San Diego Dinner Cruise

Pricing Details

Price: $1245 for a Couple

On Sale Price: $1150 for a Couple

Optional Photography Packages $155 & $275 Read more

San Diego Dinner Cruise offers: 

    • Totally Private
    • Complimentary Dinner
    • Gourmet meal and dessert
    • 51-foot Classic Yacht
    • Sunset Sail
    • Anchor on remote beaches
    • Personalized service
    • 4-hr flexible time window
    • USCG Licensed Captain

Sail Away San Diego invites you to experience the most unique dining experience on the San Diego bay.  A totally private San Diego Dinner Cruise that takes place in the most spectacular location possible.

Imagine you and your special someone sailing on a yacht that has the charm and quality of a bygone era under the impressive classic pacific sunset. And that is just the beginning.

After a relaxed and gentle sail and a glass of wine we anchor using just the sails alone. With this we provide you with a sunset dinner cruise that opens a window into nautical history and the craft of true seamanship. This is done right in front of an isolated beach, where there is not a soul around except the vastness of the sky & bay where views of the skyline burst with color as the sun’s last light lingers on the horizon.

You are viewing this from the bow of the yacht in a warm and comfortable seating arrangement with ample blankets, pillows and of course a glass of wine. It is this that makes you want to stop time forever and live in that moment again and again. The wind is generally very gentle this time of day and the water very calm providing an environment that’s almost unreal. The vastness of the harbor will feel like a comfortable living room.

It is at this time that you will hear the galley bell ring. As the deep sounding chime fades in the gentle breeze you realize that there is more to please.

Your fine dinner awaits you below deck where you will find the most charming setting for the most delicious dish. As you pass through the ships hall you notice the fantastic views from the bronze portholes surrounded by rich aged hard wood and a teak cabin sole. The ship’s fireplace provides a warm yellow dancing light and the oil lamp lights up your dining table as soft music accents your mood. Dinner is served on fine china and silverware. It is these small details that make this the most authentic and private dinner cruise on San Diego Bay. Not to mention your food. Your dish was never frozen and made with the most freshest ingredients bought that day. Desert is served as we raise the sails and start our journey back. Under the cover of the stars and the moon and the city acting as a beacon, we sail… Warm tea is served on deck as you comfortably relax on the bow in absolute privacy and enchantment.

We look forward to making your dinner cruise in San Diego as special as possible and feel fortunate to be a part of it.

Robert and Katerina


  •  I had an amazing experience booking a proposal cruise with Sail Away San Diego. Robert was very helpful in helping me set up the whole thing. I was able to enjoy an awesome cruise in the bay with my fiancee, especially with the nice breeze and setting sun. Robert did well to give us our privacy, but also provided us with a good conversation when we wanted. Then came the proposal with the pictures, which went smoothly and looked great. Dinner was also well-prepared and everything was perfect! I never felt rushed or intruded upon. I highly recommend working with Robert for all your cruising needs in San Diego!

    Peter Le

    Testimonial Source: 

  •  Ramona and I can NOT begin to describe the truly fairytale experience we had with Robert and Katrina and Sail Away San Diego! From the moment we were picked up and ferried to their sailing yacht, to sipping champagne on the bear skin rug, to dropping on my knee to ask my Sweetheart if she would marry was TRULY a magical evening that neither one of us will ever forget. Thank you to both Robert and Katrina for capturing this moment for us to treasure for a lifetime. By the way...She said "YES!"...Yeah!!! We look forward to sailing with you both again someday... With heartfelt appreciation, Tim & Ramona

    Tim Probasco

    Testimonial Source: 

  • Great experience. That's is the best way do make a proposal - very romantic and beautiful. Champagne, romantic music, sunset, beautiful yacht - no chance she will say "No". It is affordable as well. After 3 hours of sailing we were very surprised to get a free ride to our hotel - that's how good Robert treat his clients. Be sure he is the best!

    Pavel Khitrikov

    Testimonial Source: 

  • Sailaway San Diego provided us the best food and the best experience we could possibly have for an anniversary. The champagne was awesome, the salmon was perfectly cooked, and not to mention, the weather was perfect for such an occasion. I strongly recommend the photo service because the pictures he took for us were definitely better than the ones I signed up for. I strongly recommend Sail Away San Diego for a place to go for a romantic occasion. Thanks alot Robert!

    Steve Kang

     Testimonial Source: 

  • Our experience on Sail Away was Fantastic! We both truly enjoyed the experience and felt like we really had our own special moment to start this new journey in our lifetime. Captain Robert was very helpful and funny. He knew exactly where to take the photos and how to customize the proposal. We highly recommend Sail Away SD to the people out there thinking of something on their own with great sunsets and views around our beautiful city here in SD!

    Srinivas Reddy

     Testimonial Source: 


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Photos by Robert Svoboda

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    Sail Away San Diego
    2726 Shelter Island Dr. #370
    San Diego CA

    Contact Details

    Phone: (619) 723 0218

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