Book Your Next Sailing Adventure Call +1 619-297-7426

Book Your Sailing Charter or Lesson online today

We can customize ANY tour just give us a call 619-297-7426

3hr ADVENTURE DAY SAIL

$89 per person

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Duration: 3hrs

Tour Times: 4 Times a Day

Complimentary chilled beer & wine

Complimentary non-alcoholic beverages

Complimentary snacks

iPhone/Android compatible: Bring your music to make the experience truly yours!

Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

3 Hr Day Sail

3hr SUNSET SAIL

$89 per person

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Duration: 3hrs

Tour Times: 4 Times a Day

Complimentary chilled beer & wine

Complimentary non-alcoholic beverages

Complimentary snacks

iPhone/Android compatible: Bring your music to make the experience truly yours!

Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

Sunset Sail

3.5hr RUM RUNNER SAIL

$125 per person

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Duration: 3.5 hrs

Min 6 Guests Fri, Sat or Sun
Min 4 Guests Mon to Thurs

Tour Times: 11:30am, 4pm, 4:30pm

2 Bar Drinks Included! plus chilled beer and wine, non-alcoholic beverages & snacks

iPhone/Android compatible: Bring your music to make the experience truly yours!
Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

Rum Runner

3.5hr WHALE WATCHING

$90 per person

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Duration: 3hrs

Sailing or Speedboat Whale Watching Tours 

Complimentary chilled beer, wine & non-alcoholic beverages

Complimentary snacks

iPhone/Android compatible: Bring your music to make the experience truly yours!
Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

BOOK ONLINE NOW!

These are just a few of our more popular private charters. Want something totally custom? Give us a call 619-297-7426

ALL DAY GROUP SAILS

$185 per person

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Duration: 6hrs - Min 6 People

Tour Times: 11am or Noon

Complimentary chilled beer and wine

Complimentary non-alcoholic beverages

Complimentary snacks

iPhone/Android compatible: Bring your music to make the experience truly yours!

Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

6Hr All Day

PRIVATE SAILS

$505 for up to 6 people

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Duration: 3hrs

Tour Times: Anytime

Complimentary chilled beer and wine

Complimentary non-alcoholic beverages

Complimentary snacks

iPhone/Android compatible: Bring your music to make the experience truly yours!

Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

Private Sail

CORPORATE CHARTERS

Call for Details

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Duration: Call to customize

Tour Times: Anytime

Complimentary chilled beer and wine

Complimentary non-alcoholic beverages

Complimentary snacks

iPhone/Android compatible: Bring your music to make the experience truly yours!

Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

POWER WHALE WATCHING

$99 per person

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Duration: Call to customize

Tour Times: Anytime

Complimentary chilled beer and wine

Complimentary non-alcoholic beverages

Complimentary snacks

iPhone/Android compatible: Bring your music to make the experience truly yours!

Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

Power Whale Watching

"We love groups of 6 or more and will accommodate you through our bareboat program. Call for details"

Learning to sail is easy with Sail San Diego. Choose a sail below or call us to customize. 619-297-7426

40ft CATALINA LESSONS

$429 for up to 4 students

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Duration: 3hrs

Tour Times: Anytime

Complimentary chilled beer and wine

Complimentary non-alcoholic beverages

Complimentary snacks

iPhone/Android compatible: Bring your music to make the experience truly yours!

Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

22ft CATALINA LESSONS

$295 for up to 2 people

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Duration: Call to customize

Tour Times: Anytime

Complimentary chilled beer and wine

Bottled Water Onboard

Jackets, blankets, hats, binoculars, sunscreens, sunglasses, we have everything you might need

Sail San Diego Gift Cards

Give the gift of Sailing

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Choose your own amount or choose from a list of sails:

  • Adventure Day Sailing
  • Rum Runner Sail
  • Beautiful Sunset Sailing
  • Whale Watching
  • 6 Hr All day sail
  • Lessons
  • Private charters

Please Note : We do not guarantee any particular boat at any time. We do our best to accommodate individual captain requests but we do not guarantee their availability.

Got Questions or a Special Request?

Visit or Call Us

Shelter Island Marina
(behind the Western Island Palms Hotel)
2051 Shelter Island Drive, San Diego

Telephone: (619) 297-7426

Email: info@sailsandiego.flywheelsites.com

We love what we do and it translates through all the technology. So do something "Retro" and give us a call. We'd love to hear from you!

If you get voicemail, there is no automated voice responses gauntlet to get through! The people who answer the phones are involved on the docks as well, so leave a short message and we will get right back to you!

Send Us a Message

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tripadvisor2

What our guests say about Sail San Diego

Don't take our word for it...see what everyone else is saying.

Thanks- We loved it! The trip was wonderful.  The Captain was charming, A perfect afternoon.

"THE BERGMAN FAMILY"

We went whale watching new year's day and had Captain Art Harrison. he was entertaining and informative. it was very foggy so we came back in but Art took us back out even though our tour time was almost over and the fog lifted. We ended up seeing a mother and a calf Grey Whale, as well as a pod of dolphins.

Art was sensational. It was obvious our safety was his first concern but he also really wanted us to have good experience and see whales.
They boat had warm clothing and blankets as well as complimentary drinks and snacks. Wonderful experience.

"YEREMENKO SASKATOON"

Dad & I Out for a Sail

My 74 yr old dad and I took an afternoon cruise with Captain Tim a few weeks ago, and I can’t tell you how wonderful it was, and what a lovely time we all had. My dad used to sail (and race) on the Great Lakes back in the 70′s, so he has has had some experience – and *raved* about Capt. Tim’s expert skippering skills and how fabulous the boat is. In my dad’s words “It’s such a pleasure to to be on board a sailboat when the Captain knows what he’s doing!” As for me, I want to come aboard again to whale watch!

"HEATHER P."

This was a great sailing tour. Captain Art Harrison was very entertaining and knowledgeable, and managed to find a pod of 3-4 young whales, even though it was early in the season. This is a strongly recommended tour!

"COLINGON"

Before you die go sailing with Sail San Diego. Saw some whales, dolphins and were overwhelmed by the beauty of the Pacific Ocean. Had a great time with our Captain. It’s worth the extra money……great clean 40 foot sailboat. Wonderful experience!!!

"MIKE GREEN"

What an amazing time our party of eight had sailing last Tuesday.  The forty foot Catalina, the steady breeze, a great captain and constant laughter . . . the joy of being one with the water, sun and wind was transcendental.

Our friends have emailed from Eureka, CA and said the whole experience was beyond description, “You would have to experience San Diego Sail to understand the embrace of its sacred joy with friends and the earth.”  Sounds mystical but true for all of us Thanks Again.

"ALAN B."

Our second trip out on the bay with Captain Mike. This time we brought our friend Kim for her birthday. We enjoyed the company of another couple from Arkansas in town for a conference. Captain Mike gave us history and highlights of the bay area. Steered us safely beyond the point and back. A great afternoon of sunshine and relaxation. They supplied the snacks, sodas, beer and had glasses for our birthday champagne. Captain Mike told us about the whale watching so we’re sailing again in February!

"KAREN B."

We travel to San Diego every year, around Christmas, and this is the highlight of our trip. The sailing is terrific and the staff is amazing. Everyone is so friendly and knowledgeable.

The various Captains we have sailed with, are so much fun and offer all kinds of information. My son is amazed every time he steps on the boat. This is an awesome company to book with. The Best!

"VARSI M, LAS CRUCES NM"

This was by far the best experience we have had. We've never sailed before and this far exceeded expectations. You definitely get more than what you pay for. The accommodations on the boat were exceptional and the captain was an amazing guide!

We can't wait to come back and do it again. There are a lot of sailing companies, but I doubt you get treatment like this one. The extras were so great. We did have a hard time finding the location and were running late, and they were still so wonderful. Leave early to make sure you find it-it's definitely worth it!! Can't wait to go back to do it again.

"KELLY W. COLUMBUS, OHIO"

We had a first class time on the sail. There was some confusion on the day we were suppose to sail and we offered to sail the next day but they took us the day we thought. We had a great time with the Captain.

The boats are first class and the little extras-free drinks, snacks, extra jackets are a real plus. Everyone at SSD gets an A+ for customer service. We would do it again. We have sailed several times in various locations and this was by far the best.

"ED HE, BROWNSBURG INDIANA"

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2051 Shelter Island Drive, San Diego, CA 92106 | Call +1 619-297-7426 | Email: info@sailsandiego.flywheelsites.com

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