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Small-Group San Diego Afternoon Sailing Excursion

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2 travelers
Set sail from San Diego on this small-group sailing tour! This three-hour adventure on a Catalina-style sailboat is limited to just six people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the complimentary beer, wine, soft drinks and snacks as you soak in the warm sun with the glistening city lights behind you.
You'll start at
2646 Shelter Island Dr
2646 Shelter Island Dr, San Diego, CA 92106, USACruise departs from the base of Shelter Island on Point Loma. Look for the walkway between San Diego Marine Exchange and Intrepid Boat Works
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  • 1
    Harbor and Shelter Islands
    Stop: 3 hours -
    See details
  • 2
    Sail San Diego
    Stop: 3 hours - Admission included
    See details
    Pass by Point Loma
    Pass by Coronado Bridge
    Pass by Coronado Island
    Pass by USS Midway Museum
    Pass by Seaport Village
    Pass by San Diego Convention Center
You'll return to the starting point
  • Get amazing views of San Diego Harbor on an afternoon sailing tour
  • Max of six people for a semi-private tour (or book the boat with five friends)
  • Enjoy amenities such as polar fleece jackets, binoculars, and sunscreen
  • Toast your voyage with beer, wine, and soft drinks, included in tour
What to Expect
Depart from Shelter Island midday and set sail on the Beautiful San Diego Harbor with a max of six passengers for a personalized cruise. Enjoy fantastic views of the city skyline and coastal landmarks while an experienced crew navigates the Catalina-style sailboat through harbor traffic. If you like, set the scene by bringing your own music to play over the boat’s surround-sound system. Throughout the cruise, enjoy included snacks and sip your choice of beer, wine, or soft drinks from the onboard bar. Stay comfortable with amenities such as sunscreen and polar fleece jackets and wind gear for cooler days. Keep an eye out for native California marine life such as seals and pelicans using provided binoculars.
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Important Information
Departure Point
2646 Shelter Island Dr, San Diego, CA 92106, USA
Return Details
Returns to original departure point
  • 3-hour sailing cruise
  • Snacks
  • Complimentary beer, wine and soft drinks
  • Entry/Admission - Sail San Diego
  • Hotel pickup and drop-off
  • Gratuities
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Additional Info
  • Confirmation will be received at time of booking
  • Please note: Each booking is limited to six (6) passengers
  • You MUST call the local operator to confirm your departure time after booking. Departure times vary throughout the year. Guest must contact Sail San Diego after purchase for the exact departure time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveler rating
  • 122
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Popular mentions
The Captain was great, full of lots of information about what we were seeing. The boat was fully prepped for all of our potential needs.
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The cruise was absolutely tranquil and breathtaking. Captain Frank was really friendly. Totally recommend.
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Friendly, fun, great experience. Highly recommend. Forecast was for bad weather, and THEY reached out to ME to fit me in before the storms hit.
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The staff at Sail San Diego was friendly and helpful. They offered sunscreen and sun glasses if you forgot your own. Our Captain answered all our questions about the boat and his background in sailing. All this with a warm sun and gentle breeze made us not want to go back to
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Our sailing experience with Captain Theo was extremely memorable. Theo was a very accomplished sailor and made the trip a blast for everyone. One person in our party was initially uncomfortable sailing yet she had a great time. Our tour was not a putt putt around the harbor — it
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Response from Sail S, Owner at Small-Group San Diego Afternoon Sailing Excursion
Responded 13 Nov 2019
Thanks for your awesome review. Theo is one of our best. We believe in actually sailing. Go figure ;-) We hate a putt putt around the bay. They have big boats with 100 passengers on board and make you pay for everything, for that. We call that "going to sea with the unwashed public". tell your friends of the great time you had and we hope to see you back for whales watching season. The best time? Jan 5 to Feb 20th.
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About the operator
By: Sail San Diego
Lisa U
Sail whale watching
Awesome whale watching day with Captain Greg! I will always sail to view whales and Sail San Diego was incredibly
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Best Birthday Gift Ever!
Fantastic sailing adventure! Captain Frank was a great host. We were one of two couples on the boat. Saw whales
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Chattanooga, Tennessee
Intimate trip
We enjoyed our trip. Captain was great, ship was in great shape, we enjoyed just sailing. The fact we saw several
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Sail San Diego is Beautiful and Fun!
Captain Frank greeted us at the gate and took us to the sail boat. I needed assistance, being a physically limited
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Yuma, Arizona
Exactly as advertised
This is a great deal for a sail. We went it was cold windy and rainy. Despite all of that, we had an okay time.
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Winter Park, Florida
Great time on the water without the crowds
We've been on lots of whale watching cruises and this one was unique. The sailboat experience and the small number
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Dan P
Elgin, Illinois
Great whale watching experience!
Happy Captain Greg was the best! Smooth sailing and Gray Whales and sea lions. The day was fantastic!
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Dan P
Elgin, Illinois
Spectacular day on the Pacific ocean!
We had the great luck to book a sailing trip with Happy Captain Greg. The day was beautiful and sunny , Captain
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Carmel, Indiana
Overall Disappointed
We did a morning whale watching sail on January 4, 2020. Pros: -Small group; only had two other people in
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Best Birthday Surprise Ever
I booked this trip as a surprise birthday gift for my boyfriend based on all the rave reviews. It certainly did
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Key Details
  • Duration: 3h
  • Mobile Ticket Accepted
  • Instant confirmation
  • Languages Offered: English
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