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Small Group Waikiki Sunset Sailing Tour

Recommended by 97% of travelers
Badge of Excellence
Oahu, USA
Great choice
5+ bookings last month.
  • 2 hours (approx.)
  • Mobile ticket
  • Offered in: English

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/Pop
    Water, Chips and crackers Cold Soft drinks, Juices , stereo sound Restrooms below deck Amazing Captain

    Meeting and Pickup

    Meeting point

    • Hawaii Yacht Club
      1739 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 minutesAdmission Ticket Free

    3

    Magic Island

    30 minutesAdmission 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

    Cancellation Policy

    You can cancel up to 24 hours in advance of the experience for a full refund.

    Traveler Photos

    Gallery picture 1 (from a traveler's review)
    Gallery picture 2 (from a traveler's review)
    Gallery picture 3 (from a traveler's review)
    Gallery picture 4 (from a traveler's review)
    Gallery picture 5 (from a traveler's review)

    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 111 reviews
    Total reviews and rating from Viator & Tripadvisor

    Extremely arrogant and rude service

    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.

    Captain Tony took us out...

    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!

    Breathtaking Sunsets and Smooth Sailing with Experienced Captain!

    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!

    Amazing sunset cruise!!!!

    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!!!

    Amazing sunset sailboat!!!

    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!

    A Sunset to never forget

    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 🛥️

    Relaxing sunset cruise

    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!

    Highly Enjoyable.

    Bob_M, Mar 2025
    Great evening cruse. Highly enjoyable, a very nice way to spend a few hours before dinner. Thank you Capt Tony.

    Perfect Sunset experience

    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.

    Intimate and cool sail experience off Waikiki Beachikiki

    Kevin_S, Mar 2025
    Clean boat, Captain Tony is very knowledgeable and chatty, beautiful scenery - better than the "cattle" boats

    Sailing with Captain Tony...

    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!

    Great time, would book again!

    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!

    Relaxing, beautiful, and educational

    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.

    Captain Tony was great...

    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!

    Self involved

    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”.

    Sunset sail on a private boat

    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.

    Great!

    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.

    Small group is the way to go

    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.

    Beautiful views and a great captain

    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!!

    What a view!

    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.

    Wonderful sailboat experience

    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.

    True sailing from Waikiki

    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.

    Best The surveySunset Cruise in Hawaii Five stars

    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.

    Perfect sunset cruise with captain Tony.

    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.

    Highly recommend

    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!

    Beautiful sunset cruise

    Thomas_S, Dec 2023
    We really enjoyed the small group experience. Tony Montana was a great captain and he didn’t shoot us, LOL.

    Beautiful boat and great captain

    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.

    Let the Universe carry you

    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.

    Tony is the man

    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 person

    up to 24 hours before the experience starts (local time)

    Book ahead!
    On average, this is booked 28 days in advance.

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