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Best results for

Sailing in Pensacola Beach, FL

Showing 1-18 of 18 results
Blue Angels Practice Cruise in Pensacola Beach

Blue Angels Practice Cruise in Pensacola Beach

Watch Blue Angels practice from a sailboat on Pensacola Bay

5.0 • 2.1K reviews
$580
Afternoon Sail & Dolphin Watch Cruise in Pensacola Beach

Afternoon Sail & Dolphin Watch Cruise in Pensacola Beach

Stretch out on a spacious sailing raceboat, with room to relax and explore

5.0 • 137 reviews
$110/ person
Private Sunset Sail in Pensacola Beach

Private Sunset Sail in Pensacola Beach

Sail into the evening with charcuterie and sparkling wine

5.0 • 44 reviews
$477
Private Full-Day Sailing Charter in Orange Beach

Private Full-Day Sailing Charter in Orange Beach

Pair a boat-only island escape with a sunset sail

$1,994
Pensacola Beach Sunset Sail on a 27' Sailboat

Pensacola Beach Sunset Sail on a 27' Sailboat

Sail Pensacola Bay at sunset with hands-on sailing and coastal views

5.0 • 2.1K reviews
$121/ person
Morning Sail & Dolphin Watch Cruise in Pensacola Beach

Morning Sail & Dolphin Watch Cruise in Pensacola Beach

Relax on a spacious, stable sailboat with room to spread out

5.0 • 137 reviews
$110/ person
Private Sailing Charter in Pensacola Beach

Private Sailing Charter in Pensacola Beach

Relax on board or make a splash on your own private sail

5.0 • 44 reviews
$742& up
Private Sunset Sailing Charter in Orange Beach

Private Sunset Sailing Charter in Orange Beach

Share sunset views of coastal Alabama with someone you love

$532
Hobie Cat Sailboat Rental in Navarre Beach

Hobie Cat Sailboat Rental in Navarre Beach

Choose a catamaran that matches your sailing experience

4.1 • 68 reviews
$77/ boat
Sunset Sailing Cruise in Pensacola Beach

Sunset Sailing Cruise in Pensacola Beach

Find a quiet spot for two on a spacious sunset sail

5.0 • 137 reviews
$127/ person
Private Brunch Sailing Cruise on Pensacola Bay

Private Brunch Sailing Cruise on Pensacola Bay

Ease into the day with seasonal fruit and fresh-squeezed orange juice mimosas

5.0 • 44 reviews
$398
Private Sailing Charter Through Perdido Pass in Orange Beach

Private Sailing Charter Through Perdido Pass in Orange Beach

Take a break from shore with a relaxing escape under sail

$399
Sailing Cruise in Pensacola Beach for 2 Hours

Sailing Cruise in Pensacola Beach for 2 Hours

Set sail on a shaded 27-foot sailboat with drinks and Gulf Coast wildlife views

5.0 • 2.1K reviews
$121/ person
Hobie Cat Sailboat Rental Pensacola Beach

Hobie Cat Sailboat Rental Pensacola Beach

Take the helm of a Hobie sailboat on Pensacola Beach

4.7 • 640 reviews
$87/ boat
Pensacola Beach Sailing Cruise with Optional Swim Stop

Pensacola Beach Sailing Cruise with Optional Swim Stop

Sail Pensacola Bay with an optional swim stop on a 27-foot sailboat

5.0 • 2.1K reviews
$177/ person
Private Sailing Charter with Snorkel Stop in Pensacola Beach

Private Sailing Charter with Snorkel Stop in Pensacola Beach

Sail Pensacola Bay with time to take the helm, swim, or snorkel

5.0 • 2.1K reviews
$528
3.5-Hour Jolly Mon Sail and Snorkel Adventure

3.5-Hour Jolly Mon Sail and Snorkel Adventure

Sail Pensacola waters and snorkel shallow sites with gear, instruction, and a licensed captain

5.0 • 2.1K reviews
$501
Sail to Sand Island on a 7-Hour Pensacola Beach Cruise

Sail to Sand Island on a 7-Hour Pensacola Beach Cruise

Spend 7 hours sailing, swimming, and grilling on a private trip for up to 6

5.0 • 2.1K reviews
$773
Pensacola Beach Things To Do
SailingFishing Charters151Boat Tours56Boat Rentals52Dolphin Watching36
More
  • Scuba Diving23
  • Kayaking Tours18
  • Snorkeling13
  • Jet Skiing11
  • Private Fishing Charters10
  • Stand Up Paddle Boarding10
  • Yacht Charters10
  • Scavenger Hunts8
  • Parasailing7
  • Equipment Rental5
  • Ghost and Haunted4
  • Sunrise and Sunset Tours4
  • Surfing Lessons4
  • Private Boat Charters3
  • Zip Lining3