Small Group Waikiki Sunset Sailing Tour in Oahu
Oahu, United States

Small Group Waikiki Sunset Sailing Tour

Outty Ranking 74 4.9 · 118 traveler reviews2 hoursFrom $99

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September 2026

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Adults

Age 13 and over

2

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Age 12 and under

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Outty Ranking

74/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 118 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Small Group Waikiki Sunset Sailing Tour worth booking?

Small Group Waikiki Sunset Sailing Tour is a 2-hour experience in Oahu, United States, from $99 per person. It scores 74 out of 100 on the Outty Ranking, which we label “Strongly Recommended, based on a 4.9/5 rating across 118 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
74 / 100
Rating
4.9/5 (118)
Duration
2 hours
From
$99 per person

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go

What you get

    About this experience

    Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overcrowded catamarans or power boats ,when you come with us in small 6 people intimate group for more personal experience. The beauty of Oahu's south shore as you sail towards the volcanic tuff cone of Le'ahi (Diamond Head) as the sun dips below the horizon on this tour from Honolulu. Leave with a newfound appreciation for the people and marine life of Hawaii, and then gaze in awe as the sun reflects off the city skyline, overlooked by the towering peak of Diamond Head, at magical sunset hour.

    What's included

    Included

    • Carbonated beverages

    What you'll see and do

    1. Diamond Head State Monument

      Watch a spectacular sunset over the Pacific Ocean , with Waikiki and Diamond Head as an iconic backdrop to a perfect evening on a sailboat with friends and family in small groups

      60 minutes here

    2. Waikiki Beach

      Waikiki shoreline Leave with a newfound appreciation for the people and marine life of Hawaii, and then gaze in awe as the sun reflects off the city skyline, overlooked by the towering peak of Diamond Head, at magical sunset hour.

      30 minutes here

    3. Magic Island

      Watch the sunset you can take pictures of the spectacular views of the ALA Moana beach park next to magic island, on a right then on a left the Hawaiian Hilton village

      30 minutes here

    Where it starts and ends

    Meeting point

    Oahu

    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

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    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

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 6 travelers per booking
    Operated by
    Waikikisailingtours

    Know before you go

    • Public transportation options are available nearby
    • Suitable for all physical fitness levels

    Photos

    On honeymoonFamily vacationSmall Group Waikiki Sunset Sailing Tour in Oahu, photo 4On honeymoonSmall Group Waikiki Sunset Sailing Tour in Oahu, photo 6Small Group Waikiki Sunset Sailing Tour in Oahu, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 118 traveler reviews. Written by us, not quoted from reviewers.

    Photo opportunities

    5 mentions

    The views and photo stops come up again and again.

    Knowledge and storytelling

    2 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Organization

    2 mentions

    Pickup, timing, and logistics are described as running smoothly.

    Traveler reviews

    118 verified traveler reviews for Small Group Waikiki Sunset Sailing Tour. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    113
    4 star
    2
    3 star
    0
    2 star
    0
    1 star
    3
    Sort
    Haley_G · August 2026

    The best sunset cruise in Waikiki!

    We had such a wonderful experience on our sunset cruise off the coast of Waikiki with Captain Tony! We booked through Viator, and it was such a fun surprise to realize that Captain Tony had actually taken my friends and me out on a cruise back in 2023 as well, although we had booked through a different company at the time. Captain Tony was incredibly sweet, personable, and professional. He pointed out different sights along the coast, took photos of us, gave us great recommendations for things to do and places to visit, and was genuinely so kind and polite throughout the entire experience. The ride itself was peaceful and relaxing, and watching the sunset from the water was absolutely beautiful. We had such a great time and would definitely book with Captain Tony again. Highly recommend!

    via Viator

    haleyg703 · August 2026

    Captain Tony is the best!

    We had such a wonderful experience on our sunset cruise off the coast of Waikiki with Captain Tony! We booked through Viator, and it was such a fun surprise to realize that Captain Tony had actually taken my friends and me out on a cruise back in 2023 as well, although we had booked through a different company at the time. Captain Tony was incredibly sweet, personable, and professional. He pointed out different sights along the coast, took photos of us, gave us great recommendations for things to do and places to visit, and was genuinely so kind and polite throughout the entire experience. The ride itself was peaceful and relaxing, and watching the sunset from the water was absolutely beautiful. We had such a great time and would definitely book with Captain Tony again. Highly recommend!

    via Tripadvisor

    853alexas · July 2026

    A magical sunset on a Sailboat with the best views in Hawaii

    A magical sailboat experience to say the least. From the views to the vessel itself- sunset was absolutely beautiful on the water & Tony treated us like family. Not only is he 100% the expert in his profession - he’s been sailing for 40+ years and has the best stories. Thank you for a beautiful experience Tony, we’ll be back soon :)

    via Tripadvisor

    P2925OZanneb · May 2026

    5-Star Experience!

    Stunning views. Incredibly relaxing. We can't wait to sail with Captain Tony again. He deserves all the credit for an ultra smooth sail on a very windy day. He's a great conversationalist and respects silence--a wonderful combo.

    via Tripadvisor

    andreatR783OB · May 2026

    Beautiful evening sail

    Tony took us for a wonderful evening sail out to Diamond Head and back. He was fun, courteous, and interesting, and also no-nonsense and easy to talk to. The boat was comfortable, and we enjoyed having it to ourselves for a short amount of time. Highly recommend a private tour with Captain Tony!

    via Tripadvisor

    Good to know

    Duration
    2 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    41
    Verdict
    Strongly Recommended

    Why this scores 74

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)91
    Review evidence (18% weight)56
    Booking momentum (14% weight)50
    Value for money (12% weight)63
    Listing quality (10% weight)85
    Local standing (8% weight)71
    Booking flexibility (8% weight)100

    Small Group Waikiki Sunset Sailing Tour: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Oahu.

    How much does Small Group Waikiki Sunset Sailing Tour cost?

    +

    Prices start at $99 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Oahu usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Small Group Waikiki Sunset Sailing Tour take?

    +

    Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Oahu is not rushed.

    Is Small Group Waikiki Sunset Sailing Tour worth it?

    +

    It holds an Outty Ranking of 74 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.9/5 across 118 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Oahu, and how flexible the cancellation terms are.

    Can I cancel or reschedule Small Group Waikiki Sunset Sailing Tour?

    +

    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Small Group Waikiki Sunset Sailing Tour suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Small Group Waikiki Sunset Sailing Tour?

    +

    Around 41 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Oahu can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Oahu and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.

    Where does Small Group Waikiki Sunset Sailing Tour start and how do I get there?

    +

    The exact meeting point and directions are on your voucher once you book, and they sit in central Oahu within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Oahu?

    +

    On Outty we rank every Oahu experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Oahu: Full or Half Day Grand Circle Island Tour, Oahu Small-Group Circle Island Tour with Turtle Snorkeling, Pearl Harbor Remembered Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Oahu?

    +

    Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Oahu?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

    +

    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

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