San diego Sailing

Explore top sailing experiences in San Diego including harbor tours, whale watching, sunset sails, and private charters. Book your adventure today!

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2-Hour Morning Sail in San Diego

2-Hour Morning Sail in San Diego

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour ad

★ 4.9 (38)
From $95.00 USD
2-Hour Private Sailing Experience in San Diego Bay

2-Hour Private Sailing Experience in San Diego Bay

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's wo

★ 5.0 (183)
From $675.00 USD
2.5-Hour Small-Group Catamaran Sail with Drinks

2.5-Hour Small-Group Catamaran Sail with Drinks

Experience the ultimate San Diego sailing adventure with a spacious catamaran cruise, offering your choice of a relaxing daytime sail or a breathtaking sunset s

★ 5.0 (356)
From $119.00 USD
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. 2.5 hour tour len

★ 5.0 (112)
From $119.00 USD
Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Bachelorette Sailing Party on San Diego Bay up to 6 Guests

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destr

★ 5.0 (1)
From $800.00 USD
City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour

Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such as Seaport Vi

★ 4.5 (570)
From $38.33 USD
Daytime Sailing Along San Diego's Skyline

Daytime Sailing Along San Diego's Skyline

Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Sa

★ 4.9 (157)
From $99.00 USD
Deluxe Day Sail in San Diego

Deluxe Day Sail in San Diego

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a

★ 5.0 (79)
From $119.00 USD
Deluxe private Sunset & Day Sail

Deluxe private Sunset & Day Sail

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic la

★ 5.0 (3)
From $714.00 USD
Deluxe Sunset & Day Sail Small Group

Deluxe Sunset & Day Sail Small Group

Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the

★ 5.0 (352)
From $119.00 USD
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying th

★ 4.9 (208)
From $119.00 USD
Private Couples Sunset Sailing Tour in San Diego

Private Couples Sunset Sailing Tour in San Diego

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 differ

From $800.00 USD
Private Day Sail in San Diego up to 12 guests

Private Day Sail in San Diego up to 12 guests

This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San Diego landmarks along downtown where we

★ 5.0 (68)
From $487.50 USD
Private Morning Sail in San Diego up to 12 guests $975

Private Morning Sail in San Diego up to 12 guests $975

This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing

★ 5.0 (33)
From $487.50 USD
Private Sailing Charter on San Diego Bay

Private Sailing Charter on San Diego Bay

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing

★ 4.9 (50)
From $525.00 USD
Private Sailing Tour -2 Hour (Up to 12 Passengers)

Private Sailing Tour -2 Hour (Up to 12 Passengers)

Christened in 1934, Cloudia is a beautifully restored, rare example of a classic Norwegian double ended ketch. Inspired by the original designs of famed naval a

From $1,200.00 USD
Private Sunset Sail on San Diego Bay with Champagne

Private Sunset Sail on San Diego Bay with Champagne

What makes this experience truly unique is the combination of refined European luxury and a relaxed, intimate atmosphere. You will be sailing aboard a beautiful

From $975.00 USD
Sailing Charter on san diego bay for up to 6 guests

Sailing Charter on san diego bay for up to 6 guests

While sailing on your private boat tour on the San Diego bay, enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarine

★ 5.0 (2)
From $800.00 USD
Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests

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

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 typ

★ 4.0 (3)
From $800.00 USD
San Diego Bay Sailing Tour

San Diego Bay Sailing Tour

San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing

★ 5.0 (17)
From $135.00 USD
San Diego Harbor Cruise on the Largest Catamaran in San Diego

San Diego Harbor Cruise on the Largest Catamaran in San Diego

Enjoy a San Diego harbor cruise on San Diego's largest and newest catamaran yacht. We provide our guests with a unique way to splash by all of the amazing San D

★ 4.9 (55)
From $55.00 USD
San Diego Private Yacht Charter on a Classic Sailboat

San Diego Private Yacht Charter on a Classic Sailboat

Book the entire boat for your group — no strangers, no shared space, just your crew and Captain Phil on San Diego Bay. Liberty is a classic 41-ft Friendship slo

★ 5.0 (4)
From $810.00 USD
San Diego Sailing 4 Hours Wildlife Adventure Sign on Activity

San Diego Sailing 4 Hours Wildlife Adventure Sign on Activity

We are a hands on sailing adventure we encourage our guests to participate. Guests who chose to relax and enjoy the scenery and vibe are welcome to do so, you m

From $229.00 USD
San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Capta

★ 5.0 (85)
From $125.00 USD
San Diego Whale Watching Cruise

San Diego Whale Watching Cruise

Each year approximately 20,000 gray whales migrate from the Bering Sea to the lagoons of Baja California and back again. Come witness this amazing journey off t

★ 4.4 (720)
From $54.00 USD
San Diego Whale Watching Cruise

San Diego Whale Watching Cruise

Whale watching season is all year long in San Diego! Our team at Next Level Sailing provides the optimal experience with guides so experienced we received a 100

★ 4.8 (2536)
From $85.00 USD
San Diego Wild life Sailing Adventure Private

San Diego Wild life Sailing Adventure Private

We are a hands on sailing adventure we encourage our guests to participate. Guests who chose to relax and enjoy the scenery and vibe are welcome to do so, you m

★ 5.0 (2)
From $449.00 USD
San Salvador Spanish Galleon Adventure Day Sail with General Admission

San Salvador Spanish Galleon Adventure Day Sail with General Admission

Your 4-hour San Salvador Adventure Day Sail is your opportunity to step back into time as you step on board this 16th century Spanish galleon. The San Salvador

★ 4.8 (5)
From $85.00 USD
Small-Group San Diego Afternoon Sailing Excursion

Small-Group San Diego Afternoon Sailing Excursion

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five f

★ 4.9 (564)
From $116.00 USD
Small-Group San Diego Sunset Sailing Excursion

Small-Group San Diego Sunset Sailing Excursion

Set sail from San Diego on this small-group sailing tour on a sunset sail on the open ocean. This three-hour adventure on a Catalina sailboat is limited to six

★ 4.9 (639)
From $127.00 USD
Spectacular Afternoon Sail on San Diego Bay

Spectacular Afternoon Sail on San Diego Bay

A unique two-hour sailing Experience aboard our 35-foot sailboat, Luna. Limited to six people. Watch for playful dolphins, sea lions, and pelicans. Get hands-on

★ 5.0 (22)
From $120.00 USD
Spectacular Sunset Sail on San Diego Bay

Spectacular Sunset Sail on San Diego Bay

A rare sunset sailing adventure aboard our 35-foot sailboat, Luna: small group limited to six people, local captain sharing stories, hands-on sailing, and unfor

★ 5.0 (39)
From $120.00 USD
Sunset Sail Along the San Diego Skyline

Sunset Sail Along the San Diego Skyline

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water.  Our San Die

★ 4.9 (652)
From $99.00 USD
SunSet Sail in San Diego Private

SunSet Sail in San Diego Private

We are a small charter company we offer a personal experience that is flexible to our guests needs. Sailing Is our specialty, we always try to sail, shut down t

From $399.00 USD
Sunset Sailing Cruise on San Diego Bay | Champagne Included

Sunset Sailing Cruise on San Diego Bay | Champagne Included

What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group tour. You

★ 5.0 (1)
From $199.00 USD
Sunset Sailing Tour of San Diego Bay up to 6 Guests

Sunset Sailing Tour of San Diego Bay up to 6 Guests

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 differ

★ 5.0 (1)
From $800.00 USD
Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Top Rated San Diego Sunset Sail Classic Yacht 6 Guests

Skip the crowded tour boats. Liberty carries just six guests and that changes everything. Sail San Diego Bay aboard a classic 41-ft Friendship sloop with Capta

★ 4.9 (361)
From $125.00 USD

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Browse trusted tours and experiences in San diego. Compare options, read ratings, and book with confidence.

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