Explore Southern California's Coastline with Private Sunset, Harbor, or Multi-Day Sailing Adventures
TipToe Sailing offers personalized private sailing adventures departing from Cabrillo Marina, allowing you to explore the stunning Southern California coastline. Choose from romantic sunset cruises, lively harbor tours, or immersive multi-day expeditions tailored to your desires.
Highlights
Embark on a personalized private sailing adventure tailored to your desires along the stunning Southern California coastline.
Explore diverse nautical experiences, from romantic sunset cruises to immersive multi-day expeditions, perfect for any occasion.
Enjoy the expertise of a professional captain and crew, ensuring a safe, comfortable, and memorable journey on the Pacific.
Discover breathtaking marine life and scenic coastal views, with opportunities for swimming, snorkeling, or hands-on sailing lessons.
A perfect gift for adventurers, romantics, or families seeking a unique, unforgettable escape on the open water.
What To Expect

Plan Your Visit
- Operating HoursHours may vary. Please check the merchant's website for the most up-to-date information.
- DurationExperiences range from 2-hour private cruises to multi-day sailing tours, including 2-day/1-night and 7-day expeditions.
- Departure & ArrivalAll sailing adventures depart from and return to Cabrillo Marina in San Pedro, CA.
Ticket Options
Private Sunset Cruise
Perfect for romantic dates, anniversaries, or a serene evening with friends or family, this 2-hour private cruise allows up to 6 guests to savor the beauty of the Pacific Ocean during golden hour, with opportunities to spot dolphins and other marine life.
Private Harbor Cruise
Ideal for casual outings, family gatherings, or small group celebrations, this 3-hour private cruise for up to 6 guests explores the scenic harbor, with options to anchor in quiet coves for swimming or relaxation.
Private Day Charter
Customize your 6-hour private itinerary for up to 6 guests with options for hands-on sailing lessons, wildlife viewing, and coastal exploration, perfect for bachelor/bachelorette parties, milestone birthdays, or a luxurious getaway.
Multi-Day Sailing Tour
An ideal adventure for sailing enthusiasts, this 2-day, 1-night tour for up to 4 guests sails to destinations like Catalina Island, offering opportunities for island exploration, snorkeling, kayaking, and advanced sailing techniques.
7 Days West Coast Sailing Tour
Embark on an unforgettable 7-day journey along the West Coast of the USA's Pacific Ocean for up to 4 guests. Explore 7 unique waypoints, with opportunities to step ashore and walk around historical towns, all guided by a professional Captain.
How It Works
1. Grab the Deal
Buy your Groupon first!
2. Plan your visit
Contact the merchant following the instructions on your Groupon.
3. Redeem your Mobile Ticket
Scan your Groupon upon arrival.
4. Enjoy the Experience!
FAQs
What types of sailing experiences does TipToe Sailing offer?
TipToe Sailing offers a diverse range of private sailing experiences, including romantic sunset cruises, lively harbor tours, customizable private day charters, immersive multi-day sailing tours (2-day/1-night), and extensive 7-day West Coast expeditions.
How many guests can participate in a private sailing experience?
Most private cruises, such as the Sunset, Harbor, and Day Charters, can accommodate up to 6 guests. The Multi-Day Sailing Tours and the 7-day West Coast tour are designed for up to 4 guests, ensuring an intimate experience.
Where do the TipToe Sailing tours depart from?
All TipToe Sailing adventures conveniently depart from and return to Cabrillo Marina, located in San Pedro, CA, providing easy access to the beautiful Southern California coastline.
What can I expect to see and do on a private sunset cruise?
On a private sunset cruise, you can expect to witness the stunning beauty of the Pacific Ocean during the golden hour. It's a perfect opportunity for romantic dates and you might even spot playful dolphins or other marine life as the sun dips below the horizon.
Are the sailing tours customizable?
Yes, both the Private Day Charter and the Multi-Day Sailing Tours offer customizable itineraries. You can tailor your experience with options like hands-on sailing lessons, wildlife viewing, island exploration, snorkeling, or kayaking, depending on the tour type.
Is it possible to learn sailing techniques during a TipToe Sailing experience?
Absolutely! The Private Day Charter explicitly offers options for hands-on sailing lessons, allowing you to deepen your skills. The Multi-Day Sailing Tour also provides opportunities for learning advanced sailing techniques as you explore various destinations.
TipToe Sailing offers personalized private sailing adventures departing from Cabrillo Marina, allowing you to explore the stunning Southern California coastline. Choose from romantic sunset cruises, lively harbor tours, or immersive multi-day expeditions tailored to your desires.
Highlights
Embark on a personalized private sailing adventure tailored to your desires along the stunning Southern California coastline.
Explore diverse nautical experiences, from romantic sunset cruises to immersive multi-day expeditions, perfect for any occasion.
Enjoy the expertise of a professional captain and crew, ensuring a safe, comfortable, and memorable journey on the Pacific.
Discover breathtaking marine life and scenic coastal views, with opportunities for swimming, snorkeling, or hands-on sailing lessons.
A perfect gift for adventurers, romantics, or families seeking a unique, unforgettable escape on the open water.
What To Expect

Plan Your Visit
- Operating HoursHours may vary. Please check the merchant's website for the most up-to-date information.
- DurationExperiences range from 2-hour private cruises to multi-day sailing tours, including 2-day/1-night and 7-day expeditions.
- Departure & ArrivalAll sailing adventures depart from and return to Cabrillo Marina in San Pedro, CA.
Ticket Options
Private Sunset Cruise
Perfect for romantic dates, anniversaries, or a serene evening with friends or family, this 2-hour private cruise allows up to 6 guests to savor the beauty of the Pacific Ocean during golden hour, with opportunities to spot dolphins and other marine life.
Private Harbor Cruise
Ideal for casual outings, family gatherings, or small group celebrations, this 3-hour private cruise for up to 6 guests explores the scenic harbor, with options to anchor in quiet coves for swimming or relaxation.
Private Day Charter
Customize your 6-hour private itinerary for up to 6 guests with options for hands-on sailing lessons, wildlife viewing, and coastal exploration, perfect for bachelor/bachelorette parties, milestone birthdays, or a luxurious getaway.
Multi-Day Sailing Tour
An ideal adventure for sailing enthusiasts, this 2-day, 1-night tour for up to 4 guests sails to destinations like Catalina Island, offering opportunities for island exploration, snorkeling, kayaking, and advanced sailing techniques.
7 Days West Coast Sailing Tour
Embark on an unforgettable 7-day journey along the West Coast of the USA's Pacific Ocean for up to 4 guests. Explore 7 unique waypoints, with opportunities to step ashore and walk around historical towns, all guided by a professional Captain.
How It Works
1. Grab the Deal
Buy your Groupon first!
2. Plan your visit
Contact the merchant following the instructions on your Groupon.
3. Redeem your Mobile Ticket
Scan your Groupon upon arrival.
4. Enjoy the Experience!
FAQs
What types of sailing experiences does TipToe Sailing offer?
TipToe Sailing offers a diverse range of private sailing experiences, including romantic sunset cruises, lively harbor tours, customizable private day charters, immersive multi-day sailing tours (2-day/1-night), and extensive 7-day West Coast expeditions.
How many guests can participate in a private sailing experience?
Most private cruises, such as the Sunset, Harbor, and Day Charters, can accommodate up to 6 guests. The Multi-Day Sailing Tours and the 7-day West Coast tour are designed for up to 4 guests, ensuring an intimate experience.
Where do the TipToe Sailing tours depart from?
All TipToe Sailing adventures conveniently depart from and return to Cabrillo Marina, located in San Pedro, CA, providing easy access to the beautiful Southern California coastline.
What can I expect to see and do on a private sunset cruise?
On a private sunset cruise, you can expect to witness the stunning beauty of the Pacific Ocean during the golden hour. It's a perfect opportunity for romantic dates and you might even spot playful dolphins or other marine life as the sun dips below the horizon.
Are the sailing tours customizable?
Yes, both the Private Day Charter and the Multi-Day Sailing Tours offer customizable itineraries. You can tailor your experience with options like hands-on sailing lessons, wildlife viewing, island exploration, snorkeling, or kayaking, depending on the tour type.
Is it possible to learn sailing techniques during a TipToe Sailing experience?
Absolutely! The Private Day Charter explicitly offers options for hands-on sailing lessons, allowing you to deepen your skills. The Multi-Day Sailing Tour also provides opportunities for learning advanced sailing techniques as you explore various destinations.
Need To Know Info
- 3-day hassle-free refund guarantee - Free cancellation for up to 3 days after purchase for unredeemed vouchers.
- Limit 3 per person(s), may buy 3 additional as gift(s).
- Appointment required. Merchant contact information will be available for you after purchase in My Stuff.
- May be repurchased every 30 days.
- Subject to weather.
- Must sign waiver.
- 24-hour advance notice required.
- 24-hour cancellation notice required.
- Valid for 4 months.
- Not valid with other offers or promotions.