Looking for creative ways to spend date night in San Diego? Hop aboard a sunset sail and enjoy a private sailboat ride for you and your plus one on the San Diego Bay.
Take your lad or lass on a private 3-hour sunset sail for up to 10 guests, with cold drinks and snacks included, sailing past the Star of India, USS Midway, and the Coronado Bridge during golden hour. Couples who want a more social vibe can book the ticketed sunset sail (max 6 passengers). Pair it with Balboa Park beforehand and dinner on Shelter Island after for a complete San Diego date day.
Enjoy a romantic sunset cruise
What could be more romantic than stepping foot aboard your own private boat for a sunset sail? Just you and your date, sailing along San Diego’s coastline for a romantic way to spend the evening. With cold drinks and snacks on board, we provide everything you need for a relaxing evening on the water.
Choose your perfect sailing experience
Sail San Diego Sunset Cruise Options
| Option | Group size | Duration | Best for | Book |
|---|---|---|---|---|
| Private Sunset Sail | Up to 10 guests | 3 hours | Proposals, anniversaries, double dates | /product/sunset-sails/ |
| Ticketed Sunset Sail | Max 6 passengers (shared) | ~2 hours | Date night, smaller budgets, social vibe | /product/sunset-sails/ |
| Private All-Day Sail | Up to 10 guests | Full day | Special occasions, full-day escapes | /private-all-day-sails/ |
Ticketed Sunset Sail:
Enjoy a small-group sailing experience with a relaxed, social atmosphere. With a maximum of six passengers, it still feels personal while offering a chance to share the experience with others.
Private Sunset Sail:
Make the evening entirely your own. Spend three hours on a private boat with just your partner, or invite a small group of friends for a double date. Book private sunset sails up to 10 guests, making it perfect for proposals, anniversaries, or double dates.
What You’ll See on a Romantic Sunset Sail
Most couples go downtown San Diego for dinner reservations or happy hour, but you’ll experience America’s Finest City from the water. Take in a unique experience sailing along downtown San Diego during golden hour. You’ll see a side of San Diego you didn’t even know existed.
Sail along iconic sights like the Star of India, the U.S.S. Midway Aircraft Carrier, and the Coronado Bridge. This will be by far the most romantic location for happy hour you’ve experienced in San Diego.
You might even spot marine life like sea lions and dolphins during your sail in the San Diego Bay!
How to spend your date-day prior to your sunset cruise
Visit Balboa Park:
Spend a few hours walking around the gardens or museums at Balboa Park. Enjoy 1,200 acres of beautiful gardens and museums, including the San Diego Museum of Art, Natural History Museum, and San Diego Air & Space Museum.
Grab a mid-afternoon toast before setting sail:
Enjoy a glass of wine next door to our location at All Aboard. They offer a wonderful selection of wines, along with charcuterie boards and sandwich platters. You can even order a board or two ahead of time to bring with you on your sail.
Dinner options post-sail
Once you’ve spent three relaxing hours on the water, you can find several places to grab dinner just a few minutes walk away from our docks.
Restaurants within walking distance:
And there’s your itinerary for a fun, laid-back date-day in San Diego.