Charter Your Private Sailing Adventure with Captain Bob
Join Captain Bob on board the beautiful sailboat as you cruise around the tropical waters of Key West, Florida!
Click Here or call Captain Bob today to book your Key West charter! 305-434-0262
FREE ground transportation from your location within a 15 mile radius of Key West!
Private Key West Sunset Sail – (2 Hour Sailing Adventure)
Imagine, your own private cruise with your own sailing crew. Just you and your loved ones. You can have up to 6 people in your party. We depart from the Key West Yacht Club. Departure time varies slightly we will contact you with an exact depart time.
We provide water and soft drinks. We do not offer beer or wine, but you’re welcome to bring your own. We can put it on ice and serve it when requested. If this is a special occasion, let us know in advance so we can help to make everything perfect for you.
Click here to fill out our request form or call Captain Bob directly at 305-434-0262.
Private Key West Day Sail – (4 or 7 Hour Adventures | Sight see – Snorkel – Relax)
Sail Key West for a 4 hour half-day, morning or evening, or 8 hour full-day adventure. Take up to 6 people for an adventure they’ll never forget. Learn the fundamentals of sailing. Relax and just go for the ride. Take a dive in the crystal clear waters of the Florida Keys. This is your private sailing adventure. No crowds, no strangers, just you and your friends and family in the open ocean. We depart from the Key West Yacht Club.
Click here to fill out our request form or call Captain Bob directly for details at 305-434-0262.
Weddings & Vow Renewals
Weddings are forever, and so should the memories. Imagine how surprised your loved one will when your Captain stands up to officiate your vows. Yes, Captain Bob is licensed to marry couples. Not only that, Bob is a photographer with a mobile lab at the harbor. So if you’re feeling romantic, and you want the whole package, Captain Bob can assist in making memories that will last a lifetime.
Departures are from the Key West Yacht Club. Times vary. Please click here to fill out our request form or call Captain Bob directly for more details at 305-434-0262.
Key West Personalized Sailing Adventures
Every day it’s an adventure in the waters of Key West and surrounding Keys. There’s a wide range of reefs for snorkel adventures, small island getaways and don’t forget the Dry Tortugas nearby. Call Captain Bob and plan the perfect Key West short, long or overnight adventure for you and your party.
Click here to fill out our request form or call Captain Bob at 305-434-0262.
