Updated on Sep 29, 2026
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Type
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House boat
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Bedrooms
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3
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Bathrooms
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2
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House Rules
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No pets allowed
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Children allowed: ages 0-17
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Smoking allowed: in designated areas
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Events allowed: family gatherings and birthday parties;Maximum event attendees: 6
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Max Occupancy
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6
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Host Language
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English
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Property Id
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2492182
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Welcome aboard the The Thirsty Lady with 3 bedrooms and 3 baths, your own private Sailboat that also includes your Sailing Excursions for up to 6 people. If you were looking for a Unique, Memorable way to experience and enjoy Key West then THIS IS IT!! You stay in amazing 5 Star Marinas each night and Sail by day, all included. If you book 2 nights that includes a Sunset Sail your first night of arrival and 1 full day Reef Sail. Book 3 nights and receive 1 Sunset Sail and 2 Full day Reef Sails and so on. We book 2 nights minimum and 4 nights max.. We always do the Sunset Sail your first night of arrival and then a day Sail is included for each day.
**Please understand that even though 1 Sail is included for each day you book doesn't mean you have to use them all. We have found that guests who book 3 or 4 nights sometime forgo a Sail or 2 to have a free day to do what they wish. It is totally up to you whether or not you use all the Sails included and you can decide as you go when you arrive😊**
We have years under our belt offering these charters and have decided to join the VRBO family to extend our reach. We are here to cater to all your special needs to make sure your experience with us will land in your top favorite vacations EVER! We provide the Captain, Captain Pat, a USCG 100 Ton Master Captain.
The first night of arrival we take you on a Sunset Sail and that night you will be docked at a beautiful Upscale 5 Star Marina that boasts 6 pools, Restaurant & Bar, 24 hour pristine Bath House, and free shuttle all available for you use. There are bathrooms on the boat but you will want to use the Bath House for showering located just steps from the boat..
The 2nd day we take you on a full day Sail to the Reef where you can swim, snorkel and Just Relax! The 2nd night you will be docked at another Amazing Upscale Marina. All the marinas offer amazing amenities including pools, bars, restaurants, and free shuttles. If you stay a 3rd night we take you on another day sail the 3rd day and you will stay back at the 5 Star Marina you stayed the 1st night. We do offer free parking for your entire stay and if you are carless there are free shuttles available to you and we can help you with rides when available. We also provide all your water, ice, and sodas for the length of your stay along with all your life jackets, safety gear, fresh linens and towels and snorkeling equipment. You are responsible for your meals but there is a small kitchen aboard with a fridge, freezer, toaster, and a small stovetop/oven. There are plenty of Restaurant/ delivery options available to you as well. Most people just pick up light snacks and lunch items to make sandwiches for their Day Sails. There is also a dining table that seats up to 6 people.
You are responsible for your own alcohol but we usually have a pretty well stocked bar you are always welcome to. You are welcome to anything you see in the cabin! If you would like me to remove the alcohol from the boat please let me know.
This is your own PRIVATE SAILBOAT made available to you with your own Private Captain that is only there when you are going out Sailing. The rest of your time off the water the boat is all yours. Captain Pat will only be there when you need him. We are 100 percent on call when you are staying with us so we will always be available if you need us. This trip is perfect for couples, friend get togethers and amazing for families!! We have hosted them all and every summer we Captain the boat out to the Boy Scouts of America. Please understand this is a Sailboat so space is limited in the cabin and the rooms are small but there is cold A/C and extremely comfortable to sleep on. The Front bed is a Queen and the back bedrooms are double/fulls. The beds will sleep 2 comfortably but you better like each, lol..What we are offering is something so different from what everyone else is doing and we so look forward to hosting all of
you!! Please message us with any questions!
Sample Itinerary:
Day of Arrival:
Guests usually arrive between 1-4pm. We will greet you and show you around and get you acquainted with the area and boat.
4:30-6pmish is a Sunset Cruise (subject to change when Sunset times change)
The first night you will be docked at a 5 Star Upscale Marina which has 6 pools, a Restaurant & Bar, 24 hour bath house, Gym, and a free Shuttle that will take you downtown and back.
***You have to arrive by 4pm the latest on your arrival day if you want to take advantage of the Sunset Cruise***
The 4pm cutoff time will change throughout the year as Sunset times change. The other half of the year is a 5pm cutoff time when we leave the dock for when the Sun sets later in the evening and so on.
Day 2:
We meet you back at the boat around 9-10ish am (you let us know what works for you) and we Sail you out for a full day at The Reef where you can swim & snorkel. You dictate how long we stay out for but usually we get back to dock around 3 or 4, all up to you. The 2nd night we take you to another beautiful Marina in Key West. All the marinas have pools, restaurants, bars and free shuttles. Basically Sail by Day and then you are free to leave the boat and explore Key West by afternoon/night.
3rd day:
If you chose the 3 night stay we take you on another Day Sail to a different part of the reef and the 3rd night you will be docked where you were the first night. So basically if you book 2 nights that includes 2 Sails and 3 nights you receive 3 Sails.
We also offer 4 night stays which would include an extra Sail.
Located in Key West, this houseboat is on the waterfront. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Smathers Beach. Key West Tropical Forest and Botanical Garden and Sails To Rails Museum at Flagler Station are also worth visiting. Take an opportunity to explore the area for water adventures such as motor boating.
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