Skip to main content
27' Monterey Sport Boat: Private Charter for up to 12 People image 1
27' Monterey Sport Boat: Private Charter for up to 12 People image 2
27' Monterey Sport Boat: Private Charter for up to 12 People image 3
27' Monterey Sport Boat: Private Charter for up to 12 People image 4
27' Monterey Sport Boat: Private Charter for up to 12 People image 5
27' Monterey Sport Boat: Private Charter for up to 12 People image 6
27' Monterey Sport Boat: Private Charter for up to 12 People image 7

27' Monterey Sport Boat: Private Charter for up to 12 People

About this Experience

What you’ll do:

Set sail with Key West Captains and enjoy the Florida Keys the way it was meant to be—on a private boat charter designed just for your group. Cruise in style aboard a 27’ Monterey with 400hp, complete with a Bluetooth stereo, assortment of floats, a bathroom onboard, and coolers with ice. Whether you’re after a day of sandbar hopping, a sunset cruise, or dining dockside at a waterfront restaurant, your USCG licensed captain will ensure the experience is seamless, comfortable, and unforgettable.

Why we love it for your party:

  • It’s your own private paradise (No crowds, just you and your group enjoying the open water)

  • Choose your adventure (From snorkeling to sandbar parties, every charter is customized to your vibe)

  • Bring your own fun (Load up the cooler with your favorite food and drinks to keep the party going)

  • Perfect for any occasion (From bachelorettes to birthdays to romantic moments, this boat sets the stage)

About this experience partner:

Key West Captains makes the Florida Keys feel like your own personal playground with fully private charters led by licensed captains who know the waters best. With a focus on comfort, flexibility, and local expertise, they deliver tailor-made experiences that turn your day on the water into a memory of a lifetime.

Additional information:

  • Private charters available for 2, 4, 6, or 8 hours

  • Boat accommodates up to 12 passengers

  • Must be 21+ to rent/charter (bareboat option available)

  • Call or text directly to speak with a captain: (305) 209-3414

Provided by Key West Captains

Joined August 2025

Book This Experience

Visit the experience booking site to check availability and book your experience.

Location

Key West, FL

Key West, FL 33040, USA

Reviews

See All

5 (10 Ratings)

CD

Coleton D.

December 2025 • Other Party

team and boat was fantastic. got to see some new islands and learned about the area. accommodated every request. hopefully will get to go back out with brian and alexandra! 5 star service.

HM

Hailey M.

December 2025 • Group-Trip Party

Captain Brain was incredible! Highly recommend to anyone looking for a group outing - no one needed to lift a finger. Thanks for making our trip awesome!

JH

Jamie H.

December 2025 • Bachelorette Party

We had a great experience with Captain Brian! We were in town celebrating a bachelorette trip and set up a 4-hour charter. We were delayed by some rain, but Captain Brian shifted our window back so we still got a full four hours on the boat and was overall a super knowledgeable captain and great time. Highly recommend!

LK

Laney K.

December 2025 • Other Party

Captain Brian was the BEST !! He knew exactly where to go. Helped us with all of our stuff, and navigated us around some storms in the area! Very personable!! Ask for Captain Brian!!!

BG

Brian G.

December 2025 • Other Party

Great time with a great captain. Enjoyed the boat trip. Even with a little bit of rain, couldn't have had a better time.

CL

Chelsey L.

December 2025 • Birthday Party

Patrick & Reda we’re absolutely fantastic! Best service I have ever had on a day charter by leaps and bounds. Our group of 12 went out for the day to celebrate a birthday. Not one time did anyone want or reach for anything! They made cocktails and served all the food we could eat, everyone went home happy. Even when one of our passengers felt sea sick they took the time to nurse them back to normal. Over the top care and thoughtfulness!

AK

Ashly K.

December 2025 • Group-Trip Party

Patrick was the best captain!! He found a great spot for us for the day, was so much fun and engaged with our group so perfectly. We would 100% book again.

GB

Gray B.

December 2025 • Other Party

Could not have had a better time! This team is filled with rock stars! Can’t wait to get back and do it again! Thank you!

SK

Stan K.

December 2025 • Other Party

We had a great ride with Captain Brian! He took us to some cool spots where we could get out and explore and swim. It was a rainy day but he was able to maneuver around so that we were not impacted much at all. We'll definately choose Brian again the next time we visit Key West.

DC

Douglas C.

December 2025 • Group-Trip Party

Captain Patrick made our family trip to Key West a 10/10. We especially enjoyed the rope swing tucked back into the mangroves of Boca Chica Key. The dolphins and sand bar experiences were right behind. Captain Patrick was fun to be around and made this experience special for my entire family!