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You tell us the vibe. We build the whole day around it. 😎It starts with picking the right boat for your crew. Then we ha...
10/17/2026

You tell us the vibe. We build the whole day around it. 😎

It starts with picking the right boat for your crew. Then we handle the catering so you never have to think about food. Your captain plans the route around the tide and the weather, so every stop is at its best when you get there.

Morning? We're snorkeling reefs so clear you'll forget you're in the water. 🐠

Midday? We're cruising through dolphin playgrounds where the pods come out to say hi. 🐬

Afternoon? We're sandbar hopping until somebody declares herself mayor of the sandbar. 🏝️

You don't plan anything. You show up in your hat and we take it from there.

Bachelorettes, bachelors, family reunions, birthdays, girls' trips, "just because" trips. We've done them all, and we've never done the same day twice.

Contact the Captains First!
📲 (305) 209-3414
🌊 kwcaptains.com
👉 Or message us here and tell us the vibe

10/17/2026

Ladies, he said "someday."
We said "Saturday." 💅⛵

Private charters in Key West. Your crew, your playlist, your sandbar.

👯‍♀️ Tag the girls you're bringing
📲 Link in bio or call (305) 209-3414
🌊 kwcaptains.com

🚨 Fantasy Fest is HERE and the boats are going fast! 👉kwcaptains.com/private-charters/sandbar-hoppingDuval at night. San...
10/16/2026

🚨 Fantasy Fest is HERE and the boats are going fast! 👉kwcaptains.com/private-charters/sandbar-hopping

Duval at night. Sandbar by day. 🚤

Party on the island after dark, then spend the afternoon anchored on the sandbar with your crew, drinks in hand and music up.

That's how you do Fantasy Fest right. 😎

The island fills up this week. So do the boats. ⏳

Costumes optional. Clothing optional. Fun required. 😉

Tag the friends you're dragging onto the boat 👇

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

💬 Comment BOAT for open dates and pricing

10/16/2026

😉 Clothing optional isn't just for Duval this week.

The whole island is here to party.
But the best party is ON THE WATER.

While everyone else fights for a spot on Duval, you could be anchored on a secluded sandbar with your crew.

Private sandbar hopping charters are OPEN all week:
✅ Crystal clear water and white sand
✅ Your own boat, your own local captain
✅ Bring your own drinks and snacks
✅ Costumes welcome, swimsuits optional, sunscreen required

⚠️ Fantasy Fest is the busiest week of the year in Key West, and boats are booking fast.

Once they're gone, they're gone until next October.
Don't be the one watching the boat pics from the sidewalk. 👀

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

💬 Comment "SANDBAR" and we'll send you pricing

09/25/2026

Meanwhile in the Florida Keys… 😎

Down here, summer never ends. The water is warm, the sandbars are calling & boating season doesn’t come with an expiration date.

Take the boat. Find the clear water. Jump in. Stay for sunset. Do it again tomorrow.

Welcome to the Keys. 🌴

Ready to see it from the water?

Comment FLORIDA & we’ll help you find the right boat + experience for your crew.

09/25/2026

Some people like diamonds. We prefer ours scattered across the ocean. 😍

Clear, blue water, sunshine & a boat headed somewhere beautiful. That’s our kind of sparkle. 💎

Turns out the Florida Keys have their own kind of luxury. ✨

09/23/2026

You keep saying you want to do it…

Take the boat.
Go to the sandbar.
Snorkel the reef.
Explore the backcountry.
Make it all the way to Dry Tortugas.
Stay for sunset.

Stop waiting for the “perfect time.”

Book the trip. Make the memory.

A few hours. A full day. A multi-day escape. Sailing, fishing, exploring or doing absolutely nothing on a sandbar.

You tell us what kind of day you want. We’ll help make it happen.

So… what are you waiting for?

Book the trip. 🌴

DM TRIP and we’ll help you find the right boat + experience for your group!

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

POV: You booked the boat that can take you pretty much anywhere. 👉kwcaptains.com/explore-our-fleet/37-midnight-expressTh...
09/20/2026

POV: You booked the boat that can take you pretty much anywhere. 👉kwcaptains.com/explore-our-fleet/37-midnight-express

The 37’ Midnight Express isn’t for sitting around at the dock looking pretty.

She’s built to MOVE.

One minute you’re cruising across open water, the next you’re tucked behind an uninhabited island, swimming in waist-deep turquoise water, snorkeling a reef, finding a rope swing in the mangroves or chasing the sunset back to Key West.

And when you’re ready to go farther? She can take you all the way to the Dry Tortugas.

Sandbars.
Hidden islands.
Snorkeling.
Beach exploring.
Sunset chasing.
Dry Tortugas adventures.
Or absolutely no itinerary at all.

That’s the beauty of having your own boat for the day.

⚓ 37’ Midnight Express
🌴 Private Key West charters
👥 Up to 13 guests
📍 Lower Keys + Dry Tortugas

Where are we taking you? 👇

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

09/10/2026

Dolphin playgrounds are easily one of the best parts of our trips 🐬

There’s nothing quite like cruising through the backcountry and suddenly having dolphins show up to swim, play and race alongside the boat.

No schedule. No aquarium. Just wild dolphins doing their thing in the waters around Key West.

This is why we love getting you out exploring the places you can only experience by boat.

Come find your playground with us.

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

Address

7005 Shrimp Road
Key West, FL
33040

Opening Hours

Monday 8am - 8pm
Tuesday 8am - 8pm
Wednesday 8am - 8pm
Thursday 8am - 8pm
Friday 8am - 8pm
Saturday 8am - 8pm
Sunday 8am - 8pm

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