Enjoy 55' Cruising Ketch In San Diego

55 ft
27 Guests

About This Boat

Enjoy San Diego by boat. Charter a 55' Cruising Ketch for up to 27 people. Rates as low as $600 per hour.


  • $600 per hour - 2 hours minimum + crew gratuity


Our rates include light refreshments and beverages. Additional food items may be pre-ordered through our galley. We will also assist you with catering and music referrals.

Limited public sails available at the rate of $95 per person for a 3-hour cruise.

Additional pricing options are possible on custom cruises. Please contact us to design your specialty sail for your group or event.

We find 3 hours is the perfect cruise length for most group outings, but Romancing The Wind 's captain and crew can work with you to decide on the best cruise plan for your group.

Our 55-foot custom designed steel hull ketch is stable and strong, yet sleek and smooth at sea. Captain Jack and his crew welcome you aboard! Take part in hoisting and trimming the sails, steering through the entrance of the bay, or sit back, relax, and soak up the sun and scenery. Our three-hour excursion is just right for enjoying the views of the city of San Diego Bay and the the ocean beyond.

Enjoy San Diego Harbor and all the sites while relaxing aboard our 55' Sailing Yacht. Watch the playful Seals and Dolphins while your captain points out interesting San Diego landmarks and historical facts. Take the Helm and raise the sails as you glide with us across this Big Bay toward the beautiful setting sun.

We specialize in GROUPS!  Custom design your special occasion cruise for your group of up to 27 guests.

Need a smaller sailboat, a power boat, or a large party boat instead?  Let us connect you with our harbor partners to find the perfect vessel for your group!  Some of the other boats we can suggest include:

  • 90-foot 3-level cruising boat for up to 140 passengers
  • intimate sailing charters for up to 6 guests in either classic unique sailboats or a sleek modern sloop
  • catamarans ready to entertain up to 49 guests
  • comfortable and cushy powerboats for up to 12 passengers
  • classic wood sailing ship for a timeless experience
  • fishing trips for six


We provide:

  • Wedding on The Bay
  • Great Whale Sail Season!
  • Schooner Cup
  • Some Great Days on the Bay

If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.


  • Type: Schooner
  • Capacity: 27 People
  • Rental Minimum: 2 hours
  • Length: 55 ft

Rental Requirements


1450 Harbor Island Drive, San Diego, CA 92101


  • Life jackets/required safety gear
  • Wheel steering
  • Inboard Engine
  • Chart Plotter
  • Dinghy
  • Single Engine
  • Watersports Equipment
  • Head
  • Furling Mainsail

More Images

Meet Captain Jack

Captain Jack

Member Since Aug 2015

Contact Owner
Email Address
Request to Book Captain Jack