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Best results for

Sailing in Poway, CA

Showing 25-45 of 45 results
Sunset Sailboat Cruise in Oceanside

Sunset Sailboat Cruise in Oceanside

Wind down on deck with a sunset sail led by Captain Eric

5.0 • 419 reviews
$419
Private Sunset Sail on 36' Catalina Yacht in Oceanside

Private Sunset Sail on 36' Catalina Yacht in Oceanside

Let the wind carry you into the evening on your own private yacht

5.0 • 19 reviews
$318
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
Private Sailboat Charter with Coffee in Oceanside

Private Sailboat Charter with Coffee in Oceanside

Hold your next work meeting on the water with ocean views

5.0 • 7 reviews
$318
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 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 • 131 reviews
$116/ person
San Diego Rady Shell Concert Sailing Experience

San Diego Rady Shell Concert Sailing Experience

Sail to a Rady Shell concert and watch from the water

5.0 • 323 reviews
$795& up
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
Private Midday Sailing Charter in San Diego Bay

Private Midday Sailing Charter in San Diego Bay

Private coastal views with complimentary drinks and snacks

4.9 • 877 reviews
$631
Private Morning Sailing Charter on a 36' Yacht in Oceanside

Private Morning Sailing Charter on a 36' Yacht in Oceanside

Let the wind carry you on a private morning sail

5.0 • 19 reviews
$318
Private Coastal Sailing Charter in Oceanside

Private Coastal Sailing Charter in Oceanside

See your hometown from a fresh coastal perspective

5.0 • 7 reviews
$286
Small-Group Sailing Yacht Cruise on San Diego Bay

Small-Group Sailing Yacht Cruise on San Diego Bay

Share a relaxed yacht sail with coastal views and a group toast

$253/ person
Private Sailboat Cruise & Wine Tasting in San Diego

Private Sailboat Cruise & Wine Tasting in San Diego

Sail San Diego Bay, then savor local wine on a private outing

3.4 • 217 reviews
$529& up
Private 6-Hour Sailing Charter in San Diego

Private 6-Hour Sailing Charter in San Diego

Sail San Diego Bay on a private 6-hour charter for up to 12 guests

4.9 • 877 reviews
$954& up
3-Hour Midday Sailing Cruise In San Diego

3-Hour Midday Sailing Cruise In San Diego

Midday sail in San Diego with drinks and snacks included

4.9 • 877 reviews
$116/ person
Private Sailing Charter in San Diego

Private Sailing Charter in San Diego

Sail San Diego Bay or the open ocean with your own captain and crew

4.9 • 877 reviews
$1,675& up
Birthday Sailing Charter in San Diego

Birthday Sailing Charter in San Diego

Celebrate your birthday with a private sail on San Diego Bay

4.9 • 877 reviews
$631& up
2-Hour Morning Sail in San Diego

2-Hour Morning Sail in San Diego

Enjoy a relaxed San Diego Bay sail with snacks, drinks and family-friendly fun

4.9 • 877 reviews
$94/ person
Private Morning Sail in San Diego

Private Morning Sail in San Diego

Set sail through historic San Diego with complimentary drinks and snacks

4.9 • 877 reviews
$477& up
San Diego 3-Hour Bachelor Sailing Charter

San Diego 3-Hour Bachelor Sailing Charter

Private bachelor sail with drinks, snacks, and daytime or sunset departures

4.9 • 877 reviews
$583& up
12
Poway Things To Do
SailingYacht Charters45Boat Rentals40Bike Rentals28Whale Watching26
More
  • Animal Sanctuaries22
  • Fishing Charters22
  • Stand Up Paddle Boarding21
  • Boat Tours19
  • Equipment Rental18
  • Food Tours18
  • Surfing Lessons15
  • Wine Tours15
  • Zoo Tours15
City Tours
11
  • Ghost and Haunted10
  • Paddleboarding10
  • Bird Watching Tours9
  • Brewery Tours8
  • Guided Tours8
  • Seasonal and Holiday7
  • Axe Throwing6
  • Car Rentals6
  • Day Trips6
  • Dinner Cruises6