Seas the Bay Sailing

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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 experienced 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.

10/08/2026

Cooler weather is coming, and it’s time to slow down. We love fall sailing, especially on a sunny afternoon. It reminds you what’s important. Come sail on Southerly.

What a crew! We had the best time out on the Bay with the VRS Events team for their corporate outing. Everyone took a tu...
09/29/2026

What a crew!
We had the best time out on the Bay with the VRS Events team for their corporate outing. Everyone took a turn at the helm with Captain Chris, then settled in to relax and just enjoy being out on the water together.

We love being part of days like this. Thanks for sailing with Seas the Bay, VRS Meetings & Events, Inc. ⛵

We’ve had a lot of beautiful evenings on Southerly this season, but this one stuck with us. Calm water, warm light, and ...
09/26/2026

We’ve had a lot of beautiful evenings on Southerly this season, but this one stuck with us.

Calm water, warm light, and a couple who had something bigger planned than a sunset cruise.

More photos soon!!!

Throwback to last year’s Annapolis Sailboat Show.Old friends, new friends, a lot of laughs, and more people below deck t...
09/22/2026

Throwback to last year’s Annapolis Sailboat Show.

Old friends, new friends, a lot of laughs, and more people below deck than we thought would fit. Best kind of chaos!!

We’ll be back this October. Coming to the show? Drop a comment or DM us so we know to look for you. ⛵😊

Even captains need a break. ⛵We snuck away this month to Maui, and even better, Susan’s son flew in from Chicago and her...
09/11/2026

Even captains need a break. ⛵

We snuck away this month to Maui, and even better, Susan’s son flew in from Chicago and her daughter made the trip all the way from Australia to join us. It’s funny, we spend all season on the water back in Annapolis, and somehow we still can’t stay away from it on vacation.

Waterfalls, rainbow eucalyptus trees, and more blue water than we could ask for, made even better with family typically on the other side of the world finally in one place. Grateful for the time together and for localmauitours for showing us around.

Back on Southerly this week, ready for fall sailing. 🌺

Southerly, catching the last light of the day.You can’t pick a better spot to enjoy the sunset on the Chesapeake Bay! 🌅
09/06/2026

Southerly, catching the last light of the day.

You can’t pick a better spot to enjoy the sunset on the Chesapeake Bay! 🌅

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!

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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