Oahu Sailing Trips

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun....

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (3)
from
$1,199
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
Likely to Sell Out
Likely to Sell Out

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (2)
from
$1,200
Private South Shore Sail Charter

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze,...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (2)
from
$1,000
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 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
5.0 (1)
from
$1,595
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and...

2 to 3 hoursHotel pickup offeredFree Cancellation
2 to 3 hoursHotel pickup offeredFree Cancellation
2 to 3 hours • Hotel pickup offered • Free Cancellation
4.7 (2,096)
from
$84.15
Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (1,265)
from
$53.31
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
4.7 (242)
from
$79
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutesHotel pickup offeredFree Cancellation
5 hours 30 minutesHotel pickup offeredFree Cancellation
5 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (67)
from
$196.63
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
4.6 (41)
from
$93.46
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Likely to Sell Out
Likely to Sell Out

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.5 (37)
from
$101.96
Waikiki Friday Night Fireworks Cruise

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring...

1 hourFree Cancellation
1 hourFree Cancellation
1 hour • Free Cancellation
4.7 (29)
from
$60
Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.6 (9)
from
$85.09
Private Whale Watching Sailing Adventure

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)
from
$695
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
from
$1,995
Private Morning Ceremony Sailing Charter

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
from
$1,000

Frequently Asked Questions

These answers are based on answers previously given to Cool Hawaii customers' questions.

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Cool Hawaii wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Hawaii over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.