Sailing in San Diego

PLAN EARLY, BOOK EARLY. During high season (May-Oct) we sell out weekends & holidays weeks to months in advance. In addition to our hourly rate, the Port of San Diego requires us to collect an additional 11% fee which we collect directly from you. A credit card on file is required for security deposit. During high season, May-September, a minmum of three hours is required. Two hour saturday charters are subject to request and approval. We will do our best to fit you in on saturdays!

This IOR Raceboat is a classic restored 1973 Ranger 37 named Masquerade and intended for the sports enthusiast. This 37' yacht was known as "The Rocket" back in her day due to her lightning speed and innovative hull design. Much heavier than traditional boats today, Masquerade will provide a steady, smooth sail no matter what the conditions. The mythical Ranger 37 had a colorful racing history back in the 1970′s and continues to win offshore races to this day.

Embark on a breathtaking private sailing excursion in the captivating waters of San Diego. Set sail aboard a luxurious yacht, where you and your companions can enjoy the ultimate seafaring experience. With a skilled and experienced captain at the helm, you'll navigate the sparkling Pacific Ocean, taking in panoramic views of San Diego's stunning coastline, Feel the refreshing ocean breeze against your face as you glide through the water, indulging in moments of tranquility and serenity. Drinks included.

This is a fully private sailing charter designed entirely around you. Cruise San Diego Bay, passing downtown and Coronado, or tell us what your perfect day on the water looks like, and we'll make it happen. We provide light snacks and drinks, and we're happy to arrange additional food or specific beverages upon request. Whether you're relaxing, celebrating, or just enjoying the breeze, this is your custom experience from start to finish.

Enjoy a relaxing 2 Hour Sailing Trip on open water, where the wind and waves create a peaceful and refreshing escape. Feel the freedom of smooth sailing as you unwind and take in the natural rhythm of the sea. This short journey is perfect for disconnecting, recharging, and simply enjoying the art of sailing.

Set sail on a 2 Hour Luxury Sailing Adventure in beautiful Oceanside, where comfort, relaxation, and stunning coastal views come together on the open water. This experience is designed for effortless enjoyment, whether you're celebrating something special or simply escaping the everyday. Available anytime during the day, it's the perfect way to enjoy the ocean on your own schedule, with calm seas, fresh air, and a truly elevated sailing experience. Morning sails recomended for those prone to sea sickness.

**Captain's fees are paid directly to the captain. $75/hour is a good estimate (not including gratuity) Enjoy a private day or sunset sail on San Diego Bay, the perfect way to unwind, celebrate, or simply take in the views from the water. Our charters are designed for comfort, relaxation, and great vibes. Whether you're planning a romantic evening, a casual gathering with friends, or a special celebration, our professional crew takes care of everything so you can sit back and enjoy the moment.

Enjoy a 2, 2.5, or a 3 hour sail adventure along San Diego's coastline. Relax onboard with cityscape ocean views and a fresh sea breeze, or enjoy snorkeling, paddleboards, and kayaks (by special request and seasonal). Keep an eye out for dolphins, sea lions or other wildlife along the way. Departure times are flexible, contact the captain to customize the trip, including sunset options depending on timing. Perfect for families, friends, or couples seeking a quick, unforgettable ocean experience.

Morning sails with Winedown Charters offer a calm, refreshing escape where the ocean is quiet and the air is crisp. As you step aboard, you’ll feel the peaceful rhythm of the morning and the gentle light breeze as we cruise the coastline in search of dolphins, whales, and other marine life.