Home > "The Big Island" of Hawaii > Sailing Charters

Big Island Sailing Charters

There are 10 tours in this category. Hawaii's Leader in Affordable Tours and Discount Activities

Sailing Charters Sorted by Specific Tour

Hawaii Sailing Tours

Big Island Sailing Charters will 'double' in a way with snorkel tours because most of the Hawaii sailing tours on the Big Island involve snorkeling as well.  This does not mean that some boats cannot be chartered simply for the purpose of sailing alone, but these are somewhat rare except in the case of a private charter.

Sailing conditions for Big Island Sailing Charters

Sailing conditions on the Big Island are generally determined by the existing wind patterns.  As a general rule the majority of the time the 'trade winds' blow consistently from the north-east.  These winds provide excellent sailing conditions and are the best conditions for Big Island sailing charters.

Trade Winds

Although the trade winds blow most of the time there is no question that some times of the year are better than others and will effect all Hawaii sailing tours.
  • In the months of May through September the average percentage of days that blow from the "trades" averages about 90% of the time.
  • In the winter months the average falls to about 60% of the time and in the month of January the percentage actually falls to about 40%. The time of day also has an effect on the amount of wind that blows and obviously affects the quality of sailing Hawaii's sailing charters can provide their clients.  
  • Mornings are generally fairly calm but as late morning comes the trade winds will pick up.
  • By mid afternoon the winds are usually at their strongest and these are the best times to catch a real stiff sail.
  • As sunset approaches the winds usually decrease and settle down to a gentle breeze which is ideal for a romantic sunset sail.      

Pride of America Cruise Ship:

Many Big Island sailing charters are close enough to the arrival pier to allow you to take a taxi to meet them for a tour. Others can be best reached by renting a car from Tom Barefoot's Tours that will pick you up via shuttle at the pier. These Hawaii sailing boats are available when you arrive in Kona on the Wednesday of your cruise itinerary.

Do you still have questions about Sailing Charters?

Sailing Charters Sorted by Company

  • 1
  • 2
  • 3
  • 4
  • 5
(1 Review, 5 Stars)

Sea Paradise Sailing and Snorkeling Tours

3 Activity Options

Sailing and Snorkeling Tours

Sea Paradise is a 45 foot sailing catamaran, the Hokulani, which explores beautiful locations along the Kona coastline. Trips depart from Keauhou Bay heading down the coastline towards the historic marine preserve, Kealakekua Bay. Dolphins or even whales when in season will often become a major focal point of these trips. Evening tours are also available to see the amazing giant Manta Rays.
More Info / Buy Now

  • 1
  • 2
  • 3
  • 4
  • 5
(16 Reviews, 4.4 Stars)

Kamanu Charters Inc.

4 Activity Options

36' Sailing Catamaran

You'll enjoy "real sailing", snorkeling and whale watching on this trip with Kamanu Charters on their 36' custom designed sailing catamaran "Kamanu" to Pawai Bay. This area, located just north of Kona, is under State Fishery Management . The bay is within the Queen Liliuokalani Trust Land at Kaiwi Point and it is private. They also offer night manta ray snorkels.
More Info / Buy Now

Hawaii Nautical

2 Activity Options

Leid Back' Dinner Cruise, Snorkeling and Dolphins, Whale Watch off the leeward coastline,Oahu Scuba

Hawaii Nautical offers a large variety of boat tours throughout the island of Oahu and on the Big Island of Hawaii. Snorkel tours and dolphin watches are offered in the mornings and the afternoons and in addition they offer sunset sails, dinner cruises, scuba and snuba options, whale watching in season and private charters.
More Info / Buy Now

Mauna Lani Sea Adventures

1 Activity Option

21' Power Catamaran, 50' Sailing Catamaran

The beautiful Mauna Loa Resort in Waikoloa is the departure point for all the activities provided by the Mauna Lani Sea Adventures. Pristine snorkel adventures, scuba diving trips, sunset sails and whale watching trips in season are all available. The 55' Polynesian style catamaran 'Winona' carries intimate groups of passengers on tours along this gorgeous coastline.
More Info / Buy Now

Wahine Charters

1 Activity Option

Dolphin Excursions, Whale Watch Tour - Wahine Charters, Snorkeling and Manta Ray trips from Honokoha

Wicked Wahine Charters operates a series of boat tours out of Kailua-Kona on the Big Island. Their 29' custom power vessel can easily traverse the 12 miles of coastline between Honokohau Harbor and the Captain Cook Monument while snorkeling and dolphin watching on the way, or it can take you out on a night time Manta Ray adventure or whale watching.
More Info / Buy Now

Recent Reviews

Video Transcript

So, how about sailing on the Big Island? We do sail there. We do have sailboats. We do have wind that can carry us along on the ocean. You may be surprised that we don't have as many strictly sailing-type ventures as you might think.

If you're a sailing purist and you just want to get out on a boat, and you want to sail, and that's what you want to do, we can do that. We do have some charters that will do that with you. The majority, however, are going to be sailing charters that actually do something else, like snorkeling or whale watching, and then do some sailing as a part of the trip, kind of on the periphery as an additional thing.

So, be careful which trips you choose, depending on what you're interested in doing. In all honesty, many people really enjoy sailing, but would want to include it with some snorkeling or some whale watching, that sort of thing, and then just have a portion of the day be sailing. But whichever category you fit in, we do have the capability of arranging this on the Big Island for you. Generally speaking, these are off the leeward coasts of Kona going up toward Waikoloa.

If you have any questions about tours or activities in Hawaii, just give us a call, or check out tom-barefoot-dot-com. We're here to help.

Sailing in Hawaii whether it be on a Hawaii sailboat charter, a Hawaii boat tour or a Hawaii yacht charter is simply a way of life in the islands. Keep in mind that the very first people to come to these islands came by virtue of a sail boat and so the sailing heritage runs deep in the waters surrounding Hawaii.

More Info / Buy Now

Take advantage of the wind on Kauai and go on a sail.

More Info / Buy Now

Oahu has some absolutely beautiful sailing vessels. You can book individual seats or charter the whole boat.

More Info / Buy Now

Maui has all the wind you need and there are lots of sailing boats to accommodate you.

More Info / Buy Now