Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Honolulu…
    3. /Water Activities
    4. /Sailing
    5. /Sail Waikiki to Diamond Head on a 1.5-Hour Cruise
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Product image 8
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Sail Waikiki to Diamond Head on a 1.5-Hour Cruise

    Sail Waikiki’s south shore with Diamond Head views and beach boarding

    4.9 stars• 917 reviews

    Duration

    1.5 hours

    Includes

    Catamaran sail, Drinks included

    Highlights

    Ride the trade winds on a 1.5-hour afternoon sail along Oahu’s south shore. Board directly from the beach and take in coastal landmarks as you cruise toward Diamond Head.

    • Board directly from the beach near Waikiki
    • Sail toward Diamond Head Lighthouse for sweeping coastline views
    • Pass the Waikiki Natatorium War Memorial from the water
    • Relax on a custom beach catamaran with spacious seating
    • Enjoy time on the netted splash area over the water

    What's Included

    • Beer
    • Wine
    • House cocktail
    • Non-alcoholic beverages

    Things to know

    Guests under 18 must be accompanied by an adult. Bring ID to enjoy alcoholic beverages. Boarding requires climbing eight steps and walking on loose sand, so it may not suit those with heavily impaired mobility.

    Cancellation Policy

    Bookings made within 24 hours of the sail are not eligible for a refund or rebook. Parties of 8 or less: cancel 24 hours prior for a full refund or rebooking. Parties of 9 or more: 48-hour policy. No show/no call is non-refundable. Full refund or option to book another day if Holokai cancels due to weather.

    Product ID: 4QYMAG

    FAQs

    Expect beach boarding with a short walk (up to 0.2 miles), climbing eight steps at the front of the boat, and walking on loose sand.

    This sail may not suit those with heavily impaired mobility, since boarding requires climbing eight steps and walking on loose sand.

    Bring an ID if you want to enjoy alcoholic beverages. Guests under 18 must be accompanied by an adult.

    Meeting details

    2169 Kalia Rd Honolulu, HI US

    Experience provided by Holokai Catamaran

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    General

    $56.86

    (13 and older)

    0

    Keiki

    $33.51

    (4 - 12 years old)

    0

    Kama'aina

    $56.86

    $10 discount available at check-in with proof of I.D.

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    917 reviews•Google Maps
    753
    31
    10
    0
    13

    The crew consistently stands out here as genuinely friendly, professional, and fun. Captain Ryan, Cole, and Kevin get specific shoutouts for making trips memorable with their relaxed, hilarious energy. People love the open bar with good drink selections, the clean and newer boat, and the chill music vibe. The sunset and Friday fireworks cruises are particular favorites, with many saying the 1.5-hour duration feels just right. One honest note: Turtle Canyon can get crowded with multiple tour boats sharing the same snorkeling spot, which some found chaotic rather than peaceful. If you've done catamaran tours in quieter locations, this may feel more mass-tourism oriented. That said, guests still spot plenty of turtles (up to seven at once), dolphins, and colorful fish. A few mention rougher waters on the way out, so seasickness-prone visitors might want to take precautions. Overall, this is a solid, well-run operation with a crew that genuinely makes the experience special.

    What people are saying

    Review 1 of 5
    5/5

    Snorkel cruise to Turtle Canyon was epic! Crew was friendly and helpful. And their signature punch was so tasty! Would definitely book with this company again.

    Photo of Erica Danielle

    Erica Danielle

    September 1, 2026

    Review 1 of 1
    5/5

    Snorkel cruise to Turtle Canyon was epic! Crew was friendly and helpful. And their signature punch was so tasty! Would definitely book with this company again.

    Photo of Erica Danielle

    Erica Danielle

    September 1, 2026

    Nearby activities

    Turtle Canyon Snorkel Sail From Waikiki Beach
    Snorkeling

    Turtle Canyon Snorkel Sail From Waikiki Beach

    Snorkel Turtle Canyon on a beach-boarding Waikiki catamaran sail

    Snorkel Turtle Canyon on a beach-boarding Waikiki catamaran sail
    4.9 • 917 reviews
    $537& up
    Watch Friday Night Fireworks on a Honolulu Sail
    Sailing

    Watch Friday Night Fireworks on a Honolulu Sail

    Sail Friday night and watch Honolulu fireworks from the water

    Sail Friday night and watch Honolulu fireworks from the water
    4.9 • 917 reviews
    $431& up
    Private Turtle Canyon Snorkel Cruise From Waikiki
    Snorkeling

    Private Turtle Canyon Snorkel Cruise From Waikiki

    Snorkel Turtle Canyon and sail Waikiki’s coastline on your private catamaran

    Snorkel Turtle Canyon and sail Waikiki’s coastline on your private catamaran
    4.9 • 917 reviews
    $3,419
    Waikiki Sunset Gondola Cruise
    Boat Tours

    Waikiki Sunset Gondola Cruise

    Drift through Waikiki Harbor with Diamond Head views, desserts, and sparkling cider

    Drift through Waikiki Harbor with Diamond Head views, desserts, and sparkling cider
    5.0 • 235 reviews
    $86& up
    Waikiki 45-Minute Daytime Gondola Cruise
    Boat Tours

    Waikiki 45-Minute Daytime Gondola Cruise

    Glide through Waikiki Harbor with canal views, cider, desserts, and a gondolier

    Glide through Waikiki Harbor with canal views, cider, desserts, and a gondolier
    5.0 • 235 reviews
    $73/ person
    Waikiki Fire-Knife Dancing Luau
    Dance Performances

    Waikiki Fire-Knife Dancing Luau

    A Hawaiian feast and Polynesian dance show from middle-section seating

    A Hawaiian feast and Polynesian dance show from middle-section seating
    4.6 • 4.4K reviews
    $164/ person