Sailing in Naples, 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

$23 for Sightseeing Cruise for One from Naples Princess ($43.50 Value)

Naples Princess

Old Naples

Narrated tours aboard a 105-foot luxury yacht showcase the waterways of Naples, the Gulf of Mexico, and Port Royal

$43.50 $23

$21 for a Sightseeing Cruise for One from Pure Naples ($37.10 Value)

Pure Naples

Downtown Naples

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

$37.10 $21

Trolley Tour for One, Two, or Four from Naples Trolley Tours (Up to 41% Off)

Naples Trolley Tours

Naples Trolley Tours

Hear stories about historic landmarks while touring Naples, hopping on and off a vintage trolley at 21 stops

$27 $16

Half-Day Boat Rental for Up to 15 from Naples Extreme Family Fun Spot (Up to 28% Off). Three Options Available.

Naples Extreme Family Fun Spot

Naples Extreme Family Fun Spot

Take to the placid waters of the Gulf of Mexico with half-day boat rentals for up to 15

$165.09 $119

Two-Hour Segway Tour for One, Two, or Four at Segway of Naples (Up to 41% Off)

Segway of Naples

Naples Trolley Tours

Tour the city on a Segway i2 Generation 2 machine to see sights such as Naples Pier, Third Street South, and Cambier Park

$74 $45

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

90-Minute Segway Tour for Two or Four from Naples Extreme Family Fun Spot (Up to 38% Off)

Naples Extreme Family Fun Spot

Naples Extreme Family Fun Spot

Guides lead groups past the Naples Fishing Pier, Gallery Row, historic Palm Cottage, and other local landmarks in this fun tour

$120 $79

2.5-Hour Kayak Tour for Two, Four, or Six People from Kayakmarco.com (Up to 52% Off)

Kayakmarco.com

Isle of Capri Kayak Park

During guide-led tours, both beginner and experienced kayakers enjoy the local natural area and wildlife while paddling around Marco Island

$414 $199

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

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

Go Miami Card All-Inclusive 2-Day Pass includes admission to 25+ attractions for 2 days. Pay Nothing at The Gate.

Go City Card

Online Deal

Get admission to 25+ attractions for one low price. Save up to 55% and pay nothing at the gate. Pass is valid for 2 calendar days

$80 $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

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

$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

$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

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

  • Naples Extreme Family Fun Spot
    When you find yourself on the sun-kissed shores of the Gulf of Mexico, your first impulse might be to laugh with joy. Your second impulse, however, will likely be to run off on an outdoor adventure. That's where Naples Extreme Family Fun Spot. The company supplies visitors with rental boats, paddleboards, bikes, and kayaks ready to explore Naples and Marco Island. Visitors can also hop on a chartered fishing boat, strap on a helmet for a Segway tour, or take in the vibrant reds and oranges showcased on the leisurely sunset cruise. With custom tour options available, the Spot is often vacationers' first stop, and it's popular among locals, too, who are excited to see their area from a new vantage point. Thanks to the crew of helpful staffers, and the fleet of thoroughly maintained vehicles, customers adventure with confidence, safe in the knowledge that the logistics are totally covered.
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    423 Bayfront Place
    Naples, FL US
  • Scuba Outfitters of Naples
    It would take a massive pool to accommodate every diver who's been trained by Scuba Outfitters of Naples. To date, the company's instructors have educated and certified more than 1,000 scuba divers, and their aquatic alumni only continue to grow in numbers. PADI training begins in Scuba Outfitters' heated indoor training pool, where the experts introduce the most fundamental skills, such as how to avoid dissolving. Eventually, the instructors take students to premier diving locations, including the reefs of Key Largo.
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    1949 Davis Blvd
    Naples, FL US
  • Extreme Family Fun Spot
    Naples' Extreme Family Fun Spot is the great place for a sports fan to spend a Saturday, or any day for that matter. Pick up a tasty meal at their restaurant, located conveniently within the club. Don't leave the kids at home — youngsters will love the family-friendly activities at this club just as much as mom and dad. At Extreme Family Fun Spot, you can find nearby options for both street and lot parking. So head to Extreme Family Fun Spot for some fun, laughs, and a great experience.
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    423 Bayfront Place
    Naples, FL US
  • Conservancy of Southwest Florida
    After plans were revealed to build a road through Rookery Bay in 1964, the Conservancy of Southwest Florida formed to protect the region's environmental interests. This small group of concerned citizens mobilized the community to halt the project, protecting the land, water, and wildlife that makes southwest Florida beautiful. Today, the group continues that work on a larger scale, promoting clean water in the Everglades, treating and releasing injured animals, and protecting sea turtle hatchlings.
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    1495 Smith Preserve Way
    Naples, FL US
  • Sweet Liberty
    Whether you're a sailor, fisher, or just a pleasure-cruiser, Sweet Liberty in Naples has many vessels for rent that are sure to float your boat. Be sure to visit the restaurant at this center for a delicious meal. Bring the whole clan to this center — kids and parents will love the ambience here. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    4620 Gail Boulevard
    Naples, FL US
  • Corey Billie's Airboat Rides
    If you're looking for a great place to disconnect from your daily tasks and get your vacation on, Corey Billie's Airboat Rides in Naples is a prime choice. Corey Billie's Airboat Rides is located near a range of parking facilities, making parking during your stay quick and easy.
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    20610 Tamiami Trail
    Naples, FL US

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