Islamorada Boating Tours
Islamorada Boating Tours
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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!
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!
Trip availability and prices
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
Customer reviews
FAQs about Islamorada Boating Tours
What are the trip rates for Islamorada Boating Tours?
- US $450 per group - 2 Hour – Afternoon Trip (3 PM) (2 hours)
- US $450 per group - 2 Hour – Mid Day Trip (11 AM) (2 hours)
- US $450 per group - 2 Hour – Morning Trip (7 AM) (2 hours)
- US $750 per group - 4 Hour – Afternoon Charter (3 PM) (4 hours)
- US $750 per group - 4 Hour – Mid Day Charter (11 AM) (4 hours)
- US $750 per group - 4 Hour – Morning Charter (7 AM) (4 hours)
- US $1,100 per group - 6 Hour – Afternoon Charter (11 AM) (6 hours)
- US $1,100 per group - 6 Hour – Morning Charter (7 AM) (6 hours)
- US $150,000 per group - 8 Hour – Full Day Adventure (8 hours)
Which amenities are available onboard with Islamorada Boating Tours?
- GPS
- VHF Radio
- Radar
- Chart Plotter
- Depth Finder
- Sonar
- Bow Thruster
- Anchor
- Wheel Steering
- Life Jackets
- Wheelchair Accessible
- Shower
- Bow Sundeck
- Aft Sundeck
- WiFi
- Audio System
- Inside Speakers
- Outside Speakers
- Ice Box
- Wireless Trolling Motor
- Fishfinder
- Baitwell
- Rod Holders
What add-ons can be available with Islamorada Boating Tours?
- Fishing Equipment
- Catch cleaning & filleting
Which kinds of activities does Islamorada Boating Tours offer?
- Boat & Yacht Tours
- Canal Boat Tours
- Sunset Dinner Cruises
- Island Hopping
- Booze Cruises
- Paddleboard
- Whale & Dolphin Watching
- Fishing
- Eco-Tours
- Sandbar Tours
- Stingray Tours
Your operator
Step aboard my 2025 26ft Contender Center Console Bay Boat—your ticket to exploring the turquoise waters of the Florida Keys in style. This sleek, modern vessel comfortably accommodates up to six guests and is powered by a 300HP Yamaha outboard, cruising effortlessly at 40 knots. Perfect for families, friends, or couples, it offers the ideal mix of comfort, adventure, and safety. Enjoy top-tier amenities including SiriusXM satellite radio, a baitwell, fishfinder, rod holders, and an ice box for your refreshments. A spacious sun top provides shade on warm days, while the bow sundeck and swim platform invite you to relax and soak up the island vibe. Captain Greg Poland, a seasoned local guide, crafts every trip around your interests—whether that's fishing with the kids, island-hopping to secret spots, or kicking back on a scenic booze cruise. With an open policy for alcohol, pets, and even smoking, your day on the water is as flexible as it is fun. Safety is always a priority, with life jackets, GPS, depth finder, chart plotter, and VHF radio all on board for peace of mind. Don't wait to make memories—book your adventure today and let Captain Greg show you Islamorada's best spots, from Alligator Lighthouse to the world-famous sandbar.
Step aboard my 2025 26ft Contender Center Console Bay Boat—your ticket to exploring the turquoise waters of the Florida Keys in style. This sleek, modern vessel comfortably accommodates up to six guests and is powered by a 300HP Yamaha outboard, cruising effortlessly at 40 knots. Perfect for families, friends, or couples, it offers the ideal mix of comfort, adventure, and safety. Enjoy top-tier amenities including SiriusXM satellite radio, a baitwell, fishfinder, rod holders, and an ice box for your refreshments. A spacious sun top provides shade on warm days, while the bow sundeck and swim platform invite you to relax and soak up the island vibe. Captain Greg Poland, a seasoned local guide, crafts every trip around your interests—whether that's fishing with the kids, island-hopping to secret spots, or kicking back on a scenic booze cruise. With an open policy for alcohol, pets, and even smoking, your day on the water is as flexible as it is fun. Safety is always a priority, with life jackets, GPS, depth finder, chart plotter, and VHF radio all on board for peace of mind. Don't wait to make memories—book your adventure today and let Captain Greg show you Islamorada's best spots, from Alligator Lighthouse to the world-famous sandbar.
What the boat is like
Which kind of activities are offered
Which amenities are available onboard
What's included in the trip price
What’s allowed on the boat
What additional terms you should be aware of
Security deposit is not required
A refundable deposit is not required by the charter operator.
Fuel is included
Fuel is included in the price of the rental.
How cancellations work
Free cancellation up to 3 days prior to trip
You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
How you can pay
Reserve with a 20% booking deposit, pay the captain the rest
When the captain confirms your trip, BoatBooker charges your credit card a 20% booking deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express
When paying the remaining balance with a credit card, an additional 4% charge will apply.
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