You may qualify for a Loyalty discount with Islamorada Boating Tours. To check if the Loyalty discount is available for your selected dates, please sign in.

Step aboard our brand-new 2025 Contender 26 Bay Boat, docked at the iconic Lorelei in downtown Islamorada. Powered by a 300 HP Yamaha engine, this sleek, comfortable vessel cruises up to 40 knots and accommodates up to six guests — and yes, we’re pet friendly!

Relax with SiriusXM satellite radio or stream your favorite tunes via Bluetooth while enjoying the spacious aft and bow sundecks. An oversized sunshade keeps you cool, and our ice-filled cooler is ready for your favorite food and drinks — just bring your snacks and let the adventure begin!

I’m Captain Greg Poland, and I craft custom experiences for every trip. Whether it’s dolphin watching, island hopping, sandbar fun, family-friendly fishing, or a lively booze cruise, we’ll make your Florida Keys day unforgettable. Cruise the scenic canals and admire spectacular waterfront mansions, then take a refreshing dip at the famous Islamorada Sandbar!

Safety First: Anchor • Bow Thruster • Chart Plotter • Depth Finder • GPS • Life Jackets • Radar • Sonar • VHF Radio • Wheel Steering

Departure: The Lorelei, Downtown Islamorada
Limited spots available — reserve your adventure today and create memories that last a lifetime!

Trip availability and prices

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2 Hour – Morning Trip (7 AM)