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A gentle sail through the harbor.Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hrLet's Get This Party Started Gals!The Best Seat On The Bay

Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr

5.0(26 reviews)
81 bookings
Estimated price
USD $600 / hour (3 hours minimum)


Romancing The Wind is the Premier Luxury Sailboat for cruising San Diego Bay and nearby coastal waters! Our tiered pricing makes us very affordable for groups of all sizes! 1-10 Passengers $600hr. 11-20 Passengers $700/hr, 21-30 passengers $800/hr. Our hourly rates include all port and Marina Fees, and require a 3 hr minimum.  We feature a large and comfortable aft lounge area, great for mingling, dancing, or just taking in the beautiful views! We are the only premium sailboat with high rigid rails providing safe and comfortable access around the entire vessel and we are safe for children of all ages. We limit our regular rate capacity to 30 guests with options up to 35 guests upon request, some restrictions apply.  Enjoy sailing gracefully through San Diego Bay enjoying picture-perfect views of the downtown San Diego skyline, the historic vessels at the Maritime Museum, Coronado Bridge, Point Loma, Cabrillo National Monument, and the beautiful coastline. Every charter includes a USCG licensed Captain, professional crew, a variety of soft drinks, water, and light packaged snacks. We have JBL Party Box 300 Bluetooth speakers that play from your smart device. food & Beverages Let us do all the work by taking advantage of our Catering packages! We can fully customize our Bar Service to suit your discriminating needs! We offer menus from Local Restaurants, Deli’s and Custom Caterers! Guests may BYO for a flat rate $125 access and cleanup fee, restrictions apply.  We are conveniently located on Harbor Island near the San Diego airport! We have a great staff and crew that will help customize your charter to suit your specific needs! If you have any questions, contact us through this GetMyBoat’s messaging platform. Just select “Send an Inquiry” at the bottom of the page. We look forward to helping you create your next sailing adventure!

Captain is included.
A captain is provided by the listing owner to host and operate the trip.
30 guests

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5.0 (26 reviews)
  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

  1. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  2. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  3. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  4. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  5. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  6. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  7. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  8. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  9. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  10. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  11. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
  12. Enjoy 360 Degree Views of San Diego! Pricing Starts at $600/hr
17 photos have been added by reviewers who booked this listing.
  1. ND

    Jim and crew were awesome! Our group had a great birthday celebration and would sign up again in no time!

  2. Tara

    This was the absolute hi-light of our whole trip to San Diego! The boat was unbelievable and we loved the crew, the accommodations, the giant speakers, byob option, and the energy of our entire crew! This made our bachelor/bachelorette trip so special! We had SO much fun and made so many amazing memories on the sailboat! We will definitely be back! 10/10

  3. OA

    The experience of a lifetime! The boat was truly amazing and Jim and his staff were very friendly, accommodating, and made sure everyone had a great time. Highly recommend Jim and his boat to anyone looking to have a great time!

  4. HV

    We had a wonderful experience during this excursion. Bb was easy to communicate with, the captain, and deckhand were super helpful and delightful. Highly recommend this boat rental for any and all occasions. We hope to return someday!

  5. SR

    Great team, beautiful boat, awesome experience!



81 bookings

Our private charters are the best way to experience San Diego Bay and the beautiful coastal surroundings. Our vessel, Romancing The Wind, offers guests adventure and relaxation with our diverse capability from full speed offshore sailing, Motor Cruising through the bay, or dropping anchor for a refreshing swim. Our vessel is perfect for Birthdays, Family Gatherings, Corporate Events, Bachchelor, Bachelorette Parties, or just plain fun with friends. We also offer Ash Scattering and Full Body Green Burial services! Whatever the occasion, the crew will make your time on the water the best it can be!

Features & Details

  • Bar
  • Bluetooth
  • Galley Stove & Oven
  • Life jackets/required safety gear
  • BBQ
  • Licensing Required
  • Berth
  • Inverter
  • Furling Headsail
  • Fuel type: Diesel
  • Single Engine
  • Dinghy
  • Chart Plotter
  • Wheel steering
  • Inboard Engine
  • Head
  • Generator
  • Cabin

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

Cancellation Policy

Full refund up to 7 days prior.

Additional Terms & Information

We offer multi-tiered pricing system based on the size of your group. Pricing starts at $600 per hour for groups of 1-10 passengers, $700 per hour for groups of 11-20 passengers, $800 per hour for groups of 21-30 passengers. Groups up to 35 passengers by special request and pricing.  All price rates require a three-hour (3hr) minimum. and include all Port and Marina fees! All of our charters include an experienced USCG Certified Captain, a knowledgeable crew, a selection of light snacks consisting of packaged cookies, chips, pretzels etc., water, sodas, coolers, and ice. We have bluetooth speakers that play from any smart device ready for your enjoyment. Let us do all the work! We offer a wide variety of food and beverage catering options to suit your taste,and priced to suit your wallet! Contact us for additional details and information. All prices quoted include all Marina and Port fees. Charter guests are asked to arrive at the Marina no less than thirty (:30) minutes prior to departure for processing. In compliance with Covid-19 protocols, we ask that charter guests not participate if they have a fever, cough, sneezing, or do not feel well for any reason. All charter guests will be required to submit to a touch-less temperature screening, and to fill out, and sign, a Release of Liability Waiver prior to boarding. Any guest(s) appearing ill or having a temperature greater than 100 degrees, will not be permitted to board. The Captain has the final authority! Cancellation Policy: In addition to our cancellation policy outlined below, all cancellations may be subject to additional GMB cancellation fees! Cancellations 7 days or greater from the CHARTER START DATE will receive full refunds. Cancellations 2-6 days from the CHARTER START DATE will incur a 20% refund penalty. Cancellations 24 to 48 hours from the CHARTER START TIME will incur a 50% refund penalty. Cancellations less than 24 hours from the CHARTER START TIME will receive NO REFUND! In such cases the charter may be re-booked to a later date date however, ANY subsequent cancellation will receive NO REFUND!  Gratuities are not required but greatly appreciated! Standard charter industry gratuity rates are between 15-25% of the total charter price.   

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