Home > Sailing Charters

Hawaii Sailing Charters

See All Activities See All Activities By Vendor Sailing charters and tours in Hawaii.

There are tours in this Category that range in price from $29.90 to $4900.00

Sailing Charters

Sailing in Hawaii is a Way of Life.


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 sailboat and so the sailing heritage runs deep in the waters surrounding Hawaii.


For that matter keep in mind that each and every one of the Hawaiian Islands is completely surrounded by water and so it is natural for Hawaii sailing to be such a big portion of the culture here.


Ocean water is one thing we have plenty of in Hawaii but the other ingredient necessary for a good sailing experience is wind, and we have been blessed here in Hawaii with plenty of that as well.


The trade winds will blow from the northeast in Hawaii about 300 days a year.


A typical day will have the wind blowing between 8 and 12 mph but it can get much windier than that.


Even on normal trade wind days wind gusts can be much greater than the average of that days wind velocity.


The trade winds will generally blow strongest in the afternoon and will begin to come up in the late morning hours so sailing conditions for most Hawaii Boat Tours are usually best in the afternoon if you are truly looking for a strong sail.


The Time of Year Can Affect Sailing in Hawaii.


Sailing in Hawaii during the winter months can be affected by the wind which can often reverse itself and come from the south.


We refer to these days as having Kona weather conditions.


This is the time of the year when we can have big storms and of course those days are not ideal for sailing but moderate Kona conditions can be just fine for Hawaii sailing adventures.


Where you are on an island can also play an important part in determining if it is a good place to launch from to enjoy some sailing fun.


The heaviest winds will most often be affecting the 'windward' sides of the islands which are the north and east coastlines.


These are the areas that will get wind first but quite often the wind will wrap around to the 'leeward' coastlines later in the day.


Many sailing charters prefer to leave from a location on the leeward side of an island and work their way up to the wind line as it wraps around.


This method allows for the beginning of a sail in calmer waters and also a return to calmer waters when coming back to port.


The Strongest Sailing Breezes in Hawaii are Usually in the Afternoon.


Stiff winds are not the only type of winds that are ideal for Hawaii sailing tours as late afternoon or Sunset Sails usually occur at a time when the wind has died down and what light wind is occurring is caused by the "temperature differential' caused by the cooling of the island mass.


These gentle conditions are ideal for romantic Sunset Sails and Dinner Cruises when too much wind would have an adverse affect upon the serving of cocktails and the enjoyment of Hawaiian "pupu's".


If you are looking to find wind for your sailing tour when you are visiting the islands the highest annual wind velocity is usually found in July however it should be mentioned that the wind speeds for each month are usually pretty consistent.


Rainfall might be something that would affect a beautiful Hawaii sailing charter and rain is something you could expect to be happening during the winter months.

Look for this symbol in the tour descriptions below to indicate if it is Pride of America compatible.

Sailing Charters Sorted by Specific Tour


Sailing Charters Sorted by Company

  • 1
  • 2
  • 3
  • 4
  • 5
(9 Reviews, 5 Stars)

Blue Dolphin Charters

2 Activity Options

56 foot wide-beam sailing Trimaran, 27' Raft and 63' Catamaran

Blue Dolphin Charters offers spectacular motor sailing cruises to the NaPali Coast of Kauai and to the 'forbidden island' of Niihau. In addition Blue Dolphin also offers whale watches, snorkeling, snuba, dinner cruises, sunset sails and rafting excursions. All emphasis is placed upon customer comfort and its large boats each maintain large walk-in restrooms, fresh water showers and plenty of deck space.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(7 Reviews, 5 Stars)

North Shore Catamaran Charters

5 Activity Options

40' Sailing Catamaran, 40' Catamaran

The beautiful North Shore of Oahu provides the seascape for one of the most majestic boats on the island, the Ho'o Nanea, operated by North Shore Catamaran Charters. This 19 passenger, 40' sailing catamaran is one of the fastest on the island and offers fabulous sunset cruises, picnic snorkel sails and whale watching in season.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(7 Reviews, 5 Stars)

Port Waikiki Cruises

4 Activity Options

54' Catamaran

If sailing is truly your ultimate objective in going out on a boat you will be thrilled with a ride on the sailing boat Paragon. The Paragon is a 47' sailing catamaran that is designed for these waters and designed for speed. There are not that many boats that pass through these waters that could go faster than this one.
More Info / Buy Now


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

Makena Boat Charters

1 Activity Option

Makena Boat Charters

If you're staying on the south shore of Maui in the Kihei area, Wailea or Makena a really good choice for a snorkeling tour would be on the 65' sailing catamaran "Kai Kanani". This boat was built in 2007 and is a state of the art custom motorized sailboat. The location of the departure point for this boat is one of the very best because it is located just off the coast of Molokini, perhaps a short fifteen minute ride away.
More Info / Buy Now


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

Maui Ocean Charters

3 Activity Options

Maui Ocean Charters

Set sail with Maui Ocean Charters on their sailboat "Shadowfax". Trips are available that last anywhere from a few hours to a few days or more!
More Info / Buy Now


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

Bike Hawaii

3 Activity Options

Bike Adventures, Mountain Bike Tours

The company 'Bike Hawaii' deals with much more than just bike rides. Over their long history they have evolved to include hiking tours and kayaking trips as well as snorkeling and sailing adventures. Common ground for all these tours is a desire to take the island visitor to out of the way places and provide an ecological perspective.
More Info / Buy Now


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

Catamaran Kahanu

1 Activity Option

36' Sailing Catamaran, 36' double hull Hawaiian Catamaran

Catamaran Kahanu is a boat tour company that offers tours of the spectacular NaPali Coastline on Kauai's North Shore and also offers dinner cruises and whale watches. With a maximum capacity of only eighteen passengers these tours are very personalized and your captain and crew are of Hawaiian ancestry and have been lifelong residents of Kauai.
More Info / Buy Now


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

Gemini Charters

1 Activity Option

64' Sailing Catamaran

Gemini Charters offers sailing tours that depart off of Kaanapali Beach and has done so for over 30 years. They offer multiple tours which include a sail and snorkel up the coast to Honolua Bay when weather permits, a delightful champagne sunset sail and whale watching tours in season. Their seaworthy 64' Sea Runner Sailing Catamaran is an excellent choice for a real sail.
More Info / Buy Now


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

Tradewind Charter

5 Activity Options

Sail Oahu, Private Sail and Snorkeling, Private Sailing, Sunrise Sails, Snorkeling Tours and Memoria

Tradewind Charters specialize in private charters and can accommodate anywhere between just two to as many as twelve passengers on their 43 foot sailing yacht. Depending upon how many you may have in your party you just may be completely surprised in a favorable way by just how much money it will actually cost to charter a boat privately.
More Info / Buy Now


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

Iruka Hawaii

1 Activity Option

Dolphin Snorkel Tours, Manta Tour, Whale Watch

Iruka Hawaii offers snorkel and dolphin watch tours off the coasts of the two islands in Hawaii that provide the very best venue for observing dolphins, the Waianae Coast of Oahu and the Kona Coast of the Big Island of Hawaii.
More Info / Buy Now


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

Island Star

2 Activity Options

57' Sailing Yacht - Private charter only

The Island Star is a sail boat that is in a category of its own. This 57' sailing Columbia Yacht can accommodate as many a twenty guests and is used exclusively for private charters.
More Info / Buy Now


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

Sea Paradise

3 Activity Options

Snorkel - 50' Catamran

Sea Paradise is a 50 foot sailing catamaran, the Hokuhele, 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
(1 Review, 5 Stars)

Kainani Maui Sailing Charters

2 Activity Options

Kainani Maui Sailing Charters

Her modern yacht shape, spacious interior, and blue water sailing capabilities make her the perfect Hawaii sailing charter boat. She is also available for Memorials at Sea or Ash Scattering Services and special requests.
More Info / Buy Now


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

Holokai Catamaran

3 Activity Options

Reserve a trip with the Holokai Catamaran

Go out on an adventure with Holokai Catamarans! Discover colorful tropical fish, green sea turtles, exotic coral reef and more of Hawaii's undersea life. Dolphins are also possibilities on this incredible adventure. Snorkeling in Hawaii is very fun and easy.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(29 Reviews, 4.9 Stars)

Paragon Sailing Charters

4 Activity Options

47' Sailing Catamaran

Certainly one of the very fastest boats found in the islands is the 47' customized sailing catamaran, Paragon. Paragon Sailing Charters offers a number of choices for boat tours ranging from morning sails to Molokini; Day Trips to Lanai; Sunset Sails; and Performance Sails.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(21 Reviews, 4.9 Stars)

Scotch Mist Sailing Charters

5 Activity Options

50' Sailing Yacht, 50' Santa Cruz Sailing Yacht

The Scotch Mist is a 50' Santa Cruz Sailing Yacht which carries 18 passengers and offers sailing and snorkel charters off the coast of Maui. Having been the winner of the coveted Victoria to Maui Yacht Race in 1984, this vessel is a perfect choice to enjoy the waters off the coast of Maui and Lanai. She offers sailing and snorkel tours, sunset sails, trade wind sails and whale watching in season.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(8 Reviews, 4.9 Stars)

Fair Wind Charters

2 Activity Options

50' Sailing Catamaran, 55' Teknicraft Catamaran

Well established as a tour boat company on the Kona Coast of the Big Island, Fair Winds Charters has two beautiful and distinctive boats that offer a complement of tours which include snorkel tours to Kealakekua Bay and evening Manta Ray excursions. Also included as a part of the day snorkels are SNUBA diving and the new sea rocket underwater propulsion vehicles.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(31 Reviews, 4.8 Stars)

Trilogy Excursions

7 Activity Options

64' - 55' - 51' Sailing Catamarans, 55' Sailing Catamaran, 55' Catamaran to Molokini, 55' Sail Catam

One of the most popular and respected boating companies on Maui is the Trilogy which has been in operation here since 1973. Though being a large company now, operating six or so 50' range sailing catamarans, they are still the family owned operation that was begun by Eldon Coon and his two sons, Jim and Randy. Today they offer sailing tours to Lanai, Molokini, the West Coast of Maui and an assortment of shorter sunset and sailing options and whale watches.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(12 Reviews, 4.8 Stars)

Kauai Sea Tours

3 Activity Options

24' Rigid Hull Inflatable Rafts, Lucky Lady' 60' Sailing, Power Catamaran

Kauai Sea Tours is a large charter boat company that offers tours off the coast of Kauai and particularly the NaPali Coast with its beautiful 'signature' boat , Lucky Lady. In addition it also provides romantic dinner cruises and whale watches and also has a fleet of specially designed raft boats which are great for exploring caves, snorkeling and racing dolphins.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(6 Reviews, 4.8 Stars)

Hula Girl

2 Activity Options

65' Sailing Catamaran

You would be 'hard pressed' to find a more beautiful sailboat on Maui to take out on a snorkel sail, whale watch, dinner or sunset sail or a private charter. This multimillion dollar state of the art 65'x35', 90' wing mast sailing catamaran is designed for sailing and for maximum comfort. In addition it comes with its own full galley and private chef so all your meals will be prepared custom just for you.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(45 Reviews, 4.8 Stars)

Captain Andy's Expedition

5 Activity Options

55' Sailing Catamaran, 55' Gold Coast Yachts, 30' and 38' RAIV

Captain Andy's Sailing Adventures for years has offered tours to see the spectacular NaPali Coastline of Kauai. Sailing large and luxurious Gold Coast Yacht Sailing Catamarans, Captain Andy's will take you snorkeling and dolphin watching as well as provide romantic dinner and sunset cruises. In addition you can enjoy rafting adventures to the NaPali Coast.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(13 Reviews, 4.8 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


  • 1
  • 2
  • 3
  • 4
  • 5
(8 Reviews, 4.8 Stars)

Holo-Holo Charters

1 Activity Option

61' and 48' Sailing Catamarans, 38' Raft

Holo Holo Charters offers a variety of boat tours on Kauai on large, powerful and stable catamarans. Tours include beautiful snorkel and dolphin watch excursions to the NaPali Coastline, raft tours of NaPali during the summer months, dinner sunset cruises, whale watching and tours to the forbidden island of Niihau.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(8 Reviews, 4.8 Stars)

Pride Charters

1 Activity Option

65' Maxi Catamaran, 65' Catamaran

The Pride of Maui is one of the largest and most stable power catamarans available in Maui's fleet of boats. Leaving from Maalaea Harbor the 'Pride' offers tours to Molokini in the mornings but will also operate beautiful sunset cruises a few times a week and in addition will provide one of the most comfortable boats for whale watching in the winter months.
More Info / Buy Now


  • 1
  • 2
  • 3
  • 4
  • 5
(3 Reviews, 4.7 Stars)

Makani Catamaran

2 Activity Options

65' Sailing Catamaran

One of the most beautiful sailboats sailing the waters off the coast of Waikiki is the Makani Catamaran. This 64' x 32' Cat is one of the very fastest on Oahu often achieving speeds of over thirty knots. Flush with the most modern amenities you will be able to enjoy a wonderful sunset sail, a coastal daytime sail and a snorkeling excursion.
More Info / Buy Now


Alii Nui Sailing Charters

1 Activity Option

Dinner cruise with hotel pickup.

The one of a kind, luxury catamaran Alii Nui departs from Maui's Maalaea Harbor and offers a variety of sail options which include Molokini snorkel tours, sunset sails, dinner sails and whale watches. All the specialty details have been included on all its tours to provide a privileged ocean experience. Snorkel tours include hot showers on board and large terry beach towels for your personal use. Dinner cruises are limited to 32 guests and even complementary pick-up is included on its whale watches.
More Info / Buy Now


Hawaii Nautical

4 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


Holokai Kayak Adventure

1 Activity Option

Kayak off Kaneohe

Blessed with some of the most calm, clear and beautiful snorkeling waters in the state Kaneohe Bay is the location that is visited by Holokai Kayak and Snorkel Adventure. You will enjoy the bay and the sea life but will also get a chance to kayak out to the film location of Gilligan's Island. These guided kayak tours are wonderful but if you would like to rent a kayak on your own, that can be arranged as well.
More Info / Buy Now


Maita'i Catamaran

1 Activity Option

Waikiki Sailing Charters and Booze Cruises

The 44' sailing catamaran, Mai Tai, has been one of the most popular boats we have ever had on Waikiki Beach. Leaving right from the sand between the Sheraton and the Halekulani this 47 passenger boat will take you out for a day sail, a snorkel or a sunset sail and a view of the Waikiki Coastline and Diamond Head.
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


Pacific Whale Foundation

1 Activity Option

52' and 60' Power Catamaran, 52' and 65' Power Catamaran, 65' Power Catamaran, 65' Catamaran

The Pacific Whale Foundation is one of the main companies we have on island that goes out in search of the whales during the winter months. In addition, throughout the year they also offer boat tours to snorkel at Molokini, dolphin watches that look for dolphins and snorkel off the coast of Lanai and have rigid hull inflatable tours that visit the back side of Lanai.
More Info / Buy Now


Privacy Charters

2 Activity Options

Sailing, Power Catamaran

Privacy features a large air conditioned cabin with a couch seating for 3 guests, table seating for four, or sit in either of the two captains chairs at the lower helm station. Further forward there is a large clean restroom on the port side, and stateroom with a queen size bed on starboard side.
More Info / Buy Now


Royal Hawaiian Catamaran

1 Activity Option

52' Catamaran, 52' Catamaran - Sunset Excursions, 52' Sailing Catamaran, 52' Catamaran - Sunset Excu

One of the most beautiful catamarans to ever grace the waters off the coast of Waikiki is the 52' Rudy Choy designed custom cruising catamaran, the Royal Hawaiian. This famous boat builder built this specific boat with the expressed purpose of sailing Hawaiian waters. The boat is used for snorkel and sailing trips as well as private charters which can include dinner, sunset, star watching and whale watches.
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


Sea Maui

2 Activity Options

Make reservations for a snorkel trip or sunset sail on the Sea Maui.

Sea Maui is a beautiful 51 foot power, sailing catamaran that departs out of Kaanapali Beach. They offer a trade-wind sail every afternoon, a sunset sail in the evening and snorkel trips in the morning. Food is specially provided by renowned Chef Joey Macadangdang the former corporate executive chef of Roy's Kitchen.
More Info / Buy Now


Sail Oahu

4 Activity Options

SV Shalimar is a 67 foot Mega Yacht

Experience Hawaii and the Pacific Ocean aboard your private yacht, Shalimar. The meaning of Shalimar in Sanskrit is "Home of Love on the Water".
More Info / Buy Now




Recent Reviews


Top Activities
Customer Favorite Tours Based on Reviews