Top San Diego Sailing

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.

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 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 12 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.

This is a personal tour from one to six passengers that is engaging and diverse tailored to the specific selected tour option(s) Both private and mixed tours are available.

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.

Cruise around San Diego bay aboard an authentic 1992 America’s Cup racing yacht and travel at twice the speed of the average sailboat. The Stars and Stripes USA-11 is one of the fastest and best known America’s Cup racing yachts. It was designed and built to be raced in San Diego, and has been restored to pristine condition. Take a turn at the helm and join in grinding the winches to raise and trim the sails.

Set sail at one of the best times of day—sunset—during this San Diego Bay cruise. Board a comfortable sailing yacht and cruise along San Diego's coastline, taking in views of the scenic waterfront, military vessels, and historical landmarks. Catch sight of marine life and enjoy spectacular photo ops. Gorgeous sunset views and Wine makes this tour a great choice for couples or travelers celebrating a special occasion.

Sail Liberty offers the unforgettable experience of a beautiful sailboat touring adventure aboard a traditional sailing yacht. Our replica 1904 Yacht, offers excellent sailing for small group harbor tours and a remarkable sunset cruise all the while using traditional sailing techniques aboard a classic vessel unlike any other in San Diego.

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.

Zoom around the waters of San Diego Bay on a jet boat ride that provides speed, splashes, and spins. As you race through the scenic waterway, your captain points out landmarks including the USS Midway, Coronado Island, Seaport Village, the Embarcadero, and the city skyline. Hang on as your captain takes your boat into power slides, 360-degree spins and other thrilling maneuvers—a high-octane twist on sightseeing in San Diego.

Take an evening cruise wining and dining aboard the ‘Spirit of San Diego,’ enjoying top-notch food and drink, plus sparkling skyline views during this San Diego dinner cruise. Dig into your included gourmet meal, accompanied by a complimentary cocktail and live on-board entertainment, as you cruise 25-miles worth of California’s beautiful coastline and gaze at the twinkling stars above. You can also upgrade your cruise to include an unlimited open bar for an additional price.

Explore some of the top highlights of San Diego with your silver, gold, or platinum day pass (depending on option selected) for the city’s Hop-on, Hop-off Trolley Tour. Choose your own adventure as you get on and off the trolley at any of the 11 included stops, covering famous sights including the Gaslamp Quarter, the San Diego Zoo, USS Midway and the Cruise Ship Terminal, Little Italy, and many more. This San Diego trolley tour also features live commentary from the on-board guide during your ride.

Sail the lovely waters off San Diego on a private yacht charter. The itinerary is up to you, or your captain can suggest some places to go. You can opt for a whale watching tour (seasonal), or lay anchor and go for a swim. If you prefer, choose a bay tour; seeing the sights like the Hotel del Coronado, Point Loma Lighthouse, Tijuana, and the San Diego skyline.

A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailing charters and boat tours take you on an exciting tour of San Diego Bay. Book a sunset sailing boat charter and stretch out in the San Diego sunshine with a trusty skipper at the helm, A sunset sailing boat tour on San Diego Bay with Pacifica Sailing Charters is the perfect sailing experience for you and your guests. With over 20 years of boating on San Diego Bay and the waters surrounding the San Diego harbor, our sunset boat charters and sunset sailing boat tours are rated #1 on Google, Yelp, and TripAdvisor.

Sailing is an art, an adventure, and a great way to relax. Weather you're throwing a special event or you just want to get back to nature, the sea is the place to be. Sailing yacht 'Mojave' is the perfect place for birthday parties, anniversaries, family vacations, engagements, or just a tour of the bay. Join Captain Liz on a trip to see the icon sites of San Diego such as The USS Midway aircraft carrier, The Star of India, The Coranado Bridge, or just say hello to the sea lions. Sailors have crossed oceans to explore new places for thousands of years. The Vikings sailed to North America around 1,000 years ago! Keep the ancient tradition of sailing alive and book your trip today for legendary fun in the sun with the whole family. There are complementary snacks and beverages on board. I can even make the party special for your event with balloons, party decorations or whatever you want. It's 2021, time for some fun!!!

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.

Avoid the stress of being on a loud and crowded boat by opting to charter a private yacht instead. Admire the beauty of the San Diego coastline and get the chance to spot marine life such as whales or dolphins. Stay hydrated along the way with bottled water included, as well as snacks too.

A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sailing charters and boat tours. Sail San Diego with us. Our sailing charters and boat tours take you on an exciting tour of San Diego Bay. Book a sailing boat charter and stretch out in the San Diego sunshine with a trusty skipper at the helm, Choose from several types of yacht charters, catamaran cruises, sailboats, and powered luxury yachts. A sailing boat tour on San Diego Bay with Pacifica Sailing Charters is the perfect sailing experience for you and your guests. . With over 20 years of boating on San Diego Bay and the waters surrounding the San Diego harbor, our boat charters and sailing boat tours are rated #1 on Google, Yelp, and TripAdvisor...

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.

Claire Sailing offers a new, luxury Beneteau sailing yacht. She has a spacious comfortable cabin with new cushions, clean blankets, pillows, and bean bags on the bow. We also welcome special requests so don’t hesitate to ask!

Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 12 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea life including Sea Lions, Dolphins and Whales. Whether you need a classic sailboat or catamaran for your Bachelorette Party, we can provide a private catamaran that is roomy, comfortable and stable. Much heavier than traditional boats today, Sea Esta will provide a steady, smooth sail no matter what the conditions. This large and stable catamaran is perfect for sightseeing around San Diego Bay and the perfect bachelorette party yacht for you and your guests.