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.

Valentines Day is this week! Tag your valentines in the comments 💖 Did you know that we offer Sunset and Champagne Cruis...
02/11/2025

Valentines Day is this week! Tag your valentines in the comments 💖 Did you know that we offer Sunset and Champagne Cruises? On this excursion we leave the dock in late afternoon and cruise the Seven River where we find just the right spot to view the Chesapeake Bay sunset fill the sky with hues of red, orange and purple all the while enjoying gourmet appetizers and sipping champagne. Add the Dinner Option for two and your evening is complete! Visit our website to book now: https://www.seasthebaysailing.com/private-sailing-charters-2

01/29/2025

You can't think of DIY sailing without thinking of Mads and Ava from 🛠️ So much moments over on their channel, give it a watch!

Our   was designed and personalized for maximum comfort and safety ⛵️ SV Southerly is engineered to sail with effortless...
01/28/2025

Our was designed and personalized for maximum comfort and safety ⛵️ SV Southerly is engineered to sail with effortless grace and speed. The spacious deck boasts an easy to board walk-in cockpit for entertaining and sail handling.

Some of the features that make our boat so special are the electrically operated sails, and “elevator” like folding swim/dive platform in the transom, as well as comfortable and well-placed stern rail seats for enjoying cocktails and views.

Below deck, the feeling of warmth and generous lay-out makes this vessel welcoming to all who board. The richly varnished teak, along with color-coordinated décor make this a home away from home. The salon is elegantly appointed with two handsome L-shaped settees, an elaborate and sophisticated navigation station, liquor lockers, and a serving bar with a swiveling captain's chair. The galley is a gourmet's dream with a generous amount of space for food preparation and storage. The dining salon comfortably accommodates six to eight guests.

Southerly is a sailing vessel like no other and we can’t wait to share it with you! Visit our website for booking details ⛵️

MEET THE CREW 🌟 Seas the Bay Sailing isn’t just about seeing the Chesapeake Bay; it’s about feeling it. 🌊⛵ As a family-o...
01/22/2025

MEET THE CREW 🌟 Seas the Bay Sailing isn’t just about seeing the Chesapeake Bay; it’s about feeling it. 🌊⛵ As a family-owned business, we’re dedicated to giving you a day of authentic sailing, breathtaking views, and unforgettable memories. Meet Captain Chris, with 40+ years of sailing experience, and Susan, co-owner of Rosapepe Retreats in Italy, who bring their passion for unique experiences to every charter. 🛥️ Email [email protected] or call 410-881-3264 to book your adventure!

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Celebrate life's special moments with a customized cruise on the Chesapeake Bay. 🥂✨ Whether it’s an anniversary, proposa...
01/20/2025

Celebrate life's special moments with a customized cruise on the Chesapeake Bay. 🥂✨ Whether it’s an anniversary, proposal, or bachelorette soiree, we’ll make it unforgettable. Email [email protected] or call 410-881-3264 to book your specialty cruise today!

Happy   everyone! How will you spend your weekend? Planning a unique outing? 🌟 Our Specialty Cruises can accommodate up ...
01/18/2025

Happy everyone! How will you spend your weekend? Planning a unique outing? 🌟 Our Specialty Cruises can accommodate up to 6 guests for birthdays, bachelorette parties, and more. Looking for a private dinner for two? We’ve got you covered. 🥂 Email [email protected] or call 410-881-3264 to book your custom sailing

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Surprise your loved one with a romantic proposal cruise or celebrate life’s milestones on the water. 🌊✨ Fine wine, champ...
01/16/2025

Surprise your loved one with a romantic proposal cruise or celebrate life’s milestones on the water. 🌊✨ Fine wine, champagne, and gourmet appetizers are just the beginning. Let us make your special moments unforgettable. Contact us now: [email protected] | 410-881-3264.

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Fine wine, gourmet appetizers, and breathtaking views. 🌅🍷 Perfect for anniversaries, birthdays, or even an intimate dinn...
01/11/2025

Fine wine, gourmet appetizers, and breathtaking views. 🌅🍷 Perfect for anniversaries, birthdays, or even an intimate dinner for two. 💕 Reserve your specialty cruise now: [email protected] or 410-881-3264.

01/07/2025

We hope you have all had a wonderful start to the New Year! We are still reminising about all of the wonderful new friends we met at the , like Warren and Erica from ⛵️ Who do you want to see an interview with? Tell us below! ⬇️

Set sail into the Annapolis sunset with us! 🌅🛥️ Book your unforgettable private charter today at seasthebaysailing.com or call us at (410) 555-1234.

BEST HOLIDAY GIFT- Buy an adventure for your loved ones today! 🎄🎅🏻🎁⛵️⛵️🌊.Don't know what to get for your daughter and he...
12/10/2024

BEST HOLIDAY GIFT- Buy an adventure for your loved ones today! 🎄🎅🏻🎁⛵️⛵️🌊.
Don't know what to get for your daughter and her boyfriend, parents, spouse, friends? Purchase a gift certificate for a private charter for our 2025 sailing season at our 2024 prices. Buy today as availability is limited.
If you would like to purchase, please go to our website in our bio for instructions. You can also email [email protected] or text 513-604-1387 and we will take care of this for you today!

Thanks for stopping by Southerly ! I'd  go offshore in a heartbeat with either one of these salty sailors! Wouldn't you?...
10/15/2024

Thanks for stopping by Southerly !
I'd go offshore in a heartbeat with either one of these salty sailors! Wouldn't you?⛵️. Ok to be fair, one is my husband❤️ He's a superstar in my book too!



As the VIP and Cruisers Creating Content Host Boat, we have had amazing special guests who have now become amazing new f...
10/14/2024

As the VIP and Cruisers Creating Content Host Boat, we have had amazing special guests who have now become amazing new friends❤️ ( and I've adopted most of them🥰 now)

If these shoes could talk they'd have their own You Tube Channel!

Tune into all our Cruisers' You Tube Channels for the best adventures at sea!



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06/18/2024
Southerly is having a Spa Day. Stay tuned for pictures of her face , I mean, bottom lift!! 😎⛵️❤️
05/31/2024

Southerly is having a Spa Day. Stay tuned for pictures of her face , I mean, bottom lift!! 😎⛵️❤️










05/28/2024
Sunset cruises happen earlier this time of year —- simply SPECTACULAR!! Join us for a glorious fall cruise during these ...
10/20/2023

Sunset cruises happen earlier this time of year —- simply SPECTACULAR!! Join us for a glorious fall cruise during these crisp fall days! .

Address

326 First Street
Annapolis, MD
21403

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

Telephone

+14108813264

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About Us

Captain Chris has been sailing for over 40 years, and has sailed offshore for over 25 years. His sailing adventures have taken him from Maine to Key West, Bermuda, Guadalupe, Puerto Rico, and Cuba to name a few. Safety at sea is his number one priority and you will be in excellent hands.

Susan Is co-owner and operator of Rosapepe Retreats, a boutique Italian tour company that accompanies visitors to her family hotel in Italy, and provides a unique and authentic experience in southern Italy.

With her husband Chris, Susan discovered the joys of sailing many years ago, and couldn’t be happier sharing this passion and experience with anyone who dreams of a day on the Bay!

Susan and Chris will make your sailing experience a day to remember, with comfortable accommodations, wonderful food and breathtaking sights.