Key West Captains

She said "surprise us." That's our favorite thing to hear.

The bride, her girls, and a backcountry sandbar.

💍 There's no better way to spend your bachelorette than on the water.

No lines. No cover charge. No waiting on a table for twelve. Just your people, open water, and a whole day that belongs to you.

She wanted a party. We knew exactly where to take her and the crew.

And this is where we're different:
Anybody can rent you a boat. We build the day.

😎 Local captains who run this water every day and know where to go
🛥️ Full fleet of a variety of boats to choose from, so you get the right boat for your group size and adventure
🎶 Your music, your drinks, your rules
🏝️ Backcountry sandbars, snorkel stops, sunset finish, your call

👉 This is your sign, ladies. Book the boat!

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

KeyWestBoating

Planning a bachelorette party in Key West? Take notes from Allison's crew. 🥂👉kwcaptains.com/explore-our-fleet/48-leopard

Allison and her crew received the full Key West treatment aboard Southern Cross, our 48' Leopard sailing catamaran ⛵

Why this luxury catamaran was the perfect pick:

✅ 4 cabins + 4 full baths, plenty of room for the whole crew to spread out
✅ Wide bow and cockpit lounge space for sunbathing, dining, dancing, and champagne toasts
✅ Snorkel gear included for the reef stop at Western Sambo
✅ Lily Pad for open-water lounging
✅ Fully equipped galley, grill, and A/C to keep the party comfortable all day
✅ Licensed captain & crew handling everything so the bride-to-be didn't have to lift a finger

All our luxury catamarans are available for:
• Half day sails
• Full day sails
• Sunset cruises
• Multi-day excursions

Ready to plan your own? 👇

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

Your Floating Home Awaits 😍⛵

Pick your dates. We'll build the adventure. From Marathon to the Dry Tortugas, choose anywhere from 2 days, 1 night to a full week aboard.

Here's what you can experience along the way:

✅ Learn how to sail
✅ Explore remote, uninhabited islands and walk along pristine, white sand beaches
✅ Snorkel vibrant reefs and historic shipwrecks
✅ Paddleboard and kayak turquoise waters
✅ Visit the beautiful Dry Tortugas National Park
✅ Watch breathtaking sunsets and stargaze at night
✅ Hike trials and swim at Bahia Honda State Park
✅ Spot sea turtles, tropical birds, Goliath groupers, dolphins and other incredible wildlife
✅ Dine at restaurants only accessible by boat like Little Palm Island

No packing up every morning. No rushing to the next stop. Just open water, one island at a time.

Ready to plan your trip? Reach out and let's map it out!

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

This is what the "Welcome to the Fleet" party looks like from above. 🛥️🎉

Rafted up at the sandbar celebrating our newest Midnight Express boats to the fleet.

Floats out. DJ set up on the Tiki Boats. Whole squad dancing in the water. This is just how we do it. ⚡

✅ TWO new 37' Midnight Express boats, officially in the fleet
✅ Tiki boats holding down the good vibes as always
✅ Sandbar rafted up with the whole crew
✅ DJ, floats, water slides, bean bags, music and the clearest water

This is the fleet, this is the energy, and this is why people book with us.

You don't just charter a boat with us. You get THIS. Come see for yourself. ☀️😎

Best bars in Key West? Sandbar by day, Duval by night 😎👉
kwcaptains.com/private-charters/sandbar-hopping

We took our favorite local bartenders out on the Midnight Express, because the people who make your nights on Duval so fun also deserve a FUN day in the sun too.

🍸 By night, they're the heartbeat of Duval, pouring drinks and keeping the island's best street alive
🚤 By day, we traded the barstools for boat seats and pointed the Midnight Express toward open water
☀️ Cruising across turquoise flats, anchoring at the sandbar, toes in the water, drinks in hand
🐬 Because that's the secret to a Key West vacation: the fun doesn't live in one place, it flows from Duval to the deck and back again

So when you're planning your trip, remember the island's best bars come in two forms. One's lined with neon on Duval. The other floats in the middle of paradise.

Ready to find your sandbar? Let's get you out on the water!

Big crew? We were built for this. 👉kwcaptains.com

"We don't have room for your whole crew" — said no one at Key West Captains, ever. 🛥️

The bigger the crew, the better the party.

✅ Up to 13 guests on most of our vessels
✅ Group of 14+? We split you across two boats for double the fun
✅ Want to stay all together on one boat? We have a boat that fits up to 36!

Bachelorette squad. Family reunion. Corporate escape. Whatever the headcount, we've got the boat (or boats) to match.

The only thing standing between your group and open water is one message to our team to plan your amazing day on the water!

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

This Is the One Trip Everyone's Talking About. 👉kwcaptains.com/private-charters/dry-tortugas

One trip. Endless ways to make it yours.

Gorgeous reefs and historic shipwrecks. Clear blue water. A historic fort rising out of the ocean 70 miles off Key West. This is the trip that belongs on every bucket list, and we'll create your perfect day on the water around it.

✅ Shared or Private Charters
✅ Sport Utility Vessels or Luxury Catamarans
✅ Day Trips (8 to 10 hours) or Multi Day Excursions (4 Days, 3 Nights)
✅ Add Fishing 🎣
✅ BYOB, Provisioning and Catering Options
✅ Experienced USCG Licensed Captain and Crew

What you can explore:

🏰 Fort Jefferson and the moat wall
🏝️ Loggerhead Key and its lighthouse
🐠 Little Africa Reef
⚓ The Windjammer Shipwreck
🐬 Wildlife such as Goliath groupers and dolphins

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