Last Updated: December 29, 2025
While many visitors flock to the Gaslamp Quarter or La Jolla, those in search of San Diego’s true maritime soul head to Point Loma. Specifically, the neighborhood of La Playa—the “beach”—stands as one of the most historic and picturesque stretches of coastline in California.
At Sail San Diego, our family has been part of this community for over 35+ years. Operating out of Shelter Island, we have the unique privilege of sharing this historic neighborhood with guests on the largest and roomiest sailing yachts in the bay.
1. Where San Diego Began: The History of La Playa
Long before it was a premier destination for private sailing charters, Point Loma was the site of the first European landing in California. In 1542, Juan Rodriguez Cabrillo stepped ashore just a short distance from where our fleet is docked today.
- A Maritime Legacy: For centuries, La Playa served as the commercial port for the San Diego Mission.
- The Old La Playa Trail: This historic path was once the main artery between the harbor and Old Town. Today, you can still feel that heritage as you walk the shoreline of the “nautical neighborhood” before your sail.
2. Seeing Point Loma from the Water
You haven’t truly seen Point Loma until you’ve viewed it from the deck of a yacht. When you book a shared or private sail with us, you’ll witness the neighborhood’s landmarks from a perspective most people never get:
- The Point Loma Lighthouse: Perched high on the bluffs of the Cabrillo National Monument, the Old Point Loma Lighthouse has guided sailors for generations.
- Millionaire’s Row: Sail past the stunning historic estates of La Playa, where classic architecture meets modern luxury.
- Shelter Island: Our home base is a man-made marvel that serves as the gateway to the Pacific for our San Diego whale watching tours.
3. The Perfect Point Loma Itinerary
As one of San Diego’s oldest boutique sailing operations, we often get asked how to spend a day in our neighborhood. Here is our “Captain’s Recommendation” for the perfect afternoon:
- Morning Hike: Visit the tide pools at Cabrillo National Monument and take in the panoramic views of the city.
- Lunch at the Marina: Enjoy fresh seafood at a local Shelter Island eatery overlooking the yachts.
- Afternoon Sail: Board one of our modern sailing yachts for a three-hour tour. Our wide-beam boats provide the most stable and comfortable way to explore the very waters where San Diego history began.
4. Experience the Boutique Standard in a Historic Setting
At Sail San Diego, we pride ourselves on being a “boutique” experience in an increasingly commercialized world. Because we are family-run, we treat every guest like a neighbor. Whether you are celebrating a summer birthday or planning an intimate proposal, you are becoming part of Point Loma’s long nautical history.
Join Us on the Water
Ready to explore the historic beauty of Point Loma? Come see why we’ve been the local choice for over three decades.