Sunset Sail

Compass Divider

Experience the magical golden hour on the bay

Revel in the calm waters of San Diego Bay as the sun sets over the Pacific, casting a warm glow across the skyline.

This private luxury sunset sail offers an intimate and elegant setting—perfect for proposals, celebrations, or simply an extraordinary evening on the water.

Enjoy your favorite cocktails, selected wines, craft beers, and beautifully presented gourmet charcuterie as you sail through one of the most scenic harbors in the world. As the evening unfolds, relax with a glass in hand while the San Diego skyline begins to illuminate against the fading light.

For those planning a proposal, our captain and Forbes-trained crew discreetly coordinate every detail—from timing and ambiance to photography—ensuring a seamless, refined, and deeply personal experience.

Departure times are customized to align with sunset, weather conditions, and your schedule. As always, your charter is fully private, designed exclusively for you and your guests.

Riviera sailboat on the San Diego Bay at sunset, with the city in the background.

Click on images to enlarge

What to expect during your private sunset sail

Whether celebrating a special occasion or simply enjoying a refined evening on the water, a private sunset sail offers an experience unlike anything else in San Diego. From the moment you step aboard, our captain and Forbes-trained crew manage every detail—allowing you to relax and fully immerse yourself in the moment.

Your experience begins with a personal consultation, where we tailor every element of your charter—from ideal departure timing to menu preferences and the day’s sailing conditions. Each sail is thoughtfully planned to ensure optimal lighting, comfort, and flow throughout the evening.

Onboard, enjoy a curated selection of premium wines, craft cocktails, and beautifully presented gourmet appetizers featuring fresh, seasonal ingredients. Menus can be fully customized to accommodate dietary preferences, ensuring a seamless and personalized experience from start to finish.

How it works

All sails are private and planned exclusively for you and your guests.

The Riviera can accommodate a maximum of 10 passengers.

Our crew will take care of every detail for you. All you need to do is show up!

Ready to sail?

Contact us today for booking and availability

Two people on the deck of a sailboat at sunset

What our guests say

"Our sunset sail was the highlight of our trip to San Diego. We enjoyed the peaceful waters and beautiful views as we sailed the San Diego Bay. Captain Paul and Carolyn were gracious and entertaining hosts and the food and drinks were top notch. This is definitely something you will want to experience while in San Diego. Great memories made!"

Amanda Neelly, INSPIRATO Member

Sunset Sail FAQ

Curious about the Sunset Sail? This private, all-inclusive cruise is one of our most popular experiences. Check out the FAQ below to learn what to expect and how to make the most of your evening on the water. Still have questions? Captain Paul is just a message away.

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