Mar 7 – Mar 22 | $4950

Limited Availability

This trip has two blue water passages, full of warm Caribbean sailing and adventure! You’ll join the boat at Shelter Bay Marina to sail to Key West, but not without a stop at Grand Cayman.

Our visiting dates in Cayman will align with the moon cycle. This means being able to kayak one of the world’s most dazzling bioluminescent bays if you wish! With each stroke of your paddle, each touch of the water with your hand, the water is illuminated! Cayman is known for its superb underwater world, which makes it a playground for divers and snorkelers alike. Additionally, it provides plenty of white sand beaches, crystal clear water, and warm Caribbean sun. With the trade winds, it’s also the perfect spot to rent a hobie cat to sail along the shore. That’s not all! Cayman is a popular spot to swim with friendly stingrays in the shallow North Sound.

After a good stay, we’ll set sail for the second leg of the trip, riding the Gulf Stream to Key West. We’ll arrive with a bit of time to explore! Take in a sunset with the performers in Mallory Square, or a nice meal ashore at the southernmost point in the US. 

If you’d like to extend your stay for this leg aboard Sea Dragon, you have two options. Firstly, you can join us prior, on our Panama expedition as we transit the Panama Canal. Secondly, you can reserve your bunk to continue on with us from Key West to Bermuda!

All meals on board Sea Dragon are delicious and vegetarian, with the addition of fish if we catch any along the way.

This is not a trip for the infirm or physically unfit. You MUST be able to go up and down the companionway and move safely about the boat while in rough conditions. Having good balance and being in reasonably good health is a priority. Please contact us with any health concerns, or if you answer “YES” to any of the questions on our health questionnaire prior to signing up for the trip!

Ardent Training is offering a significant discount on the RYA Day Skipper Theory online course to anyone signed up for this trip. If you’re interested in taking the course, inform us at sign up and we can give you the discount code!

If you combine this voyage with Canal Crossing, that trip is only $950!


  • Distance: 1150 nautical miles
  • Cost: $4950
  • Date: Mar 7 – Mar 22, 2024 (16 Days, 15 Nights)
  • Start: Shelter Bay Marina, Colon, Panama
  • End: Stock Island Marina Village, Key West, FL

For more details, please explore the drop down menus at the bottom of the page.

Tentative Itinerary

Day 1: Arrive Sea Dragon
You will join the boat at Shelter Bay Marina in Panama between 1500-1700. Night on the dock.

Day 2: Safety Briefings/Exploration
Today is a day for going through safety briefings and getting prepped to set sail. You’ll also have some time to hang at the pool, have a wander through the jungle to the beach, or have a last meal or cold drink ashore. Night on the dock.

Day 3: Set Sail to Cayman 
Today is the day for big blue! It’s time to go sailing and we’ll get underway for the 600NM passage in the morning.

Day 4-6: Underway
Life and rhythm on Sea Dragon will quickly take shape around the watch schedule and life will be wonderfully simple and disconnected from the norm.

Day 7: Arrive Grand Cayman 
We’ll tie up to a mooring off of George Town.

Day 8-9: Exploration
There are so many things that the island offers. Options include swimming with sting rays in the north sound, snorkeling/diving, relaxing on the beach, night kayak in bioluminescent bay, and much more! 

Day 10: Set Sail to Key West  
After a wonderful few days spent in Cayman, we’ll untie from the mooring and set sail for the 550NM to Key West. 

Day 11-13: Underway 
The sailing will be fast and exciting on this leg! Everyone will be much quicker to settle in on this second leg of the trip. 

Day 14: Arrive Key West 
We will clear into the US and have free time to fill as you wish.

Day 15: Exploration ashore 
Museums, good food, sunset square performers, bike rentals, and the teal colored water are all equally a draw here! 

Day 16: Depart Sea Dragon
You will leave the boat by 0900 at The Perry Hotel & Marina.

Sign Up Now

The deposit is only $500. It’s non refundable if you back out, but if we cancel or modify the trip we are happy to return your money or apply it to a different voyage.  Please review the Crew Contract for full details. The remaining balance is due 60 days before the trip begins. Please contact us with any questions.

Contact Us

Call Us: +1 ‪(305) 330-4212‬ (Pacific Time) If we don’t pick up, please leave a message and we’ll get back to you ASAP.

What's Included
Contribution Includes:
– 16 nights accommodation on Sea Dragon
All meals (vegetarian), snacks, and drinks on board
– Sailing Instruction
– Safety equipment and foul weather gear
– Mask, fins, snorkels
– Use of inflatable paddle boards

Contribution does not include:
– Transportation to Shelter Bay Marina and from The Perry Hotel & Marina
– Transportation from Tocumen International Airport (PTY) and to Key West International Airport (EYW)
– Additional nights spent ashore
– Personal expenses while in port

Packing List

It will be a warm trip! Take a look at our Tropical packing list.

Travel Details

Tocumen International Airport Panama (PTY) is about 90 min from Shelter Bay Marina and Key West Airport is a short taxi or Uber ride from The Perry Hotel & Marina.

All Crew members are responsible for their own passports and any necessary visas. You must have at least 6 months remaining on your passport beyond our arrival in Key West.
Please look into the specific type of visa you need for arriving at these destinations by sea, or contact us directly to discuss.

Boat Tour

Your Crew

I grew up in North West England, spending every weekend outdoors in the Lake District. After attending university in Cardiff, I worked as a personal trainer, working in the Middle East for a time before discovering the Clipper Round the World Sailing race. I became completely hooked on offshore sailing and after completing half the 19-20 race (pre Covid!) I gained my Yachtmaster qualification in order to be able to work in the industry. I became the skipper for a youth trust based in the Solent, England, working with young adults in order to widen their horizons and build their confidence which I found immensely rewarding. The itch to see more of the world by sea led me to becoming a freelance cruising instructor which enabled me to work with a variety of companies on a range of boats from 20’ to 70’, cruisers to high spec race boats. I spent some time in the Caribbean and around the UK helping refit boats until the Clipper Race restarted. I returned as a first mate, helping lead a crew of amateurs from the Philippines back to the UK and also completing my own circumnavigation. Having already seen the North Pacific, I’m excited to be on board Sea Dragon and explore more of the Pacific’s waters and islands- showing others the joy of ocean sailing, discovering the world around them and our effect on it, as well as teaching them to sail and work as a team.

Mary holds her Yachtmaster Ocean with commercial endorsement as well as her MCA Proficiency in Medical Care certificate.

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