Seas the Bay Sailing

Seas the Bay Sailing Seas the Bay Sailing is a premier captained charter service that provides private day and sunset sai Not only are you on a beautiful fully equipped 54 ft.

Seas the Bay Sailing Charters is a captained charter service that provides our guests with a private day or sunset sail on the Bay without the crowds and worries of trying to sail your own boat. We provide you with an experience that has everything you need to enjoy, relax and take in all that Annapolis “on the water” has to offer. sailing vessel, you can be assured that Captain Chris is highly ex

perienced and certified for safe and deft handling of this yacht in all conditions. First Mate Susan has years of experience taking care of guests on holiday in Italy, and she will make sure you have fun memories that will last a lifetime.

Memorial Day at the Annapolis Yacht Club this past weekend! As the Commodores wife, our beautiful Susan had the honor of...
05/26/2026

Memorial Day at the Annapolis Yacht Club this past weekend! As the Commodores wife, our beautiful Susan had the honor of setting the Memorial Wreath in the water 🇺🇸❤️

🇺🇸

05/18/2026

Want an authentic experience of a lifetime in the heart of Annapolis, MD? Check out the link in our bio to book a private charter on the Southerly!!

Beautiful views of the Severn and Downtown Annapolis await!

we love being a part of magical moments like this! 💍 📸 interesting in booking your dream engagement photos on a Southerl...
05/18/2026

we love being a part of magical moments like this! 💍 📸

interesting in booking your dream engagement photos on a Southerly charter? click the link in our bio! :)

05/18/2026

Congrats to the beautiful couple! We wish them the best and couldn’t be more excited for their future together!

Clink the link in our bio to book your dream engagement photos today! ⛵️🌊💍

04/27/2026

Who doesn’t love a good boat show weekend! ☺️⛵️

Weekend charter recap from the Annapolis Spring Sailboat Show! ⛵️Use the link in our bio to book your charter today! Sum...
04/27/2026

Weekend charter recap from the Annapolis Spring Sailboat Show! ⛵️

Use the link in our bio to book your charter today!

Summertime is right around the corner in Annapolis 🦀☀️🫶🏻

04/16/2026

A little peek below… ✨
Fresh, crisp, and ready for the season!

Join us for your unforgettable escape on the Bay⛵️

Now booking private charters for the season

Southerly’s center console just got a serious refresh, bringing state-of-the-art navigation and a beautifully streamline...
03/14/2026

Southerly’s center console just got a serious refresh, bringing state-of-the-art navigation and a beautifully streamlined helm to the water this year.

Special thanks to Patrick and his team at for their timely and professional work.

Another fun day at the Annapolis Boat Show when Capt Glenn stopped by!
10/16/2025

Another fun day at the Annapolis Boat Show when Capt Glenn stopped by!

No crowds no stress just you, your loved ones, and the sea. Lets make some memories!
08/10/2025

No crowds no stress just you, your loved ones, and the sea. Lets make some memories!

Address

326 First Street
Annapolis, MD
21403

Opening Hours

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

Telephone

+14108813264

Website

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