Sailing in Villas, FL


$163 for a Half-Day Sailing Charter for Up to Six from Sundance Sailing ($330 Value)

Sundance Sailing

Estero Island

Half-day cruises piloted by a veteran sailor explore the gulf's waters, often with dolphin and local wildlife sightings

$330 $163

Admission and Skate Rental for Two or Four with Hot Chocolate and Popcorn at Fort Myers Skatium (Up to 55% Off)

Fort Myers Skatium

Fort Myers Skatium

Guests lace up rented skates and take to the ice during public-skating sessions, and enjoy delicious concessions

$29 $13

Paddleboard Rental for One or Two from Bonita Jetski and Parasail Inc (50% Off)

Bonita Jetski and Parasail Inc

Bonita Springs

Paddleboarders explore the waters off Bonita Beach

$30 $15

One-Hour of Regular or VIP Bowling for Up to Six Including Shoe Rental at Gator Lanes (Up to 52% Off)

Gator Lanes

Gator Lanes

Bowlers get access to regular lanes or a designated VIP area and play for one hour; shoe rental included

$50.50 $25

Half-Day Single or Double Kayak Rental at Salty Sam's Waterfront Adventures (Up to 53% Off)

Salty Sam's Waterfront Adventures

Fort Myers Beach

Hop in a kayak and explore the mangrove estuaries and shorelines along the Great Calusa Blueway

$29.99 $14

One-Hour Single or Double Kayak Rental, or One-Hour Paddleboard Rental from Carmen's Kayaks (Up to 58% Off)

Carmen's Kayaks

Matlacha Community Park

Kayakers and paddleboarders explore nature, which may include manatees, eagles, and dolphins, around Pine Island Sound and Matlacha Pass

$40 $17

Kayak or Standup-Paddleboard Rental from Nature Recreation Management of Lee County, LLC-Lover's Key (Up to 57% Off)

Nature Recreation Management of Lee County, LLC-Lover's Key

Bonita Springs

Get up-close & personal with wildlife kayaking around Lover's Key in a 1- or 2-person vessel; test your balance on a standup paddleboard

$50 $25

Full-Day Pontoon Rental for Six or Eight or Small Kayak Rental from Marina Mike's Boat Club (Up to 40% Off)

Marina Mike's Boat Club

Fort Myers

Groups of six or eight cruise around in a pontoon boat from 9 a.m.–4 p.m.; take out a large or small kayak for an athletic day on the water

$350 $255

$178 for 5 Rounds of Golf, 5 VIP Lessons & A ProSeries Hybrid Club at The Shell Point Golf Club ($1,020 Value)

The Shell Point Golf Club

Iona

Bundle kits out golfers with lessons, rounds, and a new hybrid club; perfect for people just getting into golf or looking to up their game

$1,020 $178

Two Hour Hydrobike Tour for One or Two at Florida Hydrobike (Up to 67% Off)

Florida Hydrobike

North Naples

Patrons skim across the waters, peddaling pontoon-floated hydrobikes

$45 $18

One Day of Unlimited Golf with Lunch for One, Two, or Four at Herons Glen Golf & Country Club (Up to 60% Off)

Herons Glen Golf & Country Club

Herons Glen Golf & Country Club

Enjoy Member-for-a-Day privileges on an 18-hole championship course, sharpen your game on a driving range, and enjoy lunch at the clubhouse

$100 $42

Introductory Indoor Archery Lesson for Two or One or Two Months of Lessons at SW Florida Budokan (Up to 59% Off)

SW Florida Budokan

Iona

Instructor teaches archery basics to two people; unlimited membership allows individual to hone their skills

$32.50 $15

Island Sunset Celebration Cruise for Two or Four at Sight Sea-R Cruises (Up to 38% Off)

Sight Sea R Cruises

Estero Island

Set off on an evening catamaran cruise that captures the beauty of Fort Myers Beach bathed in a crimson sunset

$50 $31

240 Driving-Range Balls or Golfing Gear at Golf World Discount Shop and Driving Range (Half Off)

Golf World

North Fort Myers

Well-manicured, lighted facility accommodates golfers with expansive driving range & shop stocked with gear by Callaway & Titleist.

$24 $10

Fort Myers Miracle Baseball Game for Two (June 20–September 4)

Fort Myers Miracle

Hammond Stadium at the CenturyLink Sports Complex

The Minnesots Twins affiliate Miracle faces Florida State League foes during home games throughout the summer

$22 $11

18-Hole Round of Golf with Cart Rental & Domestic Draft Beer for 2 or 4 at King's Gate Golf Club (Up to 59% Off)

Kings Gate Golf Club

King's Gate Golf Club

18-hole round of golf for two or four people includes a cart rental and one domestic draft beer per player

$46 $21

Deep-Sea Fishing Trip for One or Two from Pure Naples (Up to 33% Off)

Pure Naples

Downtown Naples

Trip includes tackle, bait, and licenses; anglers hunt redfish, grouper, mackerel, and snapper

$100.70 $69

Golf Lessons at San Carlos Golf Club or Palmetto Pine Country Club with Jordan Ball (Up to 51% Off)

Stoneybrook Junior Golf Inc

Multiple Locations

Kids practice the game’s fundamentals during Saturday lessons at San Carlos Golf Club or Palmetto Pine Country Club

$60 $30

$15 for $35 Worth of Products — Hoopster Basketball Academy

Hoopster Basketball Academy

Multiple Locations

Shooting focused personal training.

$35 $15

One-Hour Jet Ski Rental for One or Two at All Island Watersports (Up to 42% Off)

All Island Watersports

Venetian Gardens

Blast through ocean waves on a one-person jet ski, just off the coast at Fort Myers Beach

$95 $55

Tandem Hang-Gliding Flight Package for One or Two at The Florida Ridge Air Sports Park (Up to 64% Off)

The Florida Ridge Sports Air Park

The Florida Ridge Sports Air Park

Bourgeoning wind riders fly more than 1,000 ft. above Florida’s countryside under direction of skilled instructor

$184 $76

Four-Hour Kayak Excursion for One, Two, or Four from FMB FlyBoard (Up to 57% Off)

FMB FlyBoard

Getaway Marina, Fort Myers Beach

Kayakers explore the natural wonders of Fort Myers Beach, paddling past pristine beaches, lush vegetation and beautiful coastal wildlife

$40 $19

Coastal and Backwater Fishing Cruise for One or Two from Pure Naples (Up to 34% Off)

Pure Naples

Downtown Naples

Fishing cruises include tackle, bait, and licenses; anglers hunt redfish, grouper, mackerel, and more

$94.34 $63

Tandem Skydive Photo Shoot Package for One, Two, or Four at Skydive Spaceland (Up to 47% Off)

Skydive Spaceland

Clewiston

Strapped to a professional diver, beginners leap into the void as a photographer snaps 50 images on the way down

$304 $169

18-Hole Round of Golf with Cart and Balls for One, Two, or Four at Long Marsh Golf Club (Up to 59% Off)

Long Marsh Golf Club

Long Marsh Golf Club

18-hole game measures to 7,000 yards from the back set of tees, as golfers cover more than 450 acres of lolling fairways and pristine greens

$50.99 $22

One or Two Jet Skis for One-Hour Rental from Action Water Sports (Up to 41% Off)

Action Water Sports

Fort Myers Beach

On the picturesque waters of Fort Myers Beach, jet ski riders speed across waves and enjoy their time in the sun for an hour

$90 $54

Two- or Four-Hour Standup Paddleboard Rental for Two or Four from FMB FlyBoard (Up to 59% Off)

FMB FlyBoard

Getaway Marina, Fort Myers Beach

On standup paddleboards, explore the waters of Fort Myers Beach and Bunche Beach Preserve among dolphins, manatees, and sea turtles

$80 $34

Two or Four Paddleboard Rentals or a Megaboard Rental from Hop on Board Paddleboards (Up to 63% Off)

Hop on Board Paddleboards

Fort Myers / Cape Coral

From the Merchant: Deliver paddleboards and megaboards with enough room for up to six friends or family to explore the waters of Ft. Myers.

$80 $33

Tandem Skydive for One or Two or Premium Champagne Package for One or Two (Up to 41% Off)

Skydive City/Z-Hills

Zephyrhills

Connected to an instructor, skydivers hurtle toward the earth at 120 mph before opening their chutes and gliding down on a 5-minute descent

$179 $115

Stock Car Racing Experience or Ride-Along at Rusty Wallace Racing Experience (Up to 55% Off)

Rusty Wallace Racing Experience

Desoto Speedway

Professional drivers sate passengers’ need for speed in stock cars during exciting ride-alongs and racing experiences

$50 $39

Select Local Merchants

  • Adventures in Paradise
    It only took two weeks on the picturesque shores of Tahiti and Moorea to send Craig Stewart into a tailspin. He and wife Evelyn fell in love with the South Pacific’s crystalline waters and beachy breezes, so much so that the prospect of remaining in their native Oklahoma turned gloomy. Six years after the Stewarts’ Pacific vacation, they stumbled upon Sanibel Island. With a love for the waters still coursing through their veins, they uprooted and moved there, making it home base for Adventures in Paradise. In 1986, they started out with one boat—Miss Paradise—and one tour, the sunset dolphin cruise. Today, the Stewart family maintains a much larger operation. Their tour topics range from fishing and shelling to dolphin watching to historical sightseeing on a trolley.
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    Fort Myers, FL US
    +12394728443
  • Pieces of Eight Pirate Cruise
    Pirates cheer as cannons fire smoke across the sea. Yet while the pirates are actors and the cannons are just miniaturized toys, the ship they sail upon is anything but pretend—it's a 65-foot steel-hulled vessel designed by a naval architect to look like a Spanish galleon. Named for the prized Spanish currency of yore, Pieces of Eight Pirate Cruise evokes the golden age of buccaneering as it sets sail from Salty Sam’s Marina. The ship is helmed by a merry band of pirates—such as Pick Pocket Pete, Peg Leg Meg, and Fancy Face Phil—that bookends lessons on pirate history with sing-along chanteys and skits. The 90-minute family-friendly cruise also includes map-reading trivia, face painting, yo-ho-ho, and a bottle of rum. During the ride, passengers are welcome to explore the upper and lower decks or step inside the grand salon for ice cream, pretzels, and other treats. In addition to its all-ages cruises, Pieces of Eight hosts an adults-only cruise on Friday nights, which includes cocktails and its own revue. It also charters private cruises to celebrate birthdays and other special occasions.
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    Fort Myers Beach, FL US
    +12397657272
  • Mystic Charters
    What services does your business offer and what makes your business stand out from the competition? Join second generation Sailboat Master Captain Gary Barton on his private yacht, who has sailed from as far as New England to Tortola B.V.I. What is the experience customers can expect? Embark on the all in one perfect sail on the beautiful Gulf of Mexico for up to five hours with a maximum of six passengers. We will seek out the playful Dolphin (almost every cruise) and have a champagne toast to compliment our fabulous sunsets here in paradise. What was the inspiration to start or run this business? After sailing many years with family and friends I have decided to share this wonderful experience with as many people as I can. Some of you may become sailors yourself. That would be very gratifying for me. What do you love most about your job? My favorite part of sailing charters would have to be hoisting the sails and turning off the engine. And of course meeting adventurous ocean loving folks like you.
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    Fort Myers Beach, FL US
    +12398877895
  • Appledore V
    With a stable of two schooners, Appledore IV and Appledore V, which split their time between Fort Myers, Florida, and Bay City and Mackinaw City, Michigan, BaySail's captains ferry passengers about the Great Lakes and the Gulf of Mexico during leisurely and educational tours. The sea vessels depart from Bay City to wind along the Saginaw River and into open water, letting passengers soak up summer sun or, in the autumn, traveling upriver for spectacular views of changing leaves and scarecrows playing hooky on the riverbanks. Come winter, the Appledore V makes its way to Florida, where it seeks out the dolphin populations of San Carlos Bay. All of BaySail's excursions are interactive seafaring affairs in which passengers are encouraged to help to crew the watercraft, learn about fish brought into onboard tanks, and force seagulls to walk the plank.
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    Fort Myers Beach, FL US
    +12392459265
  • Salty Sam's Waterfront Adventures
    Salty Sam's Waterfront Adventures anchors the boating scene in Southwest Florida with award-winning marina services and a friendly team of boating experts. Here, customers can rent USCG-equipped boats for up to a week at a time while exploring the mangrove estuaries and shorelines along the Great Calusa Blueway. In addition to boat and kayak rentals, Salty Sam's also provides charters for fishing and sightseeing excursions, as well as state-of-the-art storage facilities so boats don't have to find their own apartments. A colorful gift shop also stocks an array of souvenirs and boating accessories, and two on-site restaurants ensure customers don't have to go far to capsize their hunger.
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    Fort Myers Beach, FL US
    +12394637333
  • Sundance Sailing
    With more than 31,000 nautical miles of sailing under his boat shoes, Captain David Richardson is more than capable of navigating his sailboat, Sundance, on the leisure cruises for which he has become known. The half-day charters he leads out of Bonita Bill's Waterfront Café take in the many moods of the Gulf of Mexico, from its tranquil disposition in the sun to the turbulent waters it experiences when it realizes it'll never be a full-grown ocean. The Sundance itself boasts comfy accommodations, from cushy seats to an on-board bathroom, and many passengers bring their own food on board to eat while ogling jumping dolphins.
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    Fort Myers Beach, FL US
    +12395655690

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