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Sail Into Adventure

Embark on a journey with TipToe Sailing and experience the beauty of sunsets, whale and dolphin watching, wedding parties, birthday celebrations, and more. Let us take you on a sailing adventure like no other.

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Our Experiences

Join us for unforgettable adventures with open sails, sailing education, multi-day tours to Catalina Island, and the stunning harbors of Southern California. Choose TipToe Sailing for a remarkable ocean experience.

Wildlife Watching

A wildlife-watching sailboat tour with TipToe Sailing in San Pedro, CA is an unforgettable way to experience marine life in its natural habitat while enjoying the beauty of the Pacific Ocean. Setting Sail from San Pedro Our journey begins at Cabrillo Marina, where we set sail along the stunning Southern California coastline. As we glide through the open water, you’ll get a hands-on sailing experience or simply relax and take in the sights. Marine Life Encounters San Pedro’s waters are home to an incredible variety of marine wildlife. Depending on the season, you may spot: •Dolphins – Playful pods of common and bottlenose dolphins often surf our wake. •Whales – Gray whales migrate along the coast in winter and spring, while blue whales, humpbacks, and fin whales make appearances in summer and fall. •Sea Lions & Seals – Watch these curious creatures bask on buoys or pop up alongside the boat. •Seabirds – Keep an eye out for pelicans, cormorants, and ospreys soaring above or diving for fish. Exploring Hidden Coves & Open Ocean We may sail toward Point Fermin, Palos Verdes, or even out to Catalina Channel, where deep waters offer excellent chances to see larger marine life. Along the way, we’ll drop anchor in a scenic spot where you can take in the peaceful surroundings. A Relaxing & Educational Adventure Our expert skippers provide insights into local wildlife, ocean conservation, and sailing techniques, making this a fun and educational experience for all ages. Whether you’re an avid nature lover or just looking for a unique day on the water, this trip offers a perfect mix of adventure and tranquility. Why Choose TipToe Sailing? •Small group experience for an intimate and personalized tour •Expert sailing and wildlife guides •A peaceful, eco-friendly way to experience marine life •Opportunities for hands-on sailing participation Ready for an unforgettable wildlife-watching adventure? Contact us at (424) 450-8504 or email tiptoesailing@gmail.com to book your trip today!

Parties on Harbor

A party tour with TipToe Sailing in San Pedro, CA is the perfect way to celebrate a special occasion while enjoying the beauty of the Pacific Ocean. Whether it’s a birthday, bachelor/bachelorette party, anniversary, or just a fun day with friends, we provide a private and unforgettable sailing experience with stunning coastal views, ocean breezes, and an incredible atmosphere. Setting Sail & Scenic Cruising Departing from Cabrillo Marina, we’ll hoist the sails and cruise along the picturesque Southern California coastline. You can soak in views of Point Fermin, Palos Verdes cliffs, and Catalina Island in the distance while sipping your favorite drinks and enjoying the ocean air. Music, Drinks & Celebration on Deck Our spacious sailboat provides a relaxed and fun environment for your party. You can: •Bring your own food, drinks, and playlists – Connect your music to our speakers and set the vibe! •Dance under the sun or stars – Smooth sailing and ocean waves create the ultimate dance floor. •Lounge & enjoy the sunset – Golden hour at sea makes for an unforgettable experience and Instagram-worthy moments. Customizable Experience Want to make it extra special? We can anchor in a calm cove for a swim, offer hands-on sailing lessons, or plan a sunset cruise for a romantic touch. If you’re celebrating a big event, let us know, and we’ll help personalize the experience. Why Choose TipToe Sailing for Your Party? •Private & exclusive experience for your group •Flexible itinerary – cruise, anchor, or even sail toward Catalina for an extended trip •BYOB & food-friendly – bring what you love •Unmatched scenic views & ocean vibes Book Your Sailing Party! Whether you want a lively celebration or a chill gathering with friends, our party sailboat tour is a one-of-a-kind experience in San Pedro. Contact us today at (424) 450-8504 or email tiptoesailing@gmail.com to book your unforgettable party on the water!

Sailing Education

At TipToe Sailing, located at 1046 S Seaside Ave, San Pedro, CA 90731, we offer personalized sailing education tailored to both beginners and seasoned sailors. Our experienced instructors provide hands-on lessons that cover essential aspects of sailing, including yacht navigation and open water sailing techniques. We emphasize a practical approach, ensuring that participants gain confidence and competence on the water. In addition to our standard lessons, we offer multi-day sailing tours to destinations like Catalina Island, allowing students to apply their skills in real-world scenarios while exploring the stunning harbors of Southern California. Our commitment is to deliver an intimate and engaging sailing experience, fostering a deep appreciation for the art of sailing. For more information or to schedule a lesson, please contact us at (424) 450-8504 or email tiptoesailing@gmail.com. We look forward to embarking on a sailing journey with you.

Multi-Day Tours

A multi-day sailing tour with TipToe Sailing from San Pedro, CA offers an unforgettable adventure on the open water. Departing from Cabrillo Marina, we set sail along the stunning Southern California coastline, heading toward Catalina Island or other scenic destinations. Day 1: Departure & Open Water Sailing We begin with a safety briefing and an overview of sailing basics before hoisting the sails. As we navigate the Pacific, you’ll get hands-on experience steering the boat, trimming sails, and learning essential navigation skills. Keep an eye out for dolphins, sea lions, and even whales along the way. After several hours at sea, we drop anchor in a quiet harbor or cove, where you can swim, snorkel, or just relax on deck. Day 2: Island Exploration & Seamanship Skills Wake up to the gentle sound of waves and enjoy breakfast on board before heading to shore. If we anchor in Avalon or Two Harbors, you’ll have time to explore the island—hike scenic trails, rent a kayak, or visit charming seaside towns. Back on the boat, we refine our sailing skills with lessons on navigation, anchoring techniques, and weather reading. As the sun sets, enjoy dinner under the stars before settling in for another peaceful night aboard. Day 3: Return Voyage to San Pedro After a leisurely morning, we set sail back toward the mainland, applying everything you’ve learned along the way. This is the perfect time to take the helm and experience the thrill of captaining a sailboat with the guidance of our experienced instructors. As we approach San Pedro, we celebrate the journey with final reflections, photos, and farewells.

Luxury Yacht Charters

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Customer Reviews

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We celebrated our anniversary on a sunset sail with TipToe Sailing. It was a magical and unforgettable experience. Thank you for the memories!

Whale Watching

South California Harbors

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The team at TipToe Sailing made our wedding party a dream come true. The setting, the service, and the overall experience were exceptional.

Wedding Parties

Knowledgeable Crew

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As locals, we've sailed with TipToe multiple times and have always had a fantastic time. Great crew, beautiful sailboats, and wonderful experiences.

Birthday Celebrations

Friendly Service

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I joined the sailing education program and was impressed by the professionalism and expertise of the instructors. A truly enriching experience.

Sailing Education

Unforgettable Memories

Book Your Sail

Join the Adventure

Experience the Pacific

Discover

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Contact Us

For inquiries, bookings, or any information, feel free to reach out to TipToe Sailing. We are here to assist you in planning your next sailing adventure in the Pacific Ocean.

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