Offshore Expeditions 2024 +2025
Start your offshore sailing adventure
Why choose an offshore expedition on a wooden Pilot Cutter? It’s about adventure, teamwork and bonding with your shipmates. Our passages are not hands off vacations. These are experiential learning opportunities for those willing.
We generally take 4 guest crew on each passage, while we have 3 professional crew onboard. This ratio allows for hands on, 1 on 1 learning experiences. Some of our passages are tamer than others. They all culminate in what should be an experience of a lifetime- A transatlantic crossing where we return Pilot Cutter Hesper to Cornwall England, where she was born.
We do not require sailing experience for these passages, but do require a certain level of physical fitness and aptitude. The booking process is simple, but thorough. We want to feel comfortable with your experience aboard, and we want you to feel comfortable with us! If you are interested in a passage, fill out our Passage Application. We generally try to set up a Zoom or Skype meeting prior to booking- This helps you answer any questions, and allows us to all get comfortable with each other.
For passages 1.1-1.4 we require a 50% deposit, with full payment due 90 days prior to departure.
For our 2.0 Passages we require a 30% non-refundable deposit, with 2/3 due at 180 days, and final due at 60 days.

Azores—> Falmouth Cornwall
Offshore Passage 2.3
1300 NM
Departure: Azores
Destination: Cornwall
Guest Crew Available: 4
Cost Per Person: $7,000
Departure: June 1st, 2025

Bermuda ---> Azores
TRANSATLANTIC CROSSING
Offshore Passage 2.2
1864 NM
Departure: Bermuda
Destination: Azores
Guest Crew Available: 4
Cost Per Person: $11,500
Departure: May 6th, 2025

Key West FLorida —> Bermuda
Offshore Passage 2.1
1086 NM
Departure: Key West Florida
Destination: Bermuda
Guest Crew Available: 4
Cost Per Person: $5,500
Departure: April 20th 2025

Charleston South Carolina —> Key West Florida
Offshore Passage 1.4
600 NM
Departure: Charleston South Carolina
Destination: Key West Florida
Guest Crew Available: 4
Cost Per Person: $3,600
Departure: November 22nd

Annapolis Maryland—> Charleston South Carolina
Offshore Passage 1.3
550 NM
Departure: Annapolis Maryland
Destination: Charleston South Carolina
Guest Crew Available: 4
Cost Per Person: $3,600
Departure: November 13th

Oyster Bay New York —> Annapolis Virgina
Offshore Passage 1.2
310 NM
Departure: Oyster Bay New York
Destination: Annapolis Maryland
Guest Crew Available: 4
Cost Per Person: $2,800
Departure: November 5th

Camden Maine—>Oyster Bay New York
Offshore Passage 1.1
356 NM
Departure: Camden Maine
Destination: Oyster Bay New York
Guest Crew Available: 4
Cost Per Person: $2,800
Departure: October 30th 2024