Bareboat Charter

For experienced sailors who want maximum freedom and flexibility, a bareboat charter gives you the boat- and the freedom to create your own adventure. You captain the yacht yourself, choose your itinerary, provision the boat, and move at your own pace.

Best for:

• Experienced sailors
• Independent travelers
• Groups comfortable handling logistics
• Adventurous families and friend groups

Considerations:

Bareboat charters offer incredible freedom — but they also require real responsibility. You’ll handle navigation, docking, weather decisions, provisioning, and day-to-day operations yourself.

Typical budget:

Approximately $3,000–$15,000+/week depending on yacht type and season.

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Skippered Charter

A skippered charter includes a professional captain who handles navigation and local knowledge while still allowing your group plenty of privacy and flexibility.

For many travelers, this is the “sweet spot” between independence and relaxation.

Best for:

• First-time charterers
• Mixed-experience groups
• Families
• Travelers who want flexibility without the pressure of operating the boat

Particularly ideal if:

• You have some sailing interest, but not enough experience to confidently bareboat
• Your group includes both sailors and non-sailors
• You want local insight without the formality of a full crewed experience
• You want a more approachable budget than a luxury crewed yacht

Typical budget:

Bareboat pricing plus approximately $1,500–$2,500/week for captain services.

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Crewed Charter

A fully crewed charter is the most effortless and luxurious way to experience the Caribbean. Depending on the yacht, your crew may include a captain, chef, steward, and/or additional staff handling everything from meals to itinerary planning.

Best for:

• Luxury travelers
• Families with children
• Milestone celebrations
• Multi-generational groups
• Travelers who want a boutique-hotel-on-the-water experience

Considerations:

Crewed charters are extraordinarily relaxing, but also come with a higher price point and slightly less spontaneity than bareboat adventures.

Typical budget:

Approximately $12,000–$40,000+/week for crewed catamarans, with luxury motor yachts ranging significantly higher.

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Which Type of Charter Is Right for You?

Choosing the right charter style matters just as much as choosing the destination. Here’s a quick guide to help narrow it down.

If this sounds like your group…	You’ll probably love…
“We’re experienced sailors and want total freedom.”	Bareboat monohull or catamaran
“We want adventure, but don’t want the stress of captaining.”	Skippered catamaran
“Some people in our group sail, others just want to relax.”	Skippered catamaran
“We want the easiest, most relaxing vacation possible.”	Fully crewed catamaran or yacht
“We’re traveling with young kids or older family members.”	Crewed or skippered catamaran
“We care more about experience than luxury.”	Bareboat or skippered monohull
“We want space, comfort, and stability.”	Catamaran
“We have a mid-level budget and mixed experience levels.”	Skippered catamaran is often the ideal fit
“We want chef-prepared meals and high-touch service.”	Luxury crewed yacht

Still unsure? That’s exactly where Caribbean Compass can help. We work with a range of trusted charter operators throughout the Caribbean and can help point you toward the right fit for your group and budget.

Not Sure Which Charter Fits Your Group?

Tell us:

• Group size
• Budget range
• Sailing experience
• Preferred destinations
• Desired vibe (luxury, adventurous, relaxed, family-friendly, etc.)

…and we’ll help connect you with the right operators and options.

Get personalized charter recommendations →