Four Days on the Chesapeake: Bareboat a 30–45' Sloop from Middle River

MIDDLE RIVER SAILING FIELD GUIDE

Four Days on the Chesapeake: Bareboat a 30–45' Sloop from Middle River

A four-day liveaboard course that teaches coastal cruising, advanced sail trim, navigation and emergency procedures and culminates in ASA 103/104 and IPC certifications.

Four Days on the Chesapeake: Bareboat a 30–45' Sloop from Middle River.

Duration
Contact operator
Location
Middle River
Operator
Starboard Sailing
Category
Sailing
Robert Eric Crews
Founder & Editor, The Adventure Collective
Published Verified

Head out of Middle River for a focused, four‑day liveaboard course that turns competent day sailors into coastal cruisers. Aboard 30'–45' sloop‑rigged, auxiliary‑powered yachts you’ll practice provisioning and boat systems, refine sail trim, learn coastal navigation and anchoring, and drill emergency procedures — all aimed at earning recognized ASA coastal cruising certifications.

Highlights

Outing Highlights

THE CERTIFICATIONS

ASA 103 & 104 plus the International Proficiency Certificate

The course culminates in formal ASA 103 and 104 certifications and the ASA International Proficiency Certificate (IPC), combining hands‑on seamanship with classroom materials to validate coastal cruising competence.

THE VESSEL

Liveaboard on a 30'–45' sloop‑rigged boat

Training is conducted aboard a sloop‑rigged, auxiliary‑powered cruiser in the 30'–45' range, giving real experience handling systems, engines and sails in moderate to heavy conditions on inland and coastal waters.

THE CRUISE

Chesapeake anchorages and overnight stops

The four‑day itinerary departs and returns to Middle River with possible overnights in Rock Hall, Annapolis, Baltimore, Kent Island or other anchorages, combining coastal passages with sheltered harbor practice.

What the day feels like

What it feels like to do this course

The pace alternates between concentrated hands‑on sailing watches and compressed classroom sessions: rig and trim sails, stand engine and helm watches, plan and execute short coastal passages, then anchor or dock for overnight instruction on navigation, provisioning and emergency procedures. By living aboard for three nights you move beyond day sailing into the rhythms and decision making required of a charter skipper.

Suitability

Who it's for

Who this course suits — and who should look elsewhere.

1
Aspiring Charter SkippersWell suited for sailors pursuing bareboat charter competency and official ASA certification; the curriculum and IPC credential are explicitly aimed at future charter skippers.
2
Certified Recreational SailorsA good next step for sailors who already hold ASA 101 (Basic Sailing) and want multi‑day, liveaboard experience in navigation and emergency procedures.
3
Independent AdultsDesigned for adults only — participants must be at least 18 years old — and for those comfortable living aboard and standing watches.
4
Families with Younger TeensNot a family program for minors; the course requires adult participants (18+) and a basic sailing certification, so it is not appropriate for children under 18.

Practical planner

Details to review before reserving

What’s provided

Two textbooks and course materials are provided; ASA 103 and 104 certifications and the ASA International Proficiency Certificate (IPC) are included along with fuel, pump outs and docking fees.

Provisions & personal costs

Provisions are not included; plan on additional provisioning costs of about $200 for food and personal supplies.

Boat & conditions

Training is aboard a 30'–45' sloop‑rigged, auxiliary‑powered boat operating on inland/coastal waters where moderate to heavy winds and sea conditions can be encountered.

Booking Notice

Review cancellation policies before reserving.

Frequently asked questions

Planning Your Outing

How long is the course?

Four days, three nights liveaboard.

Where does the cruise depart and return?

The cruise departs from and returns to the Maryland Marina in Middle River, Maryland.

What certifications are awarded on completion?

Successful completion yields ASA 103 and ASA 104 certifications and the ASA International Proficiency Certificate (IPC).

What is included and what costs extra?

Textbooks and materials, the ASA certifications and IPC, fuel, pump outs and docking fees are included; provisions are extra (about $200).

Who is eligible to participate?

Participants must be at least 18 years old and hold ASA 101 (Basic Sailing) as a prerequisite.

Where might we overnight during the cruise?

Possible overnights include Rock Hall, Annapolis, Baltimore, Kent Island or other Chesapeake anchorages; exact stops depend on the published itinerary and conditions.