Top San Diego Cruises &amp; Sailing - page 2

2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks

2 hours 30 minutesFree Cancellation

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.

San Diego Sailing Cruise Small Group 6 Guests Classic Yacht

2 hours 30 minutesFree Cancellation

Whale and Dolphin Watching in San Diego

Admire views of San Diego that many other visitors miss—and help keep your sightseeing personal—on this small-group sailing excursion that's timed for sunset. Travel aboard a Catalina–style sailboat, and soak up the peaceful ambiance, plus a photo-worthy perspective on the city skyline, Old Point Loma Lighthouse, Coronado Island, and other highlights. Along the way, enjoy beer, soft drinks, and snacks, plus blankets in case you get cold.

Small-Group San Diego Sunset Sailing Excursion

A unique two-hour sailing Experience aboard our 35-foot sailboat, Luna. Limited to six people. Watch for playful dolphins, sea lions, and pelicans. Get hands-on or sit back and enjoy breathtaking views of the city's skyline and waterfront attractions as we sail among tall ships, mega-yachts, and military vessels and your local Captain shares his knowledge of sailing and San Diego. We invite you to celebrate a special occasion with your partner, family or group and capture the moments in breathtaking photos. No sailing experience is needed for this family-friendly outing, but participation is welcome. We love sharing our knowledge and experience. Choose a public or private tour option when you book. Snacks and bottled water included. Feel free to bring your own easy to handle alcoholic/non-alcoholic beverages and snacks. Free cancellation, 100% refund up to 24 hours before your reservation.

Spectacular Afternoon Sail on San Diego Bay

Price varies by group size

City Cruises San Diego: Gourmet Dinner Cruise & Skyline Views

2 hours 30 minutesFree Cancellation

Make the most of limited time in San Diego by combining two experiences in one—a food–themed walking tour and a trip to Coronado Island. Led by a guide, discover local eateries and foodie hot spots you might miss otherwise—such as an award-winning taco shop and bites at a fish market. Conveniently, round-trip ferry transfers to Coronado Island are included, as well as all your food tastings along the way.

San Diego Walking Food Tour and Ferry to Coronado Island

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways

San Diego Whale Watching Cruise

3 hours 30 minutesFree Cancellation

Experience a luxury private wine tour in Valle de Guadalupe, Mexico’s premier wine region, with a fully customized itinerary featuring three to four amazing wineries, stunning vineyard views, and authentic Baja charm. Guests travel in style by BMW X1 (up to 4 people), XL SUV (5-8 people), or passenger van (up to 12 people) while enjoying curated tastings, boutique wineries, and the option to visit just wineries or pair their day with a Michelin-recognized lunch at Deckman’s en el Mogor, Finca Altozano, or Envero en el Valle. Perfect for romantic getaways, group celebrations, and serious food and wine lovers, this owner-curated Valle de Guadalupe wine tour delivers a personalized, seamless, and unforgettable Baja wine country experience.

Private Deluxe Wine Tour to Valle de Guadalupe by Luxury Vehicle

7 to 8 hoursFree Cancellation

Price varies by group size

With this San Diego boat trip, you don’t have to worry about encountering crowds as the group size is kept small to ensure a more personalized experience. During the tour, soak up the views of San Diego Bay, while enjoying onboard perks—such as complimentary snacks, soft drinks, and alcoholic drinks. As well as great views, the experience is the perfect way to relax on the water and see the city from a different perspective.

2-Hour Morning Sail in San Diego

If you’re looking for a personalized way to discover San Diego’s best bits, then this is it. Set off with a private guide on an adventure around the city—with private transportation included to speed up your adventures and cover more landmarks. Along the way, visit interesting locations—such as the Hotel Del Coronado, Balboa Park, and Cabrillo National Monument—with insights from your guide throughout.

San Diego Private Tour, Coronado, La Jolla, Balboa Park & More

5 hoursFree Cancellation

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 seating. Listen to our live entertainment as the attentive crew constantly top off your glass. Shouldn’t weekends always be like this?

Champagne Brunch Buffet

3-Hour Guided Whale and Dolphin Watching Experience in San Diego

San Diego provides the perfect launching point for a whale-watching tour in California. Cruise on the Pacific Ocean in a sturdy boat with a professional crew, looking for gray whales as they migrate along the coast of North America. Dolphins, seals and seabirds are often spotted during this whale-watching tour and the crew provides informative commentary about the marine animals and environment. Bonus: if the crew does not find any whales during your cruise, you receive a complimentary ticket for another trip.

City Cruises San Diego: Whale and Dolphin Watching Adventure

4 hoursFree Cancellation

San Salvador Spanish Galleon Adventure Day Sail with General Admission

Enjoy a thrilling new way to explore San Diego Bay—and enjoy speed, splashes, and spins along the way—on this high-speed jet boat tour. As you race along the scenic waterway, spot landmarks including the USS Midway, Coronado Island, Seaport Village, the Embarcadero, and the city skyline. Then, hang on as your captain takes your boat into power slides, 360-degree spins, and other high-octane maneuvers.

San Diego Bay Jet Boat Ride

30 minutesFree Cancellation

Tall Ship Adventure aboard the Schooner Californian with General Admission

San Diego Wild life Sailing Adventure Private

4 hoursFree Cancellation

Special Offer

Chauffeured Adventure to Local San Diego Vineyards

5 hoursFree Cancellation

When visiting San Diego, take a trip south of the border to Baja California on a private tour that makes it easy to experience the culture and flavor of Mexico. Border crossing on your own can be tricky, and there is no direct public transit connection, but your private driver and guide will get you there easily and safely. Enjoy a coastal lobster lunch with margaritas or craft beer tastings, accompanied by live, authentic Mariachi music.

Puerto Nuevo Lobster, Margaritas and Mariachi Private Tour

5 to 7 hoursFree Cancellation

This comprehensive city tour is ideal for first-time visitors to San Diego who want to see and experience the highlights without the hassle of finding their own way around. With a small group you'll visit the white-sand beaches of La Jolla, the Spanish settlement of Old Town, the Gaslamp Quarter, Coronado Island, and more. Hotel pickup adds convenience to your day. Find your new favorite spots to visit independently later.

Shared San Diego Tour

7 hoursFree Cancellation

Experience the best wines of the San Diego area without worrying about a designated driver on this tour through Temecula Wine Country. Visit three local wineries to taste their finest vintages while learning how the region’s unique microclimates influence flavor and tasting notes. At one winery, enjoy a behind-the-scenes tour to deepen your understanding of winemaking and enhance your tasting experience.

From San Diego Temecula Wine Country Tour

7 hours 30 minutesFree Cancellation

Price varies by group size

Put your sea legs to good use while in port and see San Diego’s sights by both land and water on a shore excursion by 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.

San Diego Shore Excursion: San Diego Seal Tour

San Diego Shore Excursion: San Diego Seal Tour

1 hour 45 minutesFree Cancellation

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Top Attractions in San Diego

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Attractions

What are people saying about San Diego

2-Hour Private Sailing Experience in San Diego Bay

Tommy_P, Sep 2026

Great afternoon on the water with Captain Liz

The entire experience with Captain Liz was perfect. Captain Liz was experienced, friendly, and extremely customer focused. The vessel was immaculate and in perfect condition. It was a wonderful 2 hour cruise in the western end of San Diego Bay - so relaxing and the perfect afternoon.

Gondola Cruise through the Coronado Cays

Aida_F, Aug 2026

It’s a must repeat experience

We got there 15 min before our experience started and was able to purchase something to drink for the ride which started right on time. The gondolier was very very nice, he answered some questions, but he let us enjoy the views and the music. This is something that I would love todo again.

San Diego Whale/Dolphin Watching Cruise Aboard Luxury Vessel

Robert_P, Aug 2026

True to their word!

It was very difficult to find the desk to sign in for the cruise. But after that, boarding the boat was smooth ( and I had a walker)! The ride was very choppy, the seas were rough. Several, including my hubby got seasick. But the staff was well prepared for all situations encountered. They were both kind and compassionate as well as professional. Unfortunately we didn’t see any whales, porpoises 🐬 or dolphins ☹️. Although the captain and staff kept looking for them. But to their credit, since they couldn’t find the aquatic life we came to see, they offered all of us a coupon to take the same excursion again free of charge in the future with no expiration date‼️I would have preferred a refund since I don’t know if I’ll ever be back in San Diego. I haven’t seen my coupon yet, but I’m sure I will, or perhaps I just don’t know where to look for it on my phone🤷🏻‍♀️.All in all, it is a well organized excursion with staff trying to orchestrate what was out of their control… choppy seas and no sightings. You also don’t have to get wet👏🏽👏🏽‼️I would definitely recommend this trip‼️

USS Midway Museum Admission: Valid Any Date

Lee_C, Jul 2026

This is a must do! We...

This is a must do! We spent 5 hours exploring and really loved it! The audio tour was great, the volunteers were friendly and knowledgable and the whole museum is very well done. Only negative was the picture they took when we entered was terrible. I always buy the pictures but didn’t buy this one. When compared to others it was easy to see something went wrong.

San Diego Shore Excursion: Hop-On Hop-Off Trolley Tour

Philip_J, Jun 2026

Worth every cent!

Worth the price and super convenient to get around the various sites of the city. I would absolutely do it again. Parking at Little Italy or the gas lamp quarter is super expensive, so, being able to just hop on and off a trolley to grab lunch and do some shopping was way more convenient. If you rented a car, I would recommend starting in old town because parking is free and the Mexican food there is amazing.

Private Sailing Charter on San Diego Bay

Nathalia_S, May 2026

One of the best days of my life.

Taking this sailing boat tour in San Diego was absolutely phenomenal, and Jason is a truly great captain! He was incredibly flexible with our arrangements and communicated so well via email leading up to the trip, making the booking process a breeze. The boat itself is beautiful, and Jason thoughtfully provided great snacks and pop drinks for us to enjoy out on the water. We had such a wonderful time soaking in the views and relaxing, the entire experience easily made this tour one of the best days of my life. I cannot recommend booking with him enough!

San Diego Walking Food Tour and Ferry to Coronado Island

Tonya_S, May 2026

My personal food tour and Ferry to Coronado Island with Maria aka MM tours

My girlfriend was coming to visit her son and new grandchild. I was so excited when she invited me to come with her to San Diego, CA. It was also her birthday and what better way to celebrate her birthday than with her grandchild. I decided to check out the different excursions they have to offer while in San Diego. I chose the San Diego walking food tour and Ferry to Coranado Island. I'm warning you don't eat because you will not be able to enjoy all the delicious food you'll partake. All the food was included in the price. Maria owner of MM Tours was our tour guide and she didn't disappoint she was very informative about old and new San Diego. Maria kept us on our toes and she really showed us a good time. Maria is so funny and and down to earth with an awesome and bubly personality. And we all fell in Iove with Coranado Island. There is a beautiful boutique called Miss Match Boutique make sure you take a look inside. The Fish Market was our first stop on our food tour. Then we took a ferry over to Coronado Island where we enjoyed delicious authentic Greek cuisine. We took the 2nd ferry back to Seaport Village. We walked off most of the food and made some space in our stomachs. Our 3rd food stop was Crack Taco Shop. I enjoyed a pork al pastor taco. It was banging my girlfriend Lele the birthday girl had the Bahia grilled shrimp taco. The food was very flavorful and filling. Maria took us to our 4th food stop Seaport Fudge Factory we enjoyed our choice of dessert. I decided to try the Vegan dole soft serve peach. It was so refreshing and my girlfriend Lele the birthday girl had the vanilla bean cheesecake. The next time you take a trip to San Diego take the food tour with Maria aka MM Tours. You will have a wonderful time.

Whale and Dolphin Watching in San Diego

Jonathan_J, May 2026

BLUE Whales are Real!!

This adventure DID NOR DISAPPOINT!! I’ve been whale watching before but here in San Diego this one must’ve been setup by Mother Nature her self!! From Humpbacks to Fins, to BLUE WHALES!!! Yes you will get a chance to catch a blue whale or two (mother can calf) without watching NatGeo. Our captain Alyssa gave us the best experience even. She was very knowledgeable of the marine wildlife, and knew exactly how to navigate to their feeding ground. The closest I’ve ever been to whales and the Blue whale IS as big as they say. Offshore Blue Adventures boats are the perfect size to handle the ocean and to get as close as possible. I’m a Texas native and will definitely be coming back again for this experience.

Glow Electric Boat night date experience in San Diego Bay

Edward_J, Mar 2026

Night Glow Boat Trip

My fiance and I had a great time...Simon, one of the proprietors, gave us some basic instruction in operating the boat, then led us out from the dock into the bay where we were able to motor around the harbor at our leisure...The total time out in the boat was an hour...When we got back to the dock, employees helped us pull the boat in and helped us out of the boat...We would definitely do this again !!!

San Diego Harbor Cruise on the Largest Catamaran in San Diego

Margot_S, Feb 2026

Perfect for impressing out of towners!

Great experience!! I was showing my cousin around San Diego and booked the sunset tour. She was blown away at the experience! The boat was clean, with friendly crew and beautiful. We decided to stay out on deck the entire time and sing along to the live music!!

3-Hour Guided Whale and Dolphin Watching Experience in San Diego

Daniela_A, Feb 2026

10/10 would recommend

It was an amazing experience for a solo traveler! Was able to walk from the airport to the meeting spot, instructions were very clear on where to meet. Now being out on the water. Incredible. Our guide was very knowledgeable. When we found the whales he kept up with them from a respectable distance. The entire encounter was wonderful.

Chauffeured Adventure to Local San Diego Vineyards

Roger_W, Feb 2026

Excellent Winery Tour

Paul Anthony was an excellent driver and guide for what turned out to be a private tour. We went to excellent wineries. Beautiful settings and great wine. Paul Anthony has great wine knowledge and a great manner in educating as well as telling good stories and information on the area.