Captained
yacht charters
All the adventure of a sailing vacation with an expert at the helm.
Captained charters are available across all Waypoints destinations — from the British Virgin Islands and the U.S. Virgin Islands to the Chesapeake Bay, the Bahamas, and beyond.
A captained charter gives you everything a bareboat charter offers — the freedom of your own private yacht, the ability to set your own itinerary, and the experience of waking up somewhere new each morning — with one important difference: a professional captain handles the sailing. You and your guests are free to relax, explore, swim, and enjoy every moment on the water without taking the wheel once if you don’t want to.
No sailing experience required. No certifications needed. Just show up, cast off, and let someone who knows these waters intimately take care of the rest.
Is a Captained Charter right for you?
A captained charter is an excellent fit if you:
- Have little or no sailing experience but want the full sailing vacation experience
- Want to focus entirely on enjoyment rather than navigation and boat management
- Are traveling with a mixed group — some sailors, some not — and want everyone equally relaxed
- Are visiting a new destination and want the benefit of local knowledge built into every day
- Prefer having a professional aboard without committing to the fully all-inclusive crewed format
If you’re a confident, experienced sailor ready to take the helm yourself, our Bareboat Charter options give you full independence. If you’d like a captain and a chef, curated meals, and a fully managed experience, our All-Inclusive crewed charters may be the better fit. Our Waypoints Yacht Charters Specialists are happy to talk through which format makes the most sense for your group.
The Booking Process
1
Tell us what you're looking for
Destination, travel dates, group size, and any preferences around pace, activities, or experience level all help us find the right combination of boat and captain for your trip.
2
Let us handle the matching
We’ll recommend both a vessel and a captain suited to your group, with up-to-date information on availability, current fleet condition, and captain fit that independent research can’t easily replicate.
3
Put an option on it
Once you’ve found the right match, we place a hold on the boat and captain while you review the charter agreement.
4
Make your deposit
You typically have up to 7 days to confirm your deposit — though high-demand boats can be challenged sooner, sometimes giving you as little as 24 hours to commit or release the option.
Standard deposit schedule:
- Booked less than 12 months from departure: 50% deposit due at booking, balance due 60 days before departure
- Booked more than 12 months out: 25% deposit at booking, next 25% due 6 months from departure, balance due 60 days before departure
What to Expect From Your Captain
Your captain handles all vessel operations: navigation, anchoring, docking, weather monitoring, and safety. Their role goes beyond that, though, because a good captain is more than a navigator.
The right person makes a captained charter feel like having a knowledgeable local friend aboard, someone who knows which anchorage to reach before the afternoon crowd, which beach bar is worth the detour, and how to read the wind so your sailing days feel effortless rather than effortful.
Frequently Asked Questions
Do I need any sailing experience for a captained charter?
None at all. Your captain manages everything on the boat. Your only job is to enjoy the destination. That said, if you’re curious about sailing and want to learn, most captains are happy to share the helm and walk you through the basics at whatever level you’re comfortable with.
Can I still take the wheel if I want to?
Absolutely. Many guests on captained charters enjoy taking turns at the helm, trimming sails, or helping with anchoring. Your captain will happily involve you as much or as little as you’d like. After all, it’s your vacation.
What does a captain cost?
Captain rates vary by destination and experience level. At our bases, rates typically range from $175 to $350 per day for a standard captain, with ASA-certified instructors available at higher rates where applicable. Plan to include meals for your captain, and tipping at 15–20% of the daily rate is customary and appreciated. Your Waypoints Yacht Charters Specialist will provide specific rates for your destination when you inquire.
Is provisioning included with a captained charter?
Provisioning — food, beverages, and sundries for the week — is typically the charterer’s responsibility on a captained charter, the same as a bareboat. If you’d prefer a fully catered experience with a chef aboard, our All-Inclusive crewed charter option covers all of this. Ask your Waypoints Yacht Charters Specialist about the options available for your destination.
How is a captained charter different from an all-inclusive charter?
A captained charter provides a professional skipper to handle the sailing — the boat, the provisioning, and the daily decisions are largely still yours. An all-inclusive crewed charter adds a chef, gourmet meals, an open bar, and a fully managed itinerary, with a crew that handles everything from departure to dinner. Both are excellent options depending on how hands-on or hands-off you want to be.
How far in advance should I book?
Our Waypoints Yacht Charters Specialists will match you with the right boat, the right captain, and the right destination for your group, and handle every detail in between.
Ready to Start Planning?
Our Waypoints Yacht Charters Specialists will match you with the right boat, the right captain, and the right destination for your group, and handle every detail in between.
CALL US
443-225-4355 ext. 1