Overnight & Inter-Island Cruises

Couples and families alike can now inexpensively charter a beautiful yacht and escape the congestion aboard a Private Overnight & Inter-Island Cruise Get away from the noise and fast pace of city life and sail off to a few of Hawaii’s “Quiet Islands.”

Your Captain shares many of the island’s secrets while you enjoy incredible snorkeling/diving, fishing, hiking, scenery, and blue-water sailing. Learn how to sail, explore our outer-islands, or just get off the beaten path and relax, we can accommodate it all! 

  • Oahu Overnight Itinerary
  • Oahu Overnight Charters allow you to escape city life for the tranquil and tropical waters surrounding Hawaii and sail off to the Gathering Place’s more discreet island locations.

    Whether you want an authentic Hawaiian sailing adventure or you want to combine sailing with other excursions, your Captain can make it happen.

    Oahu 2 Days, 2 Nights
    A great way to start or finish a vacation in Hawaii. For those arriving with late flights and a busy schedule.

    First Night: Stay aboard the yacht at Ko’olina resort. This is a beautiful resort on Oahu’s west side. A crewman meets you on board to get settled then leaves you for the night. You can catch the luau at the hotel, fine dining awaits, or if you want something special on the boat just let us know.

    Day 1:West Oahu We get a late start and sail offshore, then tack back in to the lee of the Wainae mountain range at Makaha where we stop for lunch and snorkeling. After lunch, we sail to Pokai bay, our destination for the night.

    Day 2: West Oahu We get a late start and sail close to shore working our way back to Ko’olina resort to disembark. The calm seas and gentle breeze will leave you wondering why you didn’t book a longer charter.

    Oahu Overnight Charter – 3 Days

    Day 1: West and North Shores of Oahu Depart from Ko’olina resort, the newest luxury resort on Oahu’s beautiful west side. Sail in the lee of the Waianae mountain range. We stop for lunch at Yokohama Bay, then head to Haleiwa for the night. Haleiwa is a historical town that blends old Hawaii with new. It has a relaxed country atmosphere, which is very different from the pace of Waikiki.

    Day 2: Waimea Bay We get a late start and set sail down the coast to Waimea Bay. Waimea is a beautiful location that is a sacred place in Hawaiian folklore. Once home to one of Oahu’s largest indigenous populations, today it is the home of the largest wave contest. For obvious reasons we only anchor here in the summer months when the surf is down. Go ashore and explore the sea caves, take in a show at the waterfall, or relax on the beach and watch the sunset.

    Day 3: Return to Ko’olina We get an early start and sail a different tack back around Kaena point and stop for lunch and a swim along the way. This day is a downwind run and you get a chance to sail in the trade winds. The fishing is great off the coast and we try our best to catch a big one. We arrive late in the day back at Ko’olina resort.

    Oahu Overnight Charter – 4 Days (5th Day Option)*

    Day 1: West and North Shores of Oahu Depart from Ko’olina resort, the newest luxury resort on Oahu’s beautiful west side. We sail in the lee of the Waianae mountain range and stop for lunch at Yokohama Bay, then head around Kaena point to Waimea for the night. Waimea is a beautiful location that is a sacred place in Hawaiian folklore. Once home to one of Oahu’s largest indigenous populations, today it is the home of the largest wave contest. For obvious reasons we only anchor here when the surf is down. Go ashore and explore the sea caves, take in a show at the waterfall, or relax on the beach and watch the sunset.

    Day 2: Waimea Bay We get a late start and set sail down the coast to Waimea Bay. Waimea is a beautiful location that is a sacred place in Hawaiian folklore. Once home to one of Oahu’s largest indigenous populations, today it is the home of the largest wave contest. For obvious reasons we only anchor here in the summer months when the surf is down. Go ashore and explore the sea caves, take in a show at the waterfall, or relax on the beach and watch the sunset.

    Day 2: Kaneohe Bay We get an early start and set sail along the north shore for Kaneohe Bay. The island looks decidedly different on this side, much more like French Polynesia with a barrier reef and sharp mountain ridges. Look deep into lush green valleys and try to count the waterfalls. The destination for the day is Kaneohe Bay. A beautiful location, we anchor on an island made entirely of sand that comes and goes with the tide.

    Day 4: Honolulu We get an early start, sail through Kaneohe Bay and back into the Pacific. We sail past numerous small offshore islets teeming with wild tropical seabirds, and an abundance of sea life, whales, dolphins, and turtles. We round Makapu’u point and pick up the trade winds for a fast sail back to Diamond Head and anchor off Waikiki for the night. The city lights are great at night and if we are there on a Friday, there‘s even a fireworks show.

    Day 5: Pearl Harbor We get a late start and sail past Honolulu and down the main channel of Pearl Harbor. It is quite remarkable to sail into this infamous harbor and see the landmarks from history. We stop for lunch before heading back to sea and our destination at Ko’olina.

    *Day 6: Same as above with two days in Kaneohe Bay Spend an extra day to sail and explore this beautiful bay, kayak to Coconut (Gilligan’s) Island, wait for the tide to cover up Sand Island, swim and snorkel, or just relax and enjoy.

  • Maui Inter-Island Itinerary
  • Maui and Lanai Inter-Island and  Overnight Charters allow you to get away from the noise and fast pace of city life and sail off to the Gathering Place’s more discreet island locations.

    Learn how to sail, discover more of the Hawaiian Islands and their secrets, and enjoy an unforgettable overnight sailing adventure with our private inter-island charters.

    Maui & Lanai Inter-Island and Overnight Charter – 4 Days

    Day 1: Day sail to Honolua Bay We board the vessel in Historic Lahaina Harbor, Maui and set sail for Honolua Bay. This first leg is a relaxing sail along Maui’s hotel district, enjoy the views of Molokai, Lanai, and looking back to Maui as we work our way along the coast to our destination. Honolua Bay is world-famous for it’s surfing and is also a fish preserve. It is a perfectly protected anchorage, here you can spend the day swimming with the fish, or take a walk along the top of the cliffs. Honolua is a popular local spot and one of Hawaii’s best.

    Day 2: Sailing to Lanai We get a late start and set sail towards Molokai to pick up the trade winds, then tack and sail downwind to Lanai, where we stop for lunch and a swim along the coast. After lunch, we continue toward Manele Bay, our destination for the night.

    Day 3: Lanai-Manele Bay This is a day ashore. There is a lot to see and explore on Lanai. Starting with the beach, a trip to town, golf, tennis, and then lunch in the mountains. Transportation is readily available via hotel shuttles, there is only one highway on the island and a hotel at each end.

    Day 4: Lahaina Return We get a late start and take a leisurely sail back to Maui. On this leg, we sail towards Kahoolawe, then tack in towards Maui, and make our approach to Lahaina from the South. During whale season, this area is excellent for whale watching as the seas are calm and the winds are light. We arrive in Lahaina in the afternoon to disembark.

    Maui Inter-Island and Overnight Charter – 5 Days

    Day 1: Day sail to Honolua Bay We board the vessel in Historic Lahaina Harbor, Maui and set sail for Honolua Bay. This first leg is a relaxing sail along Maui’s hotel district, enjoy the views of Molokai, Lanai, and looking back to Maui as we work our way along the coast to our destination. Honolua Bay is world-famous for its surfing and is also a fish preserve. It is a perfectly protected anchorage, here you can spend the day swimming with the fish, or take a walk along the top of the cliffs. Honolua is a popular local spot and one of Hawaii’s best.

    Day 2: Offshore Sailing We get a late start and set sail towards Molokai to pick up the trade winds, then tack and sail downwind towards Lanai, then tack again and reach in towards Kaanapali. Kaanapali is the hotel district on Maui and a great place to go ashore for shopping, dinner, head over to Lahaina, or just to hang out on the beach. We stay here for the night so go ahead and explore.

    Day 3: Molokini We get an early start and set sail for Molokini, the small crescent shaped island famous for its clear waters and fantastic snorkeling. Molokini lies between Maui, Kahoolawe, and Lanai. From this anchorage, you get great views of the islands.

    Day 4: Kihei Coast We get a late start and set sail for Maui’s Kihei coast. We drop the anchor early in the day at one of the great beaches along this coast. We stay the night here so go ahead and explore.

    Day 5: Lahaina We get an early start and set sail for Lahaina. This time we sail close to shore and stop for lunch and a swim at a great reef. We arrive in Lahaina in the afternoon to disembark.

    Maui & Lanai Inter-island and Overnight Charter – 5 days

    Day 1: Day sail to Honolua Bay We board the vessel in Historic Lahaina Harbor, Maui and set sail for Honolua Bay. This first leg is a relaxing sail along Maui’s hotel district, enjoy the views of Molokai, Lanai, and looking back to Maui as we work our way along the coast to our destination. Honolua Bay is world-famous for its surfing and is also a fish preserve. It is a perfectly protected anchorage, and here you can spend the day swimming with the fish, or take a walk along the top of the cliffs. Honolua is a popular local spot and one of Hawaii’s best.

    Day 2: Sailing to Lanai We get an early start and set sail towards Molokai to pick up the trade winds, then tack and sail downwind to far tip of Lanai, where we stop for lunch and a swim along the coast at shipwreck beach. After lunch, we continue towards the lee of Lanai. Our destination for the night is a secluded anchorage known as Pinnacles.

    Day 3: Lanai We get an early start and motor along sea cliffs to the site of an ancient Hawaiian fishing village. We stop here for lunch and snorkeling, and to take a short hike to an overlook where you can see ruins and get a great view of the island. After lunch, we head to Manele bay, where we will anchor for the night and head over to the beach to watch the sunset or up to the hotel for all the things someone could want from a 5-star hotel.

    Day 4: Lanai-Manele Bay This is a day ashore. There is a lot to see and explore on Lanai. Starting with the beach, a trip to town, golf, tennis, lunch in the mountains. Transportation is readily available via hotel shuttles, there is only one highway on the island and a hotel at each end.

    Day 5: Lahaina Return We get a late start and take a leisurely sail back to Maui. On this leg, we sail towards Kahoolawe, then tack in towards Maui, and make our approach to Lahaina from the South. During whale season, this area is excellent for whale watching as the seas are calm and the winds are light. We arrive in Lahaina in the afternoon to disembark.

    Maui & Lanai Inter-Island and Overnight Charter – 7 days

    Day 1: Sailing to Molokai Depart from Honolulu for the west end of Molokai. Sail past Waikiki, Diamond Head, and Oahu’s “gold Coast” to Koko Head. From Koko Head to Molokai is the famous Kaiwi channel, the stuff of legend, and the final run in the Transpac yacht race. After a spirited sail to Molokai, we duck behind the lee of the island and sail to our first anchorage, Hale O’ Lono harbor. Lono is far removed from civilization and the stargazing is excellent. This is the dry side of Molokai and we are a long way from the lights of civilization. The stargazing is literally “out of this world.”

    Day 2: Lanai We get an early start and sail to Lanai. This fast morning sail takes us to the lee of the island where we motor along sea cliffs to the site of an ancient Hawaiian fishing village. We stop here for lunch and snorkeling, and take a short hike to an overlook where you can see ruins and get a great view of the island. After lunch, we head to Manele bay, where we anchor for the night and head over to the beach to watch the sunset or up to the hotel for all the things someone could want from a 5-star hotel.

    Day 3: Night crossing to Maui At sunset we depart headed towards Maui for a night crossing by starlight. The channel is beautiful at night, and the light breezes and flat seas make this a great experience. We sail for Kaanapali beach and drop the anchor just off the beach.

    Day 4: Maui Kaanapli is the hotel district on Maui and a great place to go ashore for shopping, dinner, head over to Lahaina, or just to hang out on the beach. We stay here for the night so go ahead and explore.

    Day 5: Sailing to Honolua Bay We’re sailing for a couple of hours to one of the most amazing bays in the world. Honolua is a world-famous for its surfing and is also a fish preserve. It is a perfectly protected anchorage and it is our destination for day 6. Here, you can spend the day swimming with the fish, or take a walk along the top of the cliffs. Honolua is a popular local spot and one of Hawaii’s best.

    Day 6: Sailing to Molokai We get an early start and set sail for a down wind run to the western tip of Molokai back to Lono harbor.

    Day 7: Sailing to Oahu This is a great day’s run that is on a fast tack across Hawaii’s best fishing grounds. You see the island of Oahu appear from the sea mist, and try to guess which geographical feature becomes Diamond Head. We sail past Cocoa head, past Hawaii’s Gold Coast, and right under Diamond Head to Waikiki. Stop for a quick swim, a chance to collect your thoughts and things, then pull into Honolulu Harbor to disembark.

  • Lanai Inter-Island Itinerary
  • Maui and Lanai Inter-Island and  Overnight Charters lure you out to sea to experience Hawaii in a new way! For an intimate escape and exciting sailing adventure, book your Maui inter-island charter now!

    Learn how to sail, enjoy incredible snorkeling, diving, and wildlife watching as you sail past the beautiful Hawaiian Islands.

    Maui & Lanai Inter-Island and Overnight Charter – 4 Days

    Day 1: Day sail to Honolua Bay We board the vessel in Historic Lahaina Harbor, Maui and set sail for Honolua Bay. This first leg is a relaxing sail along Maui’s hotel district, enjoy the views of Molokai, Lanai, and looking back to Maui as we work our way along the coast to our destination. Honolua Bay is world-famous for its surfing and is also a fish preserve. It is a perfectly protected anchorage, here you can spend the day swimming with the fish, or take a walk along the top of the cliffs. Honolua is a popular local spot and one of Hawaii’s best.

    Day 2: Sailing to Lanai We get a late start and set sail towards Molokai to pick up the trade winds, then tack and sail downwind to Lanai, where we stop for lunch and a swim along the coast. After lunch, we continue towards Manele Bay, our destination for the night.

    Day 3: Lanai-Manele Bay This is a day ashore. There is a lot to see and explore on Lanai. Starting with the beach, you can add a trip to town, golf, tennis, or lunch in the mountains. Transportation is readily available via hotel shuttles, there is only one highway on the island and a hotel at each end.

    Day 4: Lahaina Return We get a late start and take a leisurely sail back to Maui. On this leg, we sail towards Kahoolawe, then tack in towards Maui, and make our approach to Lahaina from the South. During whale season, this area is excellent for whale watching as the seas are calm and the winds are light. We arrive in Lahaina in the afternoon to disembark.

    Maui Inter-Island and Overnight Charter – 5 Days

    Day 1: Day sail to Honolua Bay We board the vessel in Historic Lahaina Harbor, Maui and set sail for Honolua Bay. This first leg is a relaxing sail along Maui’s hotel district, enjoy the views of Molokai, Lanai, and looking back to Maui as we work our way along the coast to our destination. Honolua Bay is world-famous for its surfing and is also a fish preserve. It is a perfectly protected anchorage, here you can spend the day swimming with the fish, or take a walk along the top of the cliffs. Honolua is a popular local spot and one of Hawaii’s best.

    Day 2: Offshore Sailing We get a late start and set sail towards Molokai to pick up the trade winds, then tack and sail downwind towards Lanai, then tack again and reach in towards Kaanapali. Kaanapali is the hotel district on Maui and a great place to go ashore for shopping, dinner, head over to Lahaina, or just to hang out on the beach. We stay here for the night so go ahead and explore.

    Day 3: Molokini We get an early start and set sail for Molokini, the small crescent shaped island famous for its clear waters and fantastic snorkeling. Molokini lies between Maui, Kahoolawe, and Lanai. From this anchorage, you get great views of the islands.

    Day 4: Kihei Coast We get a late start and set sail for Maui’s Kihei coast. We drop the anchor early in the day at one of the great beaches along this coast. We stay the night here so go ahead and explore.

    Day 5: Lahaina We get an early start and set sail for Lahaina. This time we sail close to shore and stop for lunch and a swim at a great reef. We arrive in Lahaina in the afternoon to disembark.

    Maui & Lanai Inter-island and Overnight Charter – 5 days

    Day 1: Day sail to Honolua Bay We board the vessel in Historic Lahaina Harbor, Maui and set sail for Honolua Bay. This first leg is a relaxing sail along Maui’s hotel district, enjoy the views of Molokai, Lanai, and looking back to Maui as we work our way along the coast to our destination. Honolua Bay is world-famous for its surfing and is also a fish preserve. It is a perfectly protected anchorage, here you can spend the day swimming with the fish, or take a walk along the top of the cliffs. Honolua is a popular local spot and one of Hawaii’s best.

    Day 2: Sailing to Lanai We get an early start and set sail towards Molokai to pick up the trade winds, then tack and sail downwind to far tip of Lanai, where we stop for lunch and a swim along the coast at shipwreck beach. After lunch, we continue towards the lee of Lanai. Our destination for the night is a secluded anchorage known as Pinnacles.

    Day 3: Lanai We get an early start and motor along sea cliffs to the site of an ancient Hawaiian fishing village. We stop here for lunch and snorkeling, and a short hike to an overlook where you can see ruins and get a great view of the island. After lunch, we head to Manele bay, where we anchor for the night and head over to the beach to watch the sunset or up to the hotel for all the things someone could want from a 5-star hotel.

    Day 4: Lanai-Manele Bay This is a day ashore. There is a lot to see and explore on Lanai. Starting with the beach, add a trip to town, golf, tennis, or lunch in the mountains. Transportation is readily available via hotel shuttles, there is only one highway on the island and a hotel at each end.

    Day 5: Lahaina Return We get a late start and take a leisurely sail back to Maui. On this leg, we sail towards Kahoolawe, then tack in towards Maui, and make our approach to Lahaina from the South. During whale season, this area is excellent for whale watching as the seas are calm and the winds are light. We arrive in Lahaina in the afternoon to disembark.

    Maui & Lanai Inter-Island and Overnight Charter – 7 days

    Day 1: Sailing to Molokai Depart from Honolulu for the west end of Molokai. Sail past Waikiki, Diamond Head, and Oahu’s “gold Coast” to Koko Head. From Koko Head to Molokai is the famous Kaiwi channel, the stuff of legend, and the final run in the Transpac yacht race. After a spirited sail to Molokai, we duck behind the lee of the island and sail to our first anchorage, Hale O’ Lono harbor. Lono is far removed from civilization and the stargazing is excellent. This is the dry side of Molokai and we are a long way from the lights of civilization. The stargazing is literally “out of this world.”

    Day 2: Lanai We get an early start and sail to Lanai. This fast morning sail takes us to the lee of the island where we motor along sea cliffs to the site of an ancient Hawaiian fishing village. We stop here for lunch and snorkeling, and just a short hike to an overlook is where you can see ruins and get a great view of the island. After lunch, we head to Manele bay, where we anchor for the night and head over to the beach to watch the sunset or up to the hotel for all the things someone could want from a 5-star hotel.

    Day 3: Night crossing to Maui At sunset, we depart headed towards Maui for a night crossing by starlight. The channel is beautiful at night, and the light breezes and flat seas make this a great experience. We sail for Kaanapali beach and drop the anchor just off the beach.

    Day 4: Maui Kaanapli is the hotel district on Maui and a great place to go ashore for shopping, dinner, head over to Lahaina, or just to hang out on the beach. We stay here for the night so go ahead and explore.

    Day 5: Sailing to Honolua Bay We are sailing for a couple of hours to one of the most amazing bays in the world. Honolua is a world-famous for its surfing and is also a fish preserve. It is a perfectly protected anchorage and it is our destination for day 6. Here, you can spend the day swimming with the fish or take a walk along the top of the cliffs. Honolua is a popular local spot and one of Hawaii’s best.

    Day 6: Sailing to Molokai We get an early start and set sail for a down wind run to the western tip of Molokai back to Lono harbor.

    Day 7: Sailing to Oahu This is a great day’s run that is on a fast tack across Hawaii’s best fishing grounds. See the island of Oahu appear from the sea mist, and try to guess which geographical feature becomes Diamond Head. We sail past Cocoa head, past Hawaii’s Gold Coast and right under Diamond Head to Waikiki. Stop for a quick swim, a chance to collect your thoughts and things, then pull into Honolulu Harbor to disembark.

  • Kauai Inter-Island Itinerary
  • Kauai Inter-Island and Overnight Charters adds an unforgettable adventure to your Hawaiian vacation.

    View the dramatic and diverse scenery of the Emerald Isle as you learn how to sail, get out in the water for some world-class snorkeling or diving, or as you relax with a tropical drink in your hand on your private charter.

    Kauai Itinerary for Inter-Island Sail from Oahu to Kauai:

    Day 1: Sailing by the stars

    Depart from Honolulu in the afternoon and sail by the setting sun towards the western tip of Oahu in the lee of the Waianae mountain range. Sail past Pearl Harbor, Makaha, and the beautiful west side of the island, while enjoying a light dinner on the way to Kaena Point. Once past Kaena Point the channel opens up to Kaui and get ready for 60 miles of downwind sailing by the stars (it doesn’t get much better than this). By morning, the approach is made to Kauai and before noon of Day 2, the hook is in the sand at Hanalei Bay.

    Day 2 & 3: Hanalei Bay

    There is so much to explore on this part of Kauai, and Hanalei Bay is so amazing we spend two nights here before exploring the NaPali Coast.

    Day 4: NaPali Coast

    Off to an early start, we sail downwind, close to the legendary sea cliffs of the NaPali coast to really get a feel for the geography and the height of these 3,500 ft. sea cliffs, the tallest in the world, then tack out to sea for perspective, then back in close for a lunch stop and swim ashore at Kalalau beach, complete with a waterfall and valley (yes, it really is all in the same place and yes, it is paradise). From Kalalau, we sail to a protected anchorage just down the coast, the site of an ancient Hawaiian fishing village, and our stop for the night.

    Day 5: Day sail to Waimea*

    A late start to this day, we sail past the remaining sea cliffs and around to the west side of Kauai. The winds are light, and the ocean is calm. This is the dry side of the island and it’s time for serious sunbathing and swimming. We stop for lunch and snorkeling at Waimea Canyon (where Capt. Cook made his first Hawaiian landing) before heading to Port Allen Harbor for the night.

    Day 6: Waimea Canyon*

    This is a day ashore, and Waimea canyon is the grand canyon of the Pacific region and a sight to behold. You will want to see this area of Kauai and hike out to the overlooks above the NaPali Coast.

    Day 7: Day sail to Lihue

    Sailing to Nawilili Harbor, Lihue Kaui. Congratulations, you’ve circumnavigated Kauai. Go ashore here for shopping, dining, or whatever you wish to do.

    Day 8: Oahu Return

    An early start and back to Oahu we go. This is a bit more rigorous a sail since it is upwind, enjoyable yes, but we won’t be offended if you opt to take Hawaiian Air back to Oahu.

    *Day 5 & 6 Option: Niihau

    Sail to Niihau Island and anchor for the night. Depart Niihau and sail to Port Allen Harbor. –note of caution– You can’t go ashore on Niihau as it is a private and protected Hawaiian culture reserve. There is not much to see or do here and it requires a lot of sailing to go and come back.

  • Molokai Inter-Island Itinerary
  • Molokai Inter-Island and Overnight Charters provides serenity at sea as you explore Molokai aboard your own private charter.

    Whether you simply want to relax as you set sail for Molokai or you want to fill your days at sea with exceptional outdoor activities, we can accommodate your every wish.

    Molokai Itinerary for Inter-Island Sail from Oahu to Molokai:

    Day 1: Sailing to Molokai

    Depart from Honolulu for the west end of Molokai. Sail past Waikiki, Diamond Head and Oahu’s “gold Coast” to Koko Head. From Koko Head to Molokai is the famous Kaiwi channel, the stuff of legend, and the final run in the Transpac yacht race. After a spirited sail to Molokai, we duck behind the lee of the island and sail to our first anchorage, Hale O’ Lono harbor. Lono is far removed from civilization and the stargazing is excellent.

    Day 2: Sailing to Kaunakakai

    We get a late start and head up the coast between Molokai and Lanai headed for Kaunakakai, the main city on Molokai. We anchor here for the night and head to town for dinner.

    Day 3: Halawa Valley

    This is a day ashore. Molokai is a spectacular Island that remains today much as it was before people arrived. We suggest renting a car and driving to Halawa Valley and hiking back to the incredible waterfall there. Also, you won’t want to miss the overlooks to Kalaupapa and the other fascinating discoveries you make along the way.

    Day 4: Sailing to Honolua Bay

    We’re sailing between Molokai, Lanai and Maui to one of the most amazing bays in the world. Honolua is a world-famous for its surfing and is also a fish preserve. It is a perfectly protected anchorage and it is our destination for day 4.

    Day 5: North Shore of Molokai, leg one

    Depart early from Honolua bay and sail on a fast downwind run to the North coast of Molokai. Primal is how most people describe this coast, it is like stepping back in time, and the area has an awesome presence about it. We sail past Halawa valley so you can get a sea-view of the waterfall, past many other falls, and valleys. The north shore of Molokai was revered by the Hawaiian people as a magical place, when you see it, you’ll understand. Our destination for the night lies just behind a small island at the mouth of a large and uninhabited valley, we sail right between them and into a protected anchorage near Kalaupapa, you can see the original church and buildings built by Father Damien to care for the afflicted who were once marooned on these shores.

    Day 6: North Shore of Molokai, leg two

    We get a late start, and set sail around Kalaupapa, headed for the western tip of Molokai. We sail past the remaining cliffs of this coast on a fast downwind run to Ilio Point. Once around the point we tuck in close to shore and enjoy sailing in the lee of the island to our next anchorage, just off a sandy beach. From here you can see Oahu silhouetted in the setting sun, the destination for tomorrow.

    Day 7: Sailing to Oahu

    This is a great days run that is on a fast tack across Hawaii’s best fishing grounds. You see the island of Oahu appear from the sea mist, and try to guess which geographical feature becomes Diamond Head. We sail past Koko head, past Hawaii’s Gold Coast and right under Diamond Head to Waikiki. Stop for a quick swim, a chance to collect your thoughts and things, then pull into Honolulu Harbor to disembark.

  • Big Island Inter-Island Itinerary
  • Big Island Inter-Island and Overnight Charters allow you to experience more of the Big Island with an exclusive sailing charter.

    Learn all the secrets of the Hawaiian Islands as your expert Captain teaches you how to sail our vibrant blue waters. Enjoy incredible snorkeling, hiking, and other excursions while you’re anchored off the magical Big Island.

    Big Island Itinerary for Inter-Island Sail from Oahu to the Big Island:

    Day 1 & 2: Sailing

    Depart Oahu in early evening for Hawaii sailing past Lanai and Kahoolawe by morning and continuing to Kona, Hawaii arriving in the afternoon.

    Day 3: Kona Coast

    After having a chance to explore the city of Kona, we head toward Captain Cook, a beautiful bay where we anchor and stay the night.

    Day 4: Kona Coast

    After breakfast we sail along the coast gunk holing. Stopping for lunch and swimming at one of many fabulous spots. By nightfall, we’re back in Kona and you can book a luau at the hotel on shore.

    Day 5: Volcano National Park

    A day ashore to explore the active volcanoes and unique ecosystem of the Kohala coast. Rental cars are available locally and the park and lava show is just two hours away.

    Day 6: Sailing to Mauna Lani Beach

    Mauna Lani Beach is generally included in every the “best beaches of the world” publication. It is our destination for the evening. A small crescent shaped beach with a protected anchorage and unforgettable sunset.

    Day 7: Sailing to Maui

    Get an early start and we’re headed to Maui. On this leg, we sail past the wild side of Maui, past Haleakela, and make our landfall by the setting sun in Lahaina. We arrive ready for dinner and head to town.

    Day 8: Maui

    Take the morning to see the sights in Lahaina, a latte, a little shopping… Then we move the boat two miles down the coast to the hotel district and meet you there for lunch. Spend the day at the beach, swimming, snorkeling, and discovering all the clever creations of talented bartenders…

    Day 9: Sail to Molokai

    We get a late start and set sail for a down wind run to the eastern tip of Molokai where we stop for the night in a small deserted harbor. This is the dry side of Molokai and we are a long way from the lights of civilization. The star gazing is literally “out of this world.”

    Day 10: Sail to Oahu

    This is a great days run that is on a fast tack across Hawaii’s best fishing grounds. You see the island of Oahu appear from the sea mist, and try to guess which geographical feature becomes Diamond Head. We sail past Koko head, past Hawaii’s Gold Coast and right under Diamond Head to Waikiki. Stop for a quick swim, a chance to collect your thoughts and things, then pull into Honolulu Harbor to disembark.

 

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