Operations Overview

Charter & Operating Guidelines

Rabbit Hole Sailing, LLC operates under established charter and instructional guidelines developed in coordination with our insurance carrier and maritime risk partners.

These guidelines are designed to provide exceptional on-the-water experiences while maintaining strong standards for safety, professionalism, vessel care, and regulatory compliance.

Some operating limitations reflect current insurance requirements and the experience necessary to safely operate our vessels. As our programs, operational history, and insurance approvals continue to develop, these guidelines may be reviewed and updated.

No membership. No initiation fees. Simply assemble your qualified crew, choose your charter, and sail.

The primary operating requirements are summarized below.

Key Operating Guidelines

The following highlights summarize the primary operating requirements for Rabbit Hole Sailing, LLC charters and instructional programs:

• Daytime navigation only, unless part of an approved instructional course
• Maximum persons aboard based on the vessel’s approved charter capacity
• Minimum operational crew of three capable sailors for bareboat charters
• Operations limited to approved sailing areas
• Safety-first policies regarding weather conditions and impairment

Additional operational requirements are outlined below.

⚓ OPERATING RULES

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1. Navigation Time & Night Operations

By default, all charter operations are limited to daylight hours.

Navigation is permitted after dawn and before dusk only.

Unless specifically authorized as part of an instructional program, night navigation is not permitted.

Night Operations Exception

Night navigation may occur only during instructor-led instructional programs where night operations are an explicit component of the approved training curriculum.

These instructional sails are conducted under the supervision of a qualified instructor and are intended to provide training in nighttime navigation, vessel lighting, watchstanding procedures, and situational awareness.

End-of-Day Requirement

For all charters and instructional programs where night navigation is not authorized, sailing operations must be completed prior to dusk.

SV Rabbit Hole must be secured before sunset at one of the following locations:

• her home dock, or
• a pre-approved anchorage

This requirement ensures safe vessel operations and compliance with insurer operating guidelines.

2. Captained Charters

Captained charters operate under the following limitations:

• Navigation is restricted to daytime operations only
• Night navigation is not permitted
• Overnight stays may be permitted provided the vessel:

– remains at the home slip, or
– is secured at a pre-approved anchorage before dusk

3. Bareboat Charters

Bareboat charters are subject to screening and operational requirements outlined in the Charter Eligibility & Crew Requirements section below.

Operational limits include:

• Navigation restricted to daytime hours only
• Compliance with all vessel operating limits and charter policies
• Crew requirements as defined in the eligibility section below

🧭 NAVIGATION LIMITS

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4. Geographic & Navigational Limits

Vessel operations are limited to defined operating areas approved by Rabbit Hole Sailing LLC and our insurer.

Unless explicitly authorized in writing:

• Offshore or open-ocean operations are prohibited
• Crossing defined navigation boundaries is not permitted
• Entry into restricted, commercial traffic, or environmentally protected zones is prohibited

“Out-the-Gate” Operations

Transit outside the primary sailing area (“Out-the-Gate”) is limited to:

• Approved instructional courses where increased navigational boundaries are a formal component of the curriculum, or
• Bareboat charters that have received prior written approval to navigate west of the Golden Gate Bridge

All vessel operations must comply with local, state, and federal maritime regulations.

5. Weather & Sea State Restrictions

Operations will not occur under unsafe environmental conditions.

This includes, but is not limited to:

• sustained or forecast winds exceeding approved limits
• sea state or swell conditions beyond vessel or operator capability
• reduced visibility caused by fog, precipitation, or similar conditions

The acting operator (captain or primary charterer) is responsible for making conservative go / no-go decisions based on current and forecast conditions.

🛟SAFETY & COMPLIANCE

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6. Impairment & Substance Restrictions

Safety requires strict adherence to impairment policies.

• Zero tolerance for impairment while underway
• No person may operate or control the vessel while impaired by alcohol or illegal drugs
• Alcohol consumption by operators is prohibited while navigating
• Alcohol must not be consumed prior to assuming navigational control

Rabbit Hole Sailing, LLC reserves the right to immediately terminate any charter if impairment is suspected.

7. Compliance & Enforcement

All charter operations must comply with the guidelines outlined above unless explicit written authorization is provided.

Violations may result in:

• Immediate termination of the charter
• Suspension or revocation of future charter privileges

These restrictions are designed to meet or exceed insurer requirements and recognized maritime industry best practices.

8. Vessel Tracking & Monitoring

All Rabbit Hole Sailing, LLC vessels are equipped with redundant tracking and monitoring systems.

Operational data may include:

• vessel location
• vessel movement and speed
• navigational activity

Tracking information may be reviewed during or after a charter for purposes including:

• safety oversight
• training feedback
• operational monitoring
• compliance with charter guidelines and insurance requirements

Use of company vessels constitutes acknowledgment and acceptance of this monitoring as part of standard operating procedures.

👨‍✈️ CHARTER ELIGIBILITY & CREW REQUIREMENTS

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Every bareboat charter aboard SV Rabbit Hole requires a minimum operational crew of three capable sailors.

Approved to Charter Sailors

At least two sailors must be approved by Rabbit Hole Sailing, LLC prior to charter.

Approval is based on your sailing certifications, documented experience, local knowledge, and overall seamanship. Many experienced sailors are approved through their sailing resume, while others complete a Check-Out Sail to demonstrate competency aboard SV Rabbit Hole.

US Sailing Bareboat Cruising (BBC) certification—or equivalent experience—is an excellent place to start. If you’re unsure whether you qualify, we encourage you to contact us. We’d be happy to discuss your experience and the best path to approval.

Supporting Sailor

The third required sailor must hold at least US Sailing Basic Cruising (BC) certification or possess equivalent sailing experience acceptable to Rabbit Hole Sailing, LLC.

Additional Guests

Once the minimum operational crew has been met, additional family members, friends, or guests may join your charter, subject to the vessel’s approved capacity.

Maximum persons aboard: 8

📋 CHECK-OUT SAILS

Not sure whether you’re ready to charter?

Our Check-Out Sail provides experienced sailors with an opportunity to demonstrate their skills aboard SV Rabbit Hole while becoming familiar with the vessel and our operating procedures.

A typical Check-Out Sail includes:

Vessel orientation
Docking and close-quarters maneuvering
Sail handling and reefing
Navigation and safety procedures
General seamanship and vessel systems

Most evaluations take 4–6 hours, and one or two sailors may be evaluated during the same session.

A successful Check-Out Sail may qualify you for bareboat charter privileges, subject to Rabbit Hole Sailing’s screening and approval process.

🌊 Out-the-Gate Charters

Most Rabbit Hole charters operate within our standard Inshore operating area.

Charters west of the Golden Gate Bridge require additional screening and approval and are generally limited to licensed captains, qualified instructors, and charterers with advanced offshore experience and certifications.

If you’re interested in an Out-the-Gate charter, we’d love to discuss your experience and help determine the appropriate approval pathway.

Your Input Matters

These guidelines represent our initial operational framework as Rabbit Hole Sailing, LLC launches its charter and instructional programs.

We value feedback from our sailing community as we refine our offerings, expand training opportunities, and plan future operational capabilities.

Your input helps us better understand:

• interest in charter opportunities
• preferences regarding navigation boundaries and potential expansion
• sailing experience levels
• training goals
• priorities for future program development

Please take a few moments to share your feedback.

Take the Survey → [HERE]