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All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

Page 1 of 233 listings

Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling
Sailing in Honolulu · 6 guests

Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

5.0
Best of 2025
$180/hour
 A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!
Sailing in Honolulu · 12 guests

A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!

5.0
Superowner
$185/hour
Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!
Tours in Honolulu · 6 guests

Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!

4.9
Superowner
$185/hour
Instant Book
40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu
Sailing in Honolulu · 12 guests

40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu

4.8
Superowner
$185/hour
Private sail on Luxury 43' Yacht! Best of GetMyBoat 2021, 2022, and 2023! 🥇
Sailing in Honolulu · 12 guests

Private sail on Luxury 43' Yacht! Best of GetMyBoat 2021, 2022, and 2023! 🥇

4.9
Superowner
$185/hour
Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii
Sailing in Honolulu · 15 guests

Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

5.0
Superowner
Best of 2025
$400/hour
Sailing and Snorkeling Adventures on Maui on 27 Foot HunterX Monohull
Sailing in Maalaea · 6 guests

Sailing and Snorkeling Adventures on Maui on 27 Foot HunterX Monohull

5.0
Superowner
$475/hour
The best sunset sail! Very private! Best of GetMyBoat 2021, 2022 and 2023! 🥇
Sailing in Honolulu · 12 guests

The best sunset sail! Very private! Best of GetMyBoat 2021, 2022 and 2023! 🥇

4.4
Superowner
$185/hour
Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii
Sailing in Honolulu · 30 guests

Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii

5.0
$650/hour
42 ft Beneteau, located in Kewalo Basin, 2 miles from Waikiki.
Sailing in Honolulu · 6 guests

42 ft Beneteau, located in Kewalo Basin, 2 miles from Waikiki.

5.0
$235/hour
ONE OF A KIND, exhilarating trimaran sailing and swimming experience in Waikiki
Sailing in Honolulu · 6 guests

ONE OF A KIND, exhilarating trimaran sailing and swimming experience in Waikiki

4.9
$250/hour
43' Jeanneau Cruising Monohull Charter in Honolulu
Sailing in Honolulu · 6 guests

43' Jeanneau Cruising Monohull Charter in Honolulu

5.0
$165/hour
Scape 40' Sailing Catamaran Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$500+/hour
BYOB Private Waikīkī Catamaran Charters
Sailing in Honolulu · 35 guests

BYOB Private Waikīkī Catamaran Charters

5.0
$600+/hour
41ft Smooth Sailing Trimaran Charters & Adventures Oahu's North Shore, Haleiwa
Sailing in Haleiwa · 6 guests

41ft Smooth Sailing Trimaran Charters & Adventures Oahu's North Shore, Haleiwa

5.0
$250+/hour
Sunset Sails💥$295💥
Sailing in Honolulu · 6 guests

Sunset Sails💥$295💥

New
$165/hour
46ft Luxe Private Sailing Catamaran Charter in Ko Olina, Hawaii
Sailing in Kapolei · 6 guests

46ft Luxe Private Sailing Catamaran Charter in Ko Olina, Hawaii

5.0
$700/hour
Stunning Beneteau 42 Experience in Honolulu, Oahu
Sailing in Honolulu · 6 guests

Stunning Beneteau 42 Experience in Honolulu, Oahu

4.0
$1,550/day
Waikīkī’s Premier Catamaran Experience
Sailing in Honolulu · 12 guests

Waikīkī’s Premier Catamaran Experience

New
$350+/hour
50ft Hans Christian Yacht
Sailing in Lahaina · 6 guests

50ft Hans Christian Yacht

New
$150/hour
Maui, private 49 tour, snorkel, whale watch catamaran
Events in Kula · 49 guests

Maui, private 49 tour, snorkel, whale watch catamaran

New
$1,950/hour
Sunreef 62 catamaran
Sailing in Maalaea · 12 guests

Sunreef 62 catamaran

New
$1,200/hour
Scandinavian Quality Sailboat | Nautor Swan Gecco 39 Yacht
Sailing in Honolulu · 6 guests

Scandinavian Quality Sailboat | Nautor Swan Gecco 39 Yacht

New
$1,800/day
Fountaine Pajot Helia 44 Cruising Catamaran
Sailing in Honolulu · 6 guests

Fountaine Pajot Helia 44 Cruising Catamaran

New
$900/hour

Sailing Reviews in Hawaii

  1. Rob

    Rob

    Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

    Excellent experience for our whole family. Would definitely recommend. Tony was fun and helpful. It was the first time for many of us and Tony did an excellent job of making our family feel welcome. We had an amazing time sailing, snorkeling, and sunbathing. Four hours just flew by!

  2. CJ

    Casey

    Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!

    We booked Captain Rob's sunset sail so that we could watch the fireworks from the ocean and it was such an amazing experience! Captain Rob and his crew were extremely helpful, kind, and made us all feel welcome from the second we stepped onto the boat. Would 10000% recommend this trip to anyone thinking about booking -- it was one of our favorite things we did during our visit!

  3. MB

    Megan

    Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

    Tony and his boat were wonderful. We had three kids who love to swim and they got their fill. We saw lots of fish and two turtles, the kids got to jump and dive their hearts out. Tony was very knowledgeable and kept us safe, we all had lots of fun.

  4. JD

    Judy

    Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

    The crew too care of all of our needs. They serve us, something we were not expecting. This excursion was 10 out 10. Thanks for making my mom’s 80th birthday celebration special.

  5. BS

    Beverly

    Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

    ⭐⭐⭐⭐⭐ Unforgettable Day on the Water with Captain Tony! Captain Tony delivered an absolutely perfect charter experience on his stunning 45ft yacht! From the moment we stepped aboard, his professionalism and warm hospitality made us feel like VIPs. The vessel was immaculate – spacious, well-maintained, and equipped with everything we needed for an incredible day. Our 3-hour late morning snorkel charter along the Waikiki and Diamond Head coastline was absolutely magical. Tony knew exactly where to find the best coral reefs and clearest water. The snorkeling was incredible. The views of Diamond Head from the water were breathtaking. Perfect 3-hour adventure that we’ll never forget. Highly recommend Captain Tony for anyone wanting an amazing Waikiki snorkel experience! Perfect for couples and families with a party of 5!

  6. LB

    Lynette

    Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

    Captain Tony was so accommodating. His communication and professionalism was fantastic. He provided my family and I our favorite memory of Hawaii, and was such a joy to be around. I would book over and over again. Thank you Tony!