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Best results for

Sailing in Mary Esther, FL

Showing 1-24 of 27 results
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
Private 45' Sailing Yacht Charter in Destin

Private 45' Sailing Yacht Charter in Destin

Private daytime sailing cruise with optional hands-on instruction

5.0 • 251 reviews
$456& up
Sailing Charter in Destin on a Stiletto 30 Catamaran

Sailing Charter in Destin on a Stiletto 30 Catamaran

Private catamaran sailing with dolphin watching, snorkeling, and Crab Island

5.0 • 223 reviews
$372
Private Sunset Cruise from Baytowne Wharf in Sandestin

Private Sunset Cruise from Baytowne Wharf in Sandestin

Sail into sunset views on a private captained catamaran

4.9 • 245 reviews
$786
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 Sunset Sailing Charter on a 45' Yacht in Destin

Private Sunset Sailing Charter on a 45' Yacht in Destin

Sail into the Destin sunset on a private, quiet cruise

5.0 • 251 reviews
$513& up
Sail & Swim Charter in Destin on a Stiletto 30

Sail & Swim Charter in Destin on a Stiletto 30

Sail, snorkel, and explore Crab Island from Destin

5.0 • 223 reviews
$509
Sunset Cruise in Miramar Beach

Sunset Cruise in Miramar Beach

Sail into a Gulf sunset aboard a private captained catamaran

4.9 • 245 reviews
$787
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
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
Destin Sunset Sailing Charter

Destin Sunset Sailing Charter

Sail Destin Harbor aboard a private Stiletto 30 catamaran at sunset

5.0 • 223 reviews
$412
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
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
Sunset & Fireworks Sailing Cruise in Destin

Sunset & Fireworks Sailing Cruise in Destin

Sail into Destin Harbor for a private sunset and fireworks view

5.0 • 251 reviews
$741& up
Sail, Swim & Sunset Fireworks Charter in Destin

Sail, Swim & Sunset Fireworks Charter in Destin

Private 3.5-hour catamaran sail with snorkeling, sunset, and summer fireworks

5.0 • 223 reviews
$791
2-Hour Choctawhatchee Bay Sailing Charter

2-Hour Choctawhatchee Bay Sailing Charter

Sail, sightsee, and try your hand at steering a catamaran

5.0 • 66 reviews
$371
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
Sunset Sailing Charter in Destin

Sunset Sailing Charter in Destin

Private 45-foot yacht sailing with a beach stop, waterfront lunch, and Gulf sunset

5.0 • 251 reviews
$1,824
Sunset Sailing Charter in Destin

Sunset Sailing Charter in Destin

Sail Destin waters aboard a Stiletto 30 catamaran at sunset

5.0 • 223 reviews
$525
Cruise Santa Rosa Island on a Private Sailboat Charter

Cruise Santa Rosa Island on a Private Sailboat Charter

Sail Santa Rosa Island on a private charter with a licensed captain

5.0 • 66 reviews
$482& up
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
Destin Sail & Swim Charter on a Stiletto 30

Destin Sail & Swim Charter on a Stiletto 30

Sail, snorkel, and explore Crab Island aboard a private catamaran

5.0 • 223 reviews
$678
Sunrise Sailing Charter in Destin

Sunrise Sailing Charter in Destin

Sail Choctawhatchee Bay at dawn for Mid Bay Bridge views

5.0 • 66 reviews
$345
12
Mary Esther Things To Do
SailingBoat Tours150Fishing Charters116Boat Rentals86Yacht Charters56
More
  • Dolphin Watching41
  • Sunrise and Sunset Tours23
  • Snorkeling20
  • Jet Skiing19
  • Kayaking Tours18
  • Private Fishing Charters18
  • Helicopter Tours14
Car Rentals10
  • Private Boat Charters10
  • Parasailing7
  • Private Boat Tours7
  • Dance Classes5
  • Surfing Lessons5
  • Stand Up Paddle Boarding4
  • Zip Lining4
  • Birthday Packages3
  • Climbing3
  • Engagement Packages3
  • Shuttles and Rentals3
  • Speed Boating3