Islamorada Boating Tours 

 96 Madeira Road, Islamorada, FL 33036, United States

Islamorada Boating Tours 

Islamorada, FL, United States
Bay boat silhouette
26 feet
6
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!

Onboard Perks & Policies:
Alcohol allowed | Children welcome | Pets welcome | Glass bottles allowed | Red wine allowed | Smoking allowed | Swimming allowed

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!

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Customer reviews

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Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
May 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
2 Hour – Morning Trip (7 AM)
FREE Cancellation 3 days notice
2 Hour Trip
starts at 7:00 AM
+3
US $450
Private tour: up to 6 people
2 Hour – Mid Day Trip (11 AM)
FREE Cancellation 3 days notice
2 Hour Trip
starts at 11:00 AM
+3
US $450
Private tour: up to 6 people
2 Hour – Afternoon Trip (3 PM)
FREE Cancellation 3 days notice
2 Hour Trip
starts at 3:00 PM
+6
US $450
Private tour: up to 6 people
4 Hour – Morning Charter (7 AM)
FREE Cancellation 3 days notice
4 Hour Trip
starts at 7:00 AM
+5
US $750
Private tour: up to 6 people
4 Hour – Mid Day Charter (11 AM)
FREE Cancellation 3 days notice
4 Hour Trip
starts at 11:00 AM
+5
US $750
Private tour: up to 6 people
4 Hour – Afternoon Charter (3 PM)
FREE Cancellation 3 days notice
4 Hour Trip
starts at 3:00 PM
+6
US $750
Private tour: up to 6 people
6 Hour – Morning Charter (7 AM)
FREE Cancellation 3 days notice
6 Hour Trip
starts at 7:00 AM
+6
US $1,100
Private tour: up to 6 people
6 Hour – Afternoon Charter (11 AM)
FREE Cancellation 3 days notice
6 Hour Trip
starts at 11:00 AM
+6
US $1,100
Private tour: up to 6 people
8 Hour – Full Day Adventure
FREE Cancellation 3 days notice
8 Hour Trip
starts at 7:00 AM
+6
US $150,000
Private tour: up to 6 people

Customer reviews

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FAQs about Islamorada Boating Tours

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What the boat is like

Boat category
Center console boats
Boat type
Bay boat
Boat manufacturer
Contender
Boat Model
26 Bay
Year built
2025
Boat length
26 ft
Capacity
6 persons
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