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    Sterling Sails

    5.0 (75 reviews)
    Open Open 24 hours

    Sterling Sails Photos

    Recommended Reviews - Sterling Sails

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    The Artemis II Orion capsule coming home! Epic day on the water!!

    Captain Liz was seriously the best!! She greeted us right at our designated time and made us feel comfortable as soon as boarding. She went over all safety things to ensure we had the BEST party out of there on the water. Not only was she a bada** captain but she was a hostess and a tour guide. The boat was so clean and she truly ensured we were all having an incredible day! I will definitely be booking this again!!

    Would definitely recommend Sterling Sails for a wonderful sailing experience. Captain Liz is an awesome captain and provided a great tour of the San Diego bay for our family of 5! She is very personable and friendly. Her boat is beautiful and very clean. Liz provided light snacks and refreshments. We were able to get up close to some of the ships in the bay which was an awesome experience. We all had a great time sailing into the sunset!

    Captain Liz and First Mate Sydney are the absolute best! They are both incredibly hospitable and always find a way to surprise & delight their guests. Mojave is a gorgeous vessel inside and out, from bow to stern! We have been lucky enough to take a couple of trips with Captain Liz and each time is better than the next. The trips can be customizable depending on how adventurous you're feeling. Our next goal is an overnight trip to Catalina Island! Thank you for encouraging us to have fun while also keeping us safe Captain Liz! You're a rad time and we're looking forward to hanging out with you & Sydney again!

    Lorraine F.

    I celebrated my 30th birthday with a party of six for the 2-hour sailboat ride with Captain Liz. This experience exceeded our expectations and if you are considering it, go for it - you will not regret it! We opted for a 2-hour time block that will give us both day time and sunset views. Captain Liz was very responsive as I asked a few questions before booking. On the day of our ride, she provided clear instructions on how to find her boat. The moment she helped us go on board to the moment we came back, it truly felt like an intimate, personal adventure to remember. Once on the boat, Captain Liz gave us options of which direction to go sail to - we ended up going towards Point Loma as we wanted the better sunset views (vs. Downtown SD views). We brought snacks, drinks, and a cake and although we were prepared with our own silverware, Captain Liz had a full kitchen and offered those for us. Throughout the ride, she was so personable - telling great stories and truly connecting with us. At the same time, she was good at letting our group have our alone/private time throughout the ride. Access to restroom & parking: The sailboat does have a clean restroom available for us. Parking was also fairly easy as there are lots directly in front of the marina. This experience was such a fun way to kick off my 30th and everyone in my group enjoyed it as well. I 100% recommend booking with Sterling Sails - Captain Liz will take care of you and you will have an incredible time!

    Anniversary
    Jacob L.

    Liz was great! Had a wonderful time on our sail. Will definitely be back in the near future!

    USS Midway

    We had 6 family members and took a night cruise (8:30-10:30). It was the highlight of our trip. Beautifully restored 42 ft. Catalina monohull. Had the harbor all to ourselves. Captain Liz was great in so many ways: managed to sail, even with minimal wind, knows her San Diego skyline history and naval hsitory as well as all of the Navy ships in dock. Very accomodating, went where we asked her to go as well as her own favorite places.

    I had a wonderful and fun cruise with Liz at Sterling Sails! Very relaxed atmosphere and knowledgeable sailor. Her boat was beautiful and clean. I would definitely recommend her services and return next time I want to get out on the water.

    Proposed!!
    Martha C.

    Everything was amazing! From the moment we boarded the sail boat to sailing off into the sea and the weather was amazing! Thank you captain Liz for making our sail wonderful!

    Katherina F.

    Me and my family enjoyed a sailing cruise with captain Liz a lot! The boat is super clean and spacious! Highly recommend if you are visiting San Diego or just want to see the city from the another perspective

    Hubby and I on the beautiful boat
    Anastasia N.

    If you're looking for a beautiful adventure on the bay while in San Diego, Sterling Sails is the answer! My group (6 people) has the most incredible and memorable time on Captain Liz's boat. Liz is just incredible - super nice and genuine person, very accommodating, knowledgeable and incredible kind. Her communication is wonderful and I was thankful how quickly she'd get back to me via text. The boat is spotless and in immaculate condition. I have no idea how she keeps it so clean! It's a great size for 6 people. I didn't feel cramped at any point. Love that there's a full kitchen and bathroom! Liz was really nice about offering champagne and snacks to my group and allowed us to bring pretty much whatever we wanted (besides red wine - totally understandable). The experience itself was pretty epic. My group will remember it forever. We all had a blast listening to our favorite music, while enjoying the incredible views. Highly recommend Sterling Sails and we will definitely be back!

    Sev A.

    I had the best time! Captain Liz is awesome. The boat is nice. I would definitely do this again! Make sure to bring a jacket!!

    I had a few girlfriends in town for a few days and was looking for a sailing charter for a sunset cruise. We had such an incredible evening and got a beautiful sunset. Liz and Ashley were so friendly and knowledgeable about the area and gave us an experience we definitely won't forget! The boat was so cute and clean and she had everything we needed! Will definitely be using Sterling Sails again when I have visitors in the future. Couldn't have asked for anything more.

    Picture with the captain

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    6 days ago

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    11 months ago

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    10 months ago

    Capt Liz is awesome and her about is great. Will return for another cruise! Great time!

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    10 months ago

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    2 years ago

    My family had a beautiful afternoon sailing experience with Sterling Sails. I will definitely book again.

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    3 years ago

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    1 year ago

    The sail was amazing! Captain Liz was very professional and knowledgeable. We have already booked another sail!!!

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    3 years ago

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    Awesome boat! Me and my family loved every minute. Captains where super fun and friendly. Was a nice long ride. Perfect amount of time

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    Page 1 of 2

    Ask the Community - Sterling Sails

    What is the boarding process for this vessel (ladder, over the side, etc.) and is it at all challenging to get on? Also, would you have a way to offer a gift certificate?

    We have OSHA certified steps that can hold up to 300lbs including a safety rail that puts you right in line with the vessel in order to safely walk onto the boat. Yes, we sell gift certificates on our website at www.sterlingsails.com

    Don’t See Your Question? Ask Away!

    Review Highlights - Sterling Sails

    We have been lucky enough to take a couple of trips with Captain Liz and each time is better than the next.

    Mentioned in 51 reviews

    Read more highlights

    Tiki Time Bay Tours

    Tiki Time Bay Tours

    4.7
    (145 reviews)
    1.3 mi

    I surprised my boyfriend with tickets for Tiki Time Bay Tours for his birthday and had a couple…read morewere friends with tag along as well. Whether you're a local or visiting San Diego this is a really fun activity on the weekend with yummy drinks and good vibes. Originally we were booked for a 10:30am tour that goes out to watch the sea lions out on the bay, unfortunately not enough people booked that one so it was cancelled. Even though our original plan was cancelled Tiki Time Tours went above and beyond to make sure we had a good experience and not only complimentary upgraded our tickets to a more expensive tour, they also gave our party a free round of drinks for the inconvenience! I think this speaks a lot about a company; anyone can be happy with customer service when everything goes according to plan, but the most important times to step up is when plans get cancelled/changed and that's exactly what they did for us! Instead of the sea lion tour we ended up doing the Tiki Live! tour at 3pm. This tour is about 2 hours and while you're out on the water you mingle with everyone else and play games that can win prizes for yourself, your party or the whole boat! The games were fun, interactive and silly. At some points we got close enough to shore and made people on land be a part of our games! Donny was our tiki tour master and he was really funny during the whole tour. In between games he just let the music play so we could enjoy the atmosphere and drinks. My entire group left with nothing but great things to say about the whole experience. My friend even won a free tour for another time so we will definitely be returning for more tiki fun.

    RANDOM SUNDAY -…read moreStunning Views - Drinks + shots - Stunning views - chances to win money and prizes My friends randomly saw this boat and said we should do it for fun. Tickets were around $47 per person for a 2hr water tour around the Bay in a boat decorated in tiki decor. For tourist this tour is great with a ton of fun information about San Diego and stunning views in the water. Minimum 8 people on the boat or there may be cancellation of the tour. PAY ATTENTION TO DETAILS. The guide will have some friendly trivia for a chance to win good cash prices, free drinks, gift cards, etc I think that was pretty fun to include in while getting a tour. If you are sensitive to getting seasick, I would recommend a Dramamine beforehand. Although the boat was spacious, it still felt the wakes from the other boats and you can go rocking. In addition there were slow times of moving and turning. Or you can just chuck down a few drinks and feel numb to it all! They have a Tiki Bar with a drink menu (no food) to purchase from and if you bring snacks to eat - you can't eat it on the boat. Drinks were good but their "house" made shots were pretty good! We had a couple rounds of those while on tour - paid round by a passenger or a free shot in the house by the staff. The awkward but not so awkward would be mingling with other folks on the boat that you don't know. One of my friends kept interjecting with another party and while they seem to not mind I could tell they were being polite but if it were me I'd probs be annoyed if someone kept interjecting while I'm having a good time with my friends. Although we all got along and occasionally shared cheers with shots. Luckily the boat was near empty with just a few of us to have some space to do your thing. Overall, nice little 2hr time in the water. Would highly recommend the later session to catch the sunset. Until the next review....

    Photos
    Rady's
    Rady's
    Tiki Time Bay Tours
    The Tiki boat.

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    The Tiki boat.
    San Diego Whale Watch

    San Diego Whale Watch

    4.7
    (1.1k reviews)
    3.3 mi
    15 years in business
    Free parking

    The Captain, Naturalist, crew and snack bar staff, and ticket area folks were great. I went out on…read morethe Sunset Whale Watch trip and we saw large pods of dolphins. There were many babies jumping with their moms. As many times as I have gone whale watching I still love learning new things. The Naturalist talked about how really young dolphins don't know where their blow holes are located. When the little cute babies jump out of the water they leap very high so they are sure to get their blow holes clear to breathe!

    On 06/19/26, we took the 9 am excursion. Listen to this…read moreadvice..... Upgrade to "THE BEST SEAT IN THE HOUSE "!!! You will not regret it. It will accommodate up to 6 in your group. My Husband and I got in line early to check in. We saw the opportunity to upgrade and we took it! He and I had the whole outside of the Captain's deck all to ourselves! My Husband got to fulfill his childhood dream of whale watching and boy did we see some beautiful wildlife! We saw majestic whales, dolphins, birds, sea lions, and while waiting in line to board, fish and stingrays. I got really seasick and the crew there were so kind to me...they kept checking on me, bringing me bags, peppermints and water. Allison, the wildlife narrator, was especially kind. She was also very knowledgeable and her enthusiasm to educate the public about the local wildlife was evident from the beginning! There was also a very attentive young lady crew member that would often see if we needed anything. She also kept bringing me mints, water and bags...she was even kind enough to throw away my full bag. That takes a special kind of humanity to discretely do that. There was a crew member with a beard who also checked on us. I was so seasick by that point that I failed to get their names, but I hope someone lets them know how much I appreciated their hospitality. The star of the show, of course, was Captain Mike! He came out and talked to us and as he was talking to us about his job, we could hear the sincere passion in his voice! He perfectly plotted our trip and made sure that everyone was able to have a great view of the wildlife. We were impressed by how much love and respect the crew members had for the wildlife and the ecosystem. Captain Mike spotted a Mylar balloon, stopped the engine and the team picked it up! I'm sure a beautiful sea creature was saved that day! Thank you again for the wonderful opportunity we had today! This experience is definitely going in the books!!!

    Photos
    Privateer and Whale
    Privateer and Whale
    San Diego Whale Watch
    Blue Whales off the coast of San Diego. Sept 2, 2011

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    Blue Whales off the coast of San Diego. Sept 2, 2011
    Wild Pacific Whale Watch

    Wild Pacific Whale Watch

    5.0
    (19 reviews)
    1.3 mi
    Locally owned & operated
    Family-owned & operated

    My husband and I had an incredible first whale watching experience with Wild Pacific Whale Watch!…read moreWe chose to go for our anniversary, and we are SO glad we did. We got to see humpback whales, sea lions, and so many common dolphins. The crew was all so welcoming, friendly, and happy to answer any questions you have. It was a smooth riding experience and plenty of seating. It wasn't very crowded on the boat and was very spacious. They even have a whale watching guarantee on their website that says if you don't see a whale then the next trip is free which is really neat. This is a small and locally owned business whose crew is very respectful of the wildlife. They ensure to keep a distance to keep the wildlife safe. They do offer drinks and snacks for purchase or you are free to bring your own! It lasted 3 and a half hours. It was an unbelievable experience and I highly recommend Wild Pacific Whale Watch! Pro-tip I found a great deal on Groupon for it to be more affordable for my husband and I to go. Also, they had a promo code going that Capital One shopping found for me. :)

    November 2025 First time whale watching and myself, my 5y old, and my hubs had the best and most…read moremagical time. We started with gorgeous weather on a large beautiful boat, and about an hour in we saw 3 humpback whales, a pod of 40 Lag white side dolphins (which glow!), and a pod of bottlenose dolphins. Among others were hundreds of birds and sea lions!!! Seriously we ended up staying out an hour later it was wonderful! The crew were so nice and attentive, and included a marine biologist to explain what we saw, where/how to look, and answer any questions! The snacks were great! The boat was roomy, cozy inside and out, and had seating and views from all over. Best part it was not over crowded and they were super smooth and fast sailors! Def recommended!

    Photos
    Wild Pacific Whale Watch
    Wild Pacific Whale Watch
    Bottlenose dolphins off of the coast of San Diego. One of our favorite dolphins to watch at wild pacific whale watch

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    Bottlenose dolphins off of the coast of San Diego. One of our favorite dolphins to watch at wild pacific whale watch
    Stars & Stripes USA 11

    Stars & Stripes USA 11

    4.9
    (56 reviews)
    1.8 mi

    I believe it is permanently closed. There is no way to make a reservation. I tried calling the…read morenumber that was posted on the sails when we were aboard years ago. Sounds like it is a private number for a female named, Ashley.

    From beginning to end... was an AUTHENTICALLY fun adventure learning how to actually JIBE, HOIST,…read moreand STEER (yes - STEER) a world-famous Sailing Ship that has won America's Cup - TWICE!!! With Theme Parks closed and the beaches pretty much a wash in SO CAL - getting to spend the day out on the San Diego Bay, for a day of sailing and sunning and fresh breeze ... HEAVEN. LYNNE and BEA (the Captain and Co-Captain) are kind people... and BONUS if you're a Disney fan - you're sailing the SAME HARBOR where much of the first PIRATES OF THE CARIBBEAN film was shot - doubling as THE CARIBBEAN... and (it gets better!) - you actually pass by several times "THE BLACK PEARL" - the ship's stunt double from the Film!!! But even if you could care less about Cpt. Jack Sparrow or pirates - you're in for a fun day at sea and a crew of 6 who make you feel like you're more of a sailor than you really are :) Not only was every precaution and health + safety protocol taken - they add perks included a fun, brief overview of how the art of sailing and AMERICA'S CUP evolved, how award-winning ships are built (KEVLAR, TITANIUM, and other technology to keep it sturdy but lightweight) - and a giant cooler of iced-cold beverages you (and yes - the ship has a loo - just in case :) PERFECT get-away, for a family (kids over 5), or a stay-cation!

    Photos
    A DAY OF ADVENTURE ... gorgeous!
    A DAY OF ADVENTURE ... gorgeous!
    IL Moro winning the New Years Day race on San Diego Bay.
    IL Moro winning the New Years Day race on San Diego Bay.
    Stars & Stripes takes the lead with starboard tack.

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    Stars & Stripes takes the lead with starboard tack.
    San Diego Boat Tours

    San Diego Boat Tours

    5.0
    (10 reviews)
    1.0 mi

    A lifetime goal for me was to charter a boat for my 50th birthday party. After a great deal of…read moreresearch, I was excited to meet Tawanna and the friendly staff and crew of the Aolani. She was very responsive, helpful, and supportive! I appreciated her insight and answers to all of my questions. The day of my party was perfect. The captain and crew made our outing enjoyable and everyone had a great time! I hope to have the opportunity to be on board again because they made my milestone birthday very special.

    We booked San Diego Boat Tours through Funerals Your Way for the scattering of my fathers ashes on…read more8/7/2019. All I can say is....WOW, what an amazing experience, it completely surpassed my expectations. Captain Randy with the Ocean Spirit and Host Jane Loveday were so compassionate, loving, kind, and knowledgeable. My father's ashes were scattered off of Point Loma and the memorial was exactly what was needed for myself and my family. The flowers layered with my dad's ashes were the perfect touch. Capt. Randy and Host Jane Loveday were so knowledgeable about the area and we all gained so much more love for San Diego. Thank you San Diego Boat Tours for helping me bring my dad's last wishes to fruition. My family and I strongly recommend your charter services!!! The WiggyFiggy Clan Gabriella Eileen Figueroa

    Photos
    Wedding of young couple on the yacht.  We do many small and medium size wedding - a unique venue for your wedding.
    Wedding of young couple on the yacht. We do many small and medium size wedding - a unique venue for your wedding.
    While on a yacht charter around San Diego it is necessary to keep an eye out for pirates!
    While on a yacht charter around San Diego it is necessary to keep an eye out for pirates!
    ID Analytics out on a corporate yacht charter with us.  Looks like they had a GREAT time! We do many corporate tours.

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    ID Analytics out on a corporate yacht charter with us.  Looks like they had a GREAT time! We do many corporate tours.

    Sterling Sails - sailing - Updated July 2026

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