Frequently Asked Questions – Hawaii Island Sailing / Sailing Yacht “Imagine”


How do we reserve a private charter?

To book and confirm your adventure simply give us a call at you earliest convenience and chat with one of our friendly reservation assistants at (808) 938-7272. Reservation assistants are available from 6:00am to 10:00pm HST. Or contact us at


Do we have to reserve and pay in advance?

Yes, charters are booked in advance. Upon receipt of full payment, we will confirm your charter and email you the confirmation notice. Although 48-hour notice charters are sometimes available, it’s best to book a week to a month or more in advance. Cancellation refund is available up to 24 hours prior to departure.

What kind of yacht is “Imagine”?

Imagine is a beautifully maintained 40’, 2007 Catalina 400 sloop-rigged, sailing yacht. You can view pictures and specifications at our website:  Main sail has double reefing and the head sail is a roller-furling 120% genoa.  Come aboard from the aft swim-step into the large cockpit with Bimini shade over helm station.  Below deck is spacious salon with dinette, galley and nav station. Also there are forward and aft cabins with heads (shower, lavatory & marine toilet).


Do we have to sign a liability waiver to participate in the adventure?

All adults are required to sign the Charter Agreement with waiver.  Parents will sign for any in the charter party under 18 years of age.


Will we be able to “sail” the yacht?

Any member of your party may hoist the sails, take the helm, trim the sheets and navigate Imagine under the supervision of the Captain. If you are interested in sailing lessons, we have Captains who are American Sailing Association Certified Sailing Instructors.


Where will we go on our adventure?

What would you like to do? We customize your adventure. Generally most sailors prefer to go wherever the wind is best. This is usually north along the Kohala Coast, where we will see beautiful views of the west side of Hawaii Island. There are many snorkel spots with abundant sea life along the way. We always try to swim with the dolphin, we have fishing gear and of course we’re always on the lookout for whales (Humpback whale season is Nov-Mar) and other sea life.


What is the best time to go?

Lighter wind in the morning favors snorkeling and increased wind in the afternoon favors sailing, but anytime is a good time.


How far out will we go?

We may go several miles offshore depending on what adventure you choose to do. Snorkeling is best near shore and we may hug the coastline if yours is a snorkel adventure or you would just like to view the beautiful coast of the island of Hawaii.


Should we bring cash?

Our Captains and crew depend on tips for a large portion of their income. A 15-25% gratuity is customary and much appreciated by your hardworking crew. There are no other incidental expenses.


Where do we check in?

We ask you to arrive at slip H-5, Honokohau Small Boat Harbor, 15-minutes before sailing so you may attend the orientation and safety briefing. Please see map on our website:


Is there parking nearby?

Yes, we have free parking near the slip and on either side of the restrooms.


How large of a group can you accommodate?

We can accommodate a group up to 6 persons.


Is there a bathroom aboard the yacht?

We have two marine heads on board but some prefer to use the restroom in the parking area.


Are there any age limits?

The tour is safe but very small children can be startled by the excitement and ocean spray. We allow children of all ages who may fully appreciate their adventure on “Imagine“.


Is the adventure suitable for pregnant women?

If we have strong winds it can be an exciting ride!! Pregnant women should use their own best judgment and get a doctors approval as to whether or not this is an appropriate experience for them.


Is the yacht wheelchair accessible?

The Coast Guard does not allow wheelchairs on the boat so we have a storage unit available. The seating is bench style with back support. The crew is happy to assist passengers in boarding and help them navigate to a seat in the cockpit.


Are strollers allowed on the yacht?

We will gladly store your stroller at the dock. The Coast Guard does not allow strollers on the yacht.


Are the Captains licensed?

All Captains who sail for Hawaii Island Sailing are current United States Coast Guard licensed Captains with sailing endorsements. All of our Captains are highly qualified with thousands of miles and years of sailing experience, they are very knowledgeable of the yacht, the area and the local conditions.


Do the Captain and crew know first Aid and CPR?

Our Captains and crew are all currently certified in First Aid, CPR and AED.

What should we wear?

Most people wear a pair of shorts and a T-shirt. If you plan to swim, wear a swimsuit underneath. We will go barefoot on the boat and leave our shoes safely locked in our dock box back at the harbor. It is cooler on the water and our weather can change in a moment’s notice, so some people like to bring a windbreaker and some sweatpants, just in case.


Should we bring snorkel equipment and towels?

Imagine is fully equipped with snorkels, masks and fins for your snorkel adventure. She also has a fresh water shower at the swim-step and towels ready for you when you come back on board however, if you are partial to your own equipment, please bring it along. We do not have prescription lenses in any of our masks so we suggest you rent special masks if you need to.


Are there any food and beverages included?

All food and nonalcoholic beverages are included. Look on our homepage for complete listing of foods offered:

If you have any special requests or dietary restrictions, please let us know at least 24 hours before your adventure. The Coast Guard does not allow us to provide and serve alcohol, but you may bring your own and serve yourselves. We have a full and completely equipped galley.


Can we bring our own food and beverages?

Yes, some guests have opted to bring along lunch baskets prepared at their resort.  Also with prior notice we can provide a chef on board Imagine to prepare and serve you off-shore.  Imagine has a fully equipped galley with refrigerator.

Will we get seasick?

Imagine is a heavy boat and goes through the swells smoothly. Though slightly heeled (tilted) from the wind pressure on the sails, the keel hold the boat laterally stable, eliminating the rolling motion common to power boats, so seasickness is not frequent.  If however, you are prone to motion sickness or just unsure of how the ocean may affect you, you may want to take non-drowsy Dramamine or Bonine at least 2 hours before your trip, you may also ask your physician for a prescription for a motion sickness patch or, you can buy a pair of motion sickness wristbands at your local sporting goods store.


Do we need to know how to swim?

No, but you will need to be comfortable in an ocean environment. If you are fearful of the water, this might not be the choice for you. Imagine is fully equipped with U.S. Coast Guard approved life vests for your safety.


Do we have to wear life jackets?

United States Coast Guard requires children under 13 to wear a life vest when on deck. We do not require adults to wear a life jacket unless there is rough seas or an emergency.


Will we see any marine life?

We most often run into a pod or two of dolphin, you may even see a manta or two and we often see whales during whale season. Our crew likes to let a line out for fishing too!! If you choose to snorkel, Hawaii offers some of the most colorful reef fish in the world!!


Will we see sharks in the water?

Sharks are not typically seen near shore. What we do see commonly are dolphin, manta, and many species of coral and tropical fish.

Are the waters safe?

We sail on the leeward side of Hawaii Island and are protected from the rough sea conditions which are experienced on the windward side.  Usually it’s fair breezes and smooth seas.


What happens if there is bad weather?

The weather is never predictable but typically we have moderate weather here on the west side of the Hawaii Island.  In the unusual event of severe or unsafe weather conditions, we would cancel the charter and notify you immediately. You can choose to reschedule your adventure or receive a full refund.


What should we bring with us?

Besides your clothing and swimsuit, a hat, sunscreen, and definitely a camera. When it is a little cooler, some people choose to bring a windbreaker.


Are gift certificates available?

Yes, please give us a call or send us an email stating that you would like a gift certificate request. Our reservation agents are available at (808) 938-7272.


Are pets allowed?

We are unable to accommodate the unique needs of pets at this time.


Can we smoke on board?

For the safety of everyone, we ask that you do not smoke while on board “Imagine”.

What is your cancellation policy?

If you cancel 24 hours or less before your sail time there is no refund.

If you cancel 25 hours to 7 days before your sail time there is a refund of 75%.

If you cancel 8 days or more before your sail time there is a refund of 85%.