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 having 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’ 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, 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’ll 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*

Is a day ashore, 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, restaurants, etc.

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.