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Top San Diego Sailing Trips

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26 San Diego Sailing Trips

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Did you know?
You can reserve your spot today and pay when you're ready.Learn more

Classic Sailboat Sunset SailDay Cruises

Classic Sailboat Sunset Sail

star-5
Watch the sun set over San Diego during an all-inclusive small-group cruise aboard a classic sailboat. Pass landmarks such as the Maritime Museum, Coronado Bridge, and USS Midway, and look for sea lions, dolphins, and other wildlife around San Diego Harbor on the 2.5-hour cruise.
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  • 2 hours 30 minutes
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  • Free Cancellation
From  
$117.34 
From  
$117.34 
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  • 2 hours 30 minutes
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  • Free Cancellation

Harbor Sailing Experience | Private Sailing Tour in San DiegoDay Cruises

Harbor Sailing Experience | Private Sailing Tour in San Diego

Reviews at a glance
Go sailing on San Diego Bay with up to six friends on this private 2.5-hour sailboat charter. Pass by sights such as the Maritime Museum, USS Midway, Star of India, Coronado bridge, and more. Your captain shares commentary and provides refreshments such as white wine and fruit. You might see Navy ships near the Navy base, and glimpse marine life such as seals and seabirds.
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  • 2 hours
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  • Free Cancellation
From  
$299.00 
per group
From  
$299.00 
per group
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  • 2 hours
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  • Free Cancellation

San Diego Whale Watching CruiseDay Cruises

San Diego Whale Watching Cruise

Reviews at a glance
Go whale watching from San Diego aboard a replica of a historic sailing schooner that won the world’s first America’s Cup sailing competition in 1851. Throughout your cruise, your expert guide shares informative commentary about gray whales, dolphins, and other marine animals, along with details about the US Navy sites you pass as you head out on the Pacific Ocean.
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  • 4 hours 30 minutes
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  • Free Cancellation
From  
$85.00 
From  
$85.00 
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  • 4 hours 30 minutes
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  • Free Cancellation

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Sunset Sailing Experience | Private Sailboat in San DiegoSailing Trips

Sunset Sailing Experience | Private Sailboat in San Diego

Reviews at a glance
Meet your skipper at H & M Landing on Shelter Island, a well-known area of San Diego where some of the best seafood restaurants are located. The captain will meet you there & walk you to the yacht "Green Flash" After brief safety instruction, we'll set sail. Complimentary wine & beer will await you (you are welcome to bring your favorite food & drinks, too - no red wines please). We'll depart from America's Cup Harbor & cruise on San Diego Bay along Point Loma while enjoying the city’s magnificent skyline. You will enjoy a relaxing sail with a glass of good local wine & pleasant company along with a sense of unity with nature that comes with being under sail.
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  • 2 hours
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  • Free Cancellation
From  
$399.00 
per group
From  
$399.00 
per group
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  • 2 hours
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  • Free Cancellation

Affordable Luxury Sailing Tours of San Diego's Bay and Coastal Waterways!Sailing Trips

Affordable Luxury Sailing Tours of San Diego's Bay and Coastal Waterways!

Reviews at a glance
This is a personal tour from one to six passengers that is engaging and diverse tailored to the specific selected tour option(s) Both private and mixed tours are available.
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  • 2 to 3 hours
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  • Free Cancellation
From  
$112.20 
From  
$112.20 
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  • 2 to 3 hours
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  • Free Cancellation

Small-Group San Diego Sunset Sailing ExcursionSailing Trips

Small-Group San Diego Sunset Sailing Excursion

star-5
Sail into the setting sun aboard a Catalina style sailboat during this intimate cruise with a small group. Feel like you have the ship all to yourself on this trip that’s limited to just 12 total guests, watching as the last rays of the sun drop into the glistening waves. Enjoy the included beer, wine, soft drinks and snacks during the ride, as well as jackets and wind gear in case you get cold. You can even plug in your own music to add to the fun. Departure times vary throughout the year. Guest must contact Sail San Diego after purchase for the exact departure time.
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  • 3 hours
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  • Free Cancellation
From  
$107.67 
From  
$107.67 
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  • 3 hours
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  • Free Cancellation

Small-Group San Diego Afternoon Sailing ExcursionDay Cruises

Small-Group San Diego Afternoon Sailing Excursion

Reviews at a glance
Enjoy a sailing adventure on a Catalina-style sailboat with just six people for a comfortable, semi-private experience (or, find five friends and fill up the whole boat). Sail in San Diego Harbor during the day. Sit back and relax to enjoy the water views while enjoying complimentary beer, wine, soft drinks and snacks.
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  • 3 hours
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  • Free Cancellation
From  
$107.67 
From  
$107.67 
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  • 3 hours
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  • Free Cancellation

Sail Stars & Stripes America's Cup Racing Yacht in San DiegoDay Cruises

Sail Stars & Stripes America's Cup Racing Yacht in San Diego

Reviews at a glance
Cruise around San Diego bay aboard an authentic 1992 America’s Cup racing yacht and travel at twice the speed of the average sailboat. The Stars and Stripes USA-11 is one of the fastest and best known America’s Cup racing yachts. It was designed and built to be raced in San Diego, and has been restored to pristine condition. Take a turn at the helm and join in grinding the winches to raise and trim the sails.
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  • 3 hours
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  • Free Cancellation
From  
$133.34 
From  
$133.34 
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  • 3 hours
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  • Free Cancellation

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 GuestsDay Cruises

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests

Reviews at a glance
A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sailing charters and boat tours. Sail San Diego with us. Our sailing charters and boat tours take you on an exciting tour of San Diego Bay. Book a sailing boat charter and stretch out in the San Diego sunshine with a trusty skipper at the helm, Choose from several types of yacht charters, catamaran cruises, sailboats, and powered luxury yachts. A sailing boat tour on San Diego Bay with Pacifica Sailing Charters is the perfect sailing experience for you and your guests. . With over 20 years of boating on San Diego Bay and the waters surrounding the San Diego harbor, our boat charters and sailing boat tours are rated #1 on Google, Yelp, and TripAdvisor...
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  • 2 hours
From  
$80.00 
From  
$80.00 
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  • 2 hours

1/2 day Private Sailboat Adventure in San Diego Sailing Trips

1/2 day Private Sailboat Adventure in San Diego

Embark on your very own private 3, 4, or 6 hour extended San Diego sailing adventure. Enjoy an intimate sail with friends and family. Take in the coastal sights of famous San Diego landmarks from a different vantage aboard a "classic" Slocum styled vessel. She is from an era where sea-going was for exploration of new worlds. These boats were used in the popular "Captain Ron" or "50 FIRST DATES" movies due to their classic lines. Beautiful hand carved old growth Burmese teak, and bronze accents throughout. Great vessel for spectacular photo opportunities, or to venture to times long past. If you choose the open ocean route with a longer duration, you may even get to see some dolphins, whales or other unsuspecting sea-life along the way.
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  • 3 to 6 hours
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  • Free Cancellation
From  
$400.00 
per group
From  
$400.00 
per group
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  • 3 to 6 hours
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  • Free Cancellation

Private San Diego CLASSIC SAILBOAT ExperienceSailing Trips

Private San Diego CLASSIC SAILBOAT Experience

Reviews at a glance
Embark on your own "private" 2-4 hour San Diego CLASSIC sailing Experience. Enjoy an intimate sail with friends and family. Take in the coastal sights of famous San Diego landmarks from a different vantage aboard a "classic" Slocum styled vessel. She is from an era where sea-going was for exploration of new worlds. These boats were used in the popular "Captain Ron" or "50 FIRST DATES" movies due to their classic lines. Beautiful hand carved old growth Burmese teak, and bronze accents throughout. Great vessel for spectacular photo opportunities, or to venture to times long past. If you choose the open ocean route with a longer duration, you may even get to see some dolphins, whales or other unsuspecting sea-life along the way.
...  More
  • 2 to 4 hours
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  • Free Cancellation
From  
$154.67 
Price varies by group size
From  
$154.67 
Price varies by group size
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  • 2 to 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation

San Diego SUNSET Cruise ExperienceSailing Trips

San Diego SUNSET Cruise Experience

star-5
San Diego's best kept secret awaits aboard your private SUNSET cruise on San Diego Bay. See the beauty of downtown cityscape, Embarcadero, Maritime Museum from the ocean which offers a different vantage. Sip cocktails, share a romantic moment, drop a proposal for engagement, or just enjoy a one of a kind San Diego sunset. Flexibility to customize your itinerary to your own preferences, perfect for couples. Enjoy intimate moments with friends and family aboard a "classic" Slocum styled sailing vessel. She is from an era where sea-going was for exploration of new worlds and becoming a rare experience today. These classic designs were used in the popular "Captain Ron" or "50 FIRST DATES" movies due to their classic lines. Beautiful hand carved old growth Burmese teak, and bronze accents throughout. Great vessel for spectacular photo opportunities, or to venture to times long past. A Once-in-a-Lifetime Experience!
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  • 2 hours
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  • Free Cancellation
From  
$341.34 
per group
From  
$341.34 
per group
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

2 Hour San Diego Sunset SailSailing Trips

2 Hour San Diego Sunset Sail

Reviews at a glance
Set sail at one of the best times of day—sunset—during this San Diego Bay cruise. Board a comfortable sailing yacht and cruise along San Diego's coastline, taking in views of the scenic waterfront, military vessels, and historical landmarks. Catch sight of marine life and enjoy spectacular photo ops. Gorgeous sunset views and Champagne makes this tour a great choice for couples or travelers celebrating a special occasion.
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  • 2 hours
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  • Free Cancellation
From  
$95.00 
From  
$95.00 
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  • 2 hours
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  • Free Cancellation

Private Sailing Charter on San Diego BayDay Cruises

Private Sailing Charter on San Diego Bay

star-5
Sail the lovely waters off San Diego on a private yacht charter. The itinerary is up to you, or your captain can suggest some places to go. You can opt for a whale watching tour (seasonal), or lay anchor and go for a swim. If you prefer, choose a bay tour; seeing the sights like the Hotel del Coronado, Point Loma Lighthouse, Tijuana, and the San Diego skyline.
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  • 2 hours 30 minutes
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  • Free Cancellation
From  
$410.00 
per group
From  
$410.00 
per group
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  • 2 hours 30 minutes
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  • Free Cancellation

Private San Diego Day Sailing AdventureSailing Trips

Private San Diego Day Sailing Adventure

star-5
Head out onto the waters off the coast of San Diego for a private sailing adventure. Charter your own boat and bring your group of up to six to take in San Diego’s sights from the water. Enjoy a fully customizable experience—just chat with your skipper about your preferences for your sail. Feel free to bring your own wine without worrying about a corkage fee and enjoy complimentary refreshments onboard.
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  • 3 hours
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  • Free Cancellation
From  
$314.27 
per group
From  
$314.27 
per group
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  • 3 hours
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  • Free Cancellation

Luxury Catamaran Sailing Charter Sailing Trips

Luxury Catamaran Sailing Charter

star-5
Set sail from San Diego on your own private sailboat cruise that can accommodate up to 12 people. Depart from the Hyatt Regency Mission Bay and glide out to the Pacific Ocean, passing landmarks like Sunset Cliffs Natural Park, Pacific Beach, La Jolla, and Ocean Beach Pier. Get great views of southern California’s landscape and wildlife, and feel free to bring your own refreshments and music to customize your cruise.
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  • 2 to 8 hours
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  • Free Cancellation
From  
$1,100.00 
per group
From  
$1,100.00 
per group
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  • 2 to 8 hours
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  • Free Cancellation

Bachelorette Sailing Party on San Diego Bay up to 12 GuestsDay Cruises

Bachelorette Sailing Party on San Diego Bay up to 12 Guests

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea life including Sea Lions, Dolphins and Whales. Whether you need a classic sailboat or catamaran for your Bachelorette Party, we can provide a private catamaran that is roomy, comfortable and stable. Much heavier than traditional boats today, Sea Esta will provide a steady, smooth sail no matter what the conditions. This large and stable catamaran is perfect for sightseeing around San Diego Bay and the perfect bachelorette party yacht for you and your guests.
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  • 2 hours
From  
$1,200.00 
per group
From  
$1,200.00 
per group
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  • 2 hours

Sunset Sailing Tour of San Diego Bay up to 6 GuestsDay Cruises

Sunset Sailing Tour of San Diego Bay up to 6 Guests

Reviews at a glance
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailing charters and boat tours take you on an exciting tour of San Diego Bay. Book a sunset sailing boat charter and stretch out in the San Diego sunshine with a trusty skipper at the helm, A sunset sailing boat tour on San Diego Bay with Pacifica Sailing Charters is the perfect sailing experience for you and your guests. With over 20 years of boating on San Diego Bay and the waters surrounding the San Diego harbor, our sunset boat charters and sunset sailing boat tours are rated #1 on Google, Yelp, and TripAdvisor.
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  • 2 hours
From  
$136.00 
From  
$136.00 
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  • 2 hours

Private 2 Hour Day SailSailing Trips

Private 2 Hour Day Sail

Sail the magnificent San Diego Bay on this private cruise aboard a restored 1934 sailboat. A personalized alternative to crowded group outings, the cruise can be tailored to you; help sail the boat, or just relax on deck enjoying included drinks and snacks. With service from a captain and two crew members, you’ll cruise past San Diego landmarks from the Coronado Bridge to the Embarcadero.
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  • 2 to 4 hours
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  • Free Cancellation
From  
$920.00 
per group
From  
$920.00 
per group
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  • 2 to 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation

San Diego Small-Group SailSailing Trips

San Diego Small-Group Sail

Reviews at a glance
This 2 to 2.5 hour small-group sail seats up to 6 people. You can relax comfortably or invite a group of friends to sail along Point Loma in San Diego. Your guide will gracefully glide passed beautiful views and landscapes near San Diego's skyline for you to enjoy the breath talking scenery. If interested, you can also learn the basics of sailing while gazing at the glistening water and SD's spectacular scenes. Come relax and enjoy with your choice of white wine or beer, (pls specify when booking).
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
$133.32 
Price varies by group size
From  
$133.32 
Price varies by group size
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Superior SailSailing Trips

Superior Sail

Enjoy views of the Midway, Star of India, Coronado Bridge, and wildlife as you sail through San Diego Bay on our Superior Sail Tour.
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  • 3 hours
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  • Free Cancellation
From  
$1,277.92 
per group
From  
$1,277.92 
per group
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Sailboat Yacht Charter on San Diego Bay Up To 27 GuestsSailing Trips

Sailboat Yacht Charter on San Diego Bay Up To 27 Guests

Although it says only 15 guests upon check out, we actually can take up to 27 guests on this cruise, and the pricing reflects this amount of guests. Sailing San Diego Bay is an awesome way to spend an afternoon in beautiful San Diego. Whether you want to go on an exciting adventure where you take the wheel, or if you just prefer to stretch out in the San Diego sunshine with a trusty skipper at the helm, Pacifica Sailing Charters provides fun and exciting boat tours for the perfect sailing experience for you. There’s plenty of room to explore sailing san diego and everyone gets a chance at the wheel if they feel adventurous on these sailing charters located in san diego. With over 20 years of boating and sailing on San Diego Bay and the waters surrounding the San Diego harbor, we excel at ensuring each sailing tour, boat charter and catamaran cruise and sailing lesson is a memory you will cherish for a lifetime.
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  • 3 hours
From  
$3,173.34 
per group
From  
$3,173.34 
per group
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  • 3 hours

The 3 Hour TourSailing Trips

The 3 Hour Tour

star-5
A fully restored 70 foot private sailing ship for your own private group of upto 12. We can comfortably accommodate 12 passengers, we have a bluetooth stereo, and a immaculate interior belowdecks. There is a clean restroom belowdecks and we have a tremendous crew. You will have a Captain and two crew on board to assist with all the sailing, answer any questions, and to assist you in anything needed. If you would like you can assist in hoisting and trimming sail, or, you can sit back and enjoy a cold beverage and some salami, cheese, and crackers.
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  • 3 hours
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  • Free Cancellation
From  
$1,349.34 
per group
From  
$1,349.34 
per group
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private Introduction to Sailing Lesson & TourSailing Trips

Private Introduction to Sailing Lesson & Tour

This is a combination lesson & tour of the bay which gives guests the unique opportunity to learn about sailing and see the sights. It's perfect for someone who has considered learning how to sail but also wants to take friends or family members on a sightseeing tour.
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  • 2 hours 30 minutes
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  • Free Cancellation
From  
$399.00 
per group
From  
$399.00 
per group
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  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Sailing Trips in San Diego?

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