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ExtremeBoat trips & cruises30 booked in the last 90 days

Molokai Channel Crossing

Twenty-six miles of open ocean downwind. For paddlers who know what that means.

From

$495

4.9(87 reviews)7hUp to 12 guestsEnglish, Spanish, JapaneseFree cancellation · 168h

About this experience

The Kaiwi Channel is the proving ground of Pacific paddling — twenty-six miles of deep, moving water, and we run an escorted crossing for experienced paddlers in a supported fleet. Escort boat, two safety crew, water and nutrition on the hour, and a captain who has made the crossing forty-one times. Applications are reviewed; this is not a beginner trip.

  • Escorted twenty-six mile downwind channel crossing
  • Captain with forty-one Kaiwi crossings
  • Full safety escort, radio and medical kit aboard
  • Six paddlers maximum per escort vessel

Extreme. Serious commitment. Prior experience is assessed before you book. Minimum age 18.

What's included

  • Escort vessel, captain and two safety crew
  • Nutrition, electrolytes and water on the hour
  • Pre-crossing weather and route briefing
  • Return transport to Maui

Not included: Your board or ski · Flights to the start · Insurance

What to bring

  • Swimwear worn under your clothes
  • Reef-safe sunscreen (we sell it at the dock if you forget)
  • A towel and a dry change of clothes
  • Sunglasses with a retainer strap
  • A light windbreaker for the ride home

Requirements

  • Documented open-ocean downwind experience
  • Ages 18 and over
  • Application reviewed by the captain before confirmation

Not sure whether this suits your group? Call +1 (808) 555-0164 and one of the team will tell you honestly.

Meeting point

Meet here · Maui, HI
Illustrative map

Kaunakakai Wharf, Molokai — 05:00 briefing, on the water by 05:45.

101 Maalaea Boat Harbor Rd, Wailuku, HI 96793

Get directions

Cancellation policy

Free cancellation up to 7 days before

Full refund if you cancel at least 7 days before the start. After that, 50% is refunded. The deposit is not refunded.

  • Move to another time for free, once, until 14 days before the start.
  • Book with a 50% deposit; the rest is charged 30 days before.

If we cancel for weather or sea state, you choose a full refund or a free reschedule.

Guest reviews

4.9

87 verified reviews

5
100%
4
0%
3
0%
2
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1
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Ingrid S.

US · Family · 3 guests

August 2026
“Worth every cent. We rebooked for the day before we fly home.”
Leila H.

JP · Couple · 2 guests

August 2026
“Genuinely flawless from check-in to the last drink. Book it.”
Antoine S.

DE · Solo traveller

July 2026
“Worth every cent. We rebooked for the day before we fly home.”

$495per person

Next departure Sat 5:30 AM · 3 seats

Molokai Channel Crossing | Blue Horizon Watersports