yacht sailing hawaii

Hawaii Sailing Adventures, LLC

Private Charters in Maui, Oahu, Lanai, Kauai

Private Hawaiian Catamaran, Sailing and Yacht Charters

It's time for the vacation of your dreams.

1/2 day, one-day, sunset, dinner, multi-day to multi-week inter-island vacation, and trip options are available.

Hawaii Sailing Adventures offers private boats, catamaran charters, and sailing trips on our luxury fleet. We provide charter options for Maui, Kaanapali , Kauai , Niihau, Lanai , Molokai , Honolulu, Waikiki, Oahu , Kaneohe Bay, and The Big Island.   Snorkel, whale watch and visit Napali Coast, Kaanapali & Kohala Coast, exploring the beautiful "unknown" Hawaii through our one of our luxury boat trips.

Contact us  to learn more about booking a private catamaran or boat charter where you'll create a memorable adventure for your family and friends. Enjoy extraordinary encounters with whales, dolphins, and sea turtles, swim and snorkel in tropical island waters and have the best sailing experience in your lifetime!

Explore Our Fleet

Fountaine Pajot Bahia 46

Lagoon 440 Fly Bridge

Fountaine Pajot Helia 44

Excess 12 – 39’

Beneteau Oceanis 50

Beneteau Oceanis 48

Nautor Swan 46

Beneteau 42

Beneteau Oceanis 41

Beneteau 393

Beneteau 39

Ready to find out more.

Get information on prices, itineraries, private daily or weekly charters & tours in Hawaii.

Napali Coast, "The Forbidden Island", North Shore Molokai, Kanaapali, Manele Bay

Niihau, Kalalau Valley, lagoon, reefs and beaches, sea cliffs, waterfalls, snorkel, scuba, swim, sunbathe, kayak, paddleboard, surf, windsurf, fish, and dine ashore. Stay in the harbor as a pleasant, charming, quiet, relaxing home base with all the cooking and sleeping amenities, a more creative environment than a hotel or house, and explore on-island activities on a week or two sailing charter. Relax, work the sails, whale watch, extended inter-island trips, short sailing tours, sunset sail, and dinner cruise. Feel what it is like to offshore cruise in the most dramatically beautiful settings in the world. Our crewed sailing and luxury yacht charters and boat tour prices include skipper, food, fuel, gear, other vessel costs, Sail Blue Hawaii, and much more.

What our customers say...

"Thank you so much! We loved the day and the memories will be cherished. We hope to do it again some day."

The Ferrier Family

A dream wedding in hawaii.

Ask us about our tropical, romantic wedding and honeymoon packages. Then, let us arrange your marriage ceremony aboard your private yacht.

Catamaran and Monohull sailboats to; Maui , Lahaina, Molokai , Lanai , Oahu , Honolulu, Kauai , Niihau, Big Island Hawaii .

HAWAII Yacht Charter & Boat Rentals

Hawaii Yacht Rentals

50′ CORINTHIAN | 49 Guests

74′ STRIKER | 12 Guests

75′ SUNSEEKER | 12 Guests

Private yacht charter getaway – maui.

47′ Catamaran | 38 Guests

47′ Catamaran II | 38 Guests

64′ Catamaran | 38 Guests

Private yacht charter getaway – hawaii.

In the heart of the vast Pacific Ocean lies a paradise unlike any other – Hawaii. The mere mention of its name conjures images of swaying palms, pristine beaches, and a culture deeply rooted in the spirit of aloha. Now, imagine embarking on a voyage of a lifetime, a private charter that allows you to explore Hawaii’s enchanting waters, immerse yourself in its vibrant marine life, and experience the essence of aloha in a way that only the ocean can reveal.

As your private charter sets sail on the turquoise waters of Hawaii, a world of natural marvels unveils itself before you. Majestic cliffs rise from the sea, adorned with lush vegetation that seems to defy gravity. Hidden coves with powdery white sands invite you to step ashore, each beach a pristine canvas waiting to be explored. This is a land of contrasts, where the verdant mountains meet the azure ocean in a breathtaking embrace.

Hawaii’s waters are a playground of marine majesty, a realm where dolphins dance in the wake of your vessel and sea turtles glide gracefully through the sea. Snorkel into an underwater kingdom where corals bloom in a riot of colors and schools of fish move in choreographed harmony. Every moment spent beneath the waves is a reminder of the intricate beauty that thrives beneath the surface, a world that exists in perfect harmony with Hawaii’s terrestrial wonders.

Hawaii’s sunsets are nothing short of celestial masterpieces. From the deck of your private charter, watch as the sun dips below the horizon, painting the sky with hues that range from soft pinks to fiery oranges. It’s a moment of pure magic, when time stands still and the world around you is bathed in a warm, golden glow. As darkness falls, the stars emerge to create a celestial panorama, reminding you of the vastness of the universe.

Sailing on a private charter in Hawaii is a voyage of awe, wonder, and deep connection. It’s an invitation to witness the marriage of land and sea, to embrace the magic of marine life, and to experience the spirit of aloha in its purest form. As you sail into the horizon, with the wind in your hair and the ocean at your feet, you’ll find yourself captivated by the beauty, mystery, and allure of Hawaii’s boundless waters.

Whale Watching in Hawaii | Romantic Getaways

Corporate Events

Plan your party yacht charter with us!

Hawaii Yacht Charter

Luxury Liners offers yacht charters, boat rentals, and private chef services for groups of all sizes. Our Hawaii yachts are well maintained for the perfect yacht charter experience traveling to in and around the islands of Hawaii the perfect destination.

A Hawaii yacht charter is perfect for family vacations , fishing trips , and whale watching , and more!

HAWAII PRIVATE YACHT CHARTER

Our yachts are perfect for birthdays parties, corporate events, and dinner cruises. Luxury Liners offers exciting private yacht charter getaways like no other. Plan your yacht party with us!

Hawaii Yacht Charter Destinations

• (808) 664-1164
• [email protected]
• Ko Olina / Waikiki

PRIVATE & SHARED YACHT CHARTERS

We specialize in providing private and shared yacht charters in hawaii, from ko olina and waikiki. with a passenger limit of six, we cater to families, couples, corporate suites and more.  browse from our three vessels, two oahu locations, and various experiences to find the perfect match for you. trust in our genuine service and aloha from beginning to end..

MANA Cruises + Charters

92-100 Waipahe Place, Kapolei

5.0 214 reviews

Top Hawaii Activities

Top Hawaii Activities At MANA Cruises, we know that the beauty of Hawaii goes beyond the traditional sun, sand, and sea. While these are definitely some of the best things to experience in Hawaii, there are also plenty of unique and exciting activities to do

Spotting the Big M

The Iconic MANAKAHI Sail off Ko Olina’s Coast Have you ever gazed out from the sun-kissed beaches of Ko Olina and spotted a majestic sailboat with a striking ‘M’ emblem billowing in the wind? It’s a sight that captivates both locals and tourists alike, often

Why do Whales Migrate to Hawaii?

Humpback whales Northern Pacific Humpback Whales (Megaptera novaeangliae) are migratory mammals that travel long distances every year between their feeding and breeding grounds. The northern Pacific population of humpback whales, which includes whales that migrate to Hawaii, feed in the cold, nutrient-rich waters of the

Explore Your Options

Ko Olina: Ko Olina Marina 92-100 Waipahe Place, Kapolei, HI 96707 Waikiki: Ala Wai Boat Harbor 5 Holomoana St, Honolulu, HI 96815

Native Hawaiian Owned & Operated

OFFICE HOURS

Daily 8 AM - 5 PM

Experiences Locations Ko Olina Waikiki Gallery FAQ About Fleet Contact Privacy Policy

• © MANA CRUISES AND CHARTERS - 2024
• ALL RIGHTS RESERVED

Private Luxury Yacht Charters Based in Waikiki, HI

Choose a sailing charter.

• Most Popular

Enjoy the sun, surf, and spectacular views aboard your own luxury yacht. With a variety of options to customize your day sail, you can experience the day of your dreams aboard the SV Pau Hana.

• Hour Glass 2 Hours , 3 Hours , 4 Hours
• Hour Glass 2.5 Hours

Friday Fireworks Sail

Watch the Friday night fireworks in Waikiki from the SV Pau Hana. Leave the crowds behind and enjoy your own private fireworks show as our crew caters to your every need.

• Hour Glass 2 Hours

Ash Scattering

We would be honored to help you say goodbye to a loved one with a beautiful ash scattering ceremony on the Pacific Ocean.

Why Sail Oahu?

We offer the finest in luxury performance sailing on one of the newest sailing catamarans in Waikiki. Our Captain and crew are here to see to your every need while providing the highest level of comfort possible aboard a yacht of this caliber.

We will present you with the finest selection freshly prepared local food and beverage customized for you. Whether you are a first-time sailor or a seasoned “Shellback,” relax in comfort and pleasure as the Hawaiian trade winds blow us favorably past Diamond Head.

Customize Your Sail!

Have a special day in mind? Tell us about it. We can provide a no-obligation quote tailored to your perfect day in paradise. We also guarantee our quote for 60 days to give you plenty of time to decide.

Set Sail On Your Adventure

We ensure that your day in our blue paradise is spent the way you always dreamed it could be. Experience Hawaii and the Pacific Ocean aboard your private yacht.

All of our charter guests rate us 5 stars on TripAdvisor

Can't say enough good things about Alan and his crew!! So kind. So knowledgeable of the island. We swam up close with turtles and had a freshly made lunch served. We felt like celebrities. Highly recommend!!

What an awesome afternoon with Sail Oahu! Captain Alan, First Mate Wanda, and crew are first class in every way. We had a beautiful day with stunning views of Waikiki and Diamond Head - with wine, beer, and a delicious lunch to top off the trip. The sailboat was impeccable, impressive and well appointed. We felt well cared for and very welcome. We are looking forward to our next visit to the island and another afternoon with Sail Oahu.

Sail Oahu was Soo Much Fun!!! I had the best day celebrating my birthday!! Captain Alan and First Mate Wanda will make your Trip so enjoyable! They are amazing hosts! And their boat is so classy! I felt like a princess! And the views of Diamond Head were breathtaking!! I will definitely Sail with them again!!

Sail Oahu was one of the most exciting, tranquil, humbling experiences of my life. Capt. Alan, his mate Wanda, and the entire crew were so welcoming & warm. They were particularly great with my nieces and nephews (ages 3-10) as well! They always put safety and comfort first! The sailboat itself is beautiful and lavish. The views of the Island from the open water were breathtaking. I will definitely Sail Oahu every trip I make to the island.

A fantastic day out with my friends with breathtaking views, lovely food, and a stunning boat. The crew were amazing people with such interesting stories, they really made us feel like a big happy family. I recommend this for all families, friend groups, young and old. A day I will never forget! Thank you Sail Oahu and hope to see you soon.

• Paradise Sailing Hawaii

Kailua Kona Sailing Catamaran Charters - Big Island Boat Tours

Enjoy a true sailing experience with a small number of passengers during a Kona sailing charter on Hawaii's Big Island! Our beautiful new sailing catamaran features plenty of shade , comfortable cushioned seating with tables, nice clean toilet facilities and the roominess, stability and speed of the newest 36' sailing catamaran offering Big Island boat tours.  We offer a variety of Kona sailing charters including a relaxing Kona Sunset Cruise and private catamaran charters.

Because we are family owned and operated , we provide the kind of personal service only a small business can and the comfort of catamaran sailing without the big boat crowds . Please check out our reviews on GOOGLE and TripAdvisor to find out how much our guests enjoy sailing with us!

Our most popular Kona Sailing tours

4 hour private catamaran charter.

Have our beautiful catamaran all to yourself and spend the morning sailing, snorkeling & looking for wildlife. Snorkel equipment and refreshments are provided. BYOB STARTING AT $1,595 Click here for more details

Private Kona Sunset Cruise

Sail into the sunset aboard Kōlea on our  Sunset Sail and enjoy the beautiful  Big Island Sunset. Refreshments are provided.  BYOB STARTING AT $995 Click here for more details

CUSTOM PRIVATE CATAMARAN CHARTERS

Starting at just $995*.

Google Rating

5.0 159 reviews

Paradise Sailing Hawaii , Honokohau Marina Slip J24, 74-380 Kealakehe Pkwy, , Kailua Kona , HI 96740 , United States (US) - Phone: (808) 883-0399

setting sail from Honolulu, Hawai’i

Your ocean adventure awaits.

Custom sailing, swimming, and romance charters on a classic sailing yacht

CUSTOM SAILING CHARTERS ON A CLASSIC YACHT

Leave the crowd at the beach & escape to the sea.

Step aboard Blue Planet  – a newly renovated classic, 1978 sailing yacht! Enjoy the Waikiki skyline on private sailing, swimming, and science charters. Or, experience an unforgettable romantic evening with our Romance Charters or Elopements at sea.

Get ready to experience the thrill of a lifetime!

Sail & Swim Charters

Romance charters, elopements at sea, group science charters, learn to sail, what our clients say, “truly a once in a lifetime experience, just wow.🤩🤩 easily the most beautiful moment of my life., what a beautiful experience, recent news & updates.

Read the latest news and updates from Sailing Eternal Tides. Check out articles, insights, our research initiatives, and more. For even more content and information, click the link below.

Exploring Hawai’i’s Whale Watching: A Comprehensive Guide

Prepping for a Sailing Charter: 5 Essential Things to Know

Where to Eat Near Kewalo Basin Harbor

Learn How To Sail In Honolulu

Become a vip, adventure with o’ahu’s premier sailing charter in honolulu and take the trip of a lifetime.

Get a dose of stunning sailing photography, stay updated on our latest blogs, and enjoy exclusive behind-the-scenes content delivered straight to your inbox. Sign up today!

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Explore our charters

Private sail, romance charters, elope at sea, shared science sail, stickers & merch, tour the boat, meet the crew, citizen science, news & features, join our team, our commitment, certifications & training, 808.388.7256, [email protected], kewalo basin harbor, 1125 ala moana blvd., honolulu, hawai’i.

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SPOTS FILLING QUICKLY! BOOK YOUR SUMMER CRUISE & SNORKEL TODAY

Tradewind Charters

Escape on a private charter | honolulu, hi.

• Most Popular!

Cruise & Snorkel

Perfect for visitors with a desire for real sailing in a private setting. Our luxury yachts are limited to private parties ensuring comfort and no crowds!

Fishing Adventures

Create fantastic family memories at sea on your Oahu vacation by combining a few ocean activities together.

Mimosa Sunrise Cruise

Ideal for the romantic couple who’s up at the crack of dawn during their Hawaiian vacation due to time zone changes. Witness the brilliant colors of a sunrise at sea from the deck of the Love Boat.

Sea Spa Cruise

Perfect for couples, families, and groups celebrating life events like birthdays, anniversaries, showers, and bachelor/bachelorette parties.

Aloha to Tradewind Charters

Tradewind Charters Hawaii offers visitors and Kama’ainas private sailing cruises, fishing charters, sunset dinner sails, snorkeling tours, whale watching and dolphins swims, scenic sightseeing tours, weddings at sea, sea burial services, and much more. Whether you are looking to relax for an afternoon or a whole week, host a wedding and reception at sea, entertain family, friends, and business associates for a luncheon cruise, or savor a romantic sunset dinner sail, we do it all for you.

Meet Captain Ken

Capt. Ken at the helm. Over 25 years ago, I sailed over from the West Coast and started up Tradewind Charters to provide the very best in private boat charters for clients from all over the world. Our islands’ perfect weather is ideal for sailing and living in comfort, and coupled with an unsurpassed beauty and allure, incredible marine life year-round, and neighbors full of ALOHA, it truly is Paradise. Come sail with us and let us show you the reasons why we call these islands home.

Raving Reviews

"A group of four of us took a morning sailing cruise out past the shores of Waikiki. Captain Nate was a great source of information and shared some fantastic recommendations of things to see/do. He was very personable and informative and made our trip very enjoyable."

"This was an amazing way to end our vacation in Hawaii. Our family sailed for two hours and enjoyed the sunset while eating and drinking. Best of all it was just us! Our own private cruise. Paul was an incredible captain and host who took care of all of our needs. We just sat back and enjoyed the ride."

"My family thoroughly enjoyed a three-hour sail trip on "My Sunshine." Captain Paul was amazing, as was the boat trip. Beautiful say on Waikiki swimming, sailing and enjoying the sun. Perfect cruise!!!!"

"I had a WONDERFUL experience. Captain Ken was incredibly responsive and easy to coordinate with. He and his crew made sure that we had an enjoyable and safe time out on the water. The boat was incredibly clean, and well-equipped with everything you would need - snorkels, bathrooms, and a full bar! Can't wait to sail again with Tradewind Charters."

Matt Weidert

Sailing in Hawaii: Is a Bareboat Charter Possible?

Where to go sailing in hawaii, what is it like to go sailing in hawaii, how you can take a hawaii yacht charter trip.

Week-long Kauai sailing itinerary:

Day 1: cross kauai channel, anchor at hanalei bay, day 2: hanalei bay.

Day 3: Ha’ena and Tunnels Beach

Day 4: Off to explore Napali Coast

Day 5: Polihale Beach

Day 6: Go visit the forbidden island, Ni’ihau

Day 7: cross back to oahu or disembark.

Hawaii cruising conditions

Pacific trade winds.

Hawaii’s summer season

Hawaii’s winter season, tides and current.

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Our Spirit of Aloha

Hawaii’s finest yacht chartering company has served kama’aina’s and visitors for over 50 years with dedication and pride., we offer private sailing cruises, sunset sails, snorkeling tours, whale watching, unique weddings at sea, special event planning, asa sailing classes, memorial services, and much more., come sail with us and see the other side of waikiki you’ve been missing…, meet our captains and crews.

Our Crewed Yacht Charter is an Exceptional Experience.

Our carefully selected USCG Licensed Captains and crews with years of boating experience and a wealth of local knowledge will ensure you have the best time on the water. From showing you the best snorkeling spots or choosing the best anchorage for the perfect sunset our crews are here to create a lasting memory!

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Sailing in Hawaii: Everything You Need to Know

2024 Hawaii Visitor Guides

Discount Hawaii Car Rentals

The ocean surrounding the Aloha State beckons all to sail its waters. For those who take the call, they will find ample steady breezes, the sun, and calm seas awaiting their adventure. However, the calm and beautiful ocean can be deceiving to the inexperienced. 

If you want to go sailing in Hawaii, you must come prepared with a plan, a doable destination, and enough supplies if something goes wrong. This is because the trade winds and currents near the islands can change from calm to turbulent in an instant. 

To solve some of the riddles of sailing in Hawaii, the American Sailing Association established a list of tips and accredited sailing schools so you can learn the ropes. By reading further, you will learn what these tips and schools are so you can implement them as needed.

— article continued below —

Visiting Hawaii soon? Be sure to grab a copy of one of our updated Hawaii Visitor Guides .

~ Trusted by Millions of Hawaii Visitors Annually ~

The Art of Sailing Among the Islands of Hawaii

There is no better way to see Hawaii than by sailing. The trade winds surrounding the islands make nearly perfect sailing conditions without ceasing. Plus, you can enjoy the calm waters and warm breeze all year long, especially on the western side of the archipelago. You can take out your boat or rent one to see all the islands offer, such as the Kohala Coast and Kealakekua Bay.

While the lure of the water splashing onto your boat's hull sounds inviting, the islands are notoriously challenging to sail. The breeze may be steady, but it is not a constant everywhere. The shapes of the islands create a chaotic storm of everchanging ocean currents and weather. The conditions are so bad, sailors boast that if you can sail in Hawaii, you can sail anywhere .

Each island has its unique character traits. The winds are so specific that ancient Hawaiians have 30 names for the winds around the island of Maui alone. It also takes an expert navigator to chart around the swells, currents, and rotating stars. The ancient Polynesian navigators were the best in the world for a reason. 

Therefore, you must come prepared before you embark on your journey through the waters surrounding these volcanic islands. 

Hawaiian Sailing Education Resources

Most people get the taste for sailing around Hawaii on some sunset cruise and believe they are already skilled enough to handle the Hawaiian trade winds. They feel the moist air passing over the West Maui Mountains and over the boat, forcing it to move with purpose. They think they can handle the waters and embark to go off the typical visitor tours. 

However, the Hawaiian straits can get challenging beyond the shores. General sailing skills are not enough; you need local expertise if you want to avoid Hawaii's legendary surf breaks or a free trip to Tahiti. 

You can gather this expertise by hiring a guide for a private tour of the islands, or you can attend classes at one of the three American Sailing Association (ASA) sailing schools on the island of Oahu:

• Waikiki Sailing School
• Sail Hawaii
• Honolulu Sailing

You will find all three schools centrally located at the Kewalo and Ala Wai harbor near the world-famous Waikiki Beach. 

All three schools provide instructions that lead to ASA certifications 101 and 106 using a classic Pearson Ariel 26 keelboat. You will learn your way around Hawaii with practical applications such as a liveaboard Pacific Offshore Challenge sailing adventure around the islands. They even offer courses for ASA 105 and 107 (Celestial Navigation) certifications. 

Best Places to Sail in Hawaii

With your new Hawaii sailing certification, you will want to get out on the open sea. Every Hawaiian island has unique vistas and challenges that will keep you coming back for more. If you set out with a guide, they will point you towards exciting destinations and how to get to them. If you are taking the seas alone, you will want to plan out your excursions before leaving the shore. 

Sailing Around Maui

Around Maui county's islands, the tradewinds generally come from the northeast but can have different effects if they flow from the north versus the east. Either way, they will lead you to the Auau and Pailolo Channels and Maalaea Bay which are often labeled as the best sailing places in Maui. 

The Pailolo Channel

The Pailolo Channel offers the most consistent sailing conditions of the archipelago. Situated between the mountains of the Maui and Molokai islands, the strait forms a 9-mile-wide funnel that keeps the winds going in the same path regardless of their direction. 

Reaching the channel requires knowing how the winds are blowing. With an east wind, your best bet is to start sailing towards Eastern Molokai, then turn towards Maui once you reach the middle of the channel. The winds would then cross your boat from the port side. 

With a north wind, you can go straight through the middle of the channel with the free-running breeze. You will crawl at a consistent 15-25 knots, but you will have a riveting sailing experience. 

Honolua Bay should be available to you regardless of the trade winds. 

Auau Channel

As the Pailolo Channel becomes the Auau Channel near Lanai, the winds get complicated. For example, you can cross the channel from Manele Harbor to Lahaina without much effort with a good north wind. However, crossing the channel with an east wind can challenge even native experts. 

With an east wind, your best chance is to find wind convection or a light breeze caused by the nearby hot land. Though, the occasional south wind can help as well. 

On the South Side of Maui

Maui's volcanoes turn the island into a wind funnel aimed directly at Maalaea Bay. This funneling makes the bay the windiest spot in Hawaii. As such, the bay is continuously whitecapped from dawn to dusk. To make matters worse, the north wind arrives early, rendering snorkeling and other water activities impossible. 

You also must reach the bay traveling upwind. Because of this, even the seasoned veterans will not sail into the bay and recommend using a motor along the coastline. You can bring out the sails again once you reach North Kihei. You can only sail to McGregor Point and Maalaea Harbor during light or westerly winds. Just be ready for the jump from 10 knots to 25 as you pass North Kihei. 

Cruising the Leeward Seas

The leeward side of the islands is the calmer side with much more manageable water and winds. Partly shielded from the tradewinds, these waters provide an unforgettable and unique way to see Hawaii and all that the islands offer. You can sail anywhere with little effort, even upwind. 

Kaiwi Channel

For instance, you can cross the Kaiwi Channel between Oahu and Molokai in less than half a day. Once there, you can spend the rest of the day and night enjoying life in Lono Harbor, a deserted but protected hideaway. You can then take the short-day trip to the Nanahoa pinnacles, an interesting rock formation with a nice anchoring spot for swimming and lunches. 

Lanai Island

Toward the south from Nanahoa, you will find the Island of Lanai and the Auau Channel with a more leisurely approach towards Manele Bay. The bay is Lanai's only recreational marina and has no guest slips, but it does give you access to Hulopoe Beach and the nearby hiking cliff trails. 

The only other interesting spot on the island is Lahaina Harbor. The Lahaina Yacht Club privately owns the historic harbor. As such, you need permissions from the club to dock. Even then, most of the time you will find yourself mooring your boat to a visitors' buoy or anchoring in the bay, using their provided dinghy to reach the bars on the shore. 

Luckily, ASA Hawaiian classes provide Lahaina Club membership, giving full access to the club's other amenities, including hot showers, fish taco shops, and the best view in town. 

Molokai Island

Across the channel from Lanai is Maui, which has nothing special for boaters, but beyond Maui is Molokai. Reaching Molokai requires crossing the Pailolo Channel, but you will find a reef that will lead you towards the calmer lee side of the island. 

Fortunately, there are no harbors or anchorages along Molokai's north shore. So, you can avoid most of the tradewinds and travel down the lee side until you reach Kaunakakai. Kaunakakai is the main town on Molokai, and its harbor is fully equipped. There is a guest dock with end ties and enough room in the harbor in case you must anchor offshore. 

As for the island itself, Molokai has the most native Hawaiians in the state, who prefer a more traditional lifestyle. The "Friendly Island" feels like a time capsule with only a few modern amenities. The island's major attraction is the Paddler's Inn. The popular restaurant serves as the central meeting spot for locals and visitors alike. It is open every day except Sunday and serves Molokai's famous hot bread.

The Open Sea Between Molokai and Oahu

When sailing around the Hawaiian Islands, you rarely venture out into the open ocean. Most travels keep you near the islands or in the semi-protected channels between them. The only time you will travel through the open Pacific is when you go directly between Oahu and Molokai. 

The course will take you past migrating Humpback whales as they play with spinner dolphins. However, we only recommend that you take the route going in the westward direction. This way, you will travel the 45 nautical miles with the trade winds and not against them. 

Sailing Between Hawaii and Mainland U. S.

When people talk about Sailing in Hawaii, they only mention traversing the waters between the islands. However, the open ocean between the archipelago and the mainland offers a gratifying experience on its own. Many sailors prefer the ventures so they can bring their boats with them instead of renting once they get to Hawaii. 

General Hawaii-Bound Sailing Route

Regardless of your starting location, your trip to Hawaii will be essentially the same, with a few deviations. You generally head south along the coastline until you are between 35 degrees North and 25 degrees North. From there, you can head straight westerly for Hilo. The trip will take about 2-4 weeks. While there are more direct routes, this passage is the quickest with the fewest chances for failure. 

Los Angeles is a good staging point . The city ranges from 38 degrees and 34 degrees North. From the south, you want to remain offshore and out of the surf as much as possible, but you can start heading west as soon as you see the city. 

From the north, you must choose from three different routes: 

• Slowest route: Reach Los Angeles through San Francisco. You can hop from port to port until you reach the Bay Area before heading southeasterly to join the northern route to Hawaii.
• Fastest route: Head directly towards Los Angeles, approximately 20 to 40 miles from the shore. This route lets you take advantage of the coastal current and winds. 
• Safest Route : Same as the fastest route, except you remain 50 to 100 miles out. You will find smoother sailing the farther out you are, but try to avoid the Pacific High. 

Regardless of the route you take, you want to avoid:

• Point St George
• Cape Flattery
• Cape Blanco
• Rocky Point/Honda Point

Make Sure You Always Remain South of the Pacific High

Regardless of how you plan to reach Hawaii, you want to avoid the Pacific High. This semi-permanent depression in the North Pacific gives Hawaii its tradewinds, and you need those tradewinds for your trip. The High also has light winds and rain, which will make your trip a miserable experience. 

Therefore, all recommended routes towards Hawaii send you south before you head west. However, the Pacific High moves. It shifts towards the equator in the winter and back north in the summer. The Los Angeles route is only suitable for summer sailing because of this. During any other time of the year, you must head further south before you start heading for the Hawaiian Islands. 

A general rule of thumb is:

• 20 degrees North during winter
• 30 degrees North during spring
• 35 degrees North during summer

Once you reach your travel latitude, it will take you a few days before you pick up the tradewinds for smooth sailing to Hilo. Just note that the optimal wind zone will remain small and narrow throughout the trip. 

Best Time to Sail to Hawaii

Because of the Pacific High, your best time to sail to Hawaii is in June. Setting out in June lets you take the Los Angeles route in relative comfort while avoiding the hurricane season. After June, you must deal with the hurricanes, while your trip will get cold if you venture out during the winter and spring. 

Just note that you may still deal with the occasional hurricane. Fortunately, hurricanes are easily spotted. So, you should have plenty of time to prepare for them. Pacific hurricanes tend to stay south of 20 degrees North Latitude, far away from the summer Hawaii route. 

Heading Back to the Mainland

After your many adventures around Hawaii, you take a different route back to the mainland. The tropical tradewinds only move west, and you need the jet stream which moves easterly, so you must head north of the Pacific High to reach them. 

Therefore, the only route available to you is to head straight north from Hilo until you pass the High's northern edge. This path should take you to around 47 degrees North, which is the latitude of Seattle. From there, you can turn towards the east and sail until you reach the coast. You can then travel south until you reach your home base. The 2,600-mile trip to Seattle will take you 4 to 5 weeks.

Plan for the Journey

As with any long voyages, you must prepare for your trip before setting sail to or from Hawaii. You are looking at a several-week journey through cold nights, rain, and slow winds. These conditions grow worse as you drift near the Pacific High, but you should get through the worst of it after five days of sailing. 

Once you catch the trade winds, the air gets warmer and dryer, and with winds pick up to something respectable. This part of the journey will take about two weeks, but it should be a pleasant ocean voyage. 

However, you will spend all that time on your own. There will be nothing on the horizon to break the monotony. As such, you need to bring your knowledge of sea sailing, courage to remain focused, a strong stomach, and a plan for anything that might go awry. A part of that planning is establishing a time to sleep and change the sail, as well as fixing any leaks that might spring up. Because of this, you may not want to make the journey alone. 

Sailing among the Hawaiian Islands is a fun way to enjoy the sun and the sights from the Aloha State. However, the waters around these islands can challenge even seasoned sailing veterans. To enjoy your voyages while remaining safe, you must come prepared and understand how the winds and water current flow around the islands. Only then can you sail around the archipelago with your friends.

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Private Sailing Charters, Honolulu, Oahu, Hawaii

Ocean Yacht Adventures Honolulu Oahu

Hawaii Sailing Yacht Rental

Ready for your private Hawaii sailing yacht rental is Kaikiwi, a beautiful 42-ft Beneteau. Kaikiwi is Oahu-based. When sailing in Hawaii, it is important to understand the geography of the islands. Due to the heartbreak that happened on Maui this week, I already have people asking if they should cancel their travel plans. Please don’t. While we reel with the devastation that engulfed Maui, do understand that Oahu is a separate island, 100 miles away. Oahu is physically unaffected by the fires. First the pandemic. Now this. Hawaii needs continued support from those of you who love her, and those who are planning a visit for the first time.

Where do we sail to?

Kaikiwi sails from Oahu’s south (protected) shore, not far from Waikiki. She 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. Please understand this is not “destination” sailing.  “Destination” is sailing.

How can we help Maui?

While my platform is to encourage you to sign up for a private sailing charter, today I want to use it for something way more important.

Fire destroyed Lahaina and ravaged other areas of Maui, and thousands of displaced people there are desperate for your kindness. Please do what you can. Aloha United Way Aloha United Way has set up the Maui Fire Relief Fund, where donations will go directly to Maui United Way to support Maui victims.  American Red Cross of Hawaii The American Red Cross opened five emergency shelters to provide those affected by the Maui wildfires with information, a hot meal, opportunities to charge their phone, pick up relief supplies, and get health services. More information  here .  Council for Native Hawaiian Advancement CNHA is matching up to $250,000 in community donations providing critical assistance to families and businesses in Lahaina.  The Hawaiʻi Community Foundation The Hawai’i Community Foundation’s Maui Strong Fund was created to provide community resilience with resources for disaster preparedness, response, and recovery. The fund is currently supporting communities affected by the wildfires on Maui.  The Lahui Foundation The Lāhui Foundation strives to become a dependable resource for underrepresented and underserved communities here in Hawai’i. They are asking for monetary donations that will go directly to fire recovery efforts for residents of Maui.  Maui Food Bank The Maui Food Bank collaborates with various relief organizations to distribute supplies throughout Maui County.  Maui Mutual Aid Fund The Maui Mutual Aid is a local effort run by volunteers. They are asking for donations to support vulnerable residents, such as the elderly, those with physical disabilities, renters, and individuals without insurance. More information  here .  Maui United Way Maui United Way is accepting donations to its Maui Fire and Disaster Relief fund – all donations will provide direct relief to families and nonprofits directly affected by the Maui Fire Disaster. 

California to Hawaii Yacht Journey: Tips, Stocking & Crew

Are you up for an incredible yacht journey from California to Hawaii? Before you embark on this fantastic adventure, there are some essential factors you need to consider. In this article, we’ll discuss the importance of preparation, crew dynamics, and yacht considerations for a successful trip across the Pacific.

Key Factors for a Successful Yacht Journey from California to Hawaii

When planning your journey, make sure to take into account your yacht’s mileage, gasoline intake, speed, and weather conditions. Storage, supplies, crewmates, and mental/emotional health are also crucial factors to consider. Did you know that a yacht typically needs roughly 2,000 gallons of fuel for this trip? Keep that in mind when planning!

Preparing and Stocking Your Yacht for the Journey

Before setting sail, it’s essential to stock up on all necessary supplies, including food, water, and medical supplies. Don’t forget to ensure that everyone on board is in good physical, mental, and emotional health before embarking on this adventure.

The Importance of Crew Dynamics on a Boat Trip from California to Hawaii

A smooth journey relies heavily on excellent crew dynamics. Start by establishing roles and responsibilities for everyone on board. Assign tasks such as cleaning, managing food and water supplies, serving as a doctor, and acting as a helmsman. A well-organized and efficient crew is vital for a successful trip. Plus, having friends on board can help with communication, rest, and treatment of seasickness, making the journey even more enjoyable!

General Tips for a Successful Boat Journey from California to Hawaii

Here are some general tips to ensure a smooth sailing experience:

• Believe and plan with confidence.
• Take into account your boat’s size and speed.
• Be cautious of weather conditions.
• Consider cruise ship or other alternatives if needed.
• Understand the history of the yacht trip to better prepare.

Overcoming Challenges and Embracing the Adventure of the Yacht Journey

As with any adventure, there are bound to be challenges along the way. Be prepared for potential storms, rogue waves, and wildlife encounters. Additionally, navigation can be tricky, so be cautious of other boats or ships, and ensure you have a plan in case of a lack of wind or fuel shortages. Please read this The Ultimate Guide to a Boat Ride from California to Hawaii for more info.

But most importantly, stay positive and embrace the unique experience of sailing to Hawaii! This journey is one for the books, so enjoy every moment.

Fair winds and following seas, sailors!

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