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The Best Sailboat Rentals Near Haleiwa
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Haleiwa
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$100-$2,500
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$90-$1,075
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$85-$495
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$165-$1,000
Fishing Charters
Let a captain do the driving while you do the fishing
$165-$1,000
Diving
Explore the ocean depths with trained boat operators
$200-$1,100
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$400
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150
Top Sailboat Rental Locations Near Haleiwa
Recent Reviews in Haleiwa
bd
breanna
Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii
INCREDIBLE BOATING EXPERIENCE!! We even got to sail alongside dolphins. Would advise if you are considering adding food, to bring your own rather than due catering due to portion sizes being small for the price. Otherwise, would recommend Richie's team wholeheartedly.
MD
Michael
ONE OF A KIND, exhilarating trimaran sailing and swimming experience in Waikiki
Kiah and Natalie provided exceeded all expectations on our sunset cruise. We went with her suggestion to maximize the daylight, and had plenty of time to enjoy one of the best sunsets. Kiah constantly asked if there was anything we needed, if we were comfortable, and engaged in all types of conversations! Thank you for your time and care to making our sunset cruise the highlight of our vacation!
GV
Gemma
Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling
I booked a private ride to do a photoshoot and Tony was super helpful with suggestions and what we needed. Everything went really seamless and I’m so grateful! Would definitely book again!
JO
Jeremy
The best value Sunset Cruise off Waikiki! Beneteau 43ft.
We went sailing with Captain Tom and deckhand Raul. They were fantastic! We saw the sunset, a nearly full moon over Diamond Head, and just had the most wonderful time. So much more enjoyable than a group catamaran trip. We'll be doing this again. Thank you!!
Maroun
Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling
Captain Tony went out of his way to help me with my proposal to my girlfriend. He called me a day before and he was happy to help with planning. We sailed out far enough where diamond head was in the backdrop of the proposal. While I was surprising my girlfriend he was taking photos and videos! Overall it was a great experience and highly recommend. We will certainly be touring with him again. Thank you!
SC
Stephanie
Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling
Rented Tony’s Sail boat for my sister’s 30th! We had such a great time. He was very attentive with my group and shared his life experiences with us. Pretty cool life he as! Ask him. Will rent again if we come back!
Top Sailboat Rental Locations in the United States
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
Real reviews from happy Getmyboaters.
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