Top California Sailing Trips

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San Francisco Bay Sailing Cruise

5 star rating: Highly Recommended 191 Reviews

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the ... 

Location: San Francisco, California
Duration: 90 minutes

From USD $45.00

2-Hour Sunset Sail on the San Francisco Bay

5 star rating: Highly Recommended 7 Reviews

Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous ... 

Location: San Francisco, California
Duration: 2 hours

From USD $65.00

1.5-hour San Francisco Bay Sailing Tour

For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with ... 

Location: San Francisco, California
Duration: 90 minutes

From USD $49.00

Small-Group San Diego Sailing Trip

5 star rating: Highly Recommended 1 Review

Leave the streets behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant waterfront offers expansive views of Downtown, Point Loma, ... 

Location: San Diego, California
Duration: 2 hours

From USD $91.64

Classic Sailboat Sunset Sail

5 star rating: Highly Recommended 7 Reviews

This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramatic part of a California day. The multi-colored sky is the ... 

Location: San Diego, California
Duration: 2 hours 30 minutes

From USD $110.00

America's Cup Sailing Adventure on San Francisco Bay: Day Sail

5 star rating: Highly Recommended 9 Reviews

Welcome aboard for a thrilling 2.5 hour sailing adventure aboard USA 76, an International America’s Cup Class racing yacht that challenged in 2003 for ... 

Location: San Francisco, California
Duration: 2 hours 30 minutes

From USD $150.00

Small-Group San Diego Sunset Sailing Excursion

5 star rating: Highly Recommended 16 Reviews

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-style sailboat is limited ... 

Location: San Diego, California
Duration: 3 hours

From USD $88.99

San Diego Bay Sailing Tour

5 star rating: Highly Recommended 1 Review

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 ... 

Location: San Diego, California
Duration: 3 hours

From USD $79.00

Small-Group San Diego Afternoon Sailing Excursion

5 star rating: Highly Recommended 49 Reviews

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 ... 

Location: San Diego, California
Duration: 3 hours

From USD $88.99

3 Hour Private Sail For Up To 6 People

Feel the wind in your hair as you sail through the bay as you sip on wine or champagne! With 4 different departure locations, there is an option for everyone ... 

Location: San Diego, California
Duration: 3 hours

From USD $350.00

Tall-Ship Sunset Sail on the San Francisco Bay

5 star rating: Highly Recommended 1 Review

Step aboard the beautiful Schooner Freda B and enjoy a picturesque sunset sail on San Francisco Bay! Board in downtown Sausalito, CA and cruise around the ... 

Location: Sausalito, California
Duration: 2 hours

From USD $49.00

Sunday Morning Eco Sail on the San Francisco Bay

Set sail on Sunday mornings aboard the traditional Schooner Freda B for an ecology-themed tour of the Marin Headlands! This sail features a unique route, ... 

Location: Sausalito, California
Duration: 2 hours 30 minutes

From USD $69.00

Monterey Bay Sailing Cruise With Wine

4.5 star rating: Recommended 10 Reviews

Choose from various departure times when you book 1:30 P.M-2:30 P.M, 3:00 P.M-4:00 P.M or 4:30-5:30 P.M.   Please add a note with your booking ... 

Location: Monterey, California
Duration: 60 minutes

From USD $39.00

San Diego Half-Day Marine Wildlife Tour with Lunch

5 star rating: Highly Recommended 1 Review

Experience an exciting adventure while sailing along the San Diego coastline. Venture off into the Pacific Ocean and catch a chance to see local marine ... 

Location: San Diego, California
Duration: 4 hours

From USD $172.84

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 ... 

Location: San Diego, California
Duration: 3 hours

From USD $399.00

Private Sailing Cruise on Monterey Bay

5 star rating: Highly Recommended 1 Review

Share the wonders of sailing with your family and friends on this 2-hour private sailing cruise on Monterey Bay. Keep your eyes peeled, and you may spot grey, ... 

Location: Monterey, California
Duration: 2 hours

From USD $249.00

Sail Boat Charters From Hyatt Regency Mission Bay

All inclusive! Get ready to experience the beautiful coastal blue waters of San Diego on the Sailing Vessel Venere, a beautiful 42-foot sailing yacht.

Location: San Diego, California
Duration: 2 hours

From USD $85.00

Sail Stars and Stripes America's Cup Racing Yacht

Public 3 hour sailing charters aboard the authentic 1992 America's Cup racing yacht, Stars & Stripes USA-11. Take the helm, grind the winches, or just hang ... 

Location: San Diego, California
Duration: 3 hours

From USD $125.00

Small-Group Golden Gate Bridge Sailing Tour

5 star rating: Highly Recommended 1 Review

Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views of ... 

Location: San Francisco, California
Duration: 2 hours

From USD $65.00

Private San Diego Sailing Adventure

Admire San Diego’s numerous sights by water on this private sailing tour of the San Diego Bay. On a 1914-styled Friendship sloop, your group will float past ... 

Location: San Diego, California
Duration: 2 hours 30 minutes

From USD $625.00

Monterey Bay Sunset Appetizer Cruise

3.5 star rating: Worth doing 3 Reviews

Our most-popular and romantic cruise with or without hors d’oeuvres. The appetizer option includes two hors d’oeuvres beginning with brie cheese, sliced pear, ... 

Location: Monterey, California
Duration: 2 hours

From USD $89.00

Private Day Sail for 4-6 People

5 star rating: Highly Recommended 5 Reviews

Experience an intimate group charter with up to six passengers while sailing along the San Diego Bay. If you’re looking for a day of family fun, or to ... 

Location: San Diego, California
Duration: 2 hours

From USD $323.64

2-Hour Monterey Bay Family Sailing Cruise

This cruise departs at 11 A.M and returns to port by 1 P.M! Enjoy a 2-hour captained sailing excursion with your family and friends on beautiful Monterey ... 

Location: Monterey, California
Duration: 2 hours

From USD $89.00

America's Cup Sailing Adventure on San Francisco Bay: Express Sail

Welcome aboard for a family friendly 2 hour San Francisco Bay sailing tour aboard USA 76, an International America’s Cup Class racing yacht that challenged in ... 

Location: San Francisco, California
Duration: 2 hours

From USD $100.00

Sail with Spirit - A Beautiful 54-Foot Sailing Yacht

Sailing with SPIRIT Welcome aboard the luxurious sailing yacht SPIRIT! A Beautiful 54 foot Bruce Roberts Ketch, Spirit comfortably carriers up to 24 ... 

Location: San Diego, California
Duration: 2 hours

From USD $85.00
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