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.
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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.

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
Happy   from the home of  and Southerly!⚓️🇺🇸⛵️
05/25/2024

Happy from the home of and Southerly!⚓️🇺🇸⛵️




























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! .

A man’s best friend🐾🐶⛵️
08/31/2023

A man’s best friend🐾🐶⛵️

08/12/2023

Our 54 Irwin. She’s had a major facelift this year and we are loving it!⛵️❤️

August is a perfect month to go on a sailing charter… click our link in our bio to books yours before the sailing season...
08/07/2023

August is a perfect month to go on a sailing charter… click our link in our bio to books yours before the sailing season ends this year!

Nature’s light reflection painted our grill this evening! AND another glorious sunset for our private sailing charter❤️🥂...
07/27/2023

Nature’s light reflection painted our grill this evening! AND another glorious sunset for our private sailing charter❤️🥂⛵️.

Some amazing shots from our last charter!! She said YES!🤩💍⛵️  ***eclicquot   📸:                                         ...
07/12/2023

Some amazing shots from our last charter!! She said YES!🤩💍⛵️ ***eclicquot

📸:
***e

It was all smiles today!The Healing Paws crew joined us for a gorgeous day on the bay.
06/04/2023

It was all smiles today!
The Healing Paws crew joined us for a gorgeous day on the bay.

05/01/2023

My gorgeous daughter pulled out all the stops on my bday!!! Celebrating in Oz🍾💃❤️

It won’t be long now! Left Charleston and sailing north. Beautiful conditions (for once😵‍💫⛵️🌊)                          ...
04/03/2023

It won’t be long now! Left Charleston and sailing north. Beautiful conditions (for once😵‍💫⛵️🌊)

Bahamas Bound - overnight watch. Moon-set and sunrise.  Feels like we are the only ones out here!                       ...
03/06/2023

Bahamas Bound - overnight watch. Moon-set and sunrise. Feels like we are the only ones out here!

Update for Southerly: she has been down in the Florida Keys since mid November for the winter season! 🏝️🌴☀️⛵️ she is hea...
02/01/2023

Update for Southerly: she has been down in the Florida Keys since mid November for the winter season! 🏝️🌴☀️⛵️ she is headed somewhere new on March 1… can you guess where?! ⬇️

BEST HOLIDAY GIFT ON SALE NOW!!!🎄🎅🏼🎁⛵️🦀🌊 read below for more informationDon’t know what to get your daughter and her boy...
12/06/2022

BEST HOLIDAY GIFT ON SALE NOW!!!🎄🎅🏼🎁⛵️🦀🌊 read below for more information

Don’t know what to get your daughter and her boyfriend, your parents, or other loved ones? Do you just want to gift your family an experience that won’t be forgotten? Then purchase gift certificates to charter Southerly this coming season!

We are selling private charter gift certificates for the upcoming 2023 season before prices increase next year by ~5%!

If you would like to purchase, please go to our website in our bio for instructions. All you have to do is email [email protected] or text 513-604-1387 and we will get you set up!

Today was a great success for hosting the VIPs on Southerly for the   ⛵️ we all had a lot of fun, enjoyed the food and d...
09/18/2022

Today was a great success for hosting the VIPs on Southerly for the ⛵️ we all had a lot of fun, enjoyed the food and drinks, & the amazing weather! ☀️ until next year….

Never forget.     🇺🇸 Our hearts go out to all of the victims and their families of the 9/11 attacks 21yrs ago😢   #911   ...
09/11/2022

Never forget. 🇺🇸
Our hearts go out to all of the victims and their families of the 9/11 attacks 21yrs ago😢
#911

Happy Labor Day from Seas the Bay!🇺🇸👮‍♀️👷👩‍🚒👨‍⚕️ We are SO thankful for all of our clients who make  possible!❤️ What di...
09/06/2022

Happy Labor Day from Seas the Bay!🇺🇸👮‍♀️👷👩‍🚒👨‍⚕️ We are SO thankful for all of our clients who make possible!❤️
What did you guys do this weekend? 👇🏼

Father daughter bonding on a charter❤️🥺We accommodate all types of celebrations and outings! Who’s next??               ...
09/01/2022

Father daughter bonding on a charter❤️🥺
We accommodate all types of celebrations and outings! Who’s next??

08/30/2022

Feeling spontaneous?!🧳✈️🤪🍝🤩
Always wanted to go to but you just don’t want to go alone, or know how to plan it? Then this is your SIGN!🇮🇹

Rosapepe Retreats () has just added a few more spots for a small group tour trip to Italy THIS October 15-22🥳😱🇮🇹✈️This trip gives such an authentic and local feel of Italy, which other travel companies have a hard time doing… this is what makes us SO unique!
We stay at family hotel and do wine tasting, cooking
class, buffalo Mozzarella farm, Greek and Roman historical sites, Amalfi Coast day, etc. Even if you have been to Italy before, this trip is very unique-- you will feel Italy like a local!

DM us to get your questions answered and if you’re interested in coming along! You only live once, don’t let the fear of going alone stop you 💚🤍❤️

08/22/2022

Adjacent to Washington, D.C., in the northeastern USA, Maryland is known for its historic cities like Baltimore and Annapolis, fresh seafood and spectacular ...

Happy National Senior Citizen Day!!!👴🏾🧓🏼👵🏻👴🏻👵🏿🧓🏽 Thankful for the insight and wisdom from all of our senior citizens… an...
08/21/2022

Happy National Senior Citizen Day!!!👴🏾🧓🏼👵🏻👴🏻👵🏿🧓🏽 Thankful for the insight and wisdom from all of our senior citizens… and of course they can come aboard!⛵️❤️⚓️

Happy National Aviation Day!!✈️✈️✈️✈️✈️ Enjoy these photos of the   taken by one of our clients on Southerly⛵️⚓️We are S...
08/19/2022

Happy National Aviation Day!!
✈️✈️✈️✈️✈️

Enjoy these photos of the taken by one of our clients on Southerly⛵️⚓️
We are SO thankful for the men and women who fly in the and all of the pilot selects at 💛💙💛💙

Imagine booking a sunset charter with us and experiencing these AMAZING sunsets🌅😍❤️⛵️     Check our link in our bio to b...
08/15/2022

Imagine booking a sunset charter with us and experiencing these AMAZING sunsets🌅😍❤️⛵️
Check our link in our bio to book up to 6 people on the beautiful Southerly in downtown Annapolis!🤩

A beautiful picture taken by a client of Southerly and out   🇮🇹 flying!   is today! 🤩 Did you know that Sailing is the o...
08/12/2022

A beautiful picture taken by a client of Southerly and out 🇮🇹 flying!

is today! 🤩
Did you know that Sailing is the only way to reach some off-limit places for tourists? Several islands in the world are so tiny that there are no cruises or flights able to bring tourists there. The islands are typically true hidden gems with their rare beauty, and the only way to access them is through sailing!⛵️

Happy National Coastguard Day!!!💙🛥🛟⚓️🚨         to a time the US Coast Guard stopped us on Southerly to welcome the Itali...
08/05/2022

Happy National Coastguard Day!!!💙🛥🛟⚓️🚨

to a time the US Coast Guard stopped us on Southerly to welcome the Italian citizen onboard because we were flying our 🇮🇹 We are so thankful for all of the men and women who volunteer to serve our country❤️🇺🇸 thank you for all that you do!!!

Enjoyed hosting these wonderful girls for a Bachelorette Party!🥂 🎉👰‍♀️⛵️                                                ...
07/27/2022

Enjoyed hosting these wonderful girls for a Bachelorette Party!🥂 🎉👰‍♀️⛵️

Beautiful shot of our Southerly in Annapolis on the Chesapeake Bay!⛵️😍                                                  ...
07/22/2022

Beautiful shot of our Southerly in Annapolis on the Chesapeake Bay!⛵️😍

Can you name a better way to spend summer fun with your family?!  Charter sailboat with us in Annapolis MD!⛵️☀️🦀 (click ...
07/17/2022

Can you name a better way to spend summer fun with your family?! Charter sailboat with us in Annapolis MD!⛵️☀️🦀
(click link in bio for bookings and pricing)
We had a great time chartering this weekend!❤️

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.


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