Small Group Waikiki Sunset Sailing Tour
Recommended by 97% of travelers
Badge of Excellence
Oahu, USA
- 2 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
Hop aboard The Universe, or your sailboat, to watch the sunset in Waikiki on this small-group tour. Your captain navigates, so you just need to relax. Sip on provided soda and water and snack on chips and crackers as you cruise along the water. Check out Diamond Head as the sun goes down and get some awesome photos.
- Easy to find meeting point in Waikiki
- Enjoy this small, intimate group setting (max 6)
- There’s plenty of room on your sailboat to spread out and relax
- Restrooms are available if needed, so not to worry
What's Included
- Soda/PopWater, Chips and crackers Cold Soft drinks, Juices , stereo sound Restrooms below deck Amazing Captain
Meeting and Pickup
Meeting point
- Hawaii Yacht Club1739 Ala Moana Blvd, Honolulu, HI 96815, USA
Hawaii Yacht Club ALA WAI boat harbor slip 429 it’s about 100 feet before the yacht club just follow the google map to Hawaii yacht club
End point
This activity ends back at the meeting point.Itinerary
1
Diamond Head State Monument
1 hour • Admission Ticket Free
2
Waikiki Beach
30 minutes • Admission Ticket Free
3
Magic Island
30 minutes • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Near public transportation
- Most travelers can participate
- This tour/activity will have a maximum of 6 travelers
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Brent_D
Our sunset cruise was perfect!! Communication before hand was great! Stunning views and perfect weather. The highlight of the cruise was getting to know capatain tony and hearing of his adventures and his knowledge of Hawaii. He did an amazing job of making our 4 year old feel comfortable and apart of everything!! Couldn’t have asked for a better experience!! Thank you Captain Tony!! Enjoy your time with your sister and nephew!!!
Reviews
4.9
based on 116 reviews
Sort by: Most insightful
Tina_H, May 2026
Captain Tony was great! Very friendly and the boat and sunset sail was perfect. Will definitely be a repeat for us.
linghan, Feb 2026
This was a terrible experience. It's the worst service I've ever seen on Earth. I left my phone number and email address when I booked, but no one contacted me. When I arrived at the navigation point and couldn't find the boat, no one called me to contact the operator, ultimately causing me to miss my boat. When I finally got through to the operator, he arrogantly told me, "It's all your fault." Please, get your act together. I paid you; you're obligated to provide excellent service, not just shift blame onto the customer when problems arise. We're not paying to be humiliated. You need to remember that you owe your mortgage and credit card payments to these customers; they owe you nothing. Honestly, I don't care about the few hundred dollars; I'll just consider it gone. But if you continue with this arrogant attitude, you'll get your comeuppance sooner or later. If other potential customers see this review, please think twice. If you want to pay for a terrible experience, go ahead and book this operator. If you want good service, you'd better look elsewhere.
Response from Host, Jun 2026
Sorry for not understanding the clear distinction I have send you a day before with pictures how to find the boat and the slip number like I do with every customer for over 3 years you also have a confirmation email from Viator with an easy directions, when I called you 5 minutes the tour you didn’t answer your phone I give you an extra 10 minutes after our original departure time and I left to do the tour with 4 other customers on a boat so clearly was your fault not following the google directions and you didn’t show up , and now you wanted your money back it’s a business not a charity, I could have taken 2 other customers instead you who would appreciate the service on small boats with Hawaiian hospitality . Think about it if you put Airport in your google map it will not take or direct you to the train station .. I waited 10 minutes for you the Airplane don’t wait good luck with your life
Karen_D, Nov 2025
Captain Tony took us out a beautiful sail to watch the sunset. He’s an incredible man with lots of life to share. Highly recommend. Romantic and fun!
Donna_N, Oct 2025
Captain Tony was simply outstanding!
From the moment we arrived, he was
warm, welcoming, and made us feel
completely at ease. He has a fascinating background and many years of
experience, which really shine through in
theway he runs his tours.
We had our grandson with us, and
Captain Tony immediately made a
connection with him—clearly
explaining that on his boat, he’s
the “boss.” He showed us our
seating options and went over
safety instructions before we got
underway, making sure everyone
felt comfortable.
Once we were out on the water,
the sail was raised and off we went.
We were treated to two beautiful
rainbows arching over the mountains
and could even see where it was
raining in the valley. As the sun began
to set, the glow reflecting off the
water and the Waikiki shoreline was absolutely stunning.
It’s very evident that Captain Tony
loves where he lives. He shared many
lesser-known spots around the island
that give visitors a more unique
perspective of Oahu. He also offered
excellent restaurant recommendations—
we went to Nico’s Pier 38 based on
his suggestion, and it turned out to be
one of our favorite meals of the entire trip.
If you’re looking for a personable,
knowledgeable captain and an
unforgettable sailing experience,
look no further than Captain Tony!
Brent_D, Sep 2025
Our sunset cruise was perfect!! Communication before hand was great! Stunning views and perfect weather. The highlight of the cruise was getting to know capatain tony and hearing of his adventures and his knowledge of Hawaii. He did an amazing job of making our 4 year old feel comfortable and apart of everything!! Couldn’t have asked for a better experience!! Thank you Captain Tony!! Enjoy your time with your sister and nephew!!!
Jessica_K, Jul 2025
It was really awesome to see Waikiki from the oceans perspective. And it was not on a big noisy crowded catamaran!! Very private and exclusive, Captain Tony was fantastic. Highly recommend. Kids loved it too! Take Dramamine :) we took it and had no problem!
Yerson_D, May 2025
We have such an unforgettable experience even though we booked last minute via call center with Viator
We were to see the beautiful Sunset and the captain was very nice and also helped us when locating the boat since we were kind of lost at the Marina
We were able to take amazing photos and play our favorites songs and playlists since this is an experience for few people onboard 🛥️
Angela_M, Mar 2025
Captain Tony was communicative before we arrived, giving us great parking information and clear directions to find his sailboat. We left right on time, and he got us under sail as quickly as possible. He shared lots of interesting points about the area, and gave us time just to chill and enjoy the peaceful time on the water. We would 100% book with Captain Tony again!
Bob_M, Mar 2025
Great evening cruse. Highly enjoyable, a very nice way to spend a few hours before dinner. Thank you Capt Tony.
Elizabeth_C, Mar 2025
This sunset boat ride was a top highlight of our trip. Captain Tony is very nice and makes sure to include and talk to everyone. Tony made the ride special by taking pictures for everyone at the perfect time and angle for sunset. If you’re looking for a more intimate sunset boat experience instead of being crammed on a boat with 60 other people, then this is the experience to book. You may sit on seats on the back of the boat, inside, or at the front and each provide great views of Waikiki beach & the sunset. Tony also mentioned he does private Turtle snorkeling, & creates special moments for those planning to propose and will keep it a secret to make it be perfect! We celebrated our honeymoon for this ride and it couldn’t have been any more perfect.
Kevin_S, Mar 2025
Clean boat, Captain Tony is very knowledgeable and chatty, beautiful scenery - better than the "cattle" boats
Sandy_T, Mar 2025
Sailing with Captain Tony was an unforgettable experience! From the moment we stepped on board, he made us feel welcome and at ease. With only four people on the sail, it felt personal—perfect for soaking in the stunning sunset views.
He was not only a skilled sailor but also a fantastic guide. He shared interesting stories about the area, offered great insights, and even knew the best times and angles for capturing beautiful photos. He was more than happy to take pictures for us, making sure we had great memories to take home.
The peaceful, small-group setting combined with Captain Tony’s hospitality made this sunset sail truly special. If you’re looking for a relaxed yet informative sailing experience with breathtaking views, this is definitely the way to go! Highly recommend!
Alexa_M, Feb 2025
If you hate crowds, then this experience is for you. Only a max of 6 people at a time which made the experience exactly what we wanted. Captain Tony was very knowledgeable about Hawai’i and we enjoyed our time on his boat! 10/10 recommend!
Larissa_W, Jan 2025
This was a fantastic experience. Captain Tony was friendly and knowledgeable, and he sent us detailed meet-up instructions the day before. My 11 year old said it was one of the best experiences of his life. We were able to see several whales and dolphins during the sail, as well as a beautiful sunset. This is great for a small-group setting and the perfect way for us to wrap up our time on Oahu.
Kristin_N, Jan 2025
Captain Tony was great company! It was us and another couple. We were able to sit at the stern of the ship and it felt like our own private yacht. We spotted 10-15 whales and many other animals during our cruise. Lovely conversation and company. Would book with Cap Tony again!
Meike_B, Jan 2025
The cruise itself was lovely, beautiful views of Honolulu and Diamond Head.
The problem was Captain Tony. He droned on about himself nearly the entire trip, even bringing up his political conspiracy theories. Hosting consisted of “there’s the cooler, help yourself”.
Andrew_R, Dec 2024
Beautiful experience sailing off Waikiki on a sunset tour on Tony's sailboat! There was some wind, so we put up the jib and turned off the engine. The quiet, the waves, other sailboats around us and the spectacular views of Waikiki from the water made this into one of the highlights of our vacation. Saw a humpback whale too! Tony is an experienced traveler and sailor, as well as a warm and fun person, and we enjoyed our conversation.
Francine_W, Oct 2024
The sun set was beautiful. Tony was great. We can understand why he does not uses only the jib, but we were a party of longtime sailors and would have loved a good Hawiian sleighride.
Kevin_L, Oct 2024
Very small group unlike the big operators. Great romantic experience that we will remember! Felt like a valued customer and not a number.
JewelBrooks, Aug 2024
Amazing experience with a great captain! The whole experience was relaxed and easy. Great communication with captain to find dock and boat. Small group made it a very relaxing cruise. The views were amazing!!
Karen_Z, Jul 2024
Captain Tony is an excellent captain and provided us with a fun cruise! The water was so beautiful and the view of Diamondhead was amazing.
Jennifer_O, Jul 2024
Captain Tony was great. We passed several large party boats and I was so glad I chose this sailboat experience over those type of cruises.
Don_M, Jul 2024
Excellent mono-hull sailing just a short walk from the Hilton Hawaiian Village. Boat takes 6 or fewer so it’s an intimate experience.
Linda_F, Jun 2024
Captain Tony is fun and fascinating. Silent sailing through the bay is so much better than being on a large boat will all kinds of other people.
Winnie_L, Feb 2024
A perfect tour as we ended up to be the only people on board, as planned by captain Tony. It was overcast and a rainy day but we did enjoy the beautiful view and a quick sunset.
Dilki_R, Dec 2023
My family and I had the best time in Waikiki sunset sailing tour. The experience is truly amazing. Captain Tony is such a nice guy. They offered us drinks and chips and he has many years of experience in sailing. He’s too kind to drive us back to the hotel after the tour. This was my 4 years old son’s first sailing experience and he absolutely enjoyed it.
Highly recommended!
Thomas_S, Dec 2023
We really enjoyed the small group experience. Tony Montana was a great captain and he didn’t shoot us, LOL.
Dan_W, Dec 2023
Captain Tony was a spectacular tour guide on his 42’ sailboat. If you want to avoid large groups of people ( 6 max on the boat) beautiful sunset cruise and The captain was full of interesting stories. Sea yarns and more. BYOB if that’s your style, but what a memorable evening. Limited spaces so book early You won’t b disappointed. I understand he does snorkeling trips in the morning as well.
Sarah_d, Dec 2023
Captain Tony provides one of the best semi-private sailing experiences we’ve ever encountered. His historical knowledge of the Waikiki area coupled with his enlightened energy and passion for the ocean make for an experience that is more than your standard sunset sail excursion. Let Captain Tony introduce you to his Universe. You won’t be disappointed.
Luke_P, Nov 2023
Tony was so knowledgeable and friendly. He went the extra mile, and it was an experience we will never forget!
From $99.00
per personup to 24 hours before the experience starts (local time)
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Small Group Waikiki Sunset Sailing Tour
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