Sea Safaris Sailing School

09/13/2026

09/13/2026

Only a couple more weeks of sailing season here in Milwaukee, so we’re soaking in evenings like this while we still can. ⛵🌅

There’s something special about watching the sun set over the city from Lake Michigan.

We hope everyone has had a wonderful summer and is finding time to enjoy these remaining days on the water. They go by far too quickly!

09/06/2026

⛵ Our Final ASA 101 Class of the 2026 Season is Underway!

Yesterday kicked off the first day of our final ASA 101 class of the season — and Mother Nature decided to throw in a couple of extra lessons. 😄

The morning started foggy, and when the marina tender wasn’t available to get everyone out to Hunter, our teaching boat, we adjusted! Thankfully, we had Calypso’s dinghy available to get everyone where they needed to go.

Because if there’s one thing sailing teaches you, it’s this: things don’t always go exactly according to plan.

Weather changes. Conditions change. Plans change. You assess the situation, adapt, and keep moving forward.

Honestly, that’s not a bad lesson for life, either. 😉

The fog quickly cleared, and our students had plenty of time on the water learning, practicing, and putting their new sailing skills to work.

Today they’re back for Day 2 — and by the end of the day, we’ll officially wrap up our 2026 ASA 101 season! 🎉⛵

What a great way to finish another season of introducing new sailors to life on the water. 💚

09/05/2026

⛵ Help the Calypso Crewmates Make a Difference!❤️

On September 26th, the Calypso Crewmates will be hitting the water for Louie’s Last Regatta, and we’re asking our friends, family, sailors, and supporters to help us raise money for **Children’s Wisconsin**.

Our goal is $2,000, and every contribution—big or small—helps us get there!

If you’d like to support our crew and a great cause, please consider making a donation. Let’s see how much we can raise before we cross the starting line! ⛵

Sail Fast. Give Big. Make It Count.

👉 Donate here: https://support.childrenswi.org/team/850107

Please share and help us spread the word!

09/03/2026

🎉 ASA 101 IS SOLD OUT... BUT WE’RE NOT DONE YET!

Our final ASA 101 class of the 2026 season is officially FULL! Thank you to everyone who joined us on the water this summer. ⛵

But there are still a few ways to sail with Sea Safaris before we wrap up the season:

⚓ ASA 111: Anchoring Skills Clinic
NEW DATE: Sunday, September 27
ASA 101 certification is a prerequisite.
🔥 Only TWO spots remaining! Book your spot now! >> https://www.seasafarissailingschool.com/class/asa-111-anchoring-skills-clinic-september-26th-south-shore-yacht-club-milwaukee-wi/

⛵ Private Sailing Lessons
Want some one-on-one instruction, work toward your next certification, or just build your confidence on the water? Our boat will remain in the water through the end of September, so there’s still time to schedule a private lesson.

🌴 Thinking a little farther ahead?

Our February 2027 BVI sailing trips are starting to fill, and our June 2027 Greece sailing vacation is now open for booking! 🌊☀️
https://www.seasafarissailingschool.com/flotilla-sailing/

Summer may be winding down in Wisconsin, but sailing season doesn't have to end. 😉

👉 SeaSafarisSailingSchool.com

Message us with questions or to find the right next adventure for you!

08/31/2026

⛵ I can’t believe I’m even saying this, but… we only have TWO classes left in our 2026 sailing season! 😭🌊

Seriously, where did summer go?!

The good news? Summer sailing isn’t over yet, and if you’ve been thinking about getting out on the water with us, there’s still time.

⛵ ASA 101: Keelboat 1 | September 5 & 6
🔥 ONE SPOT LEFT!

⚓ ASA 111: Anchoring Skills Clinic | September 26
🔥 TWO SPOTS LEFT!
ASA 101 certification is a prerequisite.

We’re not ready to say goodbye to sailing season just yet, so let’s make these last few days on the water count. 💚⛵

👉 SeaSafarisSailingSchool.com

08/20/2026

⛵ Day 4 of our Learn to Sail Vacation!

This is what we mean when we say Learn to Sail Vacation. You’re not just practicing sailing skills... you’re using them to go somewhere! 🌊

Yesterday, our crew had a fantastic sail south from Sheboygan aboard Calypso, eventually dropping anchor off Concordia University in Ozaukee County.

Once settled in, they took the dinghy ashore, stretched their sea legs with a walk around the beautiful campus, and enjoyed a little exploring before heading back aboard for dinner and a well-earned night at anchor.

And through it all? They're sailing, navigating, working together and putting their new skills into practice in the real world.

Today, it's time to raise anchor and point Calypso back toward the Milwaukee area for Day 4 and their final night aboard.

The adventure isn't over yet! ⚓⛵

08/19/2026

⛵ Day 3 of Learn to Sail Vacation!

Yesterday gave our crew a little bit of everything!

They woke up aboard Calypso at Port Washington Marina and spent the day sailing, learning, and getting plenty of hands-on experience. Then Mother Nature decided to add a lesson that wasn’t exactly on the syllabus. 🌧️⛈️

Storms rolled through while they were making their way north to Sheboygan, but the crew made it safely into the marina, wet, happy, and ready to enjoy the evening once the weather passed!

This morning is a completely different story. ☀️ Beautiful sunshine, beautiful weather, and another day of sailing ahead as they start making their way south.

That’s cruising! Every day brings something different, and every mile brings another opportunity to learn. ⚓️

08/18/2026

Our final scheduled Learn to Sail Vacation of the season is underway! ⛵☀️

Yesterday was Day 1 aboard Calypso, and Mother Nature certainly gave this crew a beautiful welcome to Lake Michigan!

We've got an excited group ready to learn, plenty of hands-on sailing ahead, and a beautiful weather outlook for the week. Not a bad way to spend five days! 😎🌊

Over the course of the week, they'll learn, sail, practice, explore, and enjoy life aboard Calypso, all while working toward earning their ASA 101, 103 & 104 certifications!

Here's to a fantastic week of learning and adventure on the water! ⛵

08/10/2026

A beautiful night on the water, for an even better reason. ⛵️🇺🇸

Thursday evening, Sea Safaris Sailing School had the opportunity to volunteer for a Veterans sailing event here in Milwaukee.

And what a night Lake Michigan gave us! ☀️

Beautiful weather, a light breeze, sails up, and a gorgeous sunset over the Milwaukee skyline made for a pretty special evening on the water.

We always love sailing, but getting to share an evening like this with our Veterans made it that much more meaningful.

Thank you to everyone who helped make the evening possible, and most importantly, thank you to our Veterans for your service. 🇺🇸

Sometimes the best days on the water aren't about where you're going. They're about who you get to share the sail with. ❤️⛵️