Key West Captains, Key West, FL (2025)

08/29/2025

⚓ Turn Your Boat Into a Business in Paradise 👉kwcaptains.com/join-our-charter-fleet

Owning a boat in the Keys is a dream — but it can also be a profitable investment. Partner with Key West Captains, and we’ll transform your vessel into a charter business that works for you.

Our fleet includes:
• Luxury motor yachts & sailing catamarans
• Sport utility vessels & center consoles
• Day boats (including tiki-style vessels)
• Fishing boats
•
From Dry Tortugas expeditions to reef snorkeling, sandbar lounging, sunset cruises, island-hopping adventures, lobster diving, fishing trips, and tiki bar crawls — there’s no shortage of experiences our guests are searching for. Your boat could be their ticket.

Depending on where you dock, you may even be able to list it on Airbnb for additional income streams.

We handle the hard parts — marketing, booking, crew, and management — while you enjoy direct payouts and the freedom to use your boat anytime.

Your boat. Our expertise. A partnership built for success.

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

08/28/2025

⚓ Cruise Key West in Comfort & Style 👉kwcaptains.com/explore-our-fleet/30-jeanneau

Looking for the perfect blend of adventure and relaxation? Step aboard our 30’ Jeanneau NC 895 — the ultimate express cruiser designed for comfort, speed, and unforgettable days on the water.

🎣 Reel It In – Fully equipped for fishing trips, from snapper on the reef to mahi offshore.
🦞 Dive for Dinner – Jump in during lobster season and bring home the freshest catch.
🏝 Island-Hopping – Explore hidden gems like the remote Marquesas Keys or chill at backcountry sandbars.
🍹 Tiki Bar Crawl – Cruise right up to Key West’s iconic tiki bars for a true island-style party.
🌊 Water Toys Onboard – Float the day away on the lily pad or paddle around turquoise waters on the SUP.
☀️ Comfort + Style – Spacious seating, shaded cockpit, and an air-conditioned cabin for cooling off.

From family fun to fishing runs, lobster diving to tiki bar hopping, this Jeanneau brings comfort, adventure, and the full Key West experience in one sleek ride.

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

08/26/2025

🛥️🌴 Wouldn’t you love to spend a full day in the Dry Tortugas like this? 👉kwcaptains.com/explore-our-fleet/72-marquis

A private family adventure aboard the 72' Marquis—complete with turquoise water, historic forts, and sunken treasures. Here's how we did it:

📍 Fort Jefferson — Explored the legendary 1800s fortress
🐢 Loggerhead Key — Snorkeled vibrant reefs + spotted sea turtles
⚓️ Windjammer Wreck — Discovered a ghostly shipwreck beneath the surface

This isn’t your average boat trip—
It’s a luxury yacht charter to one of the most remote and breathtaking places in Florida.

✨ Air-conditioned interior + flybridge lounge
✨ Spacious for up to 12 guests
✨ Full-day or multi-day charters only
✨ Fully crewed + customizable itinerary

Ready to make the Dry Tortugas your private playground? 👇

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

08/25/2025

🏴‍☠️🍻 Arrr, hoist yer sails and raise a toast—it be Captain Patrick Carter’s birthday! 👉kwcaptains.com/patrick-carter

From steering through turquoise seas to sandbar adventures, this Key West Captain knows how to chart a course for fun. May yer year be full of fair winds, smooth seas, and just the right amount of rum. ⚓

Drop yer birthday wishes below, mates—let’s make it a proper Key West celebration! 🎂⛵️☀️

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

08/23/2025

⛵ Sail, Snorkel, Soak It In 👉kwcaptains.com/explore-our-fleet/42-lagoon

That’s what life looks like aboard Sugar Magnolia.

Today’s charter was all about reef snorkeling, grilling on deck, and lounging with the crew — because this Lagoon 42 catamaran is built for both adventure and relaxation.

🐠 Explore vibrant reefs & shipwrecks
🔥 Fire up the grill for the ultimate sandbar feast
🌴 Chill on the Lily Pad or paddle out for some fun
☀️ Stretch out on spacious decks and soak in the Key West sunshine
🌅 Stay overnight in private cabins for the full island-hopping experience

Whether you’re planning a family trip, a birthday bash, or just a day to drift away, Sugar Magnolia is your floating island escape.

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

08/20/2025

Big shout out to our newest top fans! 💎 Christine Grincius, Margie VanderMeer, Christine Al Schmidt, Bruce Chambers, Angel Herrera, Larry Holland, Logan Newell, Don Brooks, Денис Грушко, Cliff Lanham, Jay Miller, Max Zahner, Sonny Dukes, Dan Jensen, Patrick Carter, James Mathews, Peter LaRochelle

We appreciate you!!! Thanks for your support!

08/20/2025

🚤 Boat Days Are the Best Days — Monterey Style 👉kwcaptains.com/explore-our-fleet/27-monterey

Looking for the perfect boat to spend your day in paradise? The 27' Monterey is perfect for families, friend groups, and parties who want a little bit of everything. From sandbar lounging to snorkeling reefs and shipwrecks, this boat does it all.

Here’s how you can enjoy it:
🌴 4 Hours — $375 + Taxes/Fees
Hop between a few sandbars or snorkel stunning reefs close to shore. Perfect half-day escape!

🌊 6 Hours — $575 + Taxes/Fees
Spend your day snorkeling the reef AND hitting the sandbars. The ultimate Key West sampler!

☀️ 8 Hours — $725 + Taxes/Fees
An adventure-packed day! Snorkel shipwrecks and reefs, explore uninhabited islands, kick back at sandbars AND even stop at a tiki bar.

Note: Captain’s fee and fuel are additional.

Whether you’re planning a family adventure, a birthday celebration, or a laid-back day at sea, the Monterey gives you the freedom to explore Key West like a local.

📅 Book your day on the water 👇

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

08/18/2025

💍Bachelorette in Key West? This is how you do it 👉kwcaptains.com/private-charters

At Key West Captains, your last sail before the veil isn’t just a boat day — it’s your adventure, your way. You choose your boat, and we bring the vibes.

✨ Catamarans — the ultimate floating dance floor for you + all your besties
✨ Day Boats and Sport Cruisers — sleek, fast, and perfect for sandbar-hopping adventures
✨ Luxury Yachts — sip champagne by day, toast at sunset… and keep the party going with an overnight stay at sea 🌙🍾

🍹 BYOB and let us stock the cooler or elevate the day with a private chef or catering
🚤 Add-on adventures: jet skis, e-foil lessons, paddleboards & more
🏝️ The backdrop? You choose. Sandbars, snorkeling, or chasing sunsets — we’ll customize the day around your crew

From boujee babes to wild-at-heart brides, we’ve got the boat (and the extras) that make your celebration unforgettable. 🥂✨

👯‍♀️ Bride tribe, it’s time to sea-lebrate. 👇

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

08/17/2025

🐠 Adventure Below the Surface: The Keys’ Best Reefs & Wrecks👉kwcaptains.com/private-charters/coral-reef-shipwreck-snorkeling

Did you know the Florida Keys are home to the third-largest coral reef system in the world?

Stretching 221 miles from Key Biscayne down to the Dry Tortugas, this living reef is a treasure chest of marine life, history, and hidden stories waiting to be explored.

On our private and multi-day charters, you’ll have the chance to snorkel some of the Keys’ most iconic spots:
🤿 Sand Key – famous for its historic lighthouse and vibrant coral gardens.
🤿 Western Sambo – a protected reef sanctuary, brimming with sea turtles, rays, and schools of tropical fish.
🤿 Little Africa at Dry Tortugas – an underwater paradise named for its stunning reef patterns that resemble the African continent from above.

And if shipwrecks call to your adventurous side, we’ll take you there too:
⚓ Fleming Key Wreck – a mysterious sunken vessel just off Key West.
⚓ Boca Grande Key Wreck – a shallow wreck perfect for snorkeling and discovering history up close.
⚓ Windjammer at Dry Tortugas – a majestic 19th-century sailing ship, resting beneath turquoise waters, still telling stories of the past.

Whether you’re chasing coral and wildlife, exploring shipwrecks, or simply floating in awe of the ocean, our sport cruisers, luxury catamarans, and motor yachts are your gateway to the adventure of a lifetime.

Ready to dive in? 👇

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

08/16/2025

⚠️ Warning: The Salty Bottom Boat may cause excessive laughter, spontaneous dancing, and Key West stories you’ll tell forever! 👉kwcaptains.com/explore-our-fleet/salty-bottom

36 seats. Endless deck space. Zero bad vibes.
This isn’t just a party boat — it’s a floating slice of paradise where:
🏝 Sandbars turn into dance floors
🌅 Sunsets become champagne toasts
🎶 The playlist hits just right
📺 Yes… you can even watch the game mid-ocean

Bachelorettes. Birthdays. Tuesday afternoons that feel like Friday nights.

If it’s worth celebrating, it’s worth doing on the Salty Bottom.

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

08/14/2025

🏝 Your Key to Dry Tortugas Adventure — Private Day Trip or Multi-Day Luxury 👉kwcaptains.com/private-charters/dry-tortugas

Crystal-clear waters. Remote white-sand beaches. Historic Fort Jefferson rising from the sea.

The Dry Tortugas isn’t just a destination — it’s an experience most people will never have… and we take you there in absolute comfort.

🚤 Your Vessel, Your Way
Choose your style:
• Sport Cruisers for a fast and exhilarating day trip
• Luxury Catamarans for spacious, laid-back sailing
• Motor Yachts for the ultimate in style, speed, and onboard amenities

🛥 Day & Multi-Day Charters
• Day Trips: Depart in the morning, spend hours exploring the fort, snorkeling vibrant reefs, and relaxing on secluded beaches before heading back at sunset
• Multi-Day Charters: Slow it down — explore Dry Tortugas and the Marquesas, overnight under the stars, and wake up to the sound of waves

🌊 Why Go With Us?
• Private, customizable charters — no crowds
• BYOB, cater, or bring a chef to prepare gourmet meals
• Choose from a variety of boats with premium amenities
• Snorkeling gear and water toys included on our multi day adventures
• Top-tier, experienced captains

02/22/2025

Experience Key West in Style – Private Charters Aboard the 27’ Monterey! 👉kwcaptains.com/private-charters

Looking for the perfect boat for your next adventure? This luxurious 27’ Monterey offers the ultimate way to explore Key West, whether you’re looking for relaxation, excitement, or a bit of both! With two stunning options—a sleek black or elegant white model—you can cruise in style with up to 12 passengers.

Charter Options:
⏳ 4 Hours – $655 (Includes USCG Licensed Captain) + Fuel Costs
⏳ 6 Hours – $965 (Includes USCG Licensed Captain) + Fuel Costs

Your Adventure, Your Way:
🌴 Sandbar Hopping – Relax in crystal-clear waters
🐠 Reef Snorkeling – Discover vibrant marine life
🐬 Dolphin Watching – Spot playful dolphins in their natural habitat
🎉 Perfect for Special Occasions – Bachelorette parties, birthdays, anniversaries & family gatherings

Why Choose the 27’ Monterey?
✔️ Spacious & Comfortable – Room for up to 12 guests with plenty of seating
✔️ Smooth & Stylish Ride – Sleek design and top-tier performance
✔️ Bluetooth Sound System – Set the vibe with your favorite music
✔️ Onboard Convenience – Bathroom, coolers with ice, and a variety of floats
✔️ BYO Food & Drinks – Pack your favorites and make it your own

Whether you're celebrating a special moment or just want a day of fun on the water, this private charter is the perfect way to experience Key West in comfort and style.

Book your adventure today! 👇

Contact the Captains 1st!
📲 (305) 209-3414
💻 kwcaptains.com
👉 Or just message us here

Key West Captains

08/29/2025

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08/26/2025

08/25/2025

08/23/2025

08/20/2025

08/20/2025

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08/17/2025

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08/14/2025

02/22/2025

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