Escape the Ordinary with Key West Captains:
Your Private Paradise Awaits!
Key West, with its stunning sunsets, crystal-clear waters, and laid-back island vibes, is a dream destination. But why just visit paradise when you can experience it like a VIP? Enter Key West Captains, your gateway to unforgettable adventures on the water.
Forget crowded tourist boats and cookie-cutter itineraries. Key West Captains offers private boat charters tailored to your desires. Whether you're dreaming of a 3 day trip to the Dry Tortugas, a thrilling snorkeling expedition, or a fun-filled day of sandbar hopping, we've got you covered. Call or text us to speak directly with a Captain: (305)209-3414
Choose Your Adventure!
Featured Vessels
Sandbar Hop in Style!
27' Monterey - 400hp
- Up to 12 passengers
- Bluetooth Stereo
- Assortment of floats
- Bathroom onboard
- Coolers and ice provided
- Bring your own food & beverages
- USCG Licensed Captain
Click the "Book Now" button for
pricing & real time availability
Sandbar Hop on a Tritoon!
22' Bennington Tritoon
- Up to 10 Passengers
- Bluetooth Stereo
- Coolers provided
- Bring your own food & beverages
- USCG Licensed Captain
- Large bimini for shade
Click the "Book Now" button for
pricing & real time availability
Indoses
Fountaine Pajot Elba 45
- Up to 12 passengers
- 3 bedrooms / 3 bathrooms
- Air Conditioning
- Bluetooth Stereo
- Full kitchen / cooler / grill
- Bring your own food & beverages
- Catering or Private chef available
- USCG Licensed Captain & Mate
Click the "Book Now" button for
pricing & real time availability
Key West Tiki Boat
Double decker pontoon tiki boat.
- Up to 12 passengers
- Bluetooth Stereo
- Lilly pad
- Paddleboard
- Coolers and ice provided
- Bring your own food & beverages
- USCG Licensed Captain
Click the "Book Now" button for
pricing & real time availability
SUV Of The Seas
37' Axopar
- Up to 12 passengers
- Bluetooth Stereo
- Assortment of floats
- Bathroom onboard
- Coolers and ice provided
- Bring your own food & beverages
- USCG Licensed Captain
Click the "Book Now" button for
pricing & real time availability
Duet
Seawind 1260 - 41 feet
- Up to 12 passengers
- 4 bedrooms / 4 bathrooms
- Air Conditioning
- Bluetooth Stereo
- Full kitchen / cooler / grill
- Bring your own food & beverages
- Catering or Private chef available
- USCG Licensed Captain & Mate
Click the "Book Now" button for
pricing & real time availability
32' Sea Pro
- Up to 12 passengers
- Bluetooth Stereo
- Assortment of floats
- Bathroom onboard
- Coolers and ice provided
- Bring your own food/beverages or catering options available
- USCG Licensed Captain
Click the "Book Now" button for
pricing & real time availability
Salty Bottom Boat
- Up to 36 passengers
- Bluetooth Stereo
- Assortment of floats
- Bathroom onboard
- Stay connected with WiFi onboard
- Bring your own food & beverages
- USCG Licensed Captain
Click the "Book Now" button for
pricing & real time availability
30' Jeanneau NC895
- Up to 6 passengers
- Bluetooth Stereo
- Assortment of floats
- Bathroom onboard
- Coolers and ice provided
- Bring your own food & beverages
- USCG Licensed Captain
Click the "Book Now" button for
pricing & real time availability
Southern Cross
Leopard 48
- Up to 12 passengers
- 4 bedrooms / 4 bathrooms
- Air Conditioning
- Bluetooth Stereo
- Full kitchen / cooler / grill
- Bring your own food & beverages
- Catering or Private chef available
- USCG Licensed Captain & Mate
Click the "Book Now" button for
pricing & real time availability
Sugar Magnolia
Lagoon 42
- Up to 12 passengers
- 4 bedrooms / 4 bathrooms
- Air Conditioning
- Bluetooth Stereo
- Full kitchen / cooler / grill
- Bring your own food & beverages
- Catering or Private chef available
- USCG Licensed Captain & Mate
Click the "Book Now" button for
pricing & real time availability
Dream Reach
Leopard 44
- Up to 12 passengers
- 4 bedrooms / 4 bathrooms
- Air Conditioning
- Bluetooth Stereo
- Full kitchen / cooler / grill
- Bring your own food & beverages
- Catering or Private chef available
- USCG Licensed Captain & Mate
Click the "Book Now" button for
pricing & real time availability
24' Yamaha Jet Boat
- Up to 7 passengers
- Bluetooth Stereo
- Assortment of floats
- Coolers and ice provided
- Bring your own food & beverages
- USCG Licensed Captain
Click the "Book Now" button for
pricing & real time availability
Ever Summer
Fountain Pajot MY44
- Up to 12 passengers
- 4 bedrooms / 4 bathrooms
- Air Conditioning
- Bluetooth Stereo
- Full kitchen / cooler / grill
- Bring your own food & beverages
- Catering or Private chef available
- USCG Licensed Captain & Mate
Click the "Book Now" button for
pricing & real time availability
Other Services
Professional Deliveries
Need a vessel moved? Our Captains are experienced in delivering boats both domestically & internationally throughout the US, South America & Caribbean Islands.
Owner / Operator Training
Want to operate your own vessel like a pro? This course is a customized, on-water training available aboard your vessel. The Captain will come to your location and works with you aboard your boat.
Vessel Management
Full management for any size vessel. Weekly, Bi-Weekly or Monthly Dockside Inspections that can include routine maintenance, cleaning, Captain services, hurricane preparedness, etc.
Captain's Key West Picks
Our passengers are always asking us....What else should we be doing while we're here? So, we compiled a list of our favorite bars, restaurants, beaches, equipment rentals and even helicopter rides. Be sure to check them out!
Gallery
About us
Key West Captains is as local as it gets, but has the worldwide network in place to complete even the biggest of tasks! Our backgrounds range from 100 ton Master Captains, military veterans, corporate executives, boat builders, general contractors, college athletes, retired police officers, HVAC technicians, business owners, mechanics, sailors, power boaters and even have a teammate that has biked across the world! Like seriously! On a bicycle! With the vast majority of us living aboard our own large vessels docked at marinas right here on the island..... To say that we live and breathe the boat life, would be an understatement.
Whether you are looking to snorkel the reef and sandbar hop this afternoon, schedule an overnight private charter to the Dry Tortugas next week or have your vessel moved from New York to the Bahamas next month. This is the team to contact!!!! Call/Text (305) 209-3414
Request A Quote!