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Best results for

Sailing in San Diego, CA

Showing 1-24 of 35 results
2.5-Hour Private Sunset Sail in San Diego

2.5-Hour Private Sunset Sail in San Diego

Sail San Diego Bay at sunset on a private 2.5-hour charter

5.0 • 323 reviews
$525& up
Private Sailing & Swim Charter in San Diego

Private Sailing & Swim Charter in San Diego

Pair time under sail with a swim stop and paddleboard play

5.0 • 284 reviews
$1,037
Private San Diego Bay Sailing Charter

Private San Diego Bay Sailing Charter

Make room for your own celebration on a fully private sail

5.0 • 130 reviews
$636/ boat
Private Midday Sailing Charter in San Diego

Private Midday Sailing Charter in San Diego

See San Diego’s historic waterfront on a private daytime sail

4.9 • 877 reviews
$631& up
Sail San Diego Bay Catamaran Cruise With Drinks

Sail San Diego Bay Catamaran Cruise With Drinks

Sail San Diego Bay on a small-group catamaran with drinks included

4.9 • 251 reviews
$660
Classic Yacht Afternoon Sail on San Diego Bay

Classic Yacht Afternoon Sail on San Diego Bay

Sail a classic yacht past San Diego Bay landmarks with drinks and snacks

4.9 • 113 reviews
$125/ person
2.5-Hour Private Sailing Charter in San Diego Bay

2.5-Hour Private Sailing Charter in San Diego Bay

Sail, swim, and toast aboard a private yacht

$1,018
Private Sunset Sailing Tour in San Diego

Private Sunset Sailing Tour in San Diego

Sail into sunset with views of the Pacific and San Diego skyline

$694& up
2.5-Hour Sailing Charter in San Diego

2.5-Hour Sailing Charter in San Diego

Take the helm on a private sail past San Diego’s waterfront landmarks

5.0 • 323 reviews
$525& up
Private Sail & Swim Charter With Paddle Boards in San Diego

Private Sail & Swim Charter With Paddle Boards in San Diego

Enjoy sailing and time in the water without choosing between them

5.0 • 284 reviews
$1,309
Early Afternoon Sailing Tour in San Diego

Early Afternoon Sailing Tour in San Diego

Trade the city streets for coastal views under sail

5.0 • 130 reviews
$116/ person
Private 3-Hour Sailing Lesson in San Diego

Private 3-Hour Sailing Lesson in San Diego

Learn to sail in a private 3-hour lesson with a US Coast Guard certified captain

4.9 • 877 reviews
$689
Morning Sailing Charter in San Diego

Morning Sailing Charter in San Diego

Private bay sailing with Point Loma or Coronado routes

5.0 • 323 reviews
$525& up
Private Sailing Charter to Point Loma in San Diego

Private Sailing Charter to Point Loma in San Diego

Relax at sea with your own crew and views of the California coast and Mexico

5.0 • 284 reviews
$1,091
Midday Sailing Tour in San Diego

Midday Sailing Tour in San Diego

Take in San Diego’s city views under sail

5.0 • 130 reviews
$116/ person
Private Sailing Charter in San Diego

Private Sailing Charter in San Diego

Customize a private sail with your own captain and crew

4.9 • 877 reviews
$1,198& up
Private Catamaran Sailing Charter on San Diego Bay

Private Catamaran Sailing Charter on San Diego Bay

Charter a private catamaran for your special occasion on San Diego Bay

4.9 • 251 reviews
$660
Sunset Sailing Cruise in San Diego

Sunset Sailing Cruise in San Diego

Unwind on an evening sail with drinks and skyline views

4.9 • 251 reviews
$119/ person
Sunset Sail on a Classic Yacht in San Diego Bay

Sunset Sail on a Classic Yacht in San Diego Bay

A classic-yacht sunset sail with drinks and San Diego Bay views

4.9 • 113 reviews
$125/ person
4-Hour Sailing Charter in San Diego

4-Hour Sailing Charter in San Diego

Sail the coastline, swim in a calm bay, and relax on the water

$1,479
Private Sailing Tour in San Diego

Private Sailing Tour in San Diego

Take your next date out on the Pacific

$633& up
San Diego 4-Hour Sail & Swim Charter

San Diego 4-Hour Sail & Swim Charter

Cruise San Diego Bay, swim in Glorietta Bay, and explore your preferred route

5.0 • 323 reviews
$795& up
San Diego Sunset Sail on San Diego Bay

San Diego Sunset Sail on San Diego Bay

Wind down with a sunset sail, city views, and drinks included

5.0 • 130 reviews
$116/ person
Bottomless Mimosa Sailing Cruise in San Diego

Bottomless Mimosa Sailing Cruise in San Diego

Sail San Diego Bay with bottomless mimosas on a 2-hour morning cruise

4.9 • 877 reviews
$80/ person
12
San Diego Things To Do
SailingYacht Charters45Boat Rentals35Bike Rentals25Fishing Charters22
More
  • Stand Up Paddle Boarding21
  • Whale Watching21
  • Boat Tours17
  • Equipment Rental17
  • Wine Tours14
  • Food Tours11
  • Paddleboarding10
City Tours
9
  • Ghost and Haunted8
  • Surfing Lessons8
  • Guided Tours7
  • Brewery Tours6
  • Day Trips6
  • Dinner Cruises6
  • Kayaking Tours6
  • Motorcycle Tours6
  • Scuba Diving6
  • Bike Tours5
  • Seasonal and Holiday5
  • Self Guided and Passes5