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.

Some of our favorite people said yes to forever on Southerly. We’ve hosted a lot of golden hours out here, but this one ...
09/03/2026

Some of our favorite people said yes to forever on Southerly. We’ve hosted a lot of golden hours out here, but this one hits different.

If you’re picturing your own proposal, elopement, or engagement shoot on the water, this is your sign.

Sail on Southerly for your next big moment ❤️

09/01/2026

Soaking up every bit of summer we can on Southerly. What are your Labor Day weekend plans? ⛵️ ☀️ 🌊

Downtown Annapolis at golden hour. Lucky to call this town home and soak up these views everyday!
08/29/2026

Downtown Annapolis at golden hour. Lucky to call this town home and soak up these views everyday!

Wednesday Night Races are one of our favorite reasons to be out on the water. Southerly had a front row seat this week, ...
08/23/2026

Wednesday Night Races are one of our favorite reasons to be out on the water. Southerly had a front row seat this week, watching the fleet round the marks with sails everywhere.
Captain Chris had a few friends racing out there, and there’s something fun about watching him watch them, half narrating the tactics and half just enjoying the show. Good wind, good company, and a reminder of why this is one of Annapolis’s best traditions. This is what it’s like to sail with Seas the Bay!

08/21/2026

This is what a few hours on the Bay can do for you. Book an afternoon sailing with Seas the Bay.

The best sunset views in Annapolis are with us! Soak in this beautiful weather and join us for the best seats in the hou...
08/15/2026

The best sunset views in Annapolis are with us!

Soak in this beautiful weather and join us for the best seats in the house.

Family day on Southerly. Nowhere to be, nothing to do but enjoy our time together and soak up these late summer afternoo...
08/11/2026

Family day on Southerly. Nowhere to be, nothing to do but enjoy our time together and soak up these late summer afternoons.

08/09/2026

Grab your friends and come sail with Seas the Bay for a relaxing afternoon on the water ⛵

There’s still plenty of good sailing left this summer, come catch some sun and breeze on the Bay with us.

DM us or hit the link in our bio to book. Can’t wait to have you aboard 🌅

Some nights the Bay does all the talking. Glad we got to sit back and watch this one together. 🌅 🥂
08/07/2026

Some nights the Bay does all the talking.

Glad we got to sit back and watch this one together. 🌅 🥂

08/05/2026

It doesn’t get much better than this.

Link in our bio if you would like for this to be your afternoon.

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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