A private, luxury proposal at sunset
An unforgettable engagement experience, thoughtfully designed on San Diego Bay
Transform a beautiful moment into a once-in-a-lifetime experience with a private sunset proposal on the water. Set against the backdrop of San Diego’s skyline and golden evening light, your engagement unfolds in an intimate, elegant setting designed entirely around you.
Our captain and Forbes-trained crew discreetly orchestrate every detail—from perfectly chilled champagne to a curated soundtrack and a professional photographer seamlessly integrated into the experience. The result is effortless, refined, and deeply personal—allowing you to focus on the moment that matters most.
Explore a recent proposal: Read the story of a recent proposal aboard the Riviera and discover the level of care, precision, and elevated service that defines every Sail Riviera experience.
What to expect when you sail with us
It’s all in the details. The "perfect proposal" aboard a yacht takes careful planning. However, before deciding on a sail date, let's discuss your vision. You've imagined how it will look and rehearsed what you want to say. Now let us take the wheel.
We will plan for the best weather window, sunset times, and sail route. We'll prepare everything from the perfect playlist to your favorite champagne. One of Captain Paul Barnett's professional photographers will pose as "crew" to document the moment you both decide to spend the rest of your lives together.
As with all our cruises, you'll choose your menu from options which may include hand-crafted charcuterie boards made from fresh, seasonal, farm-to-table ingredients and custom cocktails guaranteed to delight your palette. Please share any dietary restrictions or food allergies so that we may plan accordingly.
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
Proposal Sail FAQ
Planning to pop the question? We’ve helped dozens of couples create unforgettable proposal moments at sea. Browse our FAQ to learn how we handle all the details. Still wondering about something? Ask Captain Paul and he'll be happy to help.
With input from the primary guest, we customize the sail plan, the menu, the photography and of course, how the surprise will remain a surprise!
In the last five years, we’ve hosted several dozen proposals. All resulted in a responding YES!
Careful planning and attention to detail, which goes into every charter we host.
A private, sailing cruise for up to 3 hours. A fantastic appetizer menu, a full bar, and photographs provided by a professional photographer.
Absolutely! Get in touch to let us know what you have in mind.
Yes! Your proposal will be carefully planned to ensure the surprise is real. We will work with you to honor any special requests.
Weekend dates are popular, and should be booked as soon as possible.
San Diego rarely has bad weather, however, we’ll check the forecast a few days prior to the reservation and if need be, adjust the date or time.
Yes, all our sail excursions are private.
Absolutely! If you have any special drink requests please let us know.