Overnight Multi-Island Hawaii Charter

Hawaii Island Hopping

Amazing 7 day trip visiting the best islands in Hawaii

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Experience the Hawaiian Islands for 7 days and 6 nights sailing in the open sea. You can leave both from Maui or Oahu and return back to port of departure. The islands you will see include Oahu, Maui, Molokai, Lanai and Big Island.


A suggested daily itinerary could be the following (itineraries are fully customisable in collaboration with our staff): 


Activities on water and land:

On board we have many toys for the fun activities on the water, it may include snorkeling, swimming, surfing, skurfing (surfboard pulled by dingy), Snuba, paddle boarding, fishing. All activities are performed at locations that are hidden gems along the coast and away from the crowds. We have fishing equipment on board for those who want to go fishing.


There are different spots where you can watch dolphins, turtles and whales (whale season goes from October through April).



We anchor at Lahaina, a historic whaling village filled with fun souvenir shopping, classy art galleries, great seafood restaurants and cold beers at the historic Pioneer Inn. The Hawaiian Islands Humpback Whale National Marine Sanctuary is also located here. We also sail to Honolua Bay on Maui's northwest coast for some more great water activities. 



We anchor at two locations, Nahahoa Bay and Menele Bay. Nahahoa Bay is on the remote backside of Lanai, where Hawaii's "Five Needles" are located. This area has incredible snorkeling spots and is a great place to have some fun with our available water toys. A short sail away is Menele Bay, a beautiful beach where the famous Four Season's 5-star resort is located. We dock close enough to the resort where we can usher you in on our dinghy to shore so you can treat yourself to the spa at the Four Seasons or have a nice Mai Tai at the Piano Bar. We will dock overnight and you will wake up in the morning to the splash of Hawaiian spinner dolphins returning to the bay after night locking for food.



Overnight stay at Hale o Lono...a quite non- descript anchorage but a walk ashore will find you on your own beautiful, private beach. Other highlights of Molokai include Kaunakakai: the island's only town. Kalaupapa Penisula, Papohaku Beach, and of course the North shore Molokai which boasts some of the largest sea cliffs in the world that rise 3000 ft above sea level...awesome!


"The Big Island" Hawaii Island:

The Big Island is the largest island in the Hawaiian Archipelago. Its diverse terrain spans colored-sand beaches at Papakolea (green) and Punalu’u (black)

to lush rainforest. Within Volcanoes National Park, there are 2 active volcanoes, Kilauea and Mauna Loa. Hapuna Beach and Kahalu'u Beach Park in the west are popular snorkeling sites. Big Island trips are limited due to seasonality, but when we do sail Big Island, we cruise along the Kohala Coast.



The island of Oahu is known as “The Gathering Place” and is home to the largest population and the best nightlife in Hawaii. Highlights in Oahu are the North Shore, Ko'Olina (next to Disney resort), Polkai Bay, Haliewa Bay, Waimea Bay, and Kaneohe Bay which is home to the only barrier reef in the Hawaiian Islands. Waking up in Kaneohe Bay will give you an incredible view of the Kualoa Mountain range, a dramatic landscape where movies such as Jurassic Park, Pirates of the Caribbean and Jumanji were filmed. Or you can dine on your private yacht and watch the sunset over Diamond Head or try some of the finest restaurant in the world ashore.

All islands are unique in their beauty and offer so many sights on land. We are happy to explore with you the islands and offer a guided tour.



In the morning, enjoy an amazing catered breakfast with local fruit and coffee especially prepared for you by your personal chef. At lunchtime you can relax on board and enjoy the tasty catered lunch or take lunch on land. At night we anchor close to shore a serve delicious dinner at a beautiful location with a Hawaiian sunset. Post dinner options could either be karaoke, movies, and or board games. The option to venture to land for some local exploring or nightlife is also a possibility.




From $ 23'219

6 7 Days
Island Trip in Hawaii
Available with 2 yachts
Fishing Gear
Interested to know more or to book?

Yacht options

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