Five Days to Skipper: Live‑Aboard Coastal Cruising on the Chesapeake

BALTIMORE BOAT TOUR FIELD GUIDE

Five Days to Skipper: Live‑Aboard Coastal Cruising on the Chesapeake

A five‑day live‑aboard course from BaySail that teaches advanced seamanship, navigation and safety while qualifying you to skipper 30–45 ft yachts (ASA 103/104).

Five Days to Skipper: Live‑Aboard Coastal Cruising on the Chesapeake.

Duration
Contact operator
Location
Baltimore
Operator
BaySail School of Sailing LLC
Category
Boat Tour
Robert Eric Crews
Founder & Editor, The Adventure Collective
Published Verified

Over five intensive days aboard a chartered sloop on the Chesapeake Bay, this live‑aboard course immerses small groups in advanced coastal cruising—covering sail trim, docking, anchoring, navigation and safety—so students leave qualified to act as skipper of a 30–45 foot boat in coastal waters.

Highlights

Outing Highlights

THE CERTIFICATION

Skipper‑level qualification recognized worldwide

Successful completion earns ASA 103/104 certification to skipper a 30–45 foot boat by day in coastal waters and qualifies graduates to apply for the International Proficiency Certification (IPC), the credential many Mediterranean charter companies require.

THE FORMAT

Live‑aboard, hands‑on training in real conditions

Students live aboard a chartered sloop for four nights, practicing sail handling, engine systems, provisioning and meteorology while spending nights at anchor or in area marinas before returning to BaySail on day five.

THE SKILLS

Advanced seamanship and navigation

The curriculum emphasizes practical skills: sail trim, docking, anchoring and mooring, heavy‑weather sailing, chart plotting and electronic navigation alongside safety, engine and cabin systems.

What the day feels like

What five days aboard feels like

Expect an immersive schedule: you, an instructor and a small crew live on a 30–45 foot sloop for four nights while training in all aspects of coastal cruising—by day moving through Chesapeake waters and by night anchored or tied up in local marinas—returning to BaySail on the final afternoon.

Suitability

Who it's for

Who this course is best for — and who should reconsider.

1
Aspiring SkippersIdeal for sailors seeking formal ASA 103/104 certification to skipper 30–45 ft coastal boats and to qualify for the IPC.
2
Experienced Day SailorsA strong match for sailors with ASA 101 or equivalent experience who want hands‑on instruction in larger yachts, diesel engine systems and coastal navigation.
3
Couples or Small TeamsThe class is run for small groups; up to three individual students or two couples may register, making it suitable for pairs or tightly coordinated small teams.
4
Younger Sailors (16+)Minimum age for certification is 16, so competent teenagers who meet the ASA 101 prerequisite may enroll.

Practical planner

Details to review before reserving

Timing & Duration

Five days, live‑aboard: arrive at BaySail by 9:00 AM on day one; course returns to BaySail by 4:00 PM on day five.

Cost & Registration

Course fee is $1,795 per student; preregistration is required and classes require at least two enrolled participants to run.

Onboard logistics

Students and instructors live aboard the chartered sloop for four nights, with overnight stays at anchor or in area marinas.

Booking Notice

Review cancellation policies before reserving.

Frequently asked questions

Planning Your Outing

How long is the course and when do I arrive and depart?

The course is five days, live‑aboard. Students should arrive at 9:00 AM on day one and the course returns to BaySail by 4:00 PM on day five.

What certification do I earn?

Successful completion awards ASA 103/104 Basic Coastal Cruising & Bareboat Cruising certification, enabling you to act as skipper of a 30–45 foot boat by day in coastal waters and to apply for the International Proficiency Certification (IPC).

What prior experience is required?

Prerequisite is ASA 101 or equivalent experience.

What is the minimum age and class size?

Minimum age for certification is 16. Classes are small: a maximum of three individual students or two couples may register; at least two people must be enrolled for the class to run.

What happens if minimum enrollment isn’t met?

BaySail reserves the right to cancel the class and refund or reschedule if fewer than the minimum number of students are enrolled.

What topics and skills are taught?

The curriculum includes sail trim, docking, anchoring, mooring, heavy‑weather sailing, chart plotting and electronic navigation, plus safety, seamanship, provisioning, engine and cabin systems, and meteorology.

How much does the course cost?

Course fees are $1,795 per student.