Top Oahu Sailing Trips

Private Whale Watching Sailing Adventure
Special Offer
Special Offer

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
3.5 (2)
$695
$694

Private Morning Ceremony Sailing Charter
Likely to Sell Out
Likely to Sell Out

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
$1,000
$999

3 Hour Luxury Private Sailing Catamaran for 7-12 People
Likely to Sell Out
Likely to Sell Out

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
$1,995
$1,994

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