Hawaii Private Charters & Custom Events

There are 72 tours in this category with adult prices that range in price from $10.00 to $4900.00 Skip Directly to Tours.

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

Private Charters & Custom Events Sorted by Company

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(1 Review, 5 Stars)

Island Star

2 Activity Options

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.
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(1 Review, 5 Stars)

Kaanapali Ocean Adventures

3 Activity Options

Boasting two different fast and fun boats. Sanity is a very fast and comfortable boat that is designed for stability is the 46' aluminum hulled turbo charged power boat used by Kaanapali Ocean Adventures.
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(1 Review, 5 Stars)

Maui Diamond II

1 Activity Option

Maui Diamond Sea Sports offers dive and snorkel charters for the whole family. Their primary destination is the island of Molokini which is a smooth ride from its dock at Maalaea Harbor on the stable 40' dive boat with twin engines, Maui Diamond ll. Unlike most dive boats they provide room for snorkelers and 'ride-along passengers' so you can have the most experienced scuba diver on the same boat with non-divers who just want to go for the ride.
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(1 Review, 5 Stars)

Kainani Maui Sailing Charters

3 Activity Options

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.
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(1 Review, 5 Stars)

Maui Ocean Charters

4 Activity Options

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!
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(5 Reviews, 4.8 Stars)

Sea Maui

4 Activity Options

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.
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(2 Reviews, 4.5 Stars)

Scotch Mist Sailing Charters

1 Activity Option

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.
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Air Maui

1 Activity Option

Air Maui Helicopters is a long-standing member of the Maui helicopter community and over the years has flown tens of thousands of passenger to the far reaches of the island. Known widely for its congenial staff and 'laid back' company culture Air Maui has provided a faultless customer security profile in all its years of service on island. Air Maui exclusively uses the A-Star touring helicopters.


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Aloha Blue Charters

3 Activity Options

Aloha Blue Charters is unique in that it provides a 40' jet drive boat for use as a snorkel boat to Molokini and surrounding Maui snorkel locations but also is an ideal vessel for bottom fishing excursions and is also used for whale watching during whale season. It carries a maximum of 35 passengers on its snorkeling tours and has enough room on board for its fishing trips to allow for 10 separate anglers.
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Chauffeured Services, LLC

3 Activity Options

On Hawaii, Kauai and Maui choose from a chauffeured Sedan, SUV, Limousine or 10 passenger Van to get you to your vacation destination with ease and in comfort.
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Frogman Charters

1 Activity Option

The charter boat company Boss Frog's is also known by the name Frogman Charters and it operates Molokini tours, whale watches, sunset sails and dinner cruises from it departure point of Maalaea Harbor. It's two main boats are the 55' power catamaran Malolo and the 55' power catamaran Quicksilver.
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Hula Girl

1 Activity Option

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.
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Paradise Helicopters

1 Activity Option

Paradise Helicopters is one of the premier helicopter touring companies that services both the Big Island and Oahu. One of the biggest differences between this company and many others is the fact that they will offer you the opportunity to take a flight with the doors off. As nerve racking as that may sound, you are completely strapped in an just a secure as you would be in an enclosed helicopter. The big difference is that your view from this perspective will be absolutely amazing.
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Piiholo Ranch

3 Activity Options

Found of the slopes of Haleakala at about the 2500' level just a couple of miles above the 'cowboy' town of Makawao is found the Piiholo Ranch. This working cattle ranch is the home of the most beautiful meadowland horseback riding area on the island as well as the home of two of the most popular zipline courses to be found on Maui. The extreme beauty of the green rolling hills, the fresh mountain air and the scent of the mountain forests in themselves are enough of a reason to come for a visit.
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Rappel Maui

1 Activity Option

"Offers introduction rappelling adventures. All courses and tours include lunch, bottled water, insect repellent and complete outfitting, including harness, helmet and special traction water shoes. Requirements and limitations for all courses and tours: Harnesses will fit waist sizes from 22 to 54 inches. Please do not sign up if equipment will not fit you. Minors (under 18 years) must be accompanied by a responsible adult. You must sign a stringent participation agreement/waiver when you check in."
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Robert's Hawaii

1 Activity Option

Robert's Hawaii is the largest sightseeing company in Hawaii offering tour options on all the islands. In addition to running a variety of land tours on each island, they also offer "room and car" packages for inter-island travel. Robert's Hawaii has branched off into ownership of many of the other major activities found throughout the islands.
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Skyline Eco Adventures

5 Activity Options

Skyline Eco-Adventures offers a Road to Hana tour, zipline tours (originator of zipline courses in the United States) and one of the exclusive providers of tours to the Haleakala Summit.
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UFO Parasail

1 Activity Option

UFO Parasail offers exciting parasail flights on both Maui and the Big Island of Hawaii. Maui tours only operate between May and early December when the whales are not visiting these waters but the Big Island is in operation year round. You will have an opportunity to fly on a parasail pulled by 800' or 1200' of line and will be in the air either 8 to 10, or 10 to 12 minutes.
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Ultimate Rafting

1 Activity Option

Ultimate Rafting offers very exciting trips for snorkeling and whale watching off of the island of Lanai and the coast of Maui on their thirty-foot aluminum hulled rafts with inflatable surround. The engines on this boat are enormous, cranking out 400 horsepower that will get you there quick. Dolphins are commonly seen year round as are the Humpback whales during the winter months.
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Wailea Boating Company

1 Activity Option

If you're like many people you won't want to share your fantastic Maui ocean experience with others but would prefer to make it a day for just your own family or perhaps just for you and a couple other friends. The Wailea Boating Company may just be the boat for you as you'll be able to discuss the itinerary of your boating adventure with your captain and go off and enjoy the day. The 36', six passenger vessel is clean and comfortable.
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Wake Maui

3 Activity Options

Wake Maui will provide you with some real fun and excitement on the ocean. Specializing in groups of 6 or less, this wake board pulled by a boat provides just about all the fun anyone can handle. It's easy to learn, and the personalized attention by the captain will make it all that more simple. The fact that these tours are often private for your family and friends, makes it even that much more enjoyable.
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Stardust Hawaii

3 Activity Options

Stardust Hawaii considers stewardship of the environment important. Tours and activities offered offer both sightseeing and reflect a pride in the sharing of history and legends about the land "aina" and those specific to the destinations.
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Kaha Loa

1 Activity Option

Kaha Loa is a 26-foot Glacier Bay power catamaran, perfect for cruising the waters around Lahaina and Maui. This boat features a shaded canopy top, an onboard marine head, fresh water shower, a full-feature stereo (feel free to bring your own music and we play it for you) a swim platform with ladder. There is plenty of seating on this boat, capable of carrying up to 10 guests, we only take a maximum of 6 guests in the interest of your comfort. The forward bow seating area is a very popular feature and this boat will reach speeds up to 28 knots, depending on ocean conditions.
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Sea Monkey

3 Activity Options

Sea Monkey is a perfect boat for a private charter of up to 6 for your family or special small group. Spend a day or watch the sunset on the water.
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Aloha Kayaks Maui

1 Activity Option

Aloha Kayak Maui is one of Maui's premier ocean activity providers. With years of ocean kayak and snorkel experience offering PRIVATE or GROUP kayak tours, whale watching, and Maui snorkeling.
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Local Maui Tours

4 Activity Options

Local Maui Tours is a unique Maui tour company that offers private, custom tours from the perspective of a credible, professional Maui local.
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Unique Hawaii Experience

6 Activity Options

Offering Private private guided tours of Maui in an Eddie Bauer Expedition. Private transportation can also be provided as well as customized tours.
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HangLoose Maui Ocean Adventures

4 Activity Options

Hang Loose Maui Ocean Adventures is owned by a local family providing guided private Kayak and Stand Up Paddle tours of the Olowalu and Makena coastal areas off Maui.
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Haleakala Eco Tours

1 Activity Option

Haleakala Eco Tours provides quality land tours of Haleakala National Park, the Upcountry Maui area and other incredible Maui locations.
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Maui Legend Tours

1 Activity Option

Sightseeing land tours of Maui with guides that share the Legends of Hawaii, passed down through the generations, with guests as they enjoy the scenic views.
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Boogie On Wheelchair Vans

1 Activity Option

Boogie On Wheelchair Vans has a mission to enable and encourage guests with disabilities to overcome the challenges of Travel. Maui is a special island with much to share rent a Luxury ADA Conversion Van to get you there!
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Maui Reef Adventures

2 Activity Options

Maui Reef Adventures offers private charters and the Molokini Turtle Town Snorkel Tour on their exhilarating 42' Rigid Hull Rafts.
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Blue Hawaiian Helicopters

1 Activity Option

Blue Hawaiian Helicopters offers spectacular Group or Private Charter helicopter tours on Kauai, Oahu, Maui and Big Island of Hawaii. Eco-Star and A-Star Helicopters are available for privates from all locations and the Maui and Hilo tours.
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Recent Reviews

Lanai Snorkel Sail - Sea Maui

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We had a wonderful time! Perfect way to start our visit & set the pace for the rest of our stay... Lisa Kudra

Sunset Cocktail Saill - Sea Maui

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Had a great time on the cocktail cruise! Tom Barefoot's is the best place to book activities. I.. Maryken Plaia

Sunset Cocktail Saill - Sea Maui

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Great time, great crew. Well sail with them again. But first, I cannot recommend Toms Barefoot.. Earnest Luke

Sunset Cocktail Saill - Sea Maui

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Had a wonderful time! Crew was excellent, food and drinks yummy! Luanne Canestro

Island Star Half-Day Sail - Island Star and Scarab

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Our 4 hour sail with Island Star and the crew, Nick, Ian and Ryan was wonderful. It was everything.. Colleen Johnson

4 Hour Private Snorkel Sail - Maui Ocean Charters

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Mike and Malcolm were great and the trip was spectacular. There is something to be said about.. Sarah McClement

Sunset Cocktail Saill - Sea Maui

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Great trip! Crew couldn't have been more pleasant and accommodating and everything was just.. Alex Kennedy

Private Charters - Scotch Mist

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This trip was a lot of fun; my husband and I along with our wedding guests enjoyed this as a.. Lisa Cooper

Private Charters - Scotch Mist

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The tour was really great. They were SUPER attentive to our every need and super sweet! I was a.. Makalia Juarez

Top Activities
Customer Favorite Tours Based on Reviews

• Private Charter Snorkel/Whale and Dolphin Watch with Kaanapali Ocean Adventures on Maui (1 Review, 5 Star Average)

• Island Star Half-Day Sail with Island Star on Maui (1 Review, 5 Star Average)

• Lanai Snorkel Sail with Sea Maui on Maui (1 Review, 5 Star Average)

• Private Charter with Maui Diamond II on Maui (1 Review, 5 Star Average)

• 4 Hour Private Snorkel Sail with Maui Ocean Charters on Maui (1 Review, 5 Star Average)

• Kainani 43' Private Sunset Sail 3 Hour with Kainani Maui Sailing Charters on Maui (1 Review, 5 Star Average)

• Sunset Cocktail Sail with Sea Maui on Maui (4 Reviews, 4.8 Star Average)

• Private Charters with Scotch Mist Sailing Charters on Maui (2 Reviews, 4.5 Star Average)

This particular video segment is on private charters and custom events.

Now, you may have noticed on our website at tombarefoot.com that we have hundreds and hundreds and hundreds of Activities and Tours on all the major islands. These are primarily tours that are specific. They have a beginning time and an end time. They cost a specific amount of money. They go out on a certain day. They're all somewhat in the box, if you will. That's why you can just go and go to our website, decide what it is that you want to do and book it and it's just all very simple for you to do.

The other side of that is that we do have requests of all kinds that come in of people that want specific ... That want different charters, ones that are custom that are specific to their own guidelines. These can be somewhat challenging to make happen and to put together but they're something that we do at all times. A list of things that we have that we do regularly is people want to have a wedding reception, or actually a Wedding that they want to do maybe on a boat. Maybe they want to do it somewhere else and they want some information regarding using a particular facility that's run by one of our vendors or activities and they would like us to organize that. A lot of times we have people that are interested in overnight sails. We had a client last week that was interested in doing ... It was just four, mother and father and two teenage sons, they were interested in doing an overnighter on a sailboat going somewhere, staying overnight, Snorkeling, doing something different, something out of the ordinary.

We have things like bachelor parties or bachelorette parties are requested quite often. Another one that we get a lot is the spreading of ashes of a departed loved one. We get corporate groups that are coming with maybe incentive groups or some special event. They're looking to do a dinner cruise. They're looking to do whatever they're looking to do for their group that is on a specific day, maybe specific different times, maybe later at night, maybe having different forms of alcohol that they're looking for, maybe a different format than a usual Dinner Cruise, different departure point.

Anything can happen. School graduations, people want to have some kind of a special celebration for schools that are a graduating class that is just making it to the end. Even things like private Helicopters, people want to do a special tour that they can't find on the website that maybe goes between Maui and the Big Island and then comes back, but all on a helicopter. These are things you won't find on a normal, regular basis, but things that we can arrange and organize, and we regularly do. Anything that you can think of that you might be interested in, we're willing to take a shot at it.

The one thing that we do need for you to do is to go to our website and go to the private charters and custom events section. Then fill out a form that's there and fill it out, please, in detail so that we can know specifically what you are looking for. Dates, times, any special amenities that you want to have incorporated and then a price range that you're looking for. Please be candid with regard to the price range. Everybody wants to pay less rather than more, but it really is impossible in some cases to get people a custom tour that they want at a very, very low price. You need to think that these are going to be more expensive than you think, rather than less. That's just the nature of the custom animal.

Also on there it's going to give you a place for an email. It's going to give you a place to put a phone number. Please put your phone number down. If you don't do that, it's going to delay the processing of it because in most cases, before we really start to investigate, to try to figure out exactly what's going to be best for you, we're going to want to talk to you directly and make sure all is understood in terms of what it is that you realistically want to have. If you don't include a phone number, you're going to get an email, in all likelihood, saying, "Can we have your phone number? We need to talk." It's just going to set things back somewhat.

Within those parameters, we are more than willing to see what we can do and this is on all the islands. We've arranged incredibly unusual, different things over the course of time. They're kind of fun to put together. They often take a lot of time to do, but we are interested in making sure that we can get the right things for you guys. Let us know if you want a custom event and we'll organize it.

If you have any questions about Tours or Activities in Hawaii, just give us a call, or check out tombarefoot.com. We're here to help.

State Wide Private Charters & Custom Events

We've been planning vacation activities in Hawaii for over 40 years and some of our favorite packages to help clients with are the "Customized Special Requests".

More Info / Buy Now

Private Charters & Custom Events on Kauai

We've been planning vacation activities on Kauai for over 40 years and some of our favorite packages to help clients with are the "Customized Special Requests".

More Info / Buy Now

Private Charters & Custom Events on Oahu

We've been planning vacation activities on Oahu for over 40 years and some of our favorite packages to help clients with are the "Customized Special Requests".

More Info / Buy Now

Private Charters & Custom Events on "The Big Island" of Hawaii

We've been planning vacation activities on the Big Island for over 40 years and some of our favorite packages to help clients with are the "Customized Special Requests".

More Info / Buy Now