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Monday 9am - 5pm Tuesday 9am - 5pm Wednesday 9am - 5pm Thursday 9am - 5pm Friday 9am - 5pm Saturday 9am - 5pm Sunday 9am - 5pm

Sail Solomons

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Chesapeake Bay's premier Bareboat Charters & Day Rentals, and ASA Award-Winning Sail School Best sailing school on the Chesapeake. Great boats for charter.

Awarded top school and top instructors for 6 consecutive years. Everything to satisfy your sailing needs. Good facilities too. Check out our school at www.sailsi.com.

10/09/2026

There's a reason sailors talk about the water the way other people talk about therapy. 🧘

Something happens the moment you leave the dock. The inbox stops mattering, the to-do list fades. Whatever was sitting heavy on your shoulders when you stepped aboard seems to dissolve somewhere between casting off the lines and filling the sails.

Sailing demands your full attention in the best possible way. Reading the wind, trimming the sails, watching the horizon — your mind simply cannot hold onto stress and seamanship at the same time. One of them has to go, and out here, it's always the stress.

We hear it from our students and charterers constantly. People who come out tightly wound and leave loose, calm, and wondering why they don't do this every week. People book one sunset cruise and end up enrolling in ASA 101 because they can't imagine going back to weekends without the water.

If you've been running on empty lately, we've got just the prescription for you.

10/07/2026

It's different for everyone. But every sailor remembers exactly when it happened.

For some it's the first time the sails fill and the engine goes quiet — that sudden, almost startling silence where the only sound is the water moving past the hull. For others it's the moment they take the tiller for the first time and feel the boat respond, alive beneath their hands in a way no one quite warned them about.

But it always happens. And once it does, nothing is quite the same.

You start seeing wind differently. Reading the water. Looking at every body of water you pass and wondering what it would feel like to sail across it. Your weekends reorganize themselves around tide charts and weather windows. You become, quietly and without making a fuss about it, a sailor.

We get to witness that moment over and over again here at Sail Solomons, and it never gets old. Not even close.

When was yours? Tell us in the comments 👇 And if it hasn't happened yet — we'd love to be there when it does.

10/02/2026

You may think of me as the office lady here at Sail Solomons, but sometimes I help out on the water!⛵️

09/26/2026

When you earn your ASA certification here on the Chesapeake, the whole world of sailing opens up. 🌍⛵

That card — earned on our waters, aboard our boats — is recognized by charter companies across the Caribbean, the Mediterranean, the Pacific, and beyond. It's the difference between dreaming about sailing the BVI and actually booking the boat.

Charter companies in Tortola, Palma de Mallorca, Tahiti, the Whitsundays, Croatia, Greece — they all accept ASA certification as proof that you can handle their boats. You go from spectator to skipper, from vacation passenger to captain of your own adventure.

We love teaching on the Chesapeake because it's genuinely great sailing: real conditions, real seamanship, skills that transfer anywhere in the world. But what gets us most excited is knowing that the sailor who starts here with us could be anchoring in a Caribbean cove or sailing through the Greek islands a year from now.

Ready to start? October courses are still open!

09/23/2026

There's a reason people who try sailing rarely stop. It gets into you in a way that's hard to explain to someone who hasn't felt it — the alertness that comes from reading the wind, the quiet courage of handling a boat in real conditions, and that particular peace that settles over you when you're out on the water with the sails full and the engine off.

It's not just a sport or hobby. It's a way of seeing the world differently.

If you've been curious about sailing but haven't taken the first step yet, we'd love to introduce you to it. Our 2-hour Introduction to Sailing lesson is just $100 and might be the best thing you do this fall. 🍂🌊

09/21/2026

The sailing season isn't over yet — and neither is your chance to get certified before winter. 🍂⛵

Swipe through for our full October course lineup. Whether you're just getting started or ready to level up, we have something on the calendar for you.

October is packed — from Introduction to Sailing all the way through ASA 106 Advanced Coastal Cruising, plus the ASA 114 liveaboard combo for sailors ready to take on bigger waters and their first catamaran experience.

Fall on the Chesapeake is genuinely some of the best sailing of the year, and there's no better time to be on the water learning. Spots are limited and these sessions fill quickly — don't wait.

📅 Book your course today:
🌐 sailsi.com/sailing-school/schedule
📞 (410) 326-4917

09/16/2026

Let us paint you a picture. ☀️

You wake up to the sound of water against the hull. The morning is quiet — just you, a mug of coffee in the cockpit, and a view across the Bay that no hotel room has ever matched. You check the forecast over breakfast, plot a course to an anchorage you've had your eye on, and by 9am the sails are up and you're underway.

The afternoon is yours. Maybe you find a cove and drop the hook for a swim. Maybe you push further down the Bay to a waterfront town for lunch and a cold b**r at a dock bar. Maybe you just sail, letting the breeze carry you wherever it wants to go.

By evening, the anchor is down in a protected creek, the cockpit is glowing with the last of the sunset, and dinner is something simple but somehow perfect when eaten out here. The stars come out. The water goes still. You wonder, not for the first time, why you don't do this every weekend.

That's a bareboat charter day. And it's waiting for you right now. DM us today to book your perfect day.

09/11/2026

We hear it more than you'd think: "I've always wanted to learn to sail, but I think I've missed my window."

You haven't. Not even close.

Some of our most enthusiastic, most dedicated, and most capable students walked through our door for the first time after their 50th birthday. Sailing doesn't care how old you are — it cares how much you want to learn, and whether you're willing to show up and give it a go.

In fact, there are real advantages to learning later in life. Patience. Life experience. The wisdom to appreciate just how special it is to be out on the water. And often, for the first time in decades, the time to actually do it properly.

Our ASA courses are designed for adults at every stage of life. Small class sizes, experienced instructors, and a pace that works for you. If you've been carrying around a dream of sailing your own boat — or chartering in the Caribbean someday — this is your sign to start.

You have more time than you think. 🌊

09/10/2026

Every great sailor started exactly where you are right now. 🌊⛵

ASA 101 is the foundation that everything else is built on — designed specifically for novice sailors who want to build real confidence and solid skills before moving on to more advanced certifications. In just a weekend on the water, you'll go from curious to capable.

𝗔𝗻𝗱 𝘄𝗲 𝗵𝗮𝘃𝗲 𝗼𝗻𝗲 𝘀𝗽𝗼𝘁 𝗹𝗲𝗳𝘁 𝗳𝗼𝗿 𝘁𝗵𝗶𝘀 𝘄𝗲𝗲𝗸𝗲𝗻𝗱.

If you've been thinking about learning to sail, this is the sign you've been waiting for. Don't let it go to someone else.

📅 This weekend · One spot remaining
🔗 Book now: (410) 326-4917

09/09/2026

Sailors aren't just a different kind of hobbyist. They're a different kind of person.

And once you spend enough time on the water, you start to understand why.

1️⃣ They show up for each other. A sailor you've never met will catch your lines, help you anchor, and share local knowledge without being asked. It's just what you do out here.
2️⃣ They're present in a way most people aren't. When you're at the helm, the wind and the water demand your full attention. No scrolling, no distraction — just the boat, the Bay, and the moment.
3️⃣ They're endlessly resourceful. Something always needs fixing on a boat, and sailors figure it out. That problem-solving mindset carries into everything else they do.
4️⃣ They find freedom in simplicity. A good anchorage, a warm meal, a sky full of stars — sailors know that the best things in life don't require a WiFi connection.
5️⃣ They never stop learning. The sea is a lifelong teacher, and the best sailors are always the most humble ones. There's always more to know, and they love that.

Sound like your kind of people? Come find your crew at Sail Solomons.

Address

455 Lore Road
Solomons, MD
20688

Opening Hours

Monday	9am - 5pm
Tuesday	9am - 5pm
Wednesday	9am - 5pm
Thursday	9am - 5pm
Friday	9am - 5pm
Saturday	9am - 5pm
Sunday	9am - 5pm

Telephone

+14103264917

Website

http://www.sailsi.com/

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