, to ensure availability and secure your preferred sailing date.

Tradewind sailing at its best. Call Sail Blue Hawaii today for YOUR private Hawaii sailing charter.

Private sailing charter in Hawaii

There are many reasons to choose a private sailing charter in Hawaii.

You may never know why you go or how it will change you, but listen to this: last night my sunset cruise (repeat) clients said: last time, after their cruise with me, they went home and took up the boating life! Yep, they went and bought a boat! And have spent the last 4 years cruising the Chesapeake. I was thrilled to hear this. I am not saying after you sail with me you will go buy a boat. After all, the best boat to have is someone else’s. 🙂

What’s so thrilling about a boating lifestyle?

It’s not just romance but you sure can find that. It’s not just freedom but you sure will find that. It’s not just sunsets but you sure will soak them in…maybe even see the green flash. It’s not just rainbows but they will deliver your pot of gold. It’s not just hands on the wheel but YES, the wheel is yours. These are just glimpses of the boating life. Whether you are a sailor or a power boater, at the end of the day, it’s the magic there. You’ve sailed or powered to an anchorage far from everyday life. And this is therapy at its best.

Sign up today for your private sailing charter in Hawaii with Sail Blue Hawaii.

Lets Go Oahu Sailing

Kaikiwi sails from Oahu’s south shore. You will embark at Kewalo Basin boat harbor, not far from Waikiki beach hotels. We sail past beautiful coastline in the cobalt blue blue waters of our Pacific. The south shore is the protected side of Oahu: calm and crystal clear, making it the perfect sailing destination.

Why Go Sailing Oahu?

Common marine wildlife sightings on Oahu are Hawaiian green sea turtles, honu, dolphins, nai’a, and humpback whales, kohola (in winter season only). In addition, flying fish, malolo, are some of the critters we may see as we sail about the island.

Incredible Sights while Sailing

Beautiful breathtaking views of Diamond Head are just one of the highlights while sailing Oahu. On clear days, although far in the distance, Molokai and Lanai can sometimes be seen from the island of Oahu. This is not destination sailing, destination is sailing!

Let’s go Sail Oahu