Operations Overview

Initial Charter Guidelines

As Rabbit Hole Sailing, LLC launches its charter and instructional programs, we are operating under a set of initial guidelines developed in coordination with our insurance carrier and maritime risk partners.

These guidelines establish the framework under which our vessels will operate during the first phase of operations. Their purpose is to balance exceptional on-the-water experiences with a strong foundation of safety, professionalism, and regulatory compliance.

While some of these limitations are intentionally conservative, they help ensure the safety of our guests, instructors, and vessels while supporting the long-term sustainability of the program as we grow.

As our operational history develops and additional approvals are obtained, these guidelines may evolve.

Key Operating Limits

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

• Daytime navigation only, unless part of an approved instructional course
• Maximum of six persons onboard
• Minimum of three experienced sailors required for bareboat charters (see details below for experience requirements and vetting procedures)
• Operations limited to approved sailing areas
• Safety-first policies regarding weather conditions and impairment

Additional operational requirements and details 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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All charters are subject to screening, vetting, and background review by Rabbit Hole Sailing, LLC prior to approval of any charter request.

Submission of a charter request does not guarantee acceptance.

These requirements ensure safe vessel operation and maintain the high standards expected aboard SV Rabbit Hole.

Crew Composition (3–6 persons aboard)

Operations Crew

Minimum operational crew required: 3

At least two fully qualified and vetted sailors must be aboard for operations during every charter.

Sailors holding US Sailing Coastal Passage Making (CPM) or Offshore Passage Making (OPM) certifications are strongly preferred, as these certifications reflect the level of experience appropriate for operations aboard SV Rabbit Hole.

Sailors holding US Sailing Bareboat Cruising (BBC) certification or equivalent may be considered; however, all sailing resumes and experience will be reviewed for suitability.

A third crew member must hold at least US Sailing Basic Cruising (BC) certification or an equivalent level of experience.

Additional Crew

Up to three additional crew members or guests may be aboard during charter operations.

Maximum persons aboard: 6

These requirements are designed to ensure safe vessel operations and a high-quality sailing experience aboard SV Rabbit Hole.

📋 CHECK-OUT SAIL (QUALIFICATION EVALUATION)

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Sailors who are not qualified based on initial screening and vetting may demonstrate competency through a Check-Out Sail with a Rabbit Hole Sailing, LLC testing instructor.

During this evaluation, the instructor assesses seamanship, vessel handling, and operational knowledge prior to approval for bareboat charter privileges.

Format

• 4–6 hour sail aboard SV Rabbit Hole with a US Sailing Certified Instructor
• One or two sailors may attempt qualification during the session
• Includes pre-sail and post-sail competency discussions
• Evaluation covers seamanship, vessel handling, safety procedures, and operational knowledge

A Check-Out Sail is a competency evaluation only.

Completion of a Check-Out Sail does not guarantee qualification for charter privileges.

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]