Top Clearwater Cruises, Sailing & Water Tours

53 Results
Private Clearwater Beach Kayak Tour & Island Adventure

Escape the crowded group tours and experience Clearwater from the water on a more personal island adventure. Paddle across the beautiful Intracoastal Waterway to a …More

Escape the crowded group tours and experience Clearwater from the water on a more personal island adventure. Paddle across the beautiful Intracoastal Waterway to a...

2 hours 30 minutes Free Cancellation
5.0 (31)
from
$85
2.5 Hour Kayaking with Manatee and History Tour in Tarpon Springs

Experience a once in a lifetime opportunity of kayaking with Manatees. Start at our launch then paddle past the historic Sponge Docks, learning about the …More

Experience a once in a lifetime opportunity of kayaking with Manatees. Start at our launch then paddle past the historic Sponge Docks, learning about the...

2 hours 30 minutes Free Cancellation
5.0 (28)
from
$66
Half-Day Private Boating On Tahoe Funship - Indian Rocks Beach

A Boat Day offers private, customized half-day and full-day boat charters for small groups of up to 8 passengers. Sit back and relax on the …More

Likely to Sell Out
Likely to Sell Out

A Boat Day offers private, customized half-day and full-day boat charters for small groups of up to 8 passengers. Sit back and relax on the...

4 hours Free Cancellation
5.0 (28)
from
$1,050
Paddle Pub Clearwater Shared Cruise – 2 Hours (Up to 20ppl, BYOB)

Explore the vibrant heart of Clearwater in style aboard our spacious paddle pub boat! Set sail through the beautiful bay, passing luxurious yachts and picturesque …More

Likely to Sell Out
Likely to Sell Out

Explore the vibrant heart of Clearwater in style aboard our spacious paddle pub boat! Set sail through the beautiful bay, passing luxurious yachts and picturesque...

2 hours Free Cancellation
4.9 (26)
from
$49
Cruise Clearwater Beach Private Pontoon Boat Tours

Experience one of the top-rated Clearwater Beach pontoon tours with private 2-hour and 4-hour options for up to 6 guests. Choose our 2-hour evening sunset …More

Experience one of the top-rated Clearwater Beach pontoon tours with private 2-hour and 4-hour options for up to 6 guests. Choose our 2-hour evening sunset...

2 to 4 hours Free Cancellation
5.0 (24)
from
$375
Half-Day Private Boating On Premium Four Winns - Clearwater Beach

A Boat Day offers private, customized boat charters for small groups of up to 10 passengers. Sit back and relax on the very comfortable, 27 …More

Likely to Sell Out
Likely to Sell Out

A Boat Day offers private, customized boat charters for small groups of up to 10 passengers. Sit back and relax on the very comfortable, 27...

4 hours Free Cancellation
5.0 (18)
from
$950
Clearwater Dolphin Kayak Tour and Bird Island Adventure

Experience Clearwater Beach like never before on your guided two-hour Dolphin Kayak and Island Excursion departing directly from Shephard’s Beach Resort. Paddle through calm Gulf …More

Experience Clearwater Beach like never before on your guided two-hour Dolphin Kayak and Island Excursion departing directly from Shephard’s Beach Resort. Paddle through calm Gulf...

2 hours Free Cancellation
4.8 (17)
from
$55
Private Holiday Inshore Fishing Charters

Explore Florida's Gulf Coast on a private inshore fishing charter from Holiday through the waters surrounding Anclote Key and nearby backcountry. This diverse coastal fishery …More

Explore Florida's Gulf Coast on a private inshore fishing charter from Holiday through the waters surrounding Anclote Key and nearby backcountry. This diverse coastal fishery...

4 to 6 hours Free Cancellation
5.0 (16)
from
$231
Florida's Beautiful Beaches and Waterways Private Tour

We offer private, customizable, scenic boat tours, sunset cruises, and island hopping. We are all about fun, family, and being on the water. Relax and …More

We offer private, customizable, scenic boat tours, sunset cruises, and island hopping. We are all about fun, family, and being on the water. Relax and...

4 hours Free Cancellation
5.0 (15)
from
$485
Private Clearwater Beach Tandem Kayak & Island Adventure

* PRICE IS PER TANDEM KAYAK FOR 2 PEOPLE! * Skip the crowded group tours and experience Clearwater from the water at your own pace. …More

* PRICE IS PER TANDEM KAYAK FOR 2 PEOPLE! * Skip the crowded group tours and experience Clearwater from the water at your own pace....

2 hours 30 minutes Free Cancellation
5.0 (12)
from
$165
Dolphin Excursions, Sunset Tours and Snorkeling & Shelling Tours

Embark on an unforgettable adventure with ParrotDise Express Boat Tours, offering premier Dolphin Excursions and captivating Sunset Tours in Clearwater and Dunedin. Cruise aboard the …More

Embark on an unforgettable adventure with ParrotDise Express Boat Tours, offering premier Dolphin Excursions and captivating Sunset Tours in Clearwater and Dunedin. Cruise aboard the...

2 hours 30 minutes Free Cancellation
5.0 (11)
from
$43
Half-Day Private Boating On Black Hurricane - Indian Rocks Beach

A Boat Day offers private, customized boat charters for small groups of 1-6 passengers. Sit back and relax on the very comfortable, 24 foot Hurricane …More

Likely to Sell Out
Likely to Sell Out

A Boat Day offers private, customized boat charters for small groups of 1-6 passengers. Sit back and relax on the very comfortable, 24 foot Hurricane...

4 hours Free Cancellation
5.0 (9)
from
$850
Go Tiki Tours Clearwater"#1 Floating Tiki Boat" Bathroom on Board

We provide the perfect 2 hour Floating Tiki Boat for any of your event needs… whether you're celebrating birthdays, anniversaries, graduations, retirements, or bachelor/bachelorette parties, …More

Likely to Sell Out
Likely to Sell Out

We provide the perfect 2 hour Floating Tiki Boat for any of your event needs… whether you're celebrating birthdays, anniversaries, graduations, retirements, or bachelor/bachelorette parties,...

2 hours
5.0 (8)
from
$60
Clearwater Sunset Cruise – October through March

Experience Clearwater’s golden hour aboard Salt Therapy with Captain Clearwater. This 2-hour private sunset cruise is pure Florida magic—dolphins playing in the fading light, the …More

Experience Clearwater’s golden hour aboard Salt Therapy with Captain Clearwater. This 2-hour private sunset cruise is pure Florida magic—dolphins playing in the fading light, the...

2 hours Free Cancellation
5.0 (8)
from
$260
Private Clearwater Inshore Fishing Charter

Experience Clearwater from the water on a private inshore fishing charter exploring Clearwater Bay, nearby barrier islands, and the waters surrounding Caladesi Island. This diverse …More

Experience Clearwater from the water on a private inshore fishing charter exploring Clearwater Bay, nearby barrier islands, and the waters surrounding Caladesi Island. This diverse...

4 to 6 hours Free Cancellation
5.0 (7)
from
$225
Paddle Pub Clearwater Private Cruise – 2 Hours (2-20ppl, BYOB)

Explore the vibrant heart of Clearwater in style aboard your own private paddle pub boat! This charter is all yours! Set sail through the beautiful …More

Likely to Sell Out
Likely to Sell Out

Explore the vibrant heart of Clearwater in style aboard your own private paddle pub boat! This charter is all yours! Set sail through the beautiful...

2 hours Free Cancellation
5.0 (5)
from
$980
2 Hour Tarpon Springs Sunset and Night Guided Kayak Tour

Leave our launch with your guide before the sun has set. Navigate through the mangroves and the shallows as you witness the surrounding ecosystems transition …More

Leave our launch with your guide before the sun has set. Navigate through the mangroves and the shallows as you witness the surrounding ecosystems transition...

2 hours Free Cancellation
5.0 (4)
from
$52
2 Hour Tandem Kayak Tour (Price for 2 People)

Experience Anclote River and everything it has to offer. You'll be guided through the mangroves spotting wildlife along the way. Learning about the Eco Systems …More

Experience Anclote River and everything it has to offer. You'll be guided through the mangroves spotting wildlife along the way. Learning about the Eco Systems...

2 hours Free Cancellation
5.0 (4)
from
$110
Clearwater Private Paddle Pub Sunset Cruise – 2 Hour (2-20ppl)

Turn up the music and turn down the lights — Clearwater from the water at night is absolutely stunning! Hop aboard our motorized party bike …More

Likely to Sell Out
Likely to Sell Out

Turn up the music and turn down the lights — Clearwater from the water at night is absolutely stunning! Hop aboard our motorized party bike...

2 hours Free Cancellation
5.0 (3)
from
$980
BYOB Tiki Cruise in Clearwater Beach with Dolphin Watching

Set sail on a lively Tiki Getaway cruise along Clearwater Beach, where you can soak in the sun and enjoy the open air. This 1.5 …More

Likely to Sell Out
Likely to Sell Out

Set sail on a lively Tiki Getaway cruise along Clearwater Beach, where you can soak in the sun and enjoy the open air. This 1.5...

90 to 120 minutes Free Cancellation
5.0 (3)
from
$25

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