Sun, Sea & Sailing in San Diego (with Coupon)

Close your eyes and imagine this: You feel the gentle warmth of the sun on your face and the cool breeze of the salty ocean on your lips while your body gently sways in the rhythmic up-and-down of the waves. Ultimate vacation vibes, right?

Greg and I love sailing. We recently got our ASA certification and now spend as much time on the water as possible. Sometimes, we rent a tiny Capri 22 or crew on a friend’s boat in one of the many sailing regattas in San Diego. A day on a boat is always a good day!

San Diego is known as one of the best sailing destinations in the country, and we couldn’t agree more. It is the perfect way to enjoy a sunny day and see the beautiful San Diego skyline from a different perspective.

Sea Monkey Adventures

Recently, we had the chance to sail with Sea Monkey Adventures for a 4-hour sail in San Diego Bay and around Point Loma, and we had the best time!!! We brought our neighbors Reggie and Taylor along and all four of us enjoyed our sailing cruise so much.

We spent about half of our cruise in the bay and about 2 hours in the open ocean, looking for whales. Unfortunately, we were not lucky this time, but we still had so much fun. We did see some wildlife, though! We saw dolphins (no photos, as I was too slow) and many sea lions and seals by the bait barges. They are always putting up a show, and it feels like they are posing just for you. Spring is pupping season, so you might get a chance to see the adorable little babies with their mothers. So cute!!!

What I loved most about them is that they only offer private sails (for up to 12 people). A sailboat can be pretty cozy, and it is just so much nicer when everyone on the boat is part of your group. And if your group is large enough, it can actually be cheaper than paying per person. And the 5% off coupon you get from us also helps a little! Just use the coupon code SanDiegoExplorer5 when you check out!

We went out with Jonathan and Maya, the owners of Sea Monkey, and they were the perfect hosts. They warmly welcomed us on the boat and made us feel at home. There are plenty of yummy snacks and soft drinks on the boat, but you can also bring your own food and drinks (no red wine or hard liquor).

The boat, a 36 ft Hunter, is a beauty and has everything you might need. I love the sunny yellow trim and cushions. Combined with the fun name and cute monkey logo, it adds to the laid-back, family-friendly vacation vibes.

Sea Monkey Sails

Sea Monkey Adventure offers several sailing tour options, so I am sure you will find something that works best with your plans and itinerary. This is a private sail. You charter the boat and hire the captain, so you have a little more flexibility than with a group sail.

For example, if this is your first time on a sailboat, you are prone to seasickness, or you have kids with you, you can tell the captain to take it easy to make the sail more comfortable. The captain can then either just motor most of the time or adjust the sails so the boat doesn’t heel as much.

On the other hand, if you have some sailing experience, you can ask the captain if you can help out and be part of the crew (if that is what you want). Greg had fun raising the main sail, and we both did a few tacks and jibes along the way. And if everyone on the boat is comfortable, you can do some more advanced sailing. This is usually not an option for many group sailings, and many of them motor most of the way and mainly use the sails as a prop.

Morning Sail – 2.5 Hours

Usually, the wind in San Diego Bay doesn’t pick up until 10 or 11 AM, so the morning sails are perfect for first-time sailors or if you have small kids in your group. Sailing might not be possible, but that depends on the day and exact time of your sail.

Depending on the time of year, visibility might be low due to the marine layer in the morning. And definitely dress in layers. Mornings on the water can be quite chilly, but as soon as the sun comes out, it can get hot fast.

A mid-day sail is probably the best time to set sails and get some good sailing in. The wind in San Diego Bay is usually highest between 12-5 PM. Remember that it is still a bay, so the wind rarely exceeds 15 knots, which is perfect for sailing and safety.

Sunset Sail – 2.5 Hours

Nothing is more romantic than sailing into the sunset. Enjoy the magical moment as the sun dips below the horizon and the sparkling lights of the city emerge. This sail is perfect for a special date, an anniversary, or maybe even a proposal. Maybe I should surprise Greg with this? What do you think? This is one of the most popular sails, so definitely book early!

Sail and Swim – 4 Hours

A perfect way to spend a summer day in San Diego, don’t you think? Sail around the bay for a while and then drop anchor to cool off with a refreshing swim. Now, that will create some unforgettable memories for the whole family! Sun, sea & sailing in San Diego! Oh yeah, babe!!!

Full Day Sail – 6 Hours

If you want to spend even more time on the water or want to leave the bay to sail the Pacific, then the 6-hour full-day sail is a fantastic option. Yes, sailing the bay is impressive, and I love the views of Coronado and the San Diego skyline. But nothing beats sailing by the stunning cliffs of Point Loma and then seeing the never-ending views of the Pacific Ocean in front of you. It’s a completely different experience and so, so worth it. I highly recommend it!

Whale Watching – 4 Hours – Seasonal

December through April is Whale Watching Season in San Diego. Almost thirty thousand grey whales migrate from the Arctic to Mexico to give birth and then travel back North for the summer.

Using a sailboat to go whale-watching is a unique and special experience. It is less disruptive and intrusive than being on an engine-powered whale-watching cruise. However, keep in mind that these are wild animals, and sightings cannot be guaranteed.

What to bring for your Sail & Helpful Tips

• Dress in Layers: It can get chilly on the water, especially with the wind. San Diego rarely gets super hot by the coast anyway, so bring a hoodie or jacket.
• Protect yourself from the sun: Bring sunscreen, a hat (one that doesn’t fly off easily), and maybe a thin shirt to wear. The sun reflects off the water and can get you a nasty sunburn in no time, if you are not careful! Ask me how I know 🙁
• Take anti-nausea medication BEFORE you get on the boat! They usually take some time to kick in and only work if you take them before you feel sick.
• Non-slip socks: Passengers are asked to take off their shoes before boarding the boat. I recommend non-slip socks or clean boat shoes with white soles.
• Sailing Gloves: This is only necessary if you want to actually work the sails.
• Food and Drinks: Sea Monkey provides snacks and soft drinks, but you are welcome to bring your own food and even alcohol (no red wine and hard liquor). Keep in mind that you are on a small boat, so packing things in containers with lids and maybe some sippy cups for the kids is a great idea.

Whether you are a seasoned sailor or this is your first time on a sailboat, Sea Monkey Adventures will make sure you have a fantastic time. Greg and I have done many different sailing tours, and this one was one of the best. We can only recommend them and can’t wait to go sailing with them again!

Last Updated on May 20, 2026 by Maria Haase