Sail in Peace
01 —Private Sailing Adventures · San Diego Bay
Six ways to sail San Diego Bay — from a peaceful two-hour sunset cruise to a full day of anchoring, swimming and grilling. Every one private, every one yours.
Whether you are chasing a golden-hour skyline, hoping to hear sea lions bark off Point Loma, or planning the proposal of a lifetime, every Sterling Sails charter is fully private — just your group, Captain Liz, and the whole of the bay. Prices are per trip, never per person.
The Fleet of Experiences
Most Popular2 hoursThe one everyone starts with
Our signature two-hour sail — glide past the downtown skyline and the USS Midway, or point the bow toward Point Loma and the sea lions. Champagne poured, playlist on, city shimmering.
From · per charter
$600
3 hoursA little more bay, a lot more time
An unhurried three hours to see it all — the downtown waterfront, harbor wildlife, the Point Loma lighthouse and a taste of open-ocean sailing beyond the bay.
From · per charter
$800
4 hoursOut where the coastline opens up
Leave the bay behind and take the crew out to sea. On a clear day the Southern California and Mexico coastlines stretch to the horizon. Fully customizable — you help chart the course.
From · per charter
$950
3 hoursDrop anchor. Dive in.
Sail out, drop the hook in a calm anchorage off Point Loma and slip into the bay. Paddleboards aboard, cold drinks waiting, the sun-deck all yours.
From · per charter
$900
Best Value4 hoursThe full afternoon on the water
Our longest swim day — anchor off Point Loma or Coronado, fire up the onboard grill, paddleboard, swim and lounge. The complete San Diego summer afternoon, private and unrushed.
From · per charter
$1,100
CustomBring the party out on the water
Birthdays, bachelorettes, engagements, anniversaries and team days — we build the whole sail around your occasion, from karaoke on the JBL party speaker to the surprise bottle chilling on ice.
Priced to suit
Custom
2–3 hoursA private sail made for romance
The full romantic evening — a private sail paired with flowers, food, champagne and a photographer to catch the moment. Proposal-ready, and unforgettable.
Priced to suit
Custom
2.5 hoursA gentle farewell beyond the bay
A dignified memorial sail beyond San Diego Bay to scatter a loved one’s ashes — with time for words, rose petals, the ringing of the bell, and the coordinates recorded for you to keep.
From · per charter
$950
Every charter is private — priced per trip, not per person. Up to 6 guests. Champagne, drinks & snacks always included.
Chart Your Course
From Harbor Island we can chase the sunset downtown, drift toward Coronado, or point the bow past the Point Loma light and out to open water. You tell us the vibe — Captain Liz sets the course.
See it for real
Mojave under sail on San Diego Bay, filmed from the air. Whichever charter you choose, this is the view that comes with it.
Sailing for Every Occasion
No Add-Ons, No Surprises
Charter Questions
Sterling Sails charters range from $600 for a 2-hour San Diego sailing cruise to $1,100 for our 4-hour Sail & Swim with an onboard grill. Every charter is private and priced per trip — not per person — for up to 6 guests, with champagne, drinks and snacks included.
Sail in Peace
Book online in a couple of taps, or message Captain Liz for a custom sail — she usually replies the same day.