Key West Sailing Charters

Key West Sailing Charters

To truly appreciate the island of Key West, see it from the sparkling waters that surround it. With a Key West sailboat vacation aboard the Lions Paw, you can experience the Southernmost City both on and off the water. Explore Key West’s lively Duval Street or enjoy a quiet night at sea under the stars. Our customizable charters offer you options for overnights at sea or in port and daytime excursions. The 45-foot Lions Paw is a first-class sailing vessel, and our crew are experienced and passionate about sailing.

Panama City Beach Vacation Rentals

The Sailboat

The Lion’s Paw

Here’s what the Lion’s Paw offers:

  • A raised deck and that translates into great views from inside the spacious salon.
  • Forward and aft cabins with full size beds and private access to bathrooms.
  • Sheets, towels, and some toiletries.
  • Two AC systems and a generator for off shore power needs
  • The kitchen includes sink, stove, small refrigerator, pots, pans, cutlery, tableware, microwave oven, and coffee pot
  • A large cooler for ice and beverages
  • Two bathrooms – called Heads – and doors to the aft and forward cabins.
  • Sound system for local radio or your personal I-Pod
  • Televisions are located in both cabins and hooked up to cable when in port
  • Wifi available via marina

Key West Harbour Marina offers:

  • Large pool with lounge chairs
  • Beach area with lounge chairs
  • Access to fishing and dive charters
  • Ships Store
  • Restaurant serving lunch and dinner
  • Fitness center and sauna
  • Seperate men and women shower facilities
  • Laundry (we provide detergent)

Captain & Crew

Experienced Captain and Crew

Capt. Nancy Beaudin: is French Canadian whose confidence, determination and perseverance led to achieving her goal of living and working on the ocean. From schooners to private charters, sailing became a passion. A spirited, high energy captain and field manager, Nancy’s experience and knowledge about sailing and the area make her a pleasure to have aboard.

Capt. Janet Hinkle : Janet is a graduate of Offshore Sailing School with certificates in Sailing, Live Aboard Cruising, and Navigation. She has over 15 years experience sailing and navigating the coast of Florida and holds both a six pack and Masters Captain’s licenses. She has lived in Key West long enough to know all the great spots for on and off the water adventures. She is the owner of The Lion’s Paw and takes great pride in maintaining a boat that is ship shape, clean, functional, and a dream to sail.

First Mates – mates are chosen for their particular expertise in sailing, wine, food, and adventure.


Nothing is more romantic than engagements and marriage at sea. Our captains will work with you to create the celebration of your dreams. Captain Janet is fully licensed to perform weddings. She is also a writer and can help shape your wedding ceremony to be a true reflection of your partnership.

Our pricing is turn key – we will do all the work for you. Cakes, champagne, the works. Call for easy, clear, and complete pricing. We are a custom charter company and can create the experience you desire.


Easy, Clear Pricing – Two Night Minimum


Per night to party of four; additional persons are $25 per person/per night. The Lion’s Paw is a 45 foot Catalina Morgan with two staterooms and two baths. Full kitchen, television, stereo, linens included. The yacht is in a slip at the Key West Harbour Yacht Club, a top tier resort with pool and fine dining.

All Stays MUST include a half day, full day, or overnight sail.


Half-Day sail – Your Captain and Mate will sail to the reef for swimming and snorkeling. Iced water and soft drinks are provided along with a refreshing fruit and cheese snack.


Full-Day Sail – the extra time allows for adventuring further away from the marina with your Captain and mate. In addition to all the benefits of the half-day sail, lunch is provided.


Island Adventure for Four – Your adventure begins with a sail to the reef for snorkeling and swimming. From there, you’ll sail further west to a remote island. During your adventure, your captain and mate will prepare and serve lunch, dinner and breakfast the following morning.

Please plan for a 15-20% of the cost of the sail combined CASH tip for your captain/mate and a Turnover Fee $250, Pet Fee $175.

Click here for Reservation Inquiry and Complete Price Quote

Key West

What’s in a Name.

When you ask boat captains about naming their boat, you can usually count on a great story to follow. At the Key West Harbour Yacht Club I have found this to be a great conversation starter.

Each morning I take my dog, Cooper, for a stroll down the dock and share a cup of coffee with folks who gather at the tiki hut. We catch a morning breeze, share marina gossip, and give our dogs a little social time. One morning I conversed with Charlie Johnson, a slim, tan gregarious talker . His live aboard boat, a power yacht, is named Ship Chaser.

Turns out he is the current among a generation of harbourmasters (yes, historically it’s one long word) who have led ships safely through the channels of Key West. The Johnsons of Key West have been chasing ships since the early 1900s.

Harbormasters are the enforcers – responsible for safe navigation, security, and correct operation of the port. Laws and traditions have kept it a family business. It’s almost like you need to secret code to get in. Charlie tells me his son is happy working as a Key West police officer but his daughter is taking an interest in following in her father’s footsteps. You go girl!

My dad had a power boat. His name is Jim. My mom’s name is Joye. They named their boat Jim’s Joye.

A lot of boats bring humor into the picture….I’m thinking of Hoof Hearted…say it fast three times and think bathroom humor. Then there’s The IJ Frog…few walking along the dock would think it’s an acronym for “I Just Freaking Ran Out of Gas” but that’s the story. Boaters tend to be a happy lot and that’s what is nice about hanging out at the marina.

My boat, The Lion’s Paw, has a story too. It’s the name of a book written by Robb White and first published in 1946. It’s a children’s classic and elementary school teachers have read it aloud to classes for decades. In fact, my fourth grade teacher read it to me and my three children’s third grade teacher read it to them.

It’s the story of two children, Penny and Nick, who escape from an orphanage and join a young man named Ben on a thrilling journey in a sloop through the oceans, inlets, and rivers of Florida encountering alligators, bounty hunters and storms along the way.

I remember loving the book and it’s my first real memory of sailing. It just may be the reason I bought a boat in the first place. I have the book on board and ask all my visitors to sign it. I open the book often and try to read it at least once a year. I encourage my company to read it while they are on board. It’s a real treat.

Key West Harbour

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    Key West Sailing Charters