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Key West Sailing Trip Details

Hi there, you've seen some preliminary information about our Key West to Dry Tortugas 4-nights, 5 days trips. Here's more details to get you motivated to come play in the sun! Love you gals. Miss you oh so much!

The Joy of Sailing Goes to Key West! Dry Tortugas National Park Here We Come!!

We have a great opportunity to do 4 nights 5 days leaving out of Stock Island in Key West and heading to Dry Tortugas National Park. Here’s more info:

Couples and singles welcome to board the very comfortable, fun, and fabulous 45' Catamaran: 3 cabins with private baths. No sailing experience necessary!

Crew/Passengers: Up to 6 each boat; 2 per cabin (singles private room $2,600).

Note: The invite list for these trips is my friends and colleagues and their guests. I’m doing this for the love of sharing sailing and to go sailing with loved ones! Suffices to say, I will be your mermaid, not your galley maid LOL. Each day we share the cooking, dishwashing, and cocktail mixing – think Big Chill movie dinner scene – it’s fun! I mention all this to set proper expectations since we are not hiring an expensive Chef.

The Boat:

We’ll be sailing with Charisma Charters on the Sailing Vessel “She”. Here’s a link where you can see lots of pictures and info on the accommodations. Three cabins; each each has a comfortable bed, closet, and private bathroom.

Our Sail Plan: subject to change of course – it is sailing after all haha

· Saturday – Depart 10 am for Sand Key

· Sunday – Depart 10 am for Dry Tortugas

· Monday – More Dry Tortuga and on to Loggerhead Key

· Tuesday – Depart 10 am for either Marquesas or back to Sand Key

· Wednesday – Depart 9 am and return to port (arrive about noon)

Captain: This is my favorite part…there will be a captain on board and he’s a friend! So I will get to join in on ALL the fun…and work a some too of course. Suffices to say you can have fun helping to work the sails or simply relax.

Base Cost: Double Occupancy Cabins: $1,300 per person

Note: I priced the market, and this charter is well below what other companies are asking. Friends in high places is always so helpful!!


ü 4 nights/5 days on the boat

ü Food/Provisions up to $750 (any additional split by crew)

ü Required sailing permits

ü Fuel up to $200 (this can be unpredictable as it is a wind-based spend but very likely not more than $300). Any fuel cost above the $200 is split be all crew.

Other Costs:

  1. Flight: I highly suggest you fly directly into Key West. It’s just so darn convenient during the high season in the Keys. The overseas highway that connects Key West to Miami airport should be a 3-hour drive but sometimes can be 5 hours with traffic. The drive is so cool but can be grueling in popular wintertime.

4 Rental cars are readily available at MIA but kind of a waste because we’ll be on the boat and walking Key West most of our time.

4 Bus Miami Airport to Key West and back – here’s the link. It’s cheap and you can relax!

4 Boat Express Shuttle out of Ft. Meyers; this is a great choice if you want to see a bit more of Florida. Fly into FTM, jump on the Express Boat, land, enjoy Key West and hop an Uber to our marina. Our Set Sail time on Saturday morning is 10 am. Here’s that link.

  1. Covid Test: If you are not vaccinated, you will need a negative Covid test within 5 days of the trip start day. We can accommodate an all-vaccinated crew so if that’s important to you, let us know.

  2. Hotel the night before Saturday departure. Right now, hotels are trending at an average $600 per night for one bed. To help reduce costs, we are offering the boat to stay on the night before. The whole boat is only $100 per person per night ($200 for a couple) so you can see that price is way better than a hotel. Totally up to you of course. If we have less than 6 people on the boat for the night before, Then we will have to split the $600/night cost and it may be more than $100/pp. We’ll see how this works out!

  3. Hotel the night of our return to Key West. This is the same situation as above and again; we can purchase this night on the boat for the same price $600 for the boat.

Dry Tortugas National Park is a about 68 miles (109 km) west of Key West in the Gulf of Mexico. The Park preserves Fort Jefferson and the seven Dry Tortugas islands, the westernmost and most isolated of the Florida Keys. Deposit Required ASAP: Reserve your spot with a deposit of $650 each person. Spots on each trip are first deposit first served.

The remaining amount of $650 pp will be due Feb 1. See “Cancellations” info below.

Dates for Sailing: Option 1: Arrive: Fri 2/25 Sail: Sat 2/26 Return: Wed 3/2

Option 2: Arrive: Fri 3/4 Sail: Sat 3/5 Return: Wed3/9

What to Do Next:

1. Choose your dates and contact me:

Please email with which weeks you can sail. If you are flexible and all dates work, let me know. Otherwise, please pick your favorite option and your second choice. This helps me organize each crew for maximum compatibility and fun!

2. Send your money to: Deposits of $650 per person required by January 15, 2022

Zelle: Phone number 562-652-7374 to find me

Venmo: The Joy of Sailing Stephens@thejoyofsailing

Check: Lynda Stephens, 4250 N. Marine Drive, #2629, Chicago IL 60613

Pre and Post Sail Plans - Once crews are set for each sail date we will coordinate our pre and post sail plans. In the meantime, here’s some helpful info

Friday before we sail on Saturday – The marina where the boat is will be about a 15 min Uber to Duvall Street (main tourist area). Coming in on this day gives us all a chance to checkout the KW sights!

Wednesday of our return – Everyone is encouraged to book flights based on a return to port time of noon. The even better option is to spend one more night on the boat in harbor and have more fun in Key West!


Full Refund – Up to the date we go under contract on the boat which is likely Jan 15.

Note: if we don’t get 6 deposits, I will not secure the boat and will definitely return any deposits received as the trip will be canceled

No Refund – Once the boat is under contract, there is no refund. We have to do this because others will lose their trip if someone ducks out, so this ensures the trip goes on, even if a conflict arises for one of the crew members. There is such a thing as travel/vacation insurance that you may want to check out to help you recover your costs in the event of an emergency.

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