Top San Diego Cruises & Sailing

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.

Cruise the coastal waters off San Diego during the sunset on this evening boat trip. Take in epic views of the sun sinking behind the Pacific Ocean's horizon and snap photos of loved ones on the boat's deck. Listen to relaxing music and sip drinks from the open bar to round out the laid-back California ambiance.

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.

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.

Take in the highlights of San Diego Bay during a sightseeing tour by amphibious vehicle. Travel on both land and water, starting on the streets of Seaport Village and rolling down Harbor Drive alongside San Diego Bay. Transition into the water after departing Seaport Village. Cruise past the SeaWorld and Vacation Isle, experiencing the best of maritime San Diego on this fun and informative tour.

See San Diego from a marine vantage point on this 2-hour harbor cruise, including a look at the marina, seabirds and potential sea lion sightings. Listen to live narration from your captain and enjoy for-purchase snacks from the onboard snack bar.

Go sightseeing on the waters of San Diego Bay during a 2-hour brunch cruise that provides a delicious seated brunch accompanied by complimentary champagne. After enjoying a lavish plated brunch dish, stay at your private table or head outside to the open air for sunshine and sightseeing.

Encounter some of Earth's most magnificent creatures on a 3-hour whale-watching cruise in San Diego. The voyage departs right from Mission Bay, so you’ll be out into the open ocean and looking for animals in just 10 short minutes. Marine biologists onboard help you spot whales and dolphins and learn about their life in the deep blue sea.

On this experience, relax in style aboard a luxury dinner cruise. Enjoy panoramic views from the boat's deck and take your time over a gourmet, 3-course meal, as you cruise past twinkling city lights that ring San Diego Bay. Listen to an entertaining DJ play music and enjoy an unforgettable evening, or celebrate a birthday, anniversary or another special occasion.

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.

Sail along the San Diego Bay on this relaxing 1-hour cruise. While aboard, enjoy views of the city, as well as US naval vessels, the Star of India, and the Coronado Bridge. Catch sight of the Hotel del Coronado, and spot sea lions in their natural habitats. Along the 1-hour route, you can pick up a snack and drink at the snack bar (own expense), and relax as you cruise the water.

Take a trip through American naval history with admission to the USS Midway Museum in San Diego. This enormous ship, known as the longest-serving aircraft carrier of the 20th century, now offers a range of interactive exhibits, a self-guided audio tour and numerous restored aircraft across its 4-acre (1.6-hectare) flight deck and sections below. It’s an essential piece of San Diego’s, and America’s, military history.

Make the most of your weekend with a 2-hour brunch cruise through San Diego Bay. Capture prime views of the city skyline and harbor from a luxury yacht, and round out your morning bliss with bottomless mimosas and our brunch menu service includes breakfast favorites, vegetarian options, and so much more. Indoor and Outdoor seating available please call Flagship Cruises & Events with seating preference. Listen to our live entertainment as the attentive crew constantly top off your glass. Shouldn’t weekends always be like this?

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.

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.

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.

See San Diego’s sights by land and water on a 1.5-hour SEAL tour independent shore excursion, and explore this picturesque port of call in an amphibious vehicle. Listen to stories that bring San Diego’s history to life as you travel along the water’s edge, then steer straight into San Diego Bay. Take in sweeping views of SeaWorld, watch for the seals and sea lions that play, eat and bask at Quivira Basin and return to your ship along the scenic Harbor Drive.

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.

Go on a whale-watching expedition in San Diego on this 3-hour cruise. Get the scoop from a guide who studies the migratory patterns of grey whales as you keep a lookout for whales in the water. Board a 2-story yacht that gives you 360-degree views of the ocean. Plus, you're guaranteed to see whales or you get to ride again for free.

Spend happy hour on the water during this San Diego sunset cruise. Enjoy views of the water and city skyline as you glide through San Diego Bay.

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.

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.

Explore San Diego at your own pace with a full-day ticket to ride a hop-on, hop-off trolley through the city. Simply board the trolley at your cruise ship’s port of call and visit historic landmarks and vibrant neighborhoods at eleven centrally-located stops. Get a glimpse of California’s past in Old Town then see the magnificent ships that moor at the bustling waterfront; grab a spot on a beach to watch surfers catch breaking waves, and try to spot the famous ghost at the elegant Hotel del Coronado.