Sail San Diego was epic! It was probably my favorite activity we did in San Diego, it was so relaxing and honestly the best way to see the city! We even saw some wildlife like sea lions. The captain is super friendly and knowledgable as well. They also provided tasty beverages and snacks. The 3 hour sail was definitely worth it and I would love to do it again! Highly recommend.

This was amazing! We had Captain Bogart for a sunset sail around the bay and it was very memorable. Not only was it beautiful and a fun, different experience, but Captain Bogart was so friendly and funny and he let our 15 year old pilot for awhile. Teenage dreams come true! Highly recommend this fun experience!

The sunset cruise was one of my favorite parts of our visit to San Diego. It was relaxing, fun and beautiful. Chris was awesome and I would highly recommend this activity while youre in San Diego!

We booked this trip last minute and were able to get almost an entire boat to ourselves. The captain was great to hang out with and the boat was immaculate. Free flowing snacks and drinks! I would do this over and over again, worth every penny.

Nice afternoon sailing for the sunset. Safe, clean boat. A nice chill time. 40 ft sail boat.

We booked a 3 hour sailing trip for my birthday and it might be one of the coolest things I’ve ever done with my family. Loved every minute!! I will be recommending Sail San Diego to all of my friends and family.

Happy Captain Greg was THE BEST!! Super funny and easy going. Really nice sail boat, bean bag lounger on the bow, snacks, beverages all in a very clean, well kept boat. Definitely recommend!

This is at least the fourth time we sailed with them when we visited San Diego. Always a great trip. This time, Captain Sean was exceptional. He is from the area and was so informative. Beautiful day, great experience. We highly recommend!

A fun little excursion to top off a birthday weekend getaway. I was a bit nervous to sail as I get very seasick, but Cal was extremely nice and helpful in preventing that from happening. Beautiful, relaxing day sailing through the marina.

Such a peaceful beautiful ride. Highly recommend for anyone wanting a romantic trip. Stocked with your basic drinks and snacks.

Well organized! Great boats and Captain Greg was excellent.We are in our very late 60s and my wife was somewhat hesitant to go but had a fabulous time! Kudos to all!

I have Sail San Diego twice now and both times are absolutely incredible!! The sailboat is clean and Captain Greg is the one you want!!! He was so positive, upbeat and just sincerely the sweetest!!! I could never right enough about the experience!!! Just do it!!Thank you again Captain Greg and Sail San Diego!!Latasha Diamond

This was the perfect few-hour getaway. Not only was the sail relaxing, but our Captain seamlessly provided the experience everyone on board was expecting...despite different people having different expectations. For some, he showed them how best to relax, almost like a private retreat. For others he showed the fundamentals of sailing and navigation.The entire experience was exactly what we were hoping for, with animal sightings, beautiful views and great company. Highly recommend!

San Diego with its beautiful summer weather, sailing with Captain Trevor combined with best friends visiting from South Carolina and champagne. . . Memories were made. Captain Trevor was very knowledgeable, personable and funny. The boat was in excellent shape and it was nice not having to pay a corkage fee on bringing in our champagne and other beverages and the snacks were a nice touch also.We all loved the evening and watching the sunset. It was worth every penny.

Every time we vacation in San Diego we make a point to schedule a 3 hour sail with Sail San Diego. This is a great way to spend an afternoon with your friends and loved ones. They have nice sailing yachts, the skippers have always been friendly, knowledgeable and cater to your needs. The price you pay for this experience is reasonable. Make sure you leave a generous tip for your skipper, they earn it.

We did one of the bachelorette 3 hour sails and it was so.much.fun!! Our Captain Theo was there for a good time and acted as DJ, photographer, bartender, whatever we needed! I would recommend this over and over again! Thank you for a great time!

Our 3 hour sail with Sail San Diego was an absolute pleasure! Our captain was very informative, gave us lots of interesting information about the sights around San Diego bay. He also gave us lots of time to just sit back, relax and enjoy the trip. The boat was very nice and well provisioned with refreshments, lots of places to sit and a great value for the price! 10 out of 10 would absolutely go sailing with them again!

Amazing sailboat cruise. Captain Greg was the best! Highly recommend this sailboat cruise. Captain Greg let Jamar captain the ship and he learned about sailing. Great experience for a teenager. Very educational and entertaining for the whole family.

First time sailing on the ocean and had a great time. Jared was an excellent captain and was able to swim around some dolphins we saw so we could get some pictures and videos. He even oriented the boat a few times so we could get some excellent background shots of Downtown. He was a funny dude and had so much history and knowledge about the area.

I had purchased a three hour sale of the San Diego harbor on Trip Advisor and my expectations were exceeded. We were visiting from NC and I wanted the kids to have something to remember and this sailboat cruise was it. The sky was overcast and cloudy, but Captains Frank and Chris went above and beyond to give us some nice views. The sailboat (Ginger) was well cared for and was spotless. The music system on the boat was great and all technology was up to date and nice. If visiting San Diego, I recommend Sail San Diego. It made me go home and tell my husband that we need to learn to sail!

We had Bogart as our Captain. He was fun and energetic the whole time. He took great pictures of us and talked to everyone the whole time. He made the experience very fun.

My daughter booked this trip for my birthday on 6/15/21. She originally booked the sunset trip online. I received a very prompt call informing me that trip was unavailable, and was asked whether I would like to reschedule, or cancel for a full refund. I’m so happy I rescheduled! The company was able to keep the date, and move the time to one in the afternoon. Myself and my family, total of four passengers, were extremely pleased with our three hour sailing day! Captain Theo, assisted by his crewman in training Liam, were the absolute best! It felt like we were out on a friends boat for the afternoon. They made myself and family feel completely comfortable while aboard. I will definitely book the sunset trip in the future!

We had a very good time with our captain Bogart. He was fun, and informative. He made us all feel very comfortable. A great time was had!

Had a great time on this boat! The captain Bogart was very friendly and informative as we went around the bay. The captain also took his time and didn’t rush back when we ran over the three hours. He gave us excellent restaurant advice for after the boat ride. It was a wonderful experience.

Sail San Diego was fabulous! It was a beautiful night and we did a slow sail while catching the scenery. Bogart was our captain and he did a great job! Thanks for a wonderful night.

Sail San Diegos two hour summer cruise was the highlight of our weekend trip to San Diego! Captain Scott was knowledgeable and adept at handling the boat smoothly while answering our many questions. From easy online booking and very clear directions to the dock with pictures, all the way through the nice refreshment selection and beautiful cabin/restroom on board, our experience with Sail San Diego was top notch. Highly recommend!

I booked a sunset sail for a bachelorette party and we had an amazing time. The boat was immaculately kept and fully stocked with snacks and drinks (way more than I was expecting!). Captain Jared was good-spirited and set a perfect tone for our cruise. I cant recommend Sail San Diego enough!

Cant recommend them enough! Perfect thing to do in San Diego.

Excellent tour, captain Greg was awesome and even let us steer a bit.Music was great, the overall mood was great, and it was nice not having to worry about refreshments. Highly recommend this tour.

The overall experience was great! My group had a slight dilemma with our scheduled date and Cal was super accommodating in helping us still make our reservation. Captain Greg was awesome and very hospitable!

We really enjoyed our 3 hour tour over the 4th of July weekend. Our captain was great and the scenery and sailing were beautiful. Everything was as expected. This tour was recommended to me and I would highly recommend it to others. Very professional and courteous. Thanks!

Fantastic sailing! Captain Mike was a great guide explaining sailing and the sights as we went. We all got a chance to take the wheel! The snacks were pretty good, nothing fancy. Beverage selection of beer, wine and soda was good.We loved the seats on the front of the boat especially once we got out into ocean.Wonderful experience! Would sail with again and very much recommend!

Excellent excursion with a Captian whom is friendly and very competent. I will definitely be back.

We had a wonderful experience sailing with Sail San Diego! Greg was our captain and he was amazing. He was very informative and pointed out sights along our sail. The service was outstanding. I highly recommend sailing with this company. Thank you so much!!

We had a spectacular experience! Captain Greg was the right balance of informative and humor. We got to see dolphins, seals, and grey whales. Loved having the small party of 6 passengers, freedom to navigate the boat, and take in the California beauty. Well-stocked boat and Captain is a very skilled sailor. When we observe the large whale-watching ships from afar, they looked packed and uncomfortable. This experience is very much worth the value!

Theo was a very professional captain, plus funny as hell! We all loved every minute of the sail. It was the highlight of our trip. Thanks.

This was in celebration of a non-traditional student (53 y/o) having earned a masters degree in Rehabilitation Counseling. This instead of walking at commencement; right choice. Waiting until finished w/ grad school; wrong choice. Should have skipped school and gone sailing. Great time. Perfect day.

Great experience on a beautiful sunset sail! Our captain was very personable, professional, and managed the excursion with ease while also teaching us some basics. Highly recommend.

Captain Frank was great for our family. SSD was flexible with our schedule and gave us a great tour of the harbor. This was one of the highlights of our trip and would not hesitate to book them again.

This was my familys favorite experience in San Diego. Captain Frank was pleasant and the sailing was awesome! The only disappointing thing was that we didnt see any animals other than sea lions, wish the dolphins would have been out!!

It was my first time visiting to San Diego and was even first time experience of sail boat. Captain Frank was very professional and kind to us and gave us the one of the most memorable experiences to my family. My mom was very satisfied. The weather was awesome and the sunset was amazing.. I already miss it! There was a time when boat was shaking a bit due to wind and wave but Captain Frank did an amazing job of calming us and he took us to the safe route. We got to see the light house and aircraft carriers which were amazing experience. I am definitely going to visit again when I am visit San Diego. Thank you for this amazing memory! :)

My friends and I went on a girls trip and booked a 3 hour sunset cruise. Although the weather decided not to cooperate so we werent able to see the sunset because it was cloudy, the sailing was amazing! We had such a great time and Captain John was so nice and fun! If I were in the area again, I would definitely do this again and highly recommend if youre looking for a unique, relaxing experience!!!

We had a wonderful, relaxing 3-hour sunset sailboat ride. The captain was knowledgeable and pleasant.

Fantastic sailing adventure! Captain Frank was a great host. We were one of two couples on the boat. Saw whales and dolphins. Beauty of the ocean can not be overstated. My husband says it was the best birthday gift ever.

Given the chilly evening weather, I was not expecting much. I was very pleasantly surprised.Scenic, informative, sea life and navy ships.Relaxing small group setting.I would highly recommend this trip for an evening out on the bay.

Did the 2 pm whale watching tour with Happy Captain Greg and it was amazing. Happy Captain Greg acts as a tour guide in addition to his captaining duties, which makes for a great trip. We did see whales, multiple times, and the ship holds just 6 per tour so we were comfortable and up close. This is now my go-to tour and I’d highly recommend it to friends and family! (My pix of the whales are in video so just posting the lovely sunset we saw as we returned to port.)

My husband and I had the BEST time on the sunset sail! Well worth the money. Beautiful sail boat with great views. Even got to see wildlife (dolphins, sea lions, birds). Our captain was so nice and informative! Free beer and snacks were a perk too!

Outstanding sail. Captain Bogart was great and worked very hard. Personally I think that it should be manned by 2 people. I’m disabled and they helped me board and disembark The drinks and snacks weren’t convenient for me. Would definitely recommend this company to others. Found the excursion through Viator.

Our experience with San Diego sail was great! It was my group’s first time sailing and we all loved it! The captains were very friendly, welcoming and knowledgeable and we all felt very safe. Would definitely recommend to anyone that is looking to go sailing in San Diego!

We had a GREAT time sailing with Sail San Diego last weekend. Boat was great, captain was excellent and the weather was perfect. I highly recommend an outing with Sail San Diego. They were very professional from the time I booked the reservation until we returned to the dock after a fun day out on the water. You wont be disappointed!

Captain Frank was great! If you want an amazing view of the San Diego sunset this is the way to do it. We brought our own snacks but it wasn’t necessary as they have snacks and drinks for you. We wanted champagne so we brought our own. It was a almost perfectly clear day and got to see the sunset! Definitely want to do again during the summer!!!

Booked the sunset sail and couldn’t have been happier. Our captain was amazing and full of great information. The trip itself was beautiful and I would highly recommend.

We did a 3 hour private sail and it was amazing. Captain Tony was teaching my husband to sail and I sat back and relaxed, enjoying the complimentary drinks and snacks. Tony was friendly, knowledgeable and patient. It was a truly enjoyable and relaxing day. Thank you Sail San Diego. We hope to be back soon.

My friends and I had a blast on our tour during my bachelorette weekend! So scenic and our Captain Bogart was seriously such a good captain/tour guide and truly such a good sport putting up with our shenanigans!!!

This was some of the most fun I have had in a while! Our captain Trevor was the best and the owner Cal was someone I would love to work with again. This was a 10 out of 10!

We had an amazing sunset sail last week! Myboyfriend and I took my mom out who was visiting town. It was our first time sailing and it was such a cool experience. We loved how it was a more intimate, unique experience with us all sitting in the back right by our captain rather than a big boat roaming on your own. Our captain, Scott, was excellent! A real local who knew my boyfriend funny enough. He told us history and stories as we sailed through the bay. We felt totally comfortable socially distanced from the other 2 guests on our boat. The cabin was really neat. Spacious with lots of snacks and drinks. Bathroom was great. I also like how you can bring your own drinks/snacks on board too. I will definitely be going back here for whale watching in the new year.

Amazing time with new friends. Captain Frank was excellent. Sunset cruise. Thank you everyone.

Great trip out on a beautiful day. Saw a whale and dolphins. Lee was very informative teaching us about the area.

Great sunset sail with Captain Trevor! We sailed and motored in the bay and just to the tip of Point Loma. Lots of good music, trivia and history provided by our captain. We would definitely sail with them again!

A great day on the bay. Thanks to Trev for oustanding service and provisions. Our second time...and well be back.

Capt. Greg was wonderful, professional, kind, safety focused and very knowledgeable. My group enjoyed every moment as we sailed toward the whale highway. We saw so many birds, sea lions, and dolphins. It was a beautiful trip for Lori, Jim and Jean! Thank you and we will certainly sail again with you!

A great experience and captain. A must do in San Diego!

Sail San Diego was a blast. Super friendly staff and captain. Gave the husband the ok to buy a boat ;)

Captain Frank is very kind, knowledgeable, and loves what he does. The boat was gorgeous and comfortable. The location is stunning especially at sunset. Just a wonderful day and the start of a passion for sailing. Please sail here, youll have a wonderful time.

We had Captain Theo! Yey! He didnt give up on finding those majestic whales :) we found a family of 3 and saw their tails as they dove to go deep. Stunning experience on the sail boat. With a lovely glass of wine as we set off. The snack bar consists of chips and crackers and nuts, perfectly fine for setting off in the afternoon.

We had an excellent time sailing with Captain Frank last week!

Best ever! Always a pleasure cruise. Highly recommend.

It was a great day. The captain was knowledgeable and friendly. Loved it!

Decided to celebrate our anniversary with a sunset cruise during our visit to San Diego - and so glad we did. Captain Mike was super friendly, very knowledgeable, and let each of us have a turn at the wheel. The ride was so calm and peaceful. Plenty of drinks and snacks, sweaters and blankets for the ride in, and very personal and uncrowded. At first I was worried 3 hrs would be a bit much - but it was perfect. Thanks for a wonderful time!

Captain Greg was amazing and gave us a memorable day on the water! Very professional, knowledgeable, fun and safe. Great company to work with and highly recommend for a private sail around San Diego, well be back!

What a beautiful boat! I personally loved the princess seat. We had a great time and came upon 2 gray whales and some dolphins too!

Had a blast. Great boat, great guide, really nice experience.

This is the third time my wife and I have sailed with sail San Diego. Each time we have had a wonderful time. Our last two sailing have been with Scott. He is knowledgeable about San Diego and its harbor. He gave us a great recommendation for a dinner restaurant that we visited the following night. Great company. Wonderful experience every time.

Fantastic trip with Captain Greg! Very knowledgeable and informative throughout our trip while taking all our requests into consideration. Cannot wait to come back and go on a longer trip!

Nice relaxing evening for this first time sailing experience.

Highly, highly recommended. We had a private charter with Captain Frank, who was awesome. Ill definitely be back - even as a local, I cant say Ive seen a better view of Point Loma or downtown. Truly one of the top experiences you can have in San Diego.

Sunset sail with Sail San Diego was thrilling and relaxing. We zig-zagged under the Coronado Bay Bridge and enjoy the skills of Captain John. Great value, worth every penny to see San Diego. A quintessential spring day!

Had a great time! Just remember to take some warm cloths.

This was our second sail with Sail San Diego and Captain John. We had such a great experience we decided to go again and take my son and his friend. Captain John was very informative and told us some great stories of his sailing experiences as well as his time spent serving in the military. Because of this he was able to tell us about everything we saw in our heavily populated military bay. The company is very professional from making the reservation to the whole experience. They have all Covid precautions in place for those who may concerned. My son is still talking about it and we can’t wait to go back again! I highly recommend!

We had a fantastic time out in the water with Captain Frank. Captain Frank was great with the kids and extremely knowledgeable. We truly enjoyed our private tour with Sail San Diego and we cant wait to go back and do it again.

I took my wife on a sailing experience for our 5 year anniversary. We had Happy Captain Greg sail our boat and who made the whole experience one to remember. Very knowledgeable, great sense of humor and a great teacher.This was the first time either of us have been on a sail boat and Sail San Diego had the best deal with the sunset cruise and the best personal working.We will be back to San Diego again soon and may just have to book another trip!Best adventure of our vacation.

I booked the private sail whale watching as a surprise for my wife on our anniversary and it was the best idea ever. We had a great time in the ocean, the captain was awesone and very friendly too. He even made us drive the sail boat! It was just wonderful especially seeing all the animals and the views. Definitely a must if youre in San Diego. My wife loved it!

This was our second time doing a private charter. It was an amazing trip both times and well worth it! If you can ask for Frank, he plays the best music and makes each trip special in its own way. Thanks for the memories that we will never forget, and we’ll be back!

We had such a wonderful time on the sunset cruise! The price was very reasonable and we were able to see so many San Diego sights and enjoy a smooth sail at sea. We were even able to help and learn about the sailing process. Beers were just basic domestic beers and wine was unfortunately unavailable (because of Covid? Doesn’t quite make sense) but we brought our own drinks including wine and local craft beers as well as cheese and crackers that made our experience much more enjoyable. We still highly recommend the trip and the value for simple drinks and snacks was unmatchable! A must for even San Diego locals. Thanks so much Capt Scott!!!

My boyfriend and I went to San Diego for an extended weekend vacation and after returning home, we said this was both of our favorite part of the trip!!! Highly recommend! And also - if you do the sunset sail, bring a jacket and a blanket!

We sailed with Happy Captain Greg last week and had an amazing experience. Greg was informative, friendly, great with the kids on our trip, and experienced. We went on the afternoon whale watching tour and he made sure we found a beautiful gray whale. We were able to experience the beauty of the whale up close and personal several times. It was the experience of a lifetime. Booking was easy, the directions to the marina were very clear and helpful, and they had everything we could have possibly needed while on the boat. Book with Sail San Diego, I promise you won’t be disappointed!

My friends and I had a fabulous time sailing with Captain Frank. He was very informative and provided us a great tour. The views were absolutely amazing and the sunset was gorgeous! Definitely will recommend Sail San Diego to anyone interested in sailing.

Captain Frank was fantastic!! We had a great afternoon sail. The boat was well stocked with soda, beer, and wine.

Booked the 3-hour sunset cruise during a stay on Shelter Island. Very professional. Good safety briefing. Captain Frank was awesome!So relaxing. Will do it again next time we’re in the area.Great job!

My wife and I went on the 3 hour sailing adventure today with Capt. Theo and had a great time. The sailing boat was nice, inside and out, drinks/ snacks all complimentary, and a very knowledgeable Captain. Theo is exactly the kind of guy I would hope to have as a captain of any vessel. He was a good sport in grabbing me napkins and a drink to settle my stomach when I got sea sick.3 hours is the perfect length and I couldnt have asked for any better of a trip. Thanks guys!!

Absolutely beautiful and relaxing experience. Extra bonus being able to see the dolphin training and a submarine departing. They limit the amount of folks on the boats to 6 or 8 at most. This made for a really enjoyable trip.

All of the friends I brought sailing had a wonderful time, and keep telling me so.

We had a wonderful sail with Captain Theo! He was very professional and gave us a great tour with informative informative. I would highly recommend this still!

Had a wonderful sunset sail with Sail San Diego! The process of booking was easy. The sail was so relaxing with good company from our captain, Theo!

Great tour! Our tour guide made it the event fun and informational. Would definitely recommend.

Captain Anthony led us on a fantastic cruise! We had a sail scheduled elsewhere that had to cancel, and Sail San Diego was able to honor our timeframe even though it wasnt one that they typically offer. The sail was perfect - a great opportunity to connect with colleagues, learn about sailing, and check out the gorgeous sunset over the San Diego skyline. Captain Anthony was a pleasure. He was relaxed, informative, and he made the trip fun for all!

Went on a 3 hour sail with Happy Captain Greg and it was a great way to cherish the beautiful city of San Diego! We got the private rental for 6, the fridge was stocked with beer, wine and snacks. We played our own music, got under blankets, sipped some wine, saw a spectacular sunset. We even saw a cruise ship real close which was cool. It is a slower paced activity, almost meditative :)

I cannot even do justice with words as to just how pleased and impressed my wife and I were with our experience with Sail San Diego! It starts with their impeccable accommodation with scheduling. My wife and I were unable to make our initial flight due to weather in the Midwest and, thus, we were unable to make our initial reservation with Sail San Diego. The GM, Cal, was extremely understanding and accommodating and kindly shifted our reservation back a day without penalty so we could still get the experience while on our getaway.The experience itself was SUPERB! We were extremely fortunate enough to get Frank as our guide. Frank, who has several decades of sailing experience, was absolutely wonderful. He was extremely knowledgeable, a terrific captain, and was one of the most personable tour guides I had ever encountered. The boats themselves are stunning. Everything from the deck to the helm and everything in between was plush and very relaxing. The hospitality they provided was beyond imagination and far superseded our anticipations. Put it this way, we left with full bellies and a good Chardonnay afternoon buzz (not to worry, we Ubered it home).We are already planning on coming back and bringing our families so they can also experience Sail San Diego, which proved to be our favorite San Diego experience! Thank you again Cal, Frank and the Sail San Diego Team!Dr. G (Solomon)

Captain Greg was awesome! We had an amazing time!!

We sailed with Theo on a sunny Saturday afternoon and it couldn’t have been better. Such a pleasant afternoon activity! We booked last minute, found the rate to be very reasonable, and really appreciated the hospitality of Theo and the other folks at Sail San Diego. Two thumbs up!