Luxury Sailing Tour of San Diego's Bay and Coastal Waterways in San Diego
San Diego, United States

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

Outty Ranking 75 4.9 · 207 traveler reviews2 hoursFrom $119

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September 2026

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Who is going?

Adults

Age 13 and over

2

Children

Age 12 and under

0

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From, per person$119
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Outty Ranking

75/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 207 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Luxury Sailing Tour of San Diego's Bay and Coastal Waterways worth booking?

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways is a 2-hour experience in San Diego, United States, from $119 per person. It scores 75 out of 100 on the Outty Ranking, which we label “Strongly Recommended, based on a 4.9/5 rating across 207 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
75 / 100
Rating
4.9/5 (207)
Duration
2 hours
From
$119 per person

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your ad

What you get

    About this experience

    This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure you'll see many types of sea life as well as learn a little about the many features of San Diego that truly make it "America's Finest City".

    What's included

    Included

    • Bottled water
    • Snacks
    • BYOB if desired. Alcohol allowed for persons over 21. Call for Catering and Special Add on's.

    What you'll see and do

    1. Experience the San Diego Downtown Skyline and Bay from aboard a beautiful Catalina Sailboat!

      Pass by without stopping

    2. Enjoy San Diego's Beautiful Bay and Coastal Waters aboard a pristine Catalina 34' Sailboat! Only up to 6 guests at a time for a personal luxury tour that will create the memories of a lifetime...

      Pass by without stopping

    Where it starts and ends

    Meeting point

    San Diego

    Meet at Cabrillo Island Marina in front of the Seal Fountain...you can't miss it!

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Meet at Cabrillo Island Marina in front of the Seal Fountain...you can't miss it!

    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
    Imagine Sailing San Diego

    Know before you go

    • Service animals allowed
    • Public transportation options are available nearby
    • Infants are required to sit on an adult’s lap
    • Not recommended for travelers with spinal injuries
    • Not recommended for travelers with poor cardiovascular health
    • Suitable for all physical fitness levels

    Photos

    Luxury Sailing Tour of San Diego's Bay and Coastal Waterways in San Diego, photo 2Luxury Sailing Tour of San Diego's Bay and Coastal Waterways in San Diego, photo 3Luxury Sailing Tour of San Diego's Bay and Coastal Waterways in San Diego, photo 4Luxury Sailing Tour of San Diego's Bay and Coastal Waterways in San Diego, photo 5Luxury Sailing Tour of San Diego's Bay and Coastal Waterways in San Diego, photo 6Luxury Sailing Tour of San Diego's Bay and Coastal Waterways in San Diego, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 206 traveler reviews. Written by us, not quoted from reviewers.

    Knowledge and storytelling

    5 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Traveler reviews

    206 verified traveler reviews for Luxury Sailing Tour of San Diego's Bay and Coastal Waterways. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    197
    4 star
    2
    3 star
    2
    2 star
    1
    1 star
    4
    Sort
    465jimmyj · August 2026

    A must do when in San Diego

    Captain Dave was fantastic. Obviously knowledgeable on the water and everything around the bay. the experience was spectacular. Highly recommend and will do it again when back in San Diego! Even though I booked it through the company direct, I ultimately got in touch with them through my concierge, Karin, at the Bay Waterfront Hilton. She was very helpful and sweet as well!

    via Tripadvisor

    Cornelius_D · August 2026

    Great sail!

    Captain Mike was full of fun facts. Great sail seeing all the sights on SD Bay. Easy & convenient trip.

    via Viator

    Michelle_G · November 2025

    Disappointed

    Ugh, No one ever showed up. Texted twice got no response. What a bummer. Quick to take my money. Please give my money back.

    Response from the operator: We are so sorry that happened and will be refunding you 100%. Also, if you have the opportunity to reach out to me we’ll arrange a free ride for you. It’s very difficult for us this time of year when the clocks change and it’s dark at 5pm. Usually that slot does not book, and if it does, we call you to arrange a 3pm departure. This unfortunate incident was compounded by the fact that I’m currently in a different time zone as well. When you booked It was close 3pm the cut off for 5pm, and midnight where I am currently. Did not get your call in time to correct the situation. I know that’s not a good excuse, but please do reach out to me for a free ride if you have the opportunity. Sincerely, Captain Mike www.ImagineSailingSanDiego.com

    via Viator

    robync574 · October 2025

    Perfect way to experience SanDiego!

    We had a fun day with beautiful wind and weather out on Dan Diego bay! Captain Mike was a blast; I even got a sailing lesson. It was the perfect way to take In the city. Thank you captain Mike!!!!

    via Tripadvisor

    Aneisa_D · October 2025

    Captain Mike was exceeded...

    Captain Mike was exceeded our expectations! The ride was smooth and relaxing. Mike gave us a lot of information about San Diego and answered any questions we had. He also had the boat stocked with snacks, drinks, blankets and even jackets/hoodies in all different sizes for us to use. He also took some great pictures of us. My husband and I had an unforgettable experience on this sailing excursion & would do it again. Definitely recommend it !!

    via Viator

    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
    72
    Verdict
    Strongly Recommended

    Why this scores 75

    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)72
    Booking momentum (14% weight)67
    Value for money (12% weight)37
    Listing quality (10% weight)70
    Local standing (8% weight)75
    Booking flexibility (8% weight)100

    Luxury Sailing Tour of San Diego's Bay and Coastal Waterways: questions travelers ask

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

    How much does Luxury Sailing Tour of San Diego's Bay and Coastal Waterways cost?

    +

    Prices start at $119 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in San Diego usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Luxury Sailing Tour of San Diego's Bay and Coastal Waterways 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 San Diego is not rushed.

    Is Luxury Sailing Tour of San Diego's Bay and Coastal Waterways worth it?

    +

    It holds an Outty Ranking of 75 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.9/5 across 207 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in San Diego, and how flexible the cancellation terms are.

    Can I cancel or reschedule Luxury Sailing Tour of San Diego's Bay and Coastal Waterways?

    +

    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 Luxury Sailing Tour of San Diego's Bay and Coastal Waterways 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 Luxury Sailing Tour of San Diego's Bay and Coastal Waterways?

    +

    Around 72 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 San Diego 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 San Diego and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.

    Where does Luxury Sailing Tour of San Diego's Bay and Coastal Waterways 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 San Diego 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 San Diego?

    +

    San Diego is an outdoor-first city: whale watching from December through April, La Jolla kayak and snorkel runs year round, harbour cruises and the USS Midway, plus Balboa Park museums when the marine layer sits low. We rank water operators on group ratios and gear quality, which is where the cheap La Jolla trips fall down. On Outty we rank every San Diego experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include USS Midway Museum Admission: Valid Any Date, Taste of Little Italy in San Diego, San Diego Whale Watching Cruise. 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 San Diego?

    +

    March to May and September to November, either side of the June overcast. 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 San Diego?

    +

    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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