We loved everything - absolutely everything - about our private sailing trip with Captain Paul. What a special and memorable way to experience Monterey!! It was worth the small extra cost to go private, have the boat for just our family, and get to know Paul. My kids and I talked about this sail as one of the highlights of our weeklong trip! We saw a beautiful sunset, got to stop for pictures, and had fun talking and laughing and learning about sailing from Captain Paul. Paul is knowledgeable, down-to-earth, a comfortable and confident captain, and just a pleasure to spend a sail with. He has a great laugh and sense of humor. He even was good-natured when I spoiled my Izze sparking drink all over the boat! We will 100% take another trip with Sail Monterey next time we visit the area!!! read more

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My family of 5 took a last minute private 1.5 hour sunset cruise and couldn't have had a better time. Captain Tiki was amazing, had a great sense of humor with the kids, and made the tour very fun. While it would've been great to be on the water longer, an hour and a half was still plenty! This was the highlight of our summer in Carmel/Monterey! read more

Our company recently booked a charter for our employees, and to say we had a wonderful experience would be an understatement--everyone absolutely loved it! Captain Vince was incredible. He was attentive, informative, and extremely kind. We felt comfortable and safe throughout the entire trip. Our employees couldn't stop raving about the experience, and many shared that they plan to book their own charters in the future for their families. It was such a peaceful and beautiful time out on the water--truly a memorable experience that will stay with you. Thank you, Captain Vince, for making our trip so memorable. You were awesome! read more

We loved the sunset cruise we recently took with Captain Vince. The weather was perfect, the scenery amazing and we were taken care of with blankets (if needed), drinks and snacks. This was a birthday gift to my husband, and he had a great time. We also thoroughly enjoyed the music selection on board. We will be back. read more

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Love the Sail Monterey crew! Everyone we have met is fun, knowledgeable, and welcoming! Customer service is super and the boats are clean and well maintained. We joined the club, have been on multiple sails, completed the ASA 101 Certification and are hooked! Looking forward to learning more, joining in the sailing events, and getting to know more people! read more

We took a 1.5 hour trip in October and were able to get up close to otters, seals, and dolphins. The employee managing our trip was very kind and attentive, and we got complimentary drinks and blankets. Shaded and open seating options! read more

Sail Monterey - Location - Boating Near Me - Monterey, California

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This is the 4 th time we've sailed with Sail Monterey and it's always amazing. Capt Vince was informative and the sailing was smooth. Sail Monterey is one of our must do places each summer read more

We booked private sail to scatter family ashes. Was a beautiful day and the staff were friendly, welcoming amd accommodating. Kiwi was our captain and she was committed to a safe, comfortable and special time for us. A nice surprise was being presented with a certificate that identifies the coordinates of where the ashes were scattered. read more

Sail Monterey - Getting ready to sail - Boating Near Me - Monterey, California

Kiwi is an amazing person. Our 3 yr old daughter got sick on the boat and Kiwi was there to help as if she was family. I can't say enough kind things about her. We saw thousands of sea lions and MANY whale sightings. I would pay double what we paid for our private whale sighting. P.S. -kiwi ask for a raise or a commissioned fee! read more

Sail Monterey - Boating Near Me - Monterey, California

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This was my fifth time sailing with Sail Monterey, and they never disappoint. No one else signed up for the Happy Hour Sunset trip and Captain Vince still took us out for what turned into a beautiful private sail. That kind of dedication and customer care is rare. He was also my instructor for the Introduction to Sailing class, and he is consistently professional, smart, patient, and kind. I always feel safe and well taken care of on board. I absolutely love this company and will continue to sail with them again and again.! read more

Loved it! Was such a great experience! Weather was not cooperative but either way had a great time! Such an amazing experience! Definitely recommended! read more

Sail Monterey - Boating Near Me - Monterey, California

My son and I had a weekend sail on a catamaran, an intro sail, completed ASA 101 and had a few intro and club sails with Sail Monterey, and rented a boat for a sail with my kids. We love sailing in Monterey Bay. The Sail Monterey team is awesome. We a learning a lot. The instructors are amazing. I highly recommend Sail Monterey. read more

Sail Monterey - Boating Near Me - Monterey, California

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Great sailing with drinks and good music, thank you Captain Vince for doing a fantastic job, you're my hero. read more

Sail Monterey - Sunset! - Boating Near Me - Monterey, California

Sometimes, it's fun to pretend to be rich. It was one of those hot days, and I wanted to sail! Unfortunately, I don't have a boat. Fortunately, I went online and found Sail Monterey, which offers affordable Catamaran Cruises. I thought it would be a perfect girl time with my daughter! The boat was beautiful! We were the first ones to check in, so we were the first ones on the boat. Whew! These three ladies cut in front of us in line. I was so relieved when the captain called us first! And it turned out the ladies were last. However, the boat was nice and spacious. Only eleven people signed up at 3:00. Free drinks and snacks were a plus! Beer, wine, juice, and water were available. I enjoyed my Italian White Wine, and my daughter enjoyed her Fizzy Grapefruit Juice. For one hour and fifteen minutes, the captain took us far into the ocean. I'm not sure if it was north or south, but it was awesome feeling the breeze on my face. We saw porpoises, whales, and sea lions. I was bummed I couldn't get a picture of the purposes and whales. They were so fast! But it was cool seeing them peeping out and then diving into the water. It was a wonderful day. My daughter couldn't stop thanking me. I was grateful, too. I'm glad I thought of this activity rather than spending it at home in 97-degree weather. Thank you, captain and Sail Monterey! read more

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We booked a private afternoon with Sail Monterey for my mothers celebration of life. They provided drinks and light snacks along with a fantastic level of professionalism and hospitality. Planning and attending a celebration of life is never easy nor enjoyable, however they did everything in their power to make this as easy as possible on us. We released (biodegradable) wreaths from the boat as my mom's favorite music played. She would have absolutely loved it every minute of it. read more

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We went on a 1 hour tour on the catamaran, it was a great trip! We saw sea otters, seals, sea lions, dolphins and lots of birds. Captain Kiwi did a fantastic job running the boat and keeping all the guest happy. We highly recommend this company. read more

Sail Monterey - Sea otters. - Boating Near Me - Monterey, California

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Such a beautiful sunset cruise and we'd definitely do it again. The captain was very friendly and complimentary drinks and blankets were provided. read more

Sail Monterey - Boating Near Me - Monterey, California

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They are amazing ! Must go ! They provided drinks and light snacks along with a fantastic level of professionalism and hospitality. Our captain was super awesome , and she even assisted me when I got sea sick, that was so kind of her! I truly appreciate it ! read more

Cannot say enough positive things about the happy hour cruise with Kiwi - it was the perfect taste of getting out on the water, great value, and she was an absolute delight! I had a friend visiting and we both agree this was the highlight of our trip. The boat was super comfortable as well. Perfect activity to pop into your afternoon for locals and tourists alike. 10/10!! read more

Took a sail with Monterey Sail on memorial weekend. Loved it. Not our first time with them. Captain Paul is a really nice guy and was so accommodating. There was a good breeze so the sail went out and we quietly and calmly cruised the bay. A beer, soda, or seltzer is part of the package offered. We will be back again. Thank you Captain Paul! read more

Captain Paul works hard, yet making everyone feel welcomed and accommodated seems effortless for him. He's one of the best captains I know--deeply knowledgeable, charismatic, and someone who inspires confidence no matter the weather. read more

Sail Monterey - Boating Near Me - Monterey, California

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Complementary drinks! Local craft beers! My wife and I got Captain Paul, We did the 11am sail and the weather was perfect. Highly recommend, we will be back for the sunset sail for sure! Thank you Sail Monterey for a wonderful morning! read more

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The trip was beautiful and relaxing. The hosts catered throughout the sailing with snacks, drinks, and blankets. A must!! read more

Great fun on the Bay. Super Captain with wonderful local knowledge. I recommend everyone take a trip. On our trip we saw Dolphins and even a mother otter with her baby. read more

We had a fantastic sail with Paul. It was supposed to be a sunset catamaran cruise and it actually got cancelled the day we were supposed to cruise, so they called me 2 hours before and let me know it would be rescheduled for the following day. I appreciated the heads up for planning purposes! The next day we sailed and I'm so glad it was saved for that day because we saw a baby humpback whale! God snuck in a little surprise for us. Thanks, Sail Monterey!! read more

Really excellent! Vince was our Captain. He gave us information and offered us beverages but was very laid back. Beautiful day with not a lot of people on a Tuesday in early October. Highly recommend. read more

Great trip. We were lucky to see a pod of dolphins and a sail boat race. And enjoyed a White Claw. read more

Sail Monterey - Boating Near Me - Monterey, California

For what it is, it is quick and informative. Positive vibe and a good time for the price. Staff is friendly.

We had an amazing sailing with Sail Monterey! Great day and Captain Tiki was the Best! We highly recommend the event!

The sunset cruise was AMAZING. The directions for the meet up point and instructions on what to wear was clear and very helpful. The crew and our captain, Paul was very friendly and knowledgeable about sea life in the bay. The drinks were flowing and we got many cute social media worthy pics. If we were from the local area, we would definitely come back! Must do! read more

Fabulous experience, luff to leech. Reservation was easy; check-in smooth; safety and boat overview clear, concise and complete. I left the dock with confidence and had a really nice sail in the bay. read more

Such a fun and beautiful experience. The staff is wonderful and knowledgeable. We had a great time and will always remember this experience. read more

Sail Monterey - Boating Near Me - Monterey, California

Life changing! We will remember it forever!! Thank you for this incredible memory. Whales all around us and my son said they were from God. Truly unforgettable and such a blessing to witness God's creation. read more

This is the very best way to see Monterey bay. Capt Paul is great and a perfect guide to the area. This is our "can't miss" experience each summer when we visit. I HIGHLY RECOMMEND Sail Monterey read more

Did a daytime private sailboat trip (up to a party of 6) and had such a blast. 4 adults and 2 kids under 3. We felt safe and Dan was a friendly captain. Definitely planning to go again. read more

Sail Monterey - Baby viewing from the boat - Boating Near Me - Monterey, California

Ahoy matey- Cap'n Paul, Ivy and Puppy Dog Coconut were the MOST amazing people we meet in Monterey. They were so kind and caring! If you are looking to be surrounded by phenomenal people and having a wonderful experience look no farther! These folks got your back. read more

These guys are awesome! I would definitely recommend taking a cruise with Sail Monterey. We took an ASA 101 course from Captain Paul who was a fantastic, thorough and patient teacher. They also do shorter "intro to sailing" classes which are super accessible and fun for those curious to learn what sailing is all about. If you don't want to learn to sail yourself, they have tons of pleasure cruises where you can see whales, have a beer and just relax. Go check them out! read more

Sail Monterey - The Peninsula from the boat - Boating Near Me - Monterey, California

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Just completed ASA 101 with Kiwi as our instructor. I am about to take an extensive sailing trip and wanted to hone my sailing skills and knowledge before doing so and this was a perfect resource. Can't recommend this group enough. They're as approachable as they are knowledgeable. I had a great afternoon of sailing for my intro class with Vince on their racing boat Tardis, and Kiwi was an amazing instructor for the three days of 101. Classes are small and everyone had a lot of individual attention and instruction. Kiwi was extremely patient and made sure everyone felt comfortable and confident in their skills. Would absolutely recommend to anyone curious about sailing regardless of experience level. read more

If you're looking a fun sunset sail around the beautiful Monterey Bay, or are interested in learning how to sail, Sail Monterey is definitely the place to go. My wife and I took a sunset catamaran cruise with Captain Paul, and we loved it so much we decided to take sailing classes. We just finished our ASA 101 course and the quality of instruction we received from Captain Paul was top notch. He is friendly, patient, knowledgeable, and has a great sense of humor, all of which make the learning process fun and enjoyable. Go check out Sail Monterey! read more

Captain Paul is outstanding. My wife and daughter loved every minute of the cruise! Sail Monterey is a must do! Great for families, couples, or anyone looking for a beautiful experience in Monterey Bay. read more