Sail the Bay on our big beautiful boat!

Custom Steel Hull Ketch (1985)

  • 55 feet

  • 27 guests

  • 1 cabins

  • 1 heads

  • Captained



Romancing The Wind is ready to welcome you aboard for a day of sailing adventure on our comfortable and stable yacht. Perfect for groups up to 27, our large open deck has room to relax and enjoy the sites of San Diego Harbor.

Watch the playful seals and dolphins while your captain points out interesting San Diego landmarks and historical facts. Or glide with us across the Big Bay toward the beautiful setting sun and the city skyline. If you want to lend a hand, our Captain will let you take the helm and raise the sails. From December through March make your plans for the best Whale Watching trip in San Diego aboard our 55-foot sailing steel hull ketch.

No overnight availability.

Rates: $1200 for 2 hours, $2,000 for 4 hours, $3000 for 8 hours. Rates include captain and 2 crew. Long distance fuel surcharge may apply. Rates include dry snack and beverages; additional food items available at additional cost.


  • Manufacturer
  • Model
    Steel Hull Ketch
  • Year
  • Guest Capacity
  • Cabins
  • Single Beds
  • Double Beds
  • Bathrooms
  • Number of engines
  • Horsepower per engine


  • Stereo AUX input mp3 hookup
  • Stove / grill
  • Autopilot
  • Microwave
  • Diving
  • Radar
Navigation & Safety
  • Autopilot
  • Radar
  • Sonar
  • Chart plotter
  • GPS
  • Generator
  • VHF Radio
  • Tender/Dinghy
  • Depth finder
  • Life jackets
  • Fire extinguisher
  • First aid kit
  • Life raft
  • Torch light
  • Stereo AUX input mp3 hookup
  • TV
  • DVD
  • CD Player
  • USB Connection
  • Speakers on deck
  • Stove / grill
  • Microwave
  • Refrigerator
  • Towels
  • Ice maker
  • Freezer
  • Inverter
  • Warm water
  • Cockpit table
  • Electricity
  • Outdoor shower
  • Diving
  • Dining
  • Cocktail parties

Boat Owner


Member since March 2015

Romancing the Wind is the ultimate sailboat for cruising San Diego Bay and nearby coastal waters! Our USCG inspected vessel can safely and comfortably hold up to 38 passengers. She sails gracefully through San Diego Bay providing our guest with views of the picture-perfect downtown San Diego skyline, the historic vessels at the Maritime Museum, Coronado Bridge, Point Loma and Cabrillo National Monument. We love hosting and making your time on San Diego Bay the best! Our charters include a variety of soft drinks, water, beer, wine and dry snacks. Guest are welcome to BYOB and food aboard or we also offer a wide variety of catering and beverage packages to suit your tastes and needs at an additional cost.
Our charters include an experienced USCG Certified Captain, and a knowledgeable crew. We also staff a friendly, fun event planner that is creative and can customize any event.

Come aboard, soak up the sun and scenery with a fresh beverage in hand.
Captain Jack and The Romancing The Wind Crew welcome you aboard.

Response rate: 53%
Response time: within 11 hours

Location and Destination Guide

Usually this boat operates around San Diego, CA.

Discover Southern California and its impressive coastline on one of Sailo’s San Diego sailing charters! If you are looking for an active day on the water, browse our San Diego fishing charters and choose the perfect one for your offshore adventure. Take a sightseeing cruise on a yacht charter from San Diego, or go for an amazing sailing trip to see gigantic whales and playful dolphins. Curious about things you can do on a yacht charter on the ultimate boating playground in California? Read on...

Customer Questions & Answers

Ask general questions about this boat. For questions related to a specific booking request directly.
Please select dates:
Boat From $1,200 per quarter day
Subtotal* Select dates
*excludes Sailo's service fee
per day


What type of yacht should I charter?

No matter what type of yacht you choose to charter, we know that you will have a fantastic time on the water. If you are more about the journey, and want a relaxing time aboard, then choose from one of the many sailboats on the platform. If you are more about the destination, and going fast, check out the powerboats on Sailo. For an exclusive experience, Sailo recommends chartering a luxurious yacht for the day. Finally, Sailo has access to many event boats as well for group outings from 50 - 1,000 guests. If you are still unsure, then just ask! more...

What should I bring?

Bring yourself, and some comfortable clothes suitable to the season you are going to be out on the water. Please keep in mind that it is often 10 degrees cooler out on the water, so a jacket or windbreaker is never a bad idea. We also recommend bringing a hat, sunscreen, and sunglasses, as well as a swimsuit if appropriate for your charter location. Please coordinate with your captain regarding any food or drinks that you wish to bring aboard. For term-charters, Sailo recommends using soft-sided luggage, and keeping it simple. more...

How long does a rental last?

The basic daily rental is structured as either a quarter-, half-, or full-day. A quarter-day is two hours, a half-day is four hours, and a full-day is eight hours. You can also discuss a custom trip with the boat by contacting the owner through Sailo. Most term charters (weekly rentals) are from Saturday to Saturday. Keep in mind that the boat generally needs to be back at the dock by Friday evening, and you will need to be off the boat on Saturday morning so they can prepare the boat for the next guests. more...