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.

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.

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 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.

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.

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.

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.

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 on the San Diego Harbor without spending a fortune on this affordable 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.

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.

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.

This is introduction to boat ocean sailing. For those who have never sailed before we will introduce you to ocean sailing by wind power, with our guests being agroup of no more than 4people we will sailAll guests are welcome to participate in the sailing activities. Guest can treat this sailing experience as a hands on adventure, We are always aware of current conditions and aim to provide an enjoyable sail for all ages Children are welcome

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!

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride without the rolling and leaning that often causes seasickness on other boats. When you are welcomed aboard, you'll feel comfortable right away because we really do like people, and with such small groups, you've escaped the crowds. We always say it's great to be a tourist, but better to not feel like a tourist. With cushioned seating with back rests, our catamarans are comfortable for all ages of guests from young kids to seniors. A perfect way to spend a lazy day, unwinding and relaxing, no cares in the world.

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...

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.

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.