TOP 30 Luxury sailing experiences in San Diego, California

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Sterling Sails is a premier travel agency located at 1880 Harbor Island Drive in San Diego, California. Specializing in boat rentals, sailing tours, and luxury yacht charters, Sterling Sails offers a variety of unique experiences on the beautiful waters of San Diego. Whether you're looking to rent a boat for a relaxing day on the water, celebrate a special occasion with a sunset cruise, or plan a memorable party or proposal, Sterling Sails has you covered. With options for bachelor and bachelorette parties, birthday celebrations, and private sailboat charters, Sterling Sails is the perfect choice for those seeking a one-of-a-kind experience in San Diego. Visit Sterling Sails today and set sail on an unforgettable adventure.

Pacifica Sailing Charters is a premier sailing school and travel agency located at 1880 Harbor Island Drive in San Diego, California. We offer a variety of sailing courses for all experience levels, from beginners to advanced sailors. Our experienced instructors provide hands-on training in a safe and supportive environment. In addition to our sailing courses, we also offer charter services for those looking to explore the beautiful waters of San Diego. Whether you're looking to learn how to sail or simply enjoy a relaxing day on the water, Pacifica Sailing Charters has something for everyone. Come sail with us and experience the beauty of the open sea!

Sail San Diego is a family-owned institution founded by San Diegans in the late ’80s. Located at 2720 Shelter Island Drive in San Diego, California, this school and travel agency offers luxury sailboat experiences with certified captains. Upon arrival, guests are welcomed by friendly staff and captains before setting sail on well-maintained modern-day sailboats from a private marina. With daily scheduled sailing charters available seven days a week, all year long, guests can choose from multiple sail times to suit their schedule and enjoy the beauty of San Diego from the water. The institution offers small and personal public sails with a maximum of 6 guests, creating an intimate and personalized experience for sailing enthusiasts of all ages. Morning sails are known for calm waters and light winds, while sunset sails provide a romantic and relaxing atmosphere. Private sailboat options are also available for up to 12 guests, making it a great option for friends, family, or special occasions.

Lucky Sol Sailing is San Diego's premier sailing tour company, located at 1880 Harbor Island Drive in San Diego, California. With a focus on providing unforgettable experiences on the waters of Southern California, Lucky Sol Sailing offers a range of sailing tours and packages for all levels of experience. Whether you're looking for a relaxing sunset cruise or an adventurous sailing excursion, Lucky Sol Sailing has something for everyone. Come sail with us and discover the beauty of San Diego's coastline from a whole new perspective.

Sail JADA Charters is a unique institution located at 1380 Harbor Island Drive in San Diego, California, United States. As a travel agency specializing in funeral charters, Sail JADA offers a peaceful and serene way to bid farewell to your loved ones. With luxurious lodging options available on board, guests can experience a comforting and intimate setting while sailing through the beautiful waters of San Diego. Let Sail JADA Charters provide a memorable and dignified farewell for your loved one.

Sail Riviera San Diego is a private, all-inclusive sailing tour agency located at 955 Harbor Island Drive in San Diego, California. Our six-passenger yacht offers personalized experiences on San Diego Bay, tailored to your specific desires. Whether you're looking for a relaxing brunch cruise, a family-friendly sail and swim adventure, or a romantic sunset cruise, we cater to your needs with exceptional service and comfort. Captain Paul, who grew up sailing on the bay, founded Sail Riviera in 2020 to share his love of sailing with others. Our experiences are fully customizable, from mimosas and brunch to cocktails and dessert while watching the sunset. We prioritize providing 5-star service on our comfortable yacht, ensuring a memorable and enjoyable sailing experience for all.

Aolani Catamaran Sailing is a luxury yacht rental located at 1380 Harbor Island Drive in San Diego, California. With 17 years of experience, this family-owned and operated business offers top-notch catamaran sailing adventures for a variety of occasions. Whether you're interested in a corporate event, day cruise, birthday party, wedding, whale watching excursion, or any other special event, Aolani Catamaran Sailing has you covered. Their 58-foot catamaran can comfortably accommodate up to 48 passengers, making it the perfect choice for intimate gatherings or larger celebrations. The professional Captain and Crew ensure a seamless and safe sailing experience, while the fully stocked premium spirits bar and catering options from local restaurants add an extra touch of luxury. With Coast Guard certification to sail in the open ocean, Aolani Catamaran Sailing offers a wide range of possibilities for custom yacht charters, including day trips, sunset cruises, overnight excursions to Catalina Island, and wildlife watching adventures. The spacious hospitality suite is ideal for corporate events and team building activities, allowing guests to relax and enjoy the stunning views while the crew takes care of the rest. Whether you're looking for a unique way to celebrate a special occasion or simply want to enjoy a day on the water, Aolani Catamaran Sailing is the perfect choice for an unforgettable experience. Contact them today to book your next adventure!

San Diego Sunset Sail is a premier travel agency located at 955 Harbor Island Drive in San Diego, California. Specializing in unforgettable sunset sailing experiences, our expert team will help you plan the perfect outing on the beautiful waters of San Diego Bay. Whether you're looking for a romantic date night or a relaxing evening with friends and family, San Diego Sunset Sail offers luxurious sailboat charters with stunning views of the sunset. Join us for a magical adventure on the water and create memories that will last a lifetime.

RockStar Yacht Charters San Diego is a premier travel agency located at 1880 Harbor Island Drive in San Diego, California. Specializing in luxury yacht charters, they offer unforgettable experiences on the stunning waters of San Diego Bay. Whether you're looking for a romantic sunset cruise, a corporate event, or a fun-filled day on the water with friends and family, RockStar Yacht Charters has the perfect vessel for you. Their fleet of top-of-the-line yachts, exceptional service, and attention to detail make them the go-to choice for those seeking a truly memorable and luxurious experience on the water. Book your charter with RockStar Yacht Charters San Diego and set sail for an unforgettable adventure.

San Diego Boat Cruise is a premier travel agency located at 1180 Rosecrans Street in San Diego, California. We specialize in providing unforgettable boat cruises along the stunning coastline of San Diego. Our experienced team is dedicated to creating the perfect cruise experience for our customers, whether they are looking for a relaxing sunset cruise, a thrilling whale watching adventure, or a festive party cruise. With a variety of boats to choose from, we can accommodate groups of all sizes. Come aboard with San Diego Boat Cruise and make memories that will last a lifetime.

The Adventuress Luxury Catamaran is a stunning 60' private yacht available for exclusive charter in San Diego, California. With a capacity for up to 48 guests, the catamaran offers customized excursions on San Diego Bay. Whether you're looking for a romantic sunset cruise, a corporate team building event, or a bachelorette party, the Adventuress is the perfect venue. The professional captain and crew ensure a first-class experience, with impeccable service and attention to detail. The spacious decks, luxurious amenities, and exceptional service make the Adventuress a top choice for any special event or outing. Don't miss the opportunity to sail in style on this beautiful catamaran.

San Diego Luxury Sailing is a prestigious institution located at 1450 Harbor Island Drive in San Diego, California. Specializing in private sailing charters, this establishment offers the best sailing experience in San Diego. Whether you're looking for a romantic sunset sail, a thrilling whale watching adventure, or an unforgettable overnight experience, San Diego Luxury Sailing has you covered. Their private sunset sails are a popular choice, allowing guests to witness the stunning San Diego sunset from the comfort of a luxury sailing yacht. For wildlife enthusiasts, their whale watching cruises provide an up-close encounter with San Diego's marine life. And for those seeking a unique overnight experience, their anchorage in Glorietta Bay offers breathtaking views of Downtown, The Hotel Del Coronado, and the Coronado Bridge.

San Diego Beach King is a premier real estate and travel agency located at 3969 Ocean Front Walk in San Diego, California. Our institution offers luxurious vacation homes with stunning ocean views and top-notch amenities. Whether you're looking to relax on the beach, go sailing, fishing, or enjoy a delicious sushi buffet, we have something for everyone. Our properties are perfect for families or groups, with options to accommodate up to 8 guests. Experience the ultimate beach getaway at San Diego Beach King and make unforgettable memories by the sea.

Cruises Inc is a premier travel agency located in San Diego, California, United States. Specializing in luxury cruises and personalized vacation packages, Cruises Inc offers unparalleled expertise and customer service to help you plan the perfect getaway. With a wide range of destinations and cruise lines to choose from, you can trust Cruises Inc to handle all the details and make your travel dreams a reality. Book your next adventure with Cruises Inc and set sail for an unforgettable experience.

Jerry & David's Cruises and Tours is a premier travel agency located in the heart of San Diego, California. Specializing in cruises and tours, our experienced team is dedicated to providing top-notch service and creating unforgettable travel experiences for our clients. Whether you're looking to set sail on a luxurious cruise or embark on an exciting guided tour, we have the expertise and resources to help you plan the perfect getaway. Visit us at 1850 Fifth Avenue and let us turn your travel dreams into reality.

Outer Limits Charters Inc. is a premier travel agency located in the heart of San Diego, California. Our experienced team specializes in providing unforgettable charter experiences for our clients, taking them to the outer limits of adventure and exploration. Whether you're looking to embark on a deep sea fishing excursion, a luxury yacht cruise, or a thrilling whale watching tour, Outer Limits Charters Inc. has you covered. Come visit us at 1717 Quivira Road and let us help you plan your next unforgettable journey.

Triton Charters and Yacht Rental is a premier travel agency located at 2700 Shelter Island Drive in San Diego, California. With the largest occupancy of any catamaran in San Diego, Triton is Coast Guard certified to accommodate up to 100 passengers. Our luxurious 75-ft catamaran features a 13-seat custom bar, built-in waterslide, plenty of seating, elegant décor, flat screen TV, dance floor, and bow trampoline. Embark on a journey through San Diego Bay and marvel at the city's iconic landmarks on our ticketed charters. Enjoy cocktails, draft beer, wine, soft drinks, and more from our fully stocked bar. Ask about our catering options to enhance your experience.

Koehler Kraft Charters is a top-rated travel agency located at 2302 Shelter Island Drive in San Diego, California. Specializing in private sailing experiences on their all wooden yacht fleet, Koehler Kraft Charters offers a luxurious and exclusive getaway for parties of 2-12 guests. Whether you're looking for a day trip, cocktail cruise, corporate event, or luxury weekend getaway, Koehler Kraft Charters has you covered. With sleek and modern yachts full of character, each experience is tailored to meet the needs and desires of their guests. From birthday celebrations to bachelorette brunch cruises, Koehler Kraft Charters creates unforgettable memories on the stunning San Diego Bay. Their dedicated team is committed to bringing your vision to life, ensuring a safe and enjoyable experience for all passengers. Book your private yacht charter with Koehler Kraft Charters for a unique ocean adventure that you and your guests will never forget.

Vintage Soul Charters is a premier travel agency located in the heart of San Diego, California. Our team of experienced professionals is dedicated to providing top-notch charter services for those looking to explore the beautiful waters of Southern California. Whether you're interested in a relaxing sunset cruise or an exhilarating deep-sea fishing adventure, we have the perfect charter for you. Come experience the luxury and elegance of Vintage Soul Charters, where every detail is carefully curated to ensure an unforgettable experience. Visit us at 2838 Garrison Street and let us help you create memories that will last a lifetime.

West Coast Multihulls is a premier institution located at 955 Harbor Island Drive in San Diego, California. As a leading school, store, and travel agency specializing in multihull sailboats, we offer top-notch instruction, a wide selection of boats and gear, and exciting travel opportunities for sailing enthusiasts of all levels. Our knowledgeable staff is dedicated to providing exceptional service and helping customers experience the thrill of multihull sailing on the beautiful West Coast. Come visit us and start your multihull adventure today!

Harbor Sailboats is a premier sailing institution located at 2040 Harbor Island Drive in San Diego, California. Offering a wide range of sailing classes, rentals, and charters, Harbor Sailboats is the perfect destination for both experienced sailors and beginners looking to explore the beautiful waters of San Diego Bay. With a fleet of well-maintained sailboats and experienced instructors, Harbor Sailboats provides a safe and enjoyable sailing experience for all. Whether you're looking to learn the ropes or simply enjoy a relaxing day on the water, Harbor Sailboats has something for everyone. Come sail with us and experience the beauty of San Diego from a whole new perspective.