Call or Text us at (305) 209-3414
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.
From luxury yachts and sporty cruisers to spacious catamarans, every charter is captained by local experts who know these waters inside and out. We’ll take you beyond the ordinary—to secret sandbars, hidden reefs, and breathtaking sunset anchorages only locals know. Your perfect day on the water starts here. Call or text us to speak directly with a Captain:
Choose Your Adventure!
Featured Vessels
After Parr T​
- Up to 12 Passengers
- Three-Deck Layout with Large Salon & Gourmet Galley
- 3 Staterooms Including Full-Beam Master Suite with His & Hers Heads
- Queen Ensuite & Double Twin Ensuite Guest Staterooms
- Below Deck Crew Quarters
- Flybridge with Wet Bar, Refrigerator, Ice Maker & BBQ Grill
- Ample Seating with Panoramic Views
- Bring Your Own Food & Drinks
- Catering & Chef Options Available
- USCG Licensed Captain & Mate
Click the "Book Now" button for pricing & real time availability
Parr T - On
- Up to 12 Passengers
- Spacious Layout with Wet Bar, Grill & Gourmet Galley
- Enclosed Sunroom with Retractable Glass Roof
- 3 Staterooms — Two Queen & One Double Twin
- Hydraulic Swim Platform for Water Sports & Snorkeling
- Ample Seating with Panoramic Views
- Bring Your Own Food & Drinks
- Catering & Chef Options Available
- USCG Licensed Captain & Mate
Click the "Book Now" button for pricing & real time availability
- Up to 12 passengers
- Triple 350hp outboards
- Spacious layout
- Cooler, Fridge, Freezer, Grill
- Coolers and Ice Provided
- Bring your own food & beverages
- Air Conditioned Cabin
- Full Bathroom
- USCG Licensed Captain
Click the "Book Now" button for pricing & real time availability
- 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
- 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
- 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
- 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
- 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
- Up to 36 passengers
- Bluetooth Stereo
- Assortment of floats
- Bathroom onboard
- Stay connected with WiFi onboard
- Bring your own food & beverages
- USCG Licensed Captain and Mate
Click the "Book Now" button for pricing & real time availability
- Up to 12 Passengers
- Custom 26' X 11' Tiki Vessel
- Twin 200HP Outboards
- Thatched Tiki Roof With Shade
- Premium Sound System
- Spacious Observation Decks
- Shallow-Draft Hull For Sandbar Access
- Bring your own food & beverages
- USCG Licensed Captain
Click the "Book Now" button for pricing & real time availability
- Up to 6 passengers per boat - 2 boats available
- Bluetooth Stereo
- Coolers & ice provided
- Bring your own food & beverages
- USCG Licensed Captain
Click the "Book Now" button for pricing & real time availability
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
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
Mystic Blue
Manta 42
- Up to 6 passengers
- 3 Bedrooms / 2 Bathrooms
- Air Conditioning
- Bluetooth Stereo
- Hammocks, Beanbags, Paddleboards
- 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
Fountaine Pajot Elba 45
- 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
London Sky
Lagoon 62
- 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
Call or text 305-209-3414 for pricing & real time availability
Captain 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