Gulf Stream Express | Grand Cayman → Key West via Cozumel

Mar 6 – Mar 20 2026 | $6,990

NEW TRIP!

Step aboard SV Sea Dragon for a fast-moving, adventurous passage from Grand Cayman to Stock Island Marina Village, Key West, taking in the turquoise seas and warm trade winds of the northern Caribbean Sea. This 700-nautical-mile journey promises thrilling offshore sailing, combined with potential stops in Cozumel, the Yucatán region and the iconic waters of the Florida Keys.

This expedition is all about the exhilaration of passage-making under the influence of the Gulf Stream. Expect lively sailing, changing conditions, and long stretches where the horizon is your only companion. Depending on weather and the skipper’s decisions, we may make landfall in Cozumel, offering a brief taste of Mexico’s coral reefs and local culture, before pressing north toward the sunny shores of Key West.

Life aboard is hands-on and immersive. Every crew member has a role, from helming to trimming sails, keeping watch, and navigating. Whether you’re seeking to build passage experience, test yourself on offshore legs, or simply enjoy the freedom of open water, this expedition delivers a rewarding mix of challenge and adventure.

You’ll also get to

Navigate lively Gulf Stream conditions under the guidance of an experienced offshore skipper
Hone offshore sailing and navigation skills in a variety of conditions
Experience potential stops in Cozumel or other secluded anchorages along the way
Enjoy fast passages with trade winds and rolling seas
Develop confidence and seamanship as part of a small, hands-on crew

Sailing with Panexplore means gaining real-world, hands-on experience, not a packaged cruise. You’ll refine your sailing skills, learn practical offshore techniques, and develop confidence in a professional, supportive environment. This sailing expedition requires you to be in good physical health and reasonably fit. Activities involve moderate to strenuous exertion, including extended hours awake and difficult physical environment to evolve in.

If you have any medical conditions, recent injuries, or concerns about your fitness level, we strongly recommend consulting with your healthcare provider before booking. This expedition is not suitable for individuals with severe mobility limitations or certain medical conditions. Your safety and enjoyment are our priority, and we want to ensure this experience is appropriate for your physical capabilities. Please contact us should you have any questions or concerns before booking.

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

Key Details

Distance: 700 nautical miles
Cost: $6,990
Dates: Mar 6 – Mar 20, 2026 (15 Days)
Start: Grand Cayman
End: Stock Island Marina Village, Key West

Tentative Itinerary

While the exact route and timing will depend on weather and skipper decisions, a typical voyage may look like this:

Days 1–2: Join SV Sea Dragon in Grand Cayman. Orientation, safety briefing, and boat familiarisation.

Days 3–7: Offshore passage north, experiencing the influence of the Gulf Stream. Crew will take turns on watches and refining seamanship skills.

Days 8–12: Depending on weather, optional stopover in Cozumel or nearby anchorages for rest, snorkeling, and exploration.

Days 13–15: Final leg into Key West, arriving at Stock Island Marina Village. Disembark by late morning on the final day, concluding the voyage.

Please note: This sailing adventure is weather-dependent. Stopovers, timing, and the exact route will be determined by the skipper to ensure safety and the best possible experience.

BOOK NOW

The deposit is only $1,000. It’s non-refundable. If you can no longer make it, or if we need to cancel or modify the trip we will either refund your deposit or apply it to a different trip. The remaining balance is due 90 days before the trip begins. The full price will be required to pay if you book within 90 days of the trip start date. Please review the Terms & Conditions.

If you have any questions or queries, please Contact us. You can also Schedule a call with us too.

What’s Included

Contribution Includes:
– 15 nights accommodation on Sea Dragon
– All meals (vegetarian), snacks, and drinks on board
– Sailing Instruction
– Safety equipment and foul weather gear

Contribution does not include:
– Transportation to departure port or onward travel from arrival port.
– Additional nights spent ashore
– Personal expenses while in port

Roles and Expectations

You are joining a working voyage as a full member of the crew. As such, you will be involved in virtually all aspects of the trip and operations. On board you will be part of a crew of up to 16 people in total, including yourself. Our expectations of you are fairly straightforward and your team will depend on you to fully participate in everything on the boat. You will be expected to work hard to the best of your ability, to be conscientious, alert, to look after the boat and to care for each other. You will not be asked to do anything you are not comfortable doing.

Tasks and activities involved in life on board SV Sea Dragon include: helming (steering), navigation, sail handling (hoisting, adjusting, stowing), keeping a look out, meal preparation and helping to keep the boat clean and tidy.

Packing List

It will be warm and the sun will be strong! Take a look at our Tropical packing list.

Travel Details

Departure: Grand Cayman 15 min from Owen Roberts International Airport (GCM).

Arrival: Stock Island Marina Village, Key West is 10 min from Key West International Airport (EYW). Taxi is fastest; crew should check passports and visa requirements for the U.S. and Mexico if stopping in Cozumel.

All crew members are responsible for their own passports and visas, which must have at least 6 months remaining beyond the trip. 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