Top San Diego Sailing Tours

Book this small group tour to get out on the San Diego Bay on a comfortable Catamaran at sunset. Your captain will make sure you are comfy with a glass of white wine, beer, and soft drinks onboard. Just relax as you sail along with your small group, checking out the San Diego skyline while looking out for friendly sea lions and sometimes dolphins.

A boat ride in San Diego Bay offers the perfect vantage point from which to view the city’s Skyline. This luxury sailing adventure on a 40-foot yacht lets visitors take in the sights in comfort and privacy, the perfect activity for those seeking an extra special addition to their San Diego trip.

Enjoy a sailing adventure on a Catalina-style sailboat with just six people for a comfortable, semi-private experience (or, find five friends and fill up the whole boat). Sail in San Diego Harbor during the day. Sit back and relax to enjoy the water views while enjoying complimentary beer, soft drinks and snacks.

Sail into the setting sun aboard a Catalina style sailboat during this intimate cruise with a small group. Feel like you have the ship all to yourself on this trip that’s limited to just 6 total guests, watching as the last rays of the sun drop into the glistening waves. Enjoy the included beer, soft drinks and snacks during the ride, as well as jackets and wind gear in case you get cold. You can even plug in your own music to add to the fun. Departure times vary throughout the year. Guest must contact Sail San Diego after purchase for the exact departure time.

Spend a few hours relaxing, sunbathing and sightseeing in the placid waters just off San Diego during this 1 or 2 hour San Diego Harbor cruise. Sit back and relax as you take in a fully-narrated tour, offering top-notch sight lines of the San Diego skyline, a cruise under Coronado Bridge, a look at the bustling US Naval fleet and a chance to spot some of the harbor’s resident sea lions. Choose between 1 and 2 hour cruise options, offering you two trips to fit your schedule and interests.

Watch the sun set over San Diego during an all-inclusive small-group cruise aboard a classic sailboat. Pass landmarks such as the Maritime Museum, Coronado Bridge, and USS Midway, and look for sea lions, dolphins, and other wildlife around San Diego Harbor on the 2.5-hour cruise.

Sail out into the San Diego Bay and take in great views of the city's skyline with this small-group tour aboard a 34-foot Catalina sailboat led by a local captain. You can choose from morning, afternoon, or evening departures and you will be welcome to bring your own drinks on board.

Go whale watching from San Diego aboard a replica of a historic sailing schooner that won the world’s first America’s Cup sailing competition in 1851. Throughout your cruise, your expert guide shares informative commentary about gray whales, dolphins, and other marine animals, along with details about the US Navy sites you pass as you head out on the Pacific Ocean.

Experience San Diego Bay the way it was meant to be seen, from the water on a private yacht. A dedicated captain handles the navigation so your group can sit back, relax, and enjoy the sights and sounds of the bay, from the USS Midway to Seaport Village and harbor seal hideouts. With room for up to six passengers, it's a great value for families, special occasions, and small groups.

Relax in the sun aboard a catamaran in San Diego Bay on this small group sailing excursion. Your captain will welcome you aboard with beer, wine, and soft drinks. You can relax, sunbathe, look at the sea life, and help sail if you like. You’ll also be keeping costs down with this small group tour.

Set sail on the San Diego Harbor without spending a fortune on this dreamy small-group sailing tour. Climb aboard a replica 1904 yacht that's unlike any other in San Diego, and enjoy several hours of cruising the bay and harbor, from Seaport Village past the USS Midway Museum and other shoreline attractions. No sailing experience is required, as a captain handles the navigation so you can enjoy the voyage.

Experience the stunning beauty of San Diego Bay at sunset! Our boat charter mono hull is the perfect vessel for a sunset sail, with space for up to 6 passengers. As we sail through the calm waters of the bay, keep your eyes peeled for the possibility of seeing playful dolphins, majestic sea lions, and colorful seabirds. The experienced crew will be on hand to point out these incredible creatures. You'll have the opportunity to witness the wonder of sea life against the backdrop of a breathtaking sunset. As we set sail towards Point Loma, greeting the rolling waves of the ocean or going towards the heart of the San Diego Bay, seeing the city towards the famous Coronado bridge, don’t miss out and anchor these memories for a lifetime. Book your sunset sailing excursion today and discover the magic of San Diego Bay!

Experience the good life on the placid waters near San Diego during this 2-hour sailing excursion with a small group. Climb aboard a vessel that seats no more than 6 guests as you navigate the waters of San Diego Harbor. As you sail you’ll have time to search for local wildlife like harbor seals, pelicans, sea lions and more, plus a chance to soak up the sun-drenched scenery of this idyllic coastal city. On-board snacks, plus wine or beer, soft drinks and water are also included.

Spend the day communing with California’s marine life during this 4-hour, small-group, wildlife and whale watching tour aboard a vintage sailing yacht. Travel in style on a boat that seats 6 guests maximum, sailing from San Diego Harbor into the Pacific to search for the tell-tale blow spouts of whales along with other sea creatures like pelicans, sea lions, cormorants and more. An included gourmet box lunch keeps you fueled up for more adventures. A guide, glass of white wine or craft beer, and other drinks are also included.

Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and knowledgeable crew, eco-friendly practices, and emphasis on creating memorable moments, we take your excursion to the next level. Come aboard for a truly unique and eco-conscious sailing adventure.

Tour San Diego Bay by boat with this small-group sailing activity for up to six passengers. You'll sail past the downtown and alongside aircraft carriers and submarines with a professional captain to take the helm. You may even spot marine life such as sea lions and dolphins along the way. Opt for a daytime departure to get time in the sun or choose an evening departure for the best shot at sunset views.

Step into the 16th century when you board the San Salvador Spanish galleon for a 4-hour sailing. The ship is a replica of Juan Rodriguez Cabrillo's ship that arrived in San Diego on September 28, 1542. For those who love history, or simply want an unforgettable San Diego sailing, this is an unconventional adventure tailor made for you.

This is the best most luxurious sailing tour in Southern California. Limited to you and 5 guests, and based on your most specific preferences, we'll make sure your time on the sailing vessel RIVIERA is the highlight of your visit. During the warm summer months, we'll anchor off of Coronado Island and you and your friends can dive into the bay for a swim. In late winter and spring, we can take to the Pacific Ocean and watch for whales, dolphins and seals off the coast of San Diego. Our Captain and crew are fun, experienced and knowledgeable. The yacht is flawless, comfortable and very well appointed. When we return to the dock, you won't want to leave.

Enjoy perfect views of the San Diego Bay with a 2-hour private sailing experience aboard a 37 foot (11.2 meter) yacht that accommodates up to six passengers. Relax on deck with a bottle of champagne and cold drinks as the captain steers the boat along the coast, and watch for dolphins and sea lions in your wake. Take the helm and learn to sail, see San Diego’s iconic skyline from the water, or just soak up the sun and serenity of a trip under sail.

With beautiful beaches and bays, navy outposts with aircraft carriers and submarines, and abundant sea life, San Diego Bay is best explored on the water. This private charter sightseeing cruise takes groups of up to six travelers around the bay in catamarans, sailboats, or powered luxury yachts. Choose between morning and afternoon trips—or evening cruises that depart just before sunset.

Cruise around San Diego Bay aboard a spacious sailboat with great views of the city skyline and Pacific Ocean during this 2-hour evening cruise. From your perch on the sailboat, take in views of downtown San Diego, Point Loma, and Coronado Island, and watch the sky change colors during the sunset. Your cruise includes commentary from your captain about the region, as well as snacks and a glass of wine, champagne, or beer.

Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour adventure on a Catalina sailboat is limited to a maximum of six (6) guests allowing you a comfortable semi-private experience (or, purchase all 6 tickets to make it a private sail for you and your friends/family!). Sit back and relax into the slower pace of your morning as you watch the sights of San Diego Bay, all while enjoying the complimentary drinks and snacks. Departure times vary throughout the year. Guest must contact Sail San Diego after purchase for the exact departure time. Please note this activity does require a minimum of 3 guests total in order to sail.

Take your bachelorette party up a notch--by renting a private catamaran. With this package for up to 12 guests, you'll get the chance to sail out on the San Diego Bay aboard the sturdy Sea Esta for fantastic views of the cityscape. Snacks and bottled water will be provided on board and you're welcome to bring your own additional food and alcohol.