Sailing in Cypress Lake, FL


$181 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 $181

$199 for a Half-Day Sail for Up to Six People from Mystic Charters ($510 Value)

Mystic Charters

Fort Myers

Sailers spend four hours exploring the barrier islands of South Florida on excursions aboard a classic American yacht

$510 $199

One-Hour Single or Double Kayak Rental, or One-Hour Paddleboard Rental from Carmen's Kayaks (Up to 51% 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 $20

$21 for a River Excursion or Sunset Cruise from Pure Fort Myers (Up to $35 Value)

Pure Fort Meyers

Ft. Myers River District

Tours include picturesque views of dolphins, manatees, eagles, and seabirds with views of the historic coastline

$35 $21

Half-Day Single or Double Kayak Rental at Salty Sam's Waterfront Adventures (Up to 45% 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 $17

$21 for Any Dolphin Tour or Sunset Party Cruise for One on The “Fort Myers Princess” ($33Value)

The Fort Myers Princess

Fort Myers Beach

The Captain Steers guests into calm waters for dolphin spotting or party cruises aboard a 75 ft. US Coast Guard–certified vessel

$33 $21

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

Orlando Explorer Pass includes admission to 3 or 5 attractions from 15 options. Pay Nothing at The Gate.

Go City Card

Online Deal

Choose 3 or 5 attractions from 15 popular options and save up to 35% off combined admission. Pay nothing at the gate

$49 $49.40

South Florida Explorer Pass includes admission to 3, 4, or 5 attractions from 25+ options. Pay Nothing at The Gate.

Go City Card

Online Deal

Choose 3, 4, or 5 attractions from 25+ popular options and save up to 40% off combined admission. Pay nothing at the gate

$85 $76.50

Adventure Thrill Ride or Sunset Tour for an Adult or Child at Jet Boat Adventures (Up to 38% Off)

Jet Boat Adventures Incorporated

Snook Bight Yacht Club & Marina

Take an adrenaline-pumping thrill ride or relaxing sunset tour on a 38-passenger, 1,200-horsepower jet boat that acts like a jet ski

$49.95 $31

Dolphin-Tour Harbor Cruise for Two, Four, or Six from Just Add Water and Sun (Up to 59% Off)

Just Add Water and Sun

Just Add Water and Sun

Boats cruise through Estero Bay/Matanzas Harbor in search of dolphins and other wildlife in their natural habitat

$240 $99

Three- or Six-Hour Kayak Rental for Two, Four, or Six from Finseeker Guided Adventures (Up to 59% Off)

Finseeker Guided Adventures

Multiple Locations

Kayakers explore southwest Florida’s coastal landscapes, catching glimpses of beautiful wildlife from stable, sit-on style 12 ft boats

$130 $59

Kayak Eco-tour or Kayak Fishing Tour for Two, Four, or Six from Nature Tours and More (Up to 50% Off)

Nature Tours and More

Multiple Locations

Guided tours explore local habitats, fishing or spotting everything from manatees and dolphins to gators and bats

$130 $69

Kayak Sightseeing Tour for Two, Four, or Six from Finseeker Guided Adventures (Up to 60% Off)

Finseeker Guided Adventures

Multiple Locations

Kayakers explore southwest Florida’s coastal landscapes, catching glimpses of beautiful wildlife from stable, sit-on style boats

$140 $59

Go Orlando Card All-Inclusive 2-Day Pass includes admission to 30+ attractions for 2 days. Pay Nothing at The Gate.

Go City Card

Online Deal

Get admission to 30+ attractions for one low price. Save up to 55% and pay nothing at the gate. Pass is valid for 2 calendar days

$105 $114

$55 for a Two-Hour Wine Tasting for 12 to 16 People from Wines for Humanity ($250 Value)

Wines for Humanity

Online Deal

Professional wine advisor teaches guests to discern distinctive notes in six exclusive vintages and pair them with appropriate dishes

$250 $55

Private Half-day Dolphin/Shell/Eco Tour for Up to Six People from Just Add Water and Sun (Up to 37% Off)

Just Add Water and Sun

Just Add Water and Sun

Boat cruise through Estero Bay to observe dolphins & Mangrove forest eco-system stopping for beachcombing, shelling or lounging on the beach

$300 $199

$119 for One-Year Ownership of Two Vines at Carneros Della Notte ($198 Value)

Own a Napa Vineyard

Carneros Della Notte

Learn how to tend and harvest grapes, access special vineyard events, and make your own wine from grapes that grow on your vines

$198 $119

One-Year Subscriptions to "Yachting", "Boating", or "Cruising World" Magazines (Up to 50% Off)

Yachting, Boating, & Cruising World Magazines

Online Deal

Get expert insight into the sailing industry & lifestyle with year-round subscriptions of Boating, Yachting, or Cruising World

$12 $6

Select Local Merchants

  • Boats Unlimited
    Take a nautical adventure around Cape Coral when you rent a vessel from The Boat House Of Cape Coral. Be sure to visit the restaurant at this center for a delicious meal. This center is kid-friendly, so little ones are welcome to tag along. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    1516 Southeast 46th Street
    Cape Coral, FL US
  • Venture Out Charters
    Leave the travel arrangements to the professionals at Cape Coral's Venture Out Charters and enjoy a luxurious vacation. The generous parking spots located in the area will make drivers feel at ease. You can travel with ease this next vacation knowing you got the best deal from Venture Out Charters in Cape Coral.
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    5828 Cape Harbour Drive
    Cape Coral, FL US
  • Action Boat Rentals Of Pine Island
    Ever wanted to experience the relaxing life of a boater? Now you can with Action Boat Rentals Of Pine Island in Bokeelia. Parking is plentiful, so guests can feel free to bring their vehicles. So get ready to sail away on a grand adventure with Action Boat Rentals Of Pine Island.
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    7447 Florence Dr
    Bokeelia, FL US
  • Neptunes Dive Service Hull Cleaning
    Whether you're a sailor, fisher, or just a pleasure-cruiser, Neptnes Dive Service Hull Cleaning in Cape Coral has many vessels for rent that are sure to float your boat. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    1143 Southwest 43rd Street
    Cape Coral, FL US
  • Paradise Boatrentals
    Get your sea legs ready! Paradise Boatrentals in Cape Coral provides quality vessels so you can have a boating experience that is both relaxing and fun. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    1733 Bikini Ct
    Cape Coral, FL US
  • Inland Marine USA
    If it's the boater's life for you, you'll want to check out the incredible seaworthy vessels for rent at Inland Marine USA in Cape Coral. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    930 Southeast 9th Lane
    Cape Coral, FL US

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