Sailing San Diego at a glance
- Our pick: San Diego Bay: Sunset & Day Sail Small Group Tour, US$ 119 per person (2h 30m, 4.99★ · 375).
- Top rated: San Diego Bay: Day Sailing Tour with Drinks & Skyline Views, US$ 119 per person (2h 30m, 5.00★ · 81).
- Best value: San Diego: 3-Hour Sailing Cruise & Harbor Views, US$ 116 per person (3h, 4.95★ · 570).
Price per person across the 16 options priced per person: US$ 54–US$ 800 (median US$ 119). With 100+ reviews: 12 of 20.
Of the 20 options: 16 with live guides in English, 18 with free cancellation, 17 with instant confirmation, 13 kid-friendly, 5 private and 17 bookable last-minute.
How we rank: quality, number of reviews, availability, booking conditions and relevance to the topic. In the comparison table, our top 3 comes first. Prices are per person, except options priced per group: that price is for the whole group, and the per-person figure assumes the group is full. “Top rated” = the highest score among options with at least 50 reviews.
Sailing San Diego — USS Midway Museum, Coronado Bridge and 8 more
Based on each operator's calendar. Confirmed when you book.
20 options
The 15 best
Ranked by quality, reviews, availability and booking conditions.
San Diego Whale Watching Cruise: Gray Whales & Marine Life Gray whale migration off San Diego Bay on a 360-degree viewing yacht with live guide, safety gear included. Morning and afternoon departures, all fitness levels welcome. Every day · 09:30 and 13:30 · All ages ★ 4.45 (720 reviews) Duration: 3h 30m Live guide: EN ✓ Free cancellation. from US$ 54 per person
San Diego Bay: Sunset & Day Sail Small Group Tour Feel the breeze as you sail San Diego Bay at sunset, spot dolphins and sea lions, sip drinks on deck, and see the Coronado Bridge: includes small group and beverages. Every day · 11:00, 11:30 and 14:30 ★ 4.99 (375 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 119 per person
San Diego Sunset Sailing: Catalina Sailboat & Drinks 3-hour sunset sail from Point Loma on a 6-person Catalina sailboat. Includes beer, soft drinks, snacks, views of USS Midway and Coronado Bridge. Small groups or fully private. Every day · 14:00 and 14:30 · All ages ★ 4.94 (642 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 127 per person
San Diego: 3-Hour Sailing Cruise & Harbor Views 3-hour sailing trip on San Diego Bay with beer, snacks & views of Coronado Bridge, USS Midway. Max 6 passengers, Shelter Island departure. Complimentary drinks included. Every day · 10:00 and 11:00 · All ages ★ 4.95 (570 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 116 per person
San Diego Catamaran Sail: 2.5-Hour Small-Group Harbor Cruise Sail San Diego Harbor on a spacious catamaran for 2.5 hours with drinks included, spotting sea lions and dolphins while the crew cuts the engine for an intimate experience. Every day · 11:30 and 14:30 · All ages ★ 4.96 (376 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 119 per person
San Diego Sunset Sail: USS Midway & Bay Views Evening sailing cruise on San Diego Bay with views of USS Midway and Maritime Museum. Includes captain, deck seating with blankets. Departs Sunroad Marina at sunset. Every day except Tuesday and Wednesday · 15:00 · All ages ★ 4.91 (662 reviews) Duration: 2h ✓ Free cancellation. from US$ 99 per person
San Diego Bay Brunch Cruise: Bottomless Mimosas & Live Music Brunch cruise on San Diego Bay with bottomless champagne and mimosas, buffet menu, and live entertainment aboard a luxury yacht. Sat and Sun · 11:00 · All ages ★ 4.52 (380 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 126 per person
San Diego Sunset Sail: Classic Yacht, 6 Guests Sail San Diego Bay aboard a 41-foot classic sloop with Captain Phil. Just six guests, craft beer and wine included, no crowds or scripts. Every day · 11:30 and 15:00 · All ages ★ 4.93 (363 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 125 per person
San Diego Bay Sailing Tour: Catalina 34' Sailboat, Small Group Sail San Diego Bay and coastal waters aboard a Catalina 34' sailboat with up to six guests, live guide, and two hours of fresh air and sea life viewing. Every day · 11:00, 14:00 and 17:00 ★ 4.88 (208 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 119 per person
2-Hour Private Sailing in San Diego Bay Sail San Diego Bay on a private yacht for two hours with champagne, snacks and water views of the Midway, sea lions and skyline. Captain Liz guides. You choose the route. Every day · Every 30 min, 10:00 to 19:00 ★ 4.99 (189 reviews) Duration: 2h Live guide: EN · ES ✓ Free cancellation. from US$ 675 per group
2.5-Hour Catamaran Sailing in San Diego: Small-Group Harbor Tour Sail San Diego Harbor on a comfortable catamaran for 2.5 hours, viewing the downtown skyline. Every day · 11:30 and 12:00 · From age 4 ★ 4.97 (114 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 119 per person
San Diego Bay: Day Sailing Tour with Drinks & Skyline Views Sail San Diego Bay past Coronado Bridge, USS Midway & Embarcadero. Relax with included drinks, local guide, and city skyline views. Small group day tour. Every day · 11:00 and 11:30 ★ 5.00 (81 reviews) Duration: 2h 30m ✓ Free cancellation. from US$ 119 per person
2-Hour Sailing Tour San Diego Bay: See the USS Midway from Water Sail San Diego Bay for 2 hours aboard a yacht with an experienced captain, departing from Harbor Island. You'll see the USS Midway Museum from the water. Every day except Tuesday and Wednesday · 12:00 · All ages ★ 4.95 (160 reviews) Duration: 2h ✓ Free cancellation. from US$ 99 per person
Private day sail San Diego: Helm the boat under Coronado Bridge Sail San Diego Bay for 2.5 hours on a private boat with up to 12 guests, passing the USS Midway, Seaport Village and under the Coronado Bridge. Every day · 13:00 ★ 4.99 (69 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 488 per person
San Diego Sailing Cruise: Classic Yacht, Six Guests Sail San Diego Bay aboard a 41-foot classic yacht with just six guests and a USCG-licensed captain: no crowded tour boats, no script, just the skyline. Every day · 11:30 and 15:00 · All ages ★ 4.98 (85 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 125 per person
Compare 5 more options for Sailing San Diego
From US$ 199 per person · 2 h to 3 h
Private Sailing Charter San Diego Bay: Set Your Own Course Sail San Diego Bay on a private yacht with captain for three hours, visiting the USS Midway, Coronado Bridge, Point Loma and historic ships. Every day · 11:00 and 14:30 ★ 4.94 (50 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 499 per group
San Diego Yacht Rental: 40-Foot Catamaran with Captain Rent the Coral Island, a 40-foot catamaran in San Diego Bay, with captain, crew and bartender included. Bring your group up to 35 and set your own pace on the water. Every day · Every 1 h, 08:00 to 19:00 ★ 4.75 (4 reviews) Duration: 2h ✓ Free cancellation. from US$ 1,210 per group
Sunset Sailing Cruise San Diego Bay: Champagne Included Sail San Diego Bay on a French yacht with champagne toast, passing Coronado Bridge, Sunset Cliffs and Point Loma. 2.5 hours with a small group or private option. Every day · Every 1 h, 10:00 to 18:00 · All ages ★ 5.00 (1 review) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 199 per person
Private Catamaran Sailing Cruise San Diego Bay: Up to 6 Guests Sail San Diego Bay on a private 32-foot catamaran with a live English-speaking guide, spotting sea lions, dolphins and whales while you steer or relax in the sun. Every day · 11:00, 14:00 and 17:00 ★ 5.00 (2 reviews) Duration: 2h Live guide: EN from US$ 800 per group
Sunset Sailing Tour San Diego Bay: Up to 6 Guests Sail San Diego Bay at sunset with a skipper, viewing downtown, naval vessels, sea lions and dolphins while enjoying refreshments and snacks. Every day · 11:00, 14:00 and 17:00 ★ 5.00 (1 review) Duration: 2h Live guide: EN from US$ 800 per person
The top 12 of 20 options, side by side
✓ 2026-11-14| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| San Diego Bay: Sunset & Day Sail Small Group TourOur pickGroup of up to 6 | US$ 119 per person | 2h 30m | 4.99★ · 375 | Every day · 11:00, 11:30 and 14:30 | English |
| San Diego Bay: Day Sailing Tour with Drinks & Skyline ViewsTop ratedGroup of up to 6 | US$ 119 per person | 2h 30m | 5.00★ · 81 | Every day · 11:00 and 11:30 | — |
| San Diego: 3-Hour Sailing Cruise & Harbor ViewsBest valueGroup of up to 6 | US$ 116 per person | 3h | 4.95★ · 570 | Every day · 10:00 and 11:00 | English |
| San Diego Whale Watching Cruise: Gray Whales & Marine Life | US$ 54 per person | 3h 30m | 4.45★ · 720 | Every day · 09:30 and 13:30 | English |
| San Diego Sunset Sailing: Catalina Sailboat & DrinksGroup of up to 6 | US$ 127 per person | 3h | 4.94★ · 642 | Every day · 14:00 and 14:30 | English |
| San Diego Catamaran Sail: 2.5-Hour Small-Group Harbor CruiseGroup of up to 6 | US$ 119 per person | 2h 30m | 4.96★ · 376 | Every day · 11:30 and 14:30 | English |
| San Diego Sunset Sail: USS Midway & Bay ViewsGroup of up to 6 | US$ 99 per person | 2h | 4.91★ · 662 | Every day except Tuesday and Wednesday · 15:00 | — |
| San Diego Bay Brunch Cruise: Bottomless Mimosas & Live Music | US$ 126 per person | 2h | 4.52★ · 380 | Sat and Sun · 11:00 | English |
| San Diego Sunset Sail: Classic Yacht, 6 GuestsGroup of up to 6 | US$ 125 per person | 2h 30m | 4.93★ · 363 | Every day · 11:30 and 15:00 | English |
| San Diego Bay Sailing Tour: Catalina 34' Sailboat, Small GroupGroup of up to 6 | US$ 119 per person | 2h | 4.88★ · 208 | Every day · 11:00, 14:00 and 17:00 | English |
| 2-Hour Private Sailing in San Diego BayPrivate | US$ 675 per group up to 6 people · ≈ US$ 113 per person if 6 go | 2h | 4.99★ · 189 | Every day · Every 30 min, 10:00 to 19:00 | English, Spanish |
| 2.5-Hour Catamaran Sailing in San Diego: Small-Group Harbor TourGroup of up to 6 | US$ 119 per person | 2h 30m | 4.97★ · 114 | Every day · 11:30 and 12:00 | English |
By what you need
- Private (5): 2-Hour Private Sailing in San Diego Bay (US$ 675 per group) · Private day sail San Diego: Helm the boat under Coronado Bridge (US$ 488 per person) · Private Sailing Charter San Diego Bay: Set Your Own Course (US$ 499 per group)
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