Chronic Sailing

Chronic Sailing Annapolis Sailboat Charters;
ASA Affiliate Sailing School;
Captain Services &
Professional Yacht Delivery
(5)

09/18/2026

Shawn and Ron said everything you need to know. We are just here to make sure you do not miss it.

Baygrass Music Festival is this weekend. Saturday and Sunday. And it kicks off Friday night at Maryland Hall at 7pm with Jammy Buffet, a Jimmy Buffett cover band that sounds exactly as good as it does, and Cumberland Honey. Tickets are $20 in advance and more at the door so get them now.

Saturday and Sunday is the full festival and you already know the lineup. What you might not know is that the Chronic Crew gets 15% off.

Use code BGFAM15 at checkout. That is B-G-F-A-M-1-5.

This is the only festival we support the way we do and it is for a reason. Baygrass gets it. The bay, the music, the community. All of it.

Come out. 🎶⛵

📅 Friday — Maryland Hall, 7pm. Doors open. $20 advance.
📅 Saturday and Sunday — Baygrass Music Festival. Full lineup. Full weekend.
🎟️ 15% off with code BGFAM15

Annapolis Baygrass Music Festival

09/15/2026

Tunesday Floating Concert Series

09/12/2026

Tunesday Floating Pop-Up Concert!!!

09/08/2026

Tunsday

09/05/2026

🚨New song debut: “Beeswax ft Big SLOP” live from the Chronic Sailing Catamaran on Back Creek Annapolis. If SLOP is MC on the floating stage concert, you best believe I’m gonna request he spit a few stanzas about vintage cucumbers. 🥒 “It might be time to refresh your philosophy if you thought your train of thought right off the rails, liberate yourself from the hypocrisy, inhale, exhale…” Video by Casey V. Bougie bootleg field recording by 3 Eyed Ghost Cat Slop (Spittin' Lyrics On Point)
⚓️

Congratulations to the first food boat in Anne Arundel County, the SS Soggy Bunz, on opening for business! We’ve been pr...
09/05/2026

Congratulations to the first food boat in Anne Arundel County, the SS Soggy Bunz, on opening for business!

We’ve been proud to support Toby and Ola Denues throughout the process, and we were excited to help them celebrate the growth of their business at our first-ever on-the-water ribbon cutting this week.

Thanks to two IVP-owned businesses, Chronic Sailing and Capital SUP, for providing the perfect platform for the fun event, and thanks to Toby and Ola for continuing to grow their family-owned business on both land and sea!

Joey Harkum 🎶at Tunesday Floating Concert Series ⛵️presented by Chronic Sailing ⚓️
09/05/2026

Joey Harkum 🎶
at Tunesday Floating Concert Series ⛵️
presented by Chronic Sailing ⚓️

06/26/2026

The bay is calling and honestly it would be rude not to go.

Charter season is here and Sea Dancer is ready. Day trips, sunset cruises, or a full day out on the Chesapeake with your whole crew. Bring the food, bring the drinks, and let us handle the rest.

Meet Sea Dancer:

🛥️ Meridian 541 Sedan power yacht
👥 Up to 13 guests
🛏️ 2 private cabins, sleeps 4-6
🚿 2 heads
🛋️ Open salon with full lounge and galley
🌅 Expansive flybridge with views for days
⚓ Multiple deck zones for lounging, dining, and swimming

Link in bio to book. 🌅⛵

06/09/2026

Part time magicians is the official titles for our team when we pull up to

Address

7082 Bembe Beach Road, #204
Annapolis, MD
21403

Telephone

+14433339113

Website

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