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All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

4.9(Average of 1,036 reviews in this area)
Page 1 of 2 (45 listings)
Private sailing on 45 foot Luxury yacht ,snorkeling ,sunset sail
Sailing in Honolulu · 6 guests

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

5.0
$180hour
Have an exciting Very Private sailing adventure on a  Beneteau 43 Foot Luxury Yacht! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Sail Away in Paradise! Kewalo Basin Honolulu!
Sailing in Honolulu · 12 guests

Have an exciting Very Private sailing adventure on a Beneteau 43 Foot Luxury Yacht! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Sail Away in Paradise! Kewalo Basin Honolulu!

5.0
Superowner
Best of 2022
$185hour
Epic 34' Catamaran Sailing in Waikiki
Sailing in Honolulu · 12 guests

Epic 34' Catamaran Sailing in Waikiki

5.0
Superowner
Best of 2022
$99person
Have an exciting Very Private sailing adventure on a  Beneteau 43 Foot Luxury Yacht! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Sail Away in Paradise! Kewalo Basin Honolulu!
Sailing in Honolulu · 12 guests

Have an exciting Very Private sailing adventure on a Beneteau 43 Foot Luxury Yacht! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Sail Away in Paradise! Kewalo Basin Honolulu!

4.9
Superowner
Best of 2022
$185hour
Private Sailing Charter only people in your party, no other people! Luxury 40 Ft Beneteau. Best of GetMyBoat 2021 and 2022 Winner! 🥇 Sail Away in Paradise! Kewalo Basin Honolulu
Sailing in Honolulu · 12 guests

Private Sailing Charter only people in your party, no other people! Luxury 40 Ft Beneteau. Best of GetMyBoat 2021 and 2022 Winner! 🥇 Sail Away in Paradise! Kewalo Basin Honolulu

4.9
Superowner
Best of 2022
$185hour
Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii
Sailing in Honolulu · 12 guests

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

5.0
Superowner
Best of 2022
$350hour
Sailing and Snorkeling Adventures in Lahaina, Hawaii on 36 Foot Lidgard Monohull
Sailing in Lahaina · 6 guests

Sailing and Snorkeling Adventures in Lahaina, Hawaii on 36 Foot Lidgard Monohull

5.0
Superowner
$475hour
The best value Sunset Cruise off Waikiki! Beneteau 43ft. Private Charter (only people in your party, no other people)! Best of GetMyBoat 2021 and 2022 Winner! 🥇!  Hawaii sailing adventures for snorkeling and swimming! Kewalo Basin Honolulu.
Sailing in Honolulu · 12 guests

The best value Sunset Cruise off Waikiki! Beneteau 43ft. Private Charter (only people in your party, no other people)! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Hawaii sailing adventures for snorkeling and swimming! Kewalo Basin Honolulu.

4.9
Superowner
Best of 2022
$185hour
Diamond Head Sunset Sail on Private 43' Luxury Yacht! Book Now!
Sailing in Honolulu · 12 guests

Diamond Head Sunset Sail on Private 43' Luxury Yacht! Book Now!

5.0
Superowner
Best of 2022
$185hour
Instant Book
Hawaii's Best Waikiki Sail and Coral Garden Snorkeling Adventure. Book Now!
Sailing in Honolulu · 12 guests

Hawaii's Best Waikiki Sail and Coral Garden Snorkeling Adventure. Book Now!

4.9
Superowner
Best of 2022
$185hour
Instant Book
Hawaii's Best Waikiki Sail Snorkel Adventure Sunset Cruise Friday Nite Fireworks
Sailing in Honolulu · 12 guests

Hawaii's Best Waikiki Sail Snorkel Adventure Sunset Cruise Friday Nite Fireworks

5.0
Superowner
Best of 2022
$300hour
Very private, only you and your party! The Best Sunset Cruise!  Beneteau 40 ft also available for adventures in snorkeling and swimming! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Kewalo Basin Honolulu
Sailing in Honolulu · 12 guests

Very private, only you and your party! The Best Sunset Cruise! Beneteau 40 ft also available for adventures in snorkeling and swimming! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Kewalo Basin Honolulu

4.2
Superowner
Best of 2022
$185hour
Adventure Awaits on Private Luxury 50' Yacht for the Ultimate Sailing Experience
Sailing in Honolulu · 12 guests

Adventure Awaits on Private Luxury 50' Yacht for the Ultimate Sailing Experience

5.0
Superowner
Best of 2022
$499hour
Instant Book
Spacious Sailing Trimaran in Honolulu, Hawaii
Sailing in Honolulu · 45 guests

Spacious Sailing Trimaran in Honolulu, Hawaii

5.0
$750hour
Custom Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii
Sailing in Honolulu · 30 guests

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

5.0
$650hour
44 foot Luxury Yacht Private Sailing Charter
Sailing in Honolulu · 6 guests

44 foot Luxury Yacht Private Sailing Charter

5.0
$250hour
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
$235hour
Authentic sailing experience on a private boat - Honolulu, HI
Sailing in Honolulu · 6 guests

Authentic sailing experience on a private boat - Honolulu, HI

4.9
$275hour
43' Jeanneau Cruising Monohull Charter in Honolulu
Sailing in Honolulu · 6 guests

43' Jeanneau Cruising Monohull Charter in Honolulu

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

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$500-750hour
40ft Luxury Catamaran for Honolulu Adventures
Honolulu · 49 guests

40ft Luxury Catamaran for Honolulu Adventures

5.0
$650hour
Waikiki boat charters
Sailing in Honolulu · 8 guests

Waikiki boat charters

5.0
$99person
Custom 38ft Private Party 33 Passenger Gorgeous Catamaran!
Sailing in Honolulu · 33 guests

Custom 38ft Private Party 33 Passenger Gorgeous Catamaran!

5.0
$990hour
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
$100-300hour

Sailing Reviews in Hawaii

  1. HL
    Hannah
    Private sailing on 45 foot Luxury yacht ,snorkeling ,sunset sail

    Tony was the best!!! My boyfriend and I had such a memorable time with him and Sean watching the sunset. He shared so many incredible stories of his life and it was truly a great way to end our last day in Waikiki. Sailing in the Universe with Captain Tony will be one of the best memories my boyfriend and I share together. Thank you Tony and we’ll be waiting for your book!!!!

  2. JJ
    Joshua
    Have an exciting Very Private sailing adventure on a Beneteau 43 Foot Luxury Yacht! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Sail Away in Paradise! Kewalo Basin Honolulu!

    Captain Tom and Kenny were both great in educating us and accommodating the whole time. I had great trust in them while sailing through the waves and watching them do what they do. The trip was exciting, relaxing and beautiful, and Captain Tom did a wonderful job in making sure we were comfortable and safe. Id definitely recommend booking with them.

  3. Marion
    Marion
    Spacious Sailing Trimaran in Honolulu, Hawaii

    We chartered Three Tiki’s for a pre-wedding event and it was the best decision we made. The crew was warm and welcoming, the boat was beautiful, and the vibes were just overall immaculate. It was a great way to kick start our wedding week and we would highly recommend this to anyone!

  4. Joanne
    Joanne
    Waikiki boat charters

    Brendan supplied us with an excellent experience on the ocean waters. He took an extra step to grab us up at our hotel so we didn’t have to walk in the sun with all our stuff to the harbor. He provided us with all the necessary equipment we needed to have while in the water, snorkeling gear, floating board etc. It was a really fun day and he made the day easy and enjoyable.

  5. TM
    Taka
    Have an exciting Very Private sailing adventure on a Beneteau 43 Foot Luxury Yacht! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Sail Away in Paradise! Kewalo Basin Honolulu!

    Awesome experience! Cap Rob and Kenny were very friendly and super flexible. We met the dolphins during our sailing time which was quite special. Our entire cruise was wonderfully tied together with the beautiful sunset at end.

  6. SW
    Stephen
    Spacious Sailing Trimaran in Honolulu, Hawaii

    We hired Matt's boat for a 3 hr sunset cruise with snorkeling around the Waikiki area.When I first saw Matt's boat on the getmyboat wesite,there was no review on this boat and I was rather apprehensive about it as there were many good reviews on other boats.My doubt quickly dissipated after talking to Matt ,he was professional and always quick to answer my questions ,he even made suggestions to fit our needs. On the day ,I was delighted to see Matt's boat as good looking as it is on the website.We are a party of 24 and I think it's just the right number for this boat.It has Bluetooth speakers ,so you can play your own music. It is also equipped with some cool LED lights which gives the boat special ambience especially after sunset. It doesn't has a lower deck area with tables and chairs like some other boats.So everything happens on the upper deck. They provide water and snorkeling gear.We did encounter some problem during our snorkeling.Even though all of us are competent swimmers,most of us have not used the snorkeling gear before.But I think the crew member who helped us with the snorkeling was a bit too eager to get us to the water where we could see turtles and fish.She didn't give us enough time to get used to breathing with the gear and as a result ,many of us were out of breath trying to keep up with her. A couple did decide to get back up to the boat as they were left too far behind .For those who could ,we did see turtles and fish.But don't expect the water as clear as you see on some websites and the turtles were rather small .But it was fun to see and swim around them.Getting back to the Harbour with the sun setting was a wonderful experience,especially with some nice music playing and his LED lights. Matt suggested that we should have dinner in the Pau Hana Place which is just next to the drop off point.It was a perfect end to a wonderful boat trip with good food around their fire pits.Overall we all had a wonderful and memorable time despite some hiccups.What makes it so special is Matt who really went above and beyond to accommodate our needs and to make sure everyone was happy.I cannot recommend him enough!