Sail in Peace

Sailing Adventures

Sterling Sails

Make Memories with a Private Sailing Adventure in San Diego

Experience the thrill of the open sea with Sterling Sails’ Sailing Adventures – your premier destination for unforgettable maritime experiences. Whether you’re planning a relaxing getaway or an exciting small boating tour, our private sailing charters promise to create memories that last a lifetime.
  • Set Sail on a San Diego Sailing Cruise
    There’s no better way to explore the sparkling waters of San Diego than with a tailored sailing cruise. From the moment you step aboard, you’ll feel the stress of daily life drift away as you take in panoramic coastline views and feel the ocean breeze on your face. Perfect for couples, families, or small groups, our San Diego sailing cruises are an ideal escape for anyone looking to enjoy the tranquility of the sea.
  • Dive into Fun with Sail & Swim Tours
    For those seeking a more active adventure, our Sail & Swim tours offer the perfect combination of sailing and splashing. Anchor in crystal-clear waters and dive right in for a refreshing swim or snorkel session. This experience is perfect for families and adventure-seekers alike who want to make the most of their time on the water.
  • Customize Your Private Sailing Charter
    Design your perfect day on the water with our private sailing charters. Whether you’re planning a romantic sunset cruise, a team-building event, or a serene morning sail, we’ll tailor your experience to suit your needs. Enjoy exclusive use of our sailboat and personalized service that ensures every detail is just right.
    We even have a JBL Party Box Speaker on board with karaoke!
  • Explore San Diego Like Never Before

    Join us for a small boating tour and discover hidden gems along the San Diego coastline. From stunning natural scenery to unique local landmarks, our knowledgeable crew will guide you on an intimate and immersive exploration of the bay and beyond.

  • Choose Your Sailing Adventure in San Diego Right Here!
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Set Sail on a San Diego Sailing Cruise

There’s no better way to explore the sparkling waters of San Diego than with a tailored sailing cruise. From the moment you step aboard, you’ll feel the stress of daily life drift away as you take in panoramic coastline views and feel the ocean breeze on your face. Perfect for couples, families, or small groups, our San Diego sailing cruises are an ideal escape for anyone looking to enjoy the tranquility of the sea.
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Celebrate with a Catalina Wine Mixer

Turn your sailing adventure into a celebration with our Catalina Wine Mixer experience. Raise a glass to stunning views, great company, and fine wine aboard our luxurious sailboat. Whether it’s a birthday, anniversary, or a well-deserved outing, this unique experience offers the perfect blend of relaxation and festivity.

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Dive into Fun with Sail & Swim Tours

For those seeking a more active adventure, our Sail & Swim tours offer the perfect combination of sailing and splashing. Anchor in crystal-clear waters and dive right in for a refreshing swim or snorkel session. This experience is perfect for families and adventure-seekers alike who want to make the most of their time on the water.

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Customize Your Private Sailing Charter

Design your perfect day on the water with our private sailing charters. Whether you’re planning a romantic sunset cruise, a team-building event, or a serene morning sail, we’ll tailor your experience to suit your needs. Enjoy exclusive use of our sailboat and personalized service that ensures every detail is just right.

binocular icon

Explore San Diego Like Never Before

Join us for a small boating tour and discover hidden gems along the San Diego coastline. From stunning natural scenery to unique local landmarks, our knowledgeable crew will guide you on an intimate and immersive exploration of the bay and beyond.

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Choose Your Sailing Adventure in San Diego Right Here!

Sterling Sails

Types of Adventures

parents with their kid

2-Hour San Diego Sailing Cruise

This 2-hour sailing adventure has two tour options! We can head downtown to check out the USS Midway, aircraft carriers, and Maritime Museum or we can sail out towards Point Loma for ocean views and visit the sea lions.

US $600

Gilligan's 3-Hour
Tour

Don’t worry! This won’t be like the 3-Hour tour on the SS MINNOW. This tour will allow you the opportunity to see and learn about all the coolest sites in the San Diego Bay.

Enjoy downtown views, see lots of wildlife, the Point Loma Lighthouse, and sail out to the ocean.

US $800

yacht sailing in the middle of sea

4-Hour
Voyage

This exciting adventure will take you and your crew out to sea. One may never know what you may discover while exploring the mysteries of the big blue. View the natural coastline of Southern California and Mexico. If your group does not want to go into the ocean, we don’t have to! Your Captain will take you anywhere you want to go for this voyage. The San Diego Bay is huge so there are many places to explore.

US $950

people in yacht

4 hour Sail & Swim

Some people want to sail, some want to jump in the water. You don’t have to choose. You can do both! Jump off the boat to swim, we even have paddle boards for you to play with in the water!

US$1,100

kids enjoying their picnic on yacht

3 hour Sail & Swim

Some people want to sail, some want to jump in the water. You don’t have to choose. You can do both! Jump off the boat to swim, we even have paddle boards for you to play with in the water!

US$900

Burial At Sea

Embark on a journey to the Pacific Ocean outside of San Diego Bay to scatter the ashes of a loved one. There will be time to say a few words if you desire during the time of the scattering. Rose petals included or bring your own flowers. Coordinates are recorded at the time of the scattering along with 8 rings of the bell for a proper maritime burial at sea

US $950

gift card

Gift Card

Give the gift of sailing to your friends and family. It will be an experience to remember! Purchase any amount of your choosing!

That someone special

The combination of a private sailing yacht in one of the most beautiful cities in the world, being with the person you love, the food, the flowers, the photos, and the celebration champagne are what makes this trip so special.