10 Incredible San Diego Sailing Tours to Get Your Sailing On

Sometimes we just want to ditch the on-land attractions and head out to the ocean for a sailing adventure. Whether you’ve never been on a boat before or you’re a seasoned sailor yourself but couldn’t get your boat down to San Diego and still need your fix of the sea breeze. Thankfully, plenty of companies offer San Diego sailing tours.

Greg and I got into sailing a few years ago. We currently don’t have our sailing certification but love spending time on the water. So until we can safely maneuver our own sailboat, we either head out with one of our friends (Big shout out to Joe! Thank you!!!) or go on a sailing tour.

Here is a list of our most loved San Diego sailing tours to get you in the mood to hit the San Diego Bay and the Pacific Ocean.

The Best San Diego Sailing Tours

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Small Group San Diego Sunset Sailing Excursion

This three-hour San Diego sunset sail tour brings lovers of the sea out on a Catalina-style sailboat to watch the last of the sun rays fall behind the ocean. The idea of this excursion is to create an intimate feeling, only allowing six guests on board.

There will be beer, soft drinks, and snacks provided by the captain during the ride. Additionally, warm jackets will be on standby in case the wind off the sea becomes too much.

Pass by San Diego’s private marina Point Loma, the USS Midway Museum, and under Coronado Bridge to the island.

The sailing boat has a modern sound system, so if anyone would like to play their favorite songs for some added ambiance, they’re free to do so.

Before you head off, meet at the Sail San Diego Office on Shelter Island. You need to receive a physical paper ticket to board the ship. It will be given to you upon check in.

Sunset Sailing Experience On San Diego Bay

Sunset is, without a doubt, the best time to take a boat out to sea. Watching the dramatic orange colors explode throughout the sky from a top deck is a blissful experience.

Hop on board a classic sailing yacht and make your way down San Diego Bay, catching glimpses of military ships and some of the city’s key sights from a unique perspective.

Take advantage of the many photo opportunities while watching the California sun slowly fades away. As well as an unforgettable sailing experience, you get some white wine, chocolates, soda, and water with your booking.

This fantastic two-hour tour is popular among those looking to celebrate something, e.g., engagement or proposal. This sunset sail in San Diego is one you won’t be soon to forget.

A maximum of six people can reserve a space on the ship which departs from Harbor Island. It’s recommended that you arrive 20 minutes beforehand, so you have time to find the gate. The company is not able to wait for anyone.

San Diego Whale Watching Cruise

Would you like to see some whales? Head out to sea with an expert guide who will provide interesting knowledge about grey whales, dolphins, and other animals that roam around San Diego.

They’ll bring you to several areas where they have spotted whales in the past. This exciting 4.5-hour whale-watching tour takes you aboard a ship modeling a sailing schooner that won a prize at the world’s first America’s Cup sailing competition in 1851. 

This outstanding whale-watching tour includes drinks and snacks, sightings of whales guaranteed, and a no-sickness promise.

Check-in is at the Next Level Sailing office. It opens an hour before departure and closes 30 minutes before. If you’re looking for a small private tour, this isn’t the one for you. The ship can hold up to 77 passengers.

Small Group Afternoon Sailing Excursion

Board a Catalina-style sailboat for six people and embark on a semi-private sailing tour of San Diego.

Get your binoculars ready because you’ll see an array of sights like the San Diego Convention Center, Seaport Village, the USS Midway, and much more.

The boat’s crew members will take good care of you for the duration of the tour, offering complimentary beer, wine, soft drinks, and snacks. If the sun gets too much for you, sunscreen will be on board too. 

Check in for this activity is at the Sail San Diego office. The captain will meet you there and bring you to the ship, where the fun will begin!

San Diego Bay Relaxing Sailing Tour

Step aboard a luxuriously designed Beneteau sailing yacht and cruise around San Diego Bay VIP style. Pop your head inside the spacious cabin kitted out with cushioned seats, soft blankets, pillows, and bean bags to relax on the bow of the boat.

The 2.5 tour starts by taking passengers to catch some gorgeous harbor views of the military ships parked up, including the USS Midway and the Star of India. After, they’ll be taken under the Coronado Bridge to see San Diego Seaport area.

The boat will then venture over the bay to the Naval Air Station and a couple of other notable attractions before making the return to land.

The tour will leave from the Claire Sailing office, only a few minutes from downtown. Beverages are provided by the company, e.g., beer and soda, and passengers can have a shot of driving the boat once given the go-ahead from the captain.

Private Sailing Charter on San Diego Bay

Enjoy a 2.5-hour private sailing charter tour along San Diego Bay.

This is different from other excursions where the company chooses the itinerary. Instead, you decide what you want to see. Whether you want to go whale watching, swimming, or lay an anchor somewhere, the sky is the limit. Additionally, if you’d like the captain to plan your time out carefully, that can be arranged too. See sights like Tijuana, Hotel del Coronado, or Point Loma Lighthouse.

Make sure you arrive outside Clayton’s Galley 10 minutes before departure time. That’s where the captain will meet you beforehand.

Look out for dolphins, sea lions, and whales when you’re out at sea. If it’s the season, you can see them.

Again, this charter sailboat tour of San Diego is private. It will only be your group on the boat with the captain and their team. Snacks and water are included with the tour.

Luxury Catamaran Sailing Charter of San Diego

Take on the San Diego waves on your private catamaran sailing charter that can hold up to 12 passengers.

Set off from the Hyatt Regency Mission Bay for an eight-hour cruise to see exciting attractions like Sunset Cliffs Natural Park, Ocean Beach Pier, La Jolla, and Pacific Beach. Soak up stunning seascapes while trying to spot aquatic animals. The captain can help you out with that one.

The crew on board will be looking after you for the day and will provide five-star, personalized service. This is the perfect tour if you have a big family and want to celebrate fashionably.

Private Luxurious Sailing Cruise in San Diego Bay

This is arguably the fanciest sailing tour you can book in California. It’s a private excursion that tailors to passengers’ needs.

Fancy a sail and swim in Glorietta Bay? Or a romantic cruise along Coronado? Pick where you’d like to see. It’s your three hours. Let the crew do the hard work while you relax, sipping on an ice-cold drink.

The tour is limited to you and 5 other guests. You’ll depart from Harbor Island at 5 pm and have three hours out at sea.

When you see inside this yacht, you won’t want to get off. Its elegant design creates a warm, homey feeling. You’ll forget you’re out on the sea.

The captain and his team are attentive and will look after your group in whatever way they can. To top it all off, alcoholic beverages are included, so grab a beer and watch the sun go down with those you love.

There’s no doubt, this is definitely one of the best sailboat tours in San Diego.

Private Sail Yacht Experience on San Diego Bay

Grab some lovely photographs of San Diego Bay on this two-hour private sailing tour.

Have a 37-foot (11.2 meters) yacht all to yourselves while you kick back with a bottle of champagne, and the captain brings you to see dolphins and other sea creatures along the coast.

The tour is suitable for a maximum of six people and comes with some luxuries such as champagne, white wine, chocolates, and soda. You’re free to bring your own food and drink as well.

Sterling Sails 2-Hour Private Sailing Experience

Did anyone ever tell you that San Diego looks better from the water? See it for yourself on this two hour private sailing experience with your own private yacht and a captain who’s well versed in handling navigation.

Sail all along San Diego Bay, scouting out sea lion hideouts and old military ships like the USS Midway.

The ship can hold six people, making this tour ideal for small families or groups on vacation looking for an ocean escape. Captain Liz will meet your group at the benches beside Marina Cortez 15 minutes before the ship’s sailing time.

San Diego is an amazing place for a sailing tour, with stable winds and a balmy climate; it’s no wonder boating enthusiasts love it here. 

When choosing a sailing tour, you’ll have to ask yourself some questions:

What’s your budget? 
Which attractions would you like to see? 
How much time do you have?

Once you’ve determined this, you’ll be on the boat, ready for your San Diego sailing tour!

Looking for more ideas? Check out these San Diego Whale Watching Tours.

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