Sail Solomons

Sail Solomons 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.

⚠️ Only 7 cabins left for our 2027 Flotilla!Our January 2027 Flotilla to Guadeloupe is nearly sold out, and once those l...
08/26/2026

⚠️ Only 7 cabins left for our 2027 Flotilla!

Our January 2027 Flotilla to Guadeloupe is nearly sold out, and once those last spots are gone, they're gone. If this has been on your radar, now is the time to stop thinking about it and make it happen.

Picture this: warm Caribbean trade winds, turquoise water, lush green islands, and a fleet of fellow Sail Solomons sailors all exploring Guadeloupe together in January — while everyone back home is dealing with cold weather and short days.

7 spots. January 2027. Guadeloupe. Don't be the one who waited too long. 👇

💰 50% deposit secures your berth · Balance due Oct. 15, 2026
📞 410-326-4917
📩 [email protected]
🌐 sailsi.com

We get this question a lot — so let's break it down. 🚢A flotilla is one of the best ways to experience sailing in a new ...
08/19/2026

We get this question a lot — so let's break it down. 🚢

A flotilla is one of the best ways to experience sailing in a new destination, especially if you've never cruised the Caribbean before. Here's how it works:

⛵ A small group of charter boats sail together as a fleet
👨‍✈️ Each boat has a professional Instructor-Captain aboard
🗺️ You have full freedom to explore — but never alone
🤝 Group anchorages, shared meals, and evening get-togethers
🛟 Support and expertise always on hand if you need it

It's the perfect balance of independence and security, and an incredible way to meet fellow sailors who quickly become lifelong friends.

Our January 2027 Flotilla to Guadeloupe is open for bookings right now. Spots are going fast. Ask us how to register today!

Our newest 103/104 graduates! 🎓 Thanks to Instructor Mark Gyorgy ! Congratulations Adam and Lee! ⚓️
08/19/2026

Our newest 103/104 graduates! 🎓 Thanks to Instructor Mark Gyorgy ! Congratulations Adam and Lee! ⚓️

There is nothing quite like waking up on a boat at anchor. No alarm. No traffic. Just the gentle sound of water against ...
08/17/2026

There is nothing quite like waking up on a boat at anchor.

No alarm. No traffic. Just the gentle sound of water against the hull, a mug of coffee in the cockpit, and a view that makes you wonder why you ever sleep ashore.

Anchoring out overnight is one of the great joys of bareboat chartering on the Chesapeake, and it's easier than most people think:

🌅 Sail to your chosen anchorage in the afternoon
⚓ Drop the hook in calm, protected water
🍷 Sundowners in the cockpit as the Bay turns golden
🌟 Fall asleep to the sound of the water
☕ Wake up and do it all again

Our bareboat charter fleet is fully equipped for overnights - everything you need to make the Bay your home for a night (or a week).

Ready to live the dream? Send us a DM.

While everyone else is scraping ice off their windshields, you could be sailing crystal-clear Caribbean waters with a cr...
08/17/2026

While everyone else is scraping ice off their windshields, you could be sailing crystal-clear Caribbean waters with a crew of fellow Sail Solomons sailors in Guadeloupe.

No experience sailing the Caribbean? No problem. That's exactly what our Instructor-Captains are there for.

Spots are limited and filling up — don't wait on this one.

📞 410-326-4917 📩 [email protected] 🌐 sailsi.com

Our newest graduates of ASA 118 Docking! Congratulations Wolfy and Deven! And “thank you”Master Instructor Andy Batchelo...
08/12/2026

Our newest graduates of ASA 118 Docking! Congratulations Wolfy and Deven! And “thank you”Master Instructor Andy Batchelor!

⛵ Sailing classes still available! ⛵Ready to level up your certifications before the season winds down? We've got six up...
08/12/2026

⛵ Sailing classes still available! ⛵

Ready to level up your certifications before the season winds down? We've got six upcoming ASA courses with open spots:
🗓️ Sept. 5–9 — ASA 103/104 Combo (Basic Coastal Cruising & Bareboat Cruising) | $1,700
🗓️ Sept. 13–15 — ASA 104: Bareboat Cruising | $1,340
🗓️ Sept. 25–27 — ASA 103: Basic Coastal Cruising | $935
🗓️ Oct. 9–12 — ASA 104/114 Combo (Bareboat Cruising & Catamaran Endorsement) | $3,200
🗓️ Oct. 9–14 — ASA 106: Advanced Coastal Cruising (DELMARVA Circumnavigation) | $2,085
🗓️ Oct. 24–25 — ASA 114: Cruising Catamaran | $1,560

Whether you're just getting started or ready to add a catamaran endorsement, there's a class for you.

Spots are limited — link in bio to book! ⚓

One of the best things about chartering from Solomons? The whole Chesapeake is your backyard. Here are 3 of our favorite...
08/10/2026

One of the best things about chartering from Solomons? The whole Chesapeake is your backyard.

Here are 3 of our favorite anchorages within reach:
📍 St. Michaels — Picturesque town and well-protected.
📍 Wye River — remote, beautiful, and excellent protection in all weather.
📍 Rhode River — Convenient to Annapolis, great holding, and gorgeous scenery all around.

Every one of these is reachable on a bareboat charter from our dock in Solomons. Drop the hook, crack open a cold one, and remember why you got into this.

We get this question more than you'd think. So, let's settle it.Why sail when you could just… power?🌬️ Because when the ...
08/05/2026

We get this question more than you'd think. So, let's settle it.

Why sail when you could just… power?
🌬️ Because when the wind fills your sails, you earned it
🔇 Because the only sound is water and wind — no engine drone
💸 Fuel is free when you're sailing
🧠 It's a skill: one that challenges and rewards you every single time
🌍 A sailboat can take you anywhere in the world
🤝 The sailing community is unlike any other

Powerboating is fun. We won't argue that. But sailing? Sailing is a way of life.

Curious what all the fuss is about? Our 2-hour Introduction to Sailing lesson is just $100 and will answer that question once and for all.

First time sailing? One of the most common questions we get is: "What should I wear?" Here's your quick-reference guide ...
08/03/2026

First time sailing? One of the most common questions we get is: "What should I wear?"

Here's your quick-reference guide before you step aboard:

👟 Shoes: soft-soled, non-marking shoes with grip (no flip flops — they go overboard!)
🧢 Hat: wide brim or a cap, the sun on the water is intense
🧴 Sunscreen: SPF 50+, and bring extra. The Bay reflects UV like a mirror
🕶️ Sunglasses: polarized lenses are a game changer on the water
👖 Layers: mornings can be cool even in summer, a light fleece or windbreaker goes a long way
💧 Water bottle: staying hydrated is more important than you think out there

Leave the heavy jewelry, loose scarves, and anything you'd be heartbroken to lose at home.

Any other questions before your first sail? Drop them in the comments 👇

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

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