Clearwater Cruises & Sailing Tours

27 experiences to discover

Day & Sunset Cruises Dinner Cruises Sailing Trips

Explore the best cruises & sailing tours tours and activities in Clearwater. Our unbiased ratings help you find the perfect experiences for your trip.

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4.74

Clearwater Beach Private Boating Adventure

From $850

1 provider live

Cruise the waterways on a private boat

Cooler with ice and bottled water

4.68

Clearwater Beach Private Boating Tour

From $950

1 provider live

Cruise on a 25-foot double-decker boat

Cooler with ice and bottled water

4.61

Clearwater Beach Tiki Cruise

From $50

1 provider live

Cruise around Clearwater Beach

USCG-certified captains

4.59

Clearwater Beach Private Pontoon Tour

$379-$549

2 providers combined

Discover remote islands around Clearwater Beach

Bottled water

4.59

Clearwater Private Sunset Cruise

From $250

1 provider live

Experience a guided boat tour

Waters and cooler access

4.58

Clearwater Floating Tiki Boat Tour 2 hr

From $60

1 provider live

Celebrate special occasions on the water

Coolers

4.55

Clearwater Tiki Boat Cruise 1.5 hr

From $299

1 provider live

Enjoy a private tiki boat cruise

USCG certified captains

4.55

Clearwater Sunset Cruise

From $400

1 provider live

Experience breathtaking sunsets

Private transportation

4.55

Clearwater Beach Tiki Boat Experience 1.5 hr

From $50

1 provider live

Cruise on a unique TIKI Boat

1.5 hour TIKI Boat cruise

4.55

Clearwater Bay Tropical Cruise & Buffet

From $58

1 provider live

Relax aboard a boat cruising Clearwater Bay

Admission to the boat cruise

4.55

Clearwater Tiki Boat Sandbar Adventure 3 hr

From $595

1 provider live

Explore two Clearwater Beach sandbars

Coastguard Certified Captains

4.55

Clearwater Island Sandbar & Swim Tiki Cruise

From $55

1 provider live

Experience lively sandbars with locals

USCG Certified Captains