Sail with us

Charters

Book by the seat or take the whole boat. Every trip is fully crewed aboard Comfortably Numb.

Sunset Sail aboard Comfortably Numb

$125 per person

Sunset Sail

Golden hour, good music and nothing to worry about. Easy sailing, open water and the kind of evening that lingers.

  • 3 hours, starting 90 minutes before sunset
  • Up to 8 guests
  • Private boat $1,000
Weekend Escape aboard Comfortably Numb

$6,000 for 4 days

Weekend Escape

Four days, a few islands and no set course. Sail, swim, drop anchor and let the days unfold.

  • Thursday to Sunday
  • Fully hosted, captain and host aboard
  • $1,500 per day
7 Day Escape aboard Comfortably Numb

$12,000 for 7 days

7 Day Escape

Cast off and settle into the rhythm of wind and sea. Live aboard, make your passage and go where it feels right.

  • 7 days aboard
  • All-inclusive, crewed experience
  • Extra days $1,700

Bring your crew

Take to the Open Water With Friends and Family

Leave everything else behind with the people who matter most. Whether it is a sunset sail, a weekend away or a full escape at sea, every trip is about shared moments, easy sailing and time well spent together. Bring your crew and we will take care of the rest.

Sailboat on calm water

FAQ

Questions Before You Step Aboard

What’s included?

Every trip includes a fully crewed experience aboard Comfortably Numb with a captain and host, fuel and the essentials for a smooth, relaxed time on the water. Depending on your trip, provisioning can be included or added on, so all you need to do is show up.

Can I book the whole boat?

Yes. Book by the seat or reserve the entire yacht for a private trip with just your group, whether it is a sunset sail or a multi-day escape. Private sunset sails are $1,000 for up to 8 guests.

What should I bring?

Keep it simple: light clothing, swimwear, sunscreen and anything personal you want on the water. Once you are aboard, everything slows down, so bring what helps you relax.

Do I need sailing experience?

No. The crew handles everything, and you are welcome to take the helm or help with the lines if you want to.

What time does the Sunset Sail leave?

Departure is about 90 minutes before sunset, so the time changes through the year. Your confirmation will have the exact time.

Do you offer group rates?

We do. Contact us for family and group pricing.

How does payment work?

Reserve your dates online with a deposit. The balance is due before your trip.

Ready to Slow Things Down?

Pick your dates online, or call the crew and we will help you plan it.