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Cast Off Sailing

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San Diego, CA, USA
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About Cast Off Sailing
Enjoy sailing San Diego Bay aboard our Beneteau Oceanis 40. We offer private and public charters for small groups with a Captain. Sunset sail, day sailing adventure, or seasonal whale watching cruises are available. We encourage our guests to take an active role sailing the vessel or sit back, sip on some win and relax while we sail effortlessly through the water.
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Hours Today: 9:00 AM - 7:00 PM
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Cast Off Sailing
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Reviews (117)
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All reviews captain aaron sunset sail san diego bay beautiful sailboat sailing adventure great captain relaxing afternoon coronado bridge a lot of fun wheel whales midway
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1 - 10 of 117 reviews
Reviewed 4 weeks ago

Book this charter - Aaron is a great captain/owner. This is such a personal experience instead of the larger charters. We're so thankful we found Cast Off! From the minute we met Aaron, we knew it would be a great time. He's friendly and personable...More

Date of experience: November 2019
Thank Sarah I
Reviewed October 2, 2019

What a way to cure a case of the Monday blues! It was an absolute pleasure to sail aboard Captain Aaron's vessel. Wine, chocolates, and a gorgeous tour of San Diego's pristine waters were just what we needed to relax! The tour includes historic San...More

Date of experience: September 2019
Thank SrfingYeti
Reviewed July 17, 2019

The owner of the boat, Aaron answered when I called. I booked over the phone via credit card and he sent me confirmation via email. The harbor is near the airport and easy to get to. Aaron's boat is immaculate and beautiful. There were 3...More

Date of experience: July 2019
Thank Susan I
Reviewed July 15, 2019

We had an amazing sunset cruise with Aaron for our honeymoon. We were lucky enough to have the boat to ourselves, which was an amazing bonus. Aaron was great company and gave us a gorgeous tour. Wine and chocs a lovely bonus! Highly recommend.

Date of experience: July 2019
Thank H3415SNalicep
Reviewed May 10, 2019

Relaxing afternoon sailing in the bay. My friend and I totally enjoyed our sale with Aaron. Highly recommend. Aaron is a great captain and a lot of fun to sail with.

Date of experience: April 2019
Thank Dufferdog
Aaron B, Owner at Cast Off Sailing, responded to this reviewResponded May 15, 2019

Thank you for the wonderful review, I hope to see you on board again sometime! Captain Aaron

Reviewed April 6, 2019

Aaron was an absolute delight to work with! I called first thing in the morning with the hopes of setting something up day of for a sunset cruise proposal (I know, I know, lack of planning…). Aaron picked up the phone immediately and talked me...More

Date of experience: March 2019
Thank Tim P
Aaron B, Owner at Cast Off Sailing, responded to this reviewResponded April 9, 2019

Congratulations Tim! I'm glad the evening went well, and even happier to hear she said yes! Captain Aaron

Reviewed April 4, 2019

I've sailed before but wanted to relax and let my young family enjoy the sailing experience. Captain Aaron was incredibly confident, professional, accommodating and easy going. Especially towards my 2 young daughters. The bay was beautiful, we saw Sea Lions, submarines, aircraft carriers lots of...More

Date of experience: March 2019
Thank PaulBann
Aaron B, Owner at Cast Off Sailing, responded to this reviewResponded April 9, 2019

Hi Paul, I'm so glad your family enjoyed sailing, I enjoyed having you all on board! Looking forward to doing it again soon. Captain Aaron

Reviewed March 13, 2019

I did research online around San Diego since I knew I wanted to propose out on a sailboat. I looked at some other options that looked cheaper but settled on Aaron because of the reviews and I'm glad I did! He was very responsive and...More

Date of experience: March 2019
Thank MarkD4988
Aaron B, Owner at Cast Off Sailing, responded to this reviewResponded March 28, 2019

Thank you Mark, it was a pleasure to have you two on board, and congratulations!!

Reviewed February 27, 2019 via mobile

Captain Aaron was professional, calm, knowledgeable, friendly and super accommodating to our family. We had a relaxing afternoon with another couple from NYC shared stories and laughs. Casually he took us to see a grey whale that was spotted in the bay and even shared...More

Date of experience: February 2019
Thank Sail W
Reviewed November 21, 2018

Second time sailing with Aaron, first doing the sunset sail. Had another awesome time and the nighttime views of San Diego are spectacular. Aaron is a laid-back as they come. Have done a few sailing trips with a few different outfits in San Diego and...More

Date of experience: November 2018
Thank KJR45K
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