Don't miss your chance for the absolute BEST way to spend an afternoon in Monterey! Sail Monterey offers a first class experience on a clean and luxurious catamaran at a reasonable price. Great for singles, couples, or friends. You will also LOVE the Sunset Cruise. Capt. Paul is totally awesome! A treat for locals and a MUST for visitors. Don't miss it! read more

Booked the 2 hour day sail for my fiancees birthday and hit traffic getting there, so we called to cancel thinking we were not going to make it. However, we ended up getting there right at our scheduled departure and they agreed to take us. Even allowed us time to use the restroom. Our captain was very nice and interactive and even let him steer the boat while she gave some quick education on sailing. Wine was included as she was very attentive, and we saw quite a few jellyfish and some dolphins. It was a beautiful day and a great experience. I would recommend to dress in layers and leaving super early as parking is a little difficult and they are all the way at the end of the warf so you will walk a few minutes. Looking forward to a sunset sail next time! read more

If you want to experience Monterey Bay in a different way, be sure to book a cruise with Monterey Bay Sailing. A very friendly front office will help you with the reservation and they will work to accommodate last minute bookings. The captain, Dutch, is quite a gentlemen and it was great to be on board with Shawn, who is a first mate with a promising future. The sail was delightful and the weather cooperated so our cruise had a beautiful view of the sunset. You can even take a hand at the helm if you are up for it! Highly recommend MBS, you will learn about the bay, see it in its full beauty, and will want to go back again real soon. Sailing calms the soul and energizes at the same time. Hope you get to sail with MBS, you will not regret it, and you will have many memories, stories, and photos to share! read more

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Captain Paul took us on a 1 hour tour... phenomenal experience, and an even better captain. Will definitely go again.

Captain Dutch is no longer with the company, but Captain Takoda (which I bet is constantly misspelled as Dakota) took us out (on short notice, too!) for a 4-hour sail. We were hoping to see some whales and boy did we! Dakota is really good not only at scoping them out, but at quickly maneuvering the vessel around to give you the best views as the whales surface in new places. He was super chill, friendly, and equally eager to converse or enjoy the quiet. He is safe, experienced, knowledgable, and clearly enjoys his profession. We can highly recommend sailing with Captain Takoda! read more

The captain, first mate and the other couple made for great conversation. My wife and I both left feeling great about our evening sail. read more

Sail Monterey - Boating Near Me - Monterey, California

Wonderful experience from start to finish. We enjoyed the one-hour trip on our first California sailing adventure and we can't wait to come back for a longer day, or for a beautiful sunset sail. Captain Paul was knowledgeable, professional, interactive, and truly made the day incredible. read more

Took a hour long bay cruise with wife, my 6 year old and 2 year old daughters. Quick reservation on the phone for the next day. Got there 45 minutes early and Takoda said we could leave early since we were the only ones on that cruise. It was a 32 foot sailboat that was nice. Motored out of the habour and were soon sailing with a gentle 8 knot wind. Skipper Takoda was great, had conversation but not too much. He looked like a 16 year old kid but it was easy to see he has done this many many times before. We saw sea lions, habour seals, sea otters and hundreds of jelly fish. My wife and 2 year old sat in the cockpit feeling sea sick and my 6 year old and I sat on the deck enjoying the sail :). There were some decent swells which meant the boat rocked a bit. Overall an awesome experience! read more

We had an amazing time on our sunset sail. Paul was so nice and friendly. It was smooth sailing. The fog bank kind of covered the sunset but being out on the water with no other boats around was so peaceful. My husband and Paul hit it off when they found out they both hiked the same area. I'd recommend Paul and sailing anytime. read more

Awesome ride! Must do if you're in Monterey! Wine, whales, sea lions. The owner was super accommodating when we missed our time. I really thank him for that! Great ride!! read more

I was disappointed with Monterey Bay Sailing. We never really sailed because the crew couldn't get the sail up so the engine ran the entire time. We did 4 small circles in the same small area over 2 hours while other boats sailed past us having fun. The captain didn't speak one word to us the entire time. The Monterey bay is beautiful, but I'll sail with someone else next time. read more

My wife and I booked a last minute cruise. Sail Monterey had us on the boat in 10 minutes. Captain Paul was energetic, entertaining and very professional. At the end of our cruise there was a kayaker in in distress and Captain Paul brought the person aboard made sure he was ok and made sure that he would meet up with the rest of his party. Captain Paul was on point. Thank you for a wonderful cruise. read more

Takota was awesome and the sailing trip was amazing. We went this past holiday weekend and it was informational and super fun. We'll be back for the dinner cruise! read more

This was a great place to go to for sailing! They are very nice, appreciate, and helpful! The captain was great, very mellow, knew his stuff and informative. Was a great time out at sea and had a fabulous time. The wine and appetizer plate was good as well. They were ready to top off your glass or take care of your needs. Comfortable, easy-going, and amazing experience! Thanks to you all!! read more

Sail Monterey - Monterey Bay Sailing! Great time! - Boating Near Me - Monterey, California

My family and I were supposed to be in Zion. However due to malfunctions we salvaged the trip and went to Monterey Ca. Best thing we did. Our kids liked the aquarium BUT, the absolute highlight of the trip was seeing a bunch of humpback whales, dolphins, sea lions, otters and jellyfish up close and personal with Monterey Bay Sailing. These guys are a class act and love what they do. We got to go on there beautiful huge catamaran. Within 3 hours our guide led us to numerous humpback whales very close up and hundreds of dolphins swimming right with boat. I will post pics from our trip. Our 7 year old boy was ecstatic as were we all. We will always use Monterey Bay Sailing for our excursions. If you are in Monterey be sure and book a sailing trip or excursion or a sunset cruise with Monterey Bay Sailing. read more

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Went on a cruise today at Monterey Bay Sailing!!! The prices were competitive and the service was phenomenal. We were taken out on a stunning catamaran, so comfortable and so luxurious. Served wine and treated like queens!!!! My girlfriends and I will definitely be coming here again. And not to mention, the staff Takota and Paul were so caring and attentive. You will not be disappointed sailing with this crew! read more

Sail Monterey - Boating Near Me - Monterey, California

Horrendous service. We were scheduled to take the 430 p.m. cruise and called ahead to notify them that we would be late and would like to reschedule to either the sunset cruise or the first cruise available the following morning. However, they told us that we would have to wait at the office until the captain came back which was in another 90 minutes. We were unable to wait around for the captain and told the office that we would call back at 6 p.m. to figure out the next available tour time. When we called back, the person at the office told us we missed our chance and hang up on us. The service at Monterey Bay sailing is amateurish and awful. Stick with the Bella on the Bay sailing. He is much more friendly and professional. read more

The Capt. & Crew where great ( Liz and Michell ) but sorry to say Monterey Bay Sailing gets a (No Star Rating ) I was very disappointed with our sunset sail , the management did a poor job in scheduling the sail with matching guess. On a small boat all the guess should either be on the same venue . My girlfriend and I booked a dinner sunset sail and and other guess on the boat did not , so when it was time to eat it became uncomfortable so to make to evening friendly we shared our food. The Capt. & Crew even offer the other guest food and of course we all shared but the in the end we paid for all the food. Monterey Bay Sailing should do a better job matching the guest , if its a sunset dinner boat then all the guest should be eating rather then a few guest enjoying dinner while other do not ..... read more

Sailed out with Captain Randy who is a very funny and friendly guy. My previous sailing experiences with darling involved a captain who didn't say 5 words the entire trip, so this was a very nice change. Informative, I learned a few things, and would highly recommend Monterey Sailing Company. read more

Sailor John and "Shrimp" are the best!! My 4 year old daughter, husband and I had a blast! We did the 2 hour and got to see 2 humpback whales! Great service! read more

Dutch was fantastic. The sailboat was perfectly maintained, we left on time, and Dutch expertly piloted us along with a pod of russo dolphins for nearly 30 minutes. Thanks Dutch! read more

Don't do business with this guy. He is an unprofessional jerk. We called about renting a bare boat for a few hours of sailing on Monterey Bay. I described our sailing experience and he said "yeah, that sounds fine." So after we arrive, he was rude, had an attitude of superiority and while we were trying to talk to him, took phone calls without putting them to hold. So when he finally does start discussing the arrangements, he asks about our experience again. Only this time, he is being completely smarmy and says "I could rent you a boat, but I have to ask you a question, do you care about your safety?" He proceeds to try and upsell us to a skippered tour of the bay. When that doesn't work, he then tries to sign us up for sailing lessons. Never mind we already have years of experience and a certification. He told us, "we don't recognize that certification here." I think this guy does sleazy business and you will be better off for having avoided him. read more

My sister and I did the locals cruise. We ended up being the only participants and it was great. We both were able to steer for a while. My sister is a professional photographer and Captain Dutch knew exactly where to take us so she could get some amazing shots of dolphins and sea lions. It was a wonderful experience and I look forward to going out again. read more

WOW!!! I bought an overnight stay aboard one of their boats followed by an "intro to Sailing" lesson for the two of us the next day.....WONDERFUL!!!! The accommodations where fun and located just a stone's throw away from many restaurants, a seasonal ice skating rink, shops, etc. We brought a bottle of bubbly with us, played a little music poker and sipped the night away. The next morning we where greeted by the proprietor (Dutch). He had us motor the boat we spent the night in over to a mooring, then to another sail boat that we spent a few hours learning the terms of sailing, how various lines, knots, winds, techniques, etc. work. Parking it in the slip might have been the most fun since we had a chance to show off our "parking a 25 foot sail boat in a slip" skills twice each. Excitement, laughs, fun, adventure.....if you seek any of them, give them a try! read more

My wife and I escaped the mad house of the valley for a day. No better way than an 11 AM sail with Captain Vinn for a couple of hours on the beautiful Bay. We even saw a couple of whale's that waved hi with their tails. My wife enjoyed the smooth ride of the catamaran and I loved being under sail. This was the perfect centerpiece to an amazing day!! read more

Dutch is a 5 star captain all the way around my mother has been sailing with him for 4 years and I for 2 every year on July 26 th the day her beloved husband and my step dad passed away we go and take a sailing trip around Monterey and throw roses overboard. Dutch is always so nice to us and of course my moms dog stewie, he always provides us with a good time and I appreciate that. read more

We chose the 30 min sailing trip. I am not a huge fan of the giant ocean in a small boat. Dutch was a great captain, he was careful with his sails and ropes and was sure not to hit anyone while dealing with it all. This was my first sailing trip, it was a pleasant experience. read more

Captain Dutch was great! super nice and easy going. Definitely had a great time. Wear layers and know the wait is worth it!!

Captain Liz and her deck hand, Michelle, took me, my husband, my sister, bro in law, and their two kids out on an hour cruise around the bay (~$240). We were able to book the cruise via online. They were very pleasant and we got to know them personally. Michelle was kind enough to let my 5 year old nephew help her put up the sail. Captain Liz was also nice enough to let him drive the boat. He really got a kick out of it. As for my niece, she wasn't feeling the ocean too much...she got seasick and threw up on the boat. They didn't make a big deal out of it and helped clean up the mess. The cruise was relaxing and fun. Not the cheapest activity to do, but well worth it. read more

Was great. Takes dogs! Had an awesome 1hr long trip. The captain was very knowledgeable about the area and pointed us in the direction of some other great camping spots and restaurants. It was great because they took our dogs which was awesome. read more

What an adventure! Went on a spontaneous sail with my friend (thanks to Captain Landon's invitation) and ended up making awesome new friends, enjoying boxed wine (it's some good boxed wine), and lots of laughs while sailing away into the sunset. Captain Landon is awesome and entertaining, and one heck of a sailor. Such a memorable experience - no regerts!! read more

I am a local in Monterey County and took advantage of the locals special with Captain Dutch. We went out for two hours on Tuesday night and had a wonderful experience. It was great to see beautiful Pacific Grove from the Bay. We enjoyed the entire experience. read more

Great to work with. Gabi and Mariah were friendly, efficient and professional. We rented a boat for a half day. Boat was ready to go, clean and well prepared. Could not have been better. read more

We were approached by the captain as we wandered down the wharf (sorry, I've forgotten his name), and he convinced us and another couple that we could do something amazing today instead of standing around and wondering what it'd be like. We did a 30 minute sail just over to cannery row area with our two kids (3 and 1 years of age), and while it was a bit cramped with lines and stuff all over, captain did a wonderful job of narrating the scenery, telling some history, and sailing us around the bay with our semi-fussy toddler and other folks too. While we saw some otters, sea lions, various birds and neat views, captain did tell us that he had some whales pass under the boat yesterday. We had a great time, and would definitely do it again. read more

The whole experience was amazing. We had reserved the 1 hr family bay cruise in the morning. We had concerns due to our three year old and this was the first time in a sail boat. Fortunately, the weather was perfect and we had a really nice trip with Captain Floyd ( the owner was on vacation). We could sail for some time as well with the motor shut off. We did not see any whales or dolphins but the trip was very refreshing. The captain also allowed our daughter to steer the boat for sometime and she enjoyed it. I would not recommend this trip if you want to see whales/dolphins. The sail boat is definitely more stable compared to the Little mermaid glass bottom boat. Would recommend for toddlers if they don't get sea sick. Will definitely come again. read more

Went on a sunset cruise around the Bay with my mom while she was in town. Captain Dutch was mellow, informative, funny, and super courteous - chatting with the passengers, explaining points of interest. We even saw sea lions, otters, and harbor seals! Mom got a little freaked out by the waves at the beginning, but by the end was enjoying herself. Captain John was also a super nice guy and made setting up our reservation very easy. read more

We had a wonderful time with Captain Takoda. We celebrated our 20 year anniversary along with Holly and Jayson (20 years too) as well as Paul and Lynn (3 yrs). We saw tons of whales, sea lions, seals and otters. Takoda was a blast!!! Well worth the money. read more

An amazing way to see my home (the Monterey Bay, California). I have just returned home from a Vacation which included "Cape San Blas, Florida" So coming from one coast back to another coast, I needed to touch the waters! I took a stroll on the Old Fisherman's Wharf, I filled my lungs with the salty air & enjoyed the sun on my coast. I was approached by a young sailor tugging on my adventerous side to take a short sail on the bay. This would be a first, I've gone Whale watching, swimming and just for nice walks on the beach, but never even considered a sail! After being on the coast of Florida I had such fond memories, so I told myself this would be a great way to connect with the home waters. So I signed the necessary paperwork, met my fellow to be sailors and then our Captain, Dutch! Captain Dutch gave me his hand as I boarded our sailboat (a gentleman from the start). He gave a few instructions, which did come in handy to be forewarned about the boat lifting up on one side & the sail coming acrossed the boat completely. Captain Dutch filled the air on deck with information regarding the bay, the scenic coastal areas & the inhabitants of our Pacific Ocean and Monterey Bay. It was only 20 minutes or so, but it is a new memory and a cherished one. I have promised myself that I will make memories when ever and where ever I can, Life can be short or long but fill it up, we only get one time around 'Live, Love & Laugh, Laugh, Laugh! If you find yourself on Fisherman's Wharf in Monterey, step outside of the ordinary, opt for a sail instead of just a boat ride. There is a difference when you sail, the sea asks much more of you (even if your a passenger and not the Captain). Thanks to Monterey Bay Sailing for a great memory to add to my good stuff! If your going to sail choose Monterey Bay Sailing 5 Stars for sure! read more

Went out on the Bay for a birthday present. Bryce was our Captain and he was GREAT! Super knowledgeable and fun. Loved the experience! read more

Sail Monterey - Just had the best time on the Bay! Bryce was our Captain and he was GREAT! Super knowledgeable and fun. Loved the experience! - Boating Near Me - Monterey, California

The people were SO nice and accommodating to a last minute reservation for a two hour sunset cruise. The water was choppy but the crew was fantastic. Free wine included and no limit there! Really fun and would do it again in a heartbeat! read more