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    Sterling Sails

    5.0 (74 reviews)
    Open Open 24 hours

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    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!

    Anniversary
    Jacob L.

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

    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!

    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!

    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.

    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!!

    Picture with the captain

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    28 days ago

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    9 months ago

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    8 months ago

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    8 months ago

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

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    Elizabeth H.

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    8 months ago

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    3 years 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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    2 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 50 reviews

    Read more highlights

    San Diego Whale Watch - The Privateer

    San Diego Whale Watch

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

    Fantastic whale watching experience in San Diego! The weather was perfect, which made the trip even…read morebetter. We were lucky enough to see a whale that truly put on an amazing show--such a memorable moment. The crew was efficient, friendly, and very informative throughout the entire trip, which made us feel comfortable and engaged. Everything was also very budget-friendly, which made it an even greater value. Overall, a great experience and absolutely worth both the time and the money. Highly recommend!

    Heard it was migration season so decided to book a 9am tour on a Friday…read more The tour was two and a half hours long and we saw so many dolphins it was bananas! We also saw a baby grey baleen whale which was such a treat. But even sightings aside it was a lovely way to be out on the water. The crew to our boat were great. Knowledgeable and ensured everyone was having a good time. They recommend you get there 45 minutes early and definitely do so! You sign in and then line up. A lot of people can be fit on their boat (if you get the group one) and the line can get pretty large and it's first come first sit. For 10 bucks a pop you can go on early. For 200 dollars you get the exclusive front top deck. I recommend sitting at the top. Please note that means sometimes no shade so bring a hat. You can sit on the first level or inside in the shade. The boat has a bathroom and after 3 miles you can get drinks! If you park in the lot attached to their location it's 10 dollars. Or you can street park on Quivera road which I recommend as it was super easy and not a walk at all. Would highly recommend regardless of if you see any whales just for the joy of being out on the water.

    Photos
    San Diego Whale Watch - Privateer and Whale

    Privateer and Whale

    San Diego Whale Watch
    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

    San Diego Boat Cruise - Interior below deck

    San Diego Boat Cruise

    5.0(75 reviews)
    1.3 miFleetridge, Point Loma

    Captain Paul was fantastic--extremely knowledgeable about the area and wonderfully accommodating,…read moreespecially with five small children in tow. He made the entire experience smooth, fun, and memorable. Couldn't recommend these folks more highly!

    I booked a yacht with San Diego Boat Cruises for my bachelorette party and it was a highlight of…read morethe trip! If you're looking for an amazing private cruise, definitely book with San Diego Boat Cruises!! We were on Miss Jen II (50' yacht) and it comfortably fit 12 women (the max occupancy). We all fit under the covered seating in the back of the boat together as well as on the bow at the same time. Below deck was nice, although we didn't spend much time down there aside from using the two bathrooms or making drinks in the kitchenette. The boat was equipped with a huge JBL speaker, phone chargers, a cooler with ice, soft drinks, water bottles, mixers, cups, and snacks (assorted chips). We brought our own alcohol, sandwiches, and extra snacks since we cruised at lunch time. We were on the water from 12-3:30pm and even though the day was cloudy, it didn't spoil our fun. The time flew by! We started the trip all seated in the covered area as we were cruising by the seals and to Point Loma. We cruised through San Diego Bay and ended up anchoring at Glorietta Bay, partying on the bow. The whole trip was a blast and Captain Paul was wonderful! He even got some great photos and videos for us! I booked the trip with Captain Glenn, who was easy to coordinate with. Overall I highly recommend San Diego Boat Cruise and would book with them again for any special occasion.

    Photos
    San Diego Boat Cruise - Exterior bow

    Exterior bow

    San Diego Boat Cruise - Captain Paul!

    Captain Paul!

    San Diego Boat Cruise - Seals

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    Seals

    Wild Pacific Whale Watch - Gray Whale Fluke

    Wild Pacific Whale Watch

    5.0(14 reviews)
    1.3 miFleetridge, Point Loma
    Locally owned & operated
    Family-owned & operated

    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!

    I called several companies to inquire about whale watching tours. I really liked the way Melissa…read morespoke to me over the phone. She was not only patient but she was also so enthusiastic and informative. The other companies I called seemed nonchalant or just very blah. So when I decided to call back to book the tour with Wild Pacific Whale Watch, Simon was the one who answered my call and was just as friendly and provided great customer service. The tour itself was so fun. We booked the 9am tour and checked in at a table situated by the H&M building in Point Loma. It was very easy to find and when it was time for the tour, the gentleman advised us to board the Peregrine. Although we didn't see any whales, we saw a bunch of dolphins and seal lions. Since we didn't see any whales they gave all the guests a 50% off voucher with no expiration date to return. The crew onboard consisted of Captain Quinn, Greg (the tour guide and naturalist) and Cameron who assisted with the snack bar and other duties. Greg was full of facts and was so nice. He knew so much about the wildlife. Everyone was wonderful! This 80 ft luxury boat is a newer boat and has stabilizers to help deter rocking which makes it less likely for seasickness. We felt fine but we did take some Dramamine just in case. I highly recommend this tour.

    Photos
    Wild Pacific Whale Watch
    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 - Grinding the winch

    Stars & Stripes USA 11

    4.9(56 reviews)
    1.8 miShelter Island, Point Loma

    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
    Stars & Stripes USA 11 - A DAY OF ADVENTURE ... gorgeous!

    A DAY OF ADVENTURE ... gorgeous!

    Stars & Stripes USA 11 - 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 USA 11 - Stars & Stripes takes the lead with starboard tack.

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    Stars & Stripes takes the lead with starboard tack.

    San Diego Boat Tours - One of our large catamaran heading out for a sail! A fantastic way to spend the day or night on a charter boat around the bay.

    San Diego Boat Tours

    5.0(10 reviews)
    1.0 miShelter Island, Point Loma

    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
    San Diego Boat Tours - 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.

    San Diego Boat Tours - 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!

    San Diego Boat Tours - 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 May 2026

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