Seas the Bay Sailing

Seas the Bay Sailing

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Thanks Washingtonian Magazine for the mention- we love our water sports!

📸 Annapolis Efoil

#annapolisefoil Seas the Bay Sailing Breakwater Adventures Z Flight Parasail and Watersports Annapolis Efoil

https://www.washingtonian.com/2021/06/21/new-chesapeake-bay-adventures/
The best way to see #Annapolis is by boat! Consider booking an intimate charter for your next event with Seas the Bay Sailing.

More details on Annapolis Discovered!

#sailing #charter #cruising #visitannapolis
Seas the Bay Sailing is a great way to enjoy a private sailing charter on the Chesapeake Bay. Learn more on Annapolis Discovered.

#sailing #boating #annapolis #VisitAnnapolis

Seas the Bay Sailing is a premier captained charter service that provides private day and sunset sails on a 54 ft. sailboat. We provide intimate cruises on the Chesapeake Bay for up to six people.

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. Not only are you on a beautiful fully equipped 54 ft. sailing vess

Operating as usual

11/05/2021

Occasionally we trade in our sea legs for land legs and take a stroll through our charming town. Make a weekend of it!! We have lots of great suggestions for eateries and charming accommodations too! #sailingtown #sailinglife #historichomes #visitannapolis #frontdoorsofannapolis #midatlanticdaytrips #daytripdc #marylandweekend

Occasionally we trade in our sea legs for land legs and take a stroll through our charming town. Make a weekend of it!! We have lots of great suggestions for eateries and charming accommodations too! #sailingtown #sailinglife #historichomes #visitannapolis #frontdoorsofannapolis #midatlanticdaytrips #daytripdc #marylandweekend

11/02/2021

……….😳When the Bay “seizes” Seas the Bay Sailing😱🌊💨💦. #chesapeakebay #annapolisweather #naptown #annapolismd #sailinglife #visitannapolis #boatlife #waterworld #marinalife #sailing

……….😳When the Bay “seizes” Seas the Bay Sailing😱🌊💨💦. #chesapeakebay #annapolisweather #naptown #annapolismd #sailinglife #visitannapolis #boatlife #waterworld #marinalife #sailing

10/16/2021

October sunsets in Annapolis ⛵️🍾❤️. Spectacular!!! #sunsetlovers #sunsetphotography #annapolissailboatshow #annapolissunset #sailingskies #mdinfocus #visitannapolis #sailinglife #chesapeakebay

October sunsets in Annapolis ⛵️🍾❤️. Spectacular!!! #sunsetlovers #sunsetphotography #annapolissailboatshow #annapolissunset #sailingskies #mdinfocus #visitannapolis #sailinglife #chesapeakebay

10/14/2021

We just sailed by the @annapolisboatshow - So beautiful at night! Seas the Bay Sailing crew can’t wait to visit our sailing “family” tomorrow on opening day!! ⛵️🥰. #annapolislifestyle #annapolisdiscovered #sailingfamily #sailboats #sailinglife #cruisinglifestyle #boatshow

We just sailed by the @annapolisboatshow - So beautiful at night! Seas the Bay Sailing crew can’t wait to visit our sailing “family” tomorrow on opening day!! ⛵️🥰. #annapolislifestyle #annapolisdiscovered #sailingfamily #sailboats #sailinglife #cruisinglifestyle #boatshow

10/12/2021

Sunrise in Whitehall Creek - home of Seas The Bay Sailing 🌅! If you are visiting @annapolisboatshow, discover hidden gems - creeks and coves around Annapolis when you take a spin on your new boat!! ⛵️❤️. #annapolissailboatshow #sailboat #visitannapolis #chesapeakebayboating #visitmaryland #visitbwi #annapolisboatshow #discoverannapolis

Sunrise in Whitehall Creek - home of Seas The Bay Sailing 🌅! If you are visiting @annapolisboatshow, discover hidden gems - creeks and coves around Annapolis when you take a spin on your new boat!! ⛵️❤️. #annapolissailboatshow #sailboat #visitannapolis #chesapeakebayboating #visitmaryland #visitbwi #annapolisboatshow #discoverannapolis

10/06/2021

What we do on our day off😵‍💫😱😊. #sailannapolis #sailing #boatingsafety #boatingdaily #boatmaintenance #annapolislife #yachtlife #severnriver #chesapeakebaysailing

What we do on our day off😵‍💫😱😊. #sailannapolis #sailing #boatingsafety #boatingdaily #boatmaintenance #annapolislife #yachtlife #severnriver #chesapeakebaysailing

09/30/2021

Just another night on Seas the Bay where the wind filled the sails and took us to the perfect place at the perfect time!! ❤️⛵️🙏. #annapolissunset #sailinglife #chesapeakebay #visitannapolis #sailingphotography #sailingdrone #marylandsailing #thomaspointlighthouse #sunsetcruise #sailingholiday

Just another night on Seas the Bay where the wind filled the sails and took us to the perfect place at the perfect time!! ❤️⛵️🙏. #annapolissunset #sailinglife #chesapeakebay #visitannapolis #sailingphotography #sailingdrone #marylandsailing #thomaspointlighthouse #sunsetcruise #sailingholiday

09/18/2021

We were honored to be a part of the Hospice Cup Regatta 40th year! These are some of the fantastic folks that give their time and support to this incredible organization. Thank you to all involved with Hospice! So happy the weather was grand😊⛵️#hospicevolunteer #hospiceregatta #visitannapolis #annapolisyachtclub #chesapeakefamily

We were honored to be a part of the Hospice Cup Regatta 40th year! These are some of the fantastic folks that give their time and support to this incredible organization. Thank you to all involved with Hospice! So happy the weather was grand😊⛵️#hospicevolunteer #hospiceregatta #visitannapolis #annapolisyachtclub #chesapeakefamily

09/12/2021

It takes a special man to craft a surprise like this! It was magnificent 🥰 Congratulations to a beautiful couple🍾⛵️❤️. @kelly.ingle.photography

It takes a special man to craft a surprise like this! It was magnificent 🥰 Congratulations to a beautiful couple🍾⛵️❤️. @kelly.ingle.photography

08/30/2021

Thank you Morgan and Parker for sharing your FIRST time sailing and FIRST time to Annapolis with Seas The Bay Sailing! 😊🥰⛵️. We hope we made you fall in love……with Annapolis 😂❤️! #visitannapolis #annapolisdiscovered #spinsheetmagazine , #summervacation,#summergetaway #weekendinannapolis #chesapeakebaysailing #couplesgetawa,#gosailing

Thank you Morgan and Parker for sharing your FIRST time sailing and FIRST time to Annapolis with Seas The Bay Sailing! 😊🥰⛵️. We hope we made you fall in love……with Annapolis 😂❤️! #visitannapolis #annapolisdiscovered #spinsheetmagazine , #summervacation,#summergetaway #weekendinannapolis #chesapeakebaysailing #couplesgetawa,#gosailing

08/12/2021

The beginning of a new chapter starts here with this beautiful fun-loving fantastic couple!! Thank you two for sharing your special moments with @seasthebaysailing !! ❤️🥰🎉🎊🍾. #proposals #specialengagement #dcengagement #mdengagement #sailingproposal #popthequestion

08/01/2021

Happy 17th Anniversary to these special guests who chose Seas the Bay charters to celebrate. We love sharing these good times and beautiful Annapolis sunsets. Happy Anniversary ❤️#familyfun, #anniversarysurprise #visitannapolis #sailingcharter #summervibes #trysailing #dayonthebay #visitmaryland

Happy 17th Anniversary to these special guests who chose Seas the Bay charters to celebrate. We love sharing these good times and beautiful Annapolis sunsets. Happy Anniversary ❤️#familyfun, #anniversarysurprise #visitannapolis #sailingcharter #summervibes #trysailing #dayonthebay #visitmaryland

07/14/2021

Making Family Memories in Annapolis with Seas The Bay Sailing! These two young men are future sailors for sure after trying their hand at the wheel on our cruise. We had a great sail with time to take a dip too! ⛵️❤️ #familyfun #chesapeakefamily #annapolismd #visitannapolis #chesapeakebayboating #sailannapolis #onthewater

Making Family Memories in Annapolis with Seas The Bay Sailing! These two young men are future sailors for sure after trying their hand at the wheel on our cruise. We had a great sail with time to take a dip too! ⛵️❤️ #familyfun #chesapeakefamily #annapolismd #visitannapolis #chesapeakebayboating #sailannapolis #onthewater

07/04/2021

Happy 4th! Thank you Sherwood Forest- we had a BLAST😊 ⛵️🍾🇺🇸celebrating the USA from the water. Join Seas The Bay Sailing for more summer sailing adventures⭐️🌈 in our beautiful city of Annapolis Maryland! #visitannapolis #sherwoodforest #weekendinannapolis #onthewater #seasthebaysailing #4thofjuly #visitmaryland #visitwashingtondc

07/01/2021

By land and by sea, Seas The Bay Sailing is thrilled to partner with Visit Annapolis. Contact us for your private cruise and special occasions to experience Annapolis on the water! Kudos to the hard- working folks at Visit Annapolis and Annapolis Discovered for bringing back the charm and sheer joy of our town❤️⛵️#visitannapolis #annapolisdiscovered #4thofjuly #annapolismaryland #chesapeakebay #onthewater #fireworks #weekendgetaway

By land and by sea, Seas The Bay Sailing is thrilled to partner with Visit Annapolis. Contact us for your private cruise and special occasions to experience Annapolis on the water! Kudos to the hard- working folks at Visit Annapolis and Annapolis Discovered for bringing back the charm and sheer joy of our town❤️⛵️#visitannapolis #annapolisdiscovered #4thofjuly #annapolismaryland #chesapeakebay #onthewater #fireworks #weekendgetaway

06/25/2021

The playful Annapolis sky delivers once again! Sunset and moonrise all at the same time. 👏⛵️🌞🌕#visitannapolis #annapolisdiscovered #sunsetcruise #chesapeakebay #sailingcharter #staycay #familyfun #romanticgetaway #cruiseideas #visitmaryland

The playful Annapolis sky delivers once again! Sunset and moonrise all at the same time. 👏⛵️🌞🌕#visitannapolis #annapolisdiscovered #sunsetcruise #chesapeakebay #sailingcharter #staycay #familyfun #romanticgetaway #cruiseideas #visitmaryland

06/22/2021

It’s V***e Time! Her SMILE and that RING shone brighter than the sun🍾❤️💍. Congrats on your dreams coming true! #proposal, #proposalideas #surpriseproposal #dcengagement #annapolisinn #annapolisengagement #howtheyasked #proposalcruise #mdproposal, #vaproposal #specialoccasionideas #chartersailboat #cruiseannapolis #smrosapepe

It’s V***e Time! Her SMILE and that RING shone brighter than the sun🍾❤️💍. Congrats on your dreams coming true! #proposal, #proposalideas #surpriseproposal #dcengagement #annapolisinn #annapolisengagement #howtheyasked #proposalcruise #mdproposal, #vaproposal #specialoccasionideas #chartersailboat #cruiseannapolis #smrosapepe

New Chesapeake Bay Adventures | Washingtonian (DC) 06/21/2021

New Chesapeake Bay Adventures | Washingtonian (DC)

Thank you Washingtonian Magazine for the mention- we love taking people out #sailing on the #chesapeakebay.

New Chesapeake Bay Adventures | Washingtonian (DC) “Water water everywhere” could arguably be the motto for the Chesapeake Bay area here in Maryland. From beautiful natural lakes boasting vast and serene

06/19/2021

Seas the Bay Sailing congratulates this Ironman family and Karis and Macy for their impressive completion of this incredible event in Cambridge MD. Way to go girls👏🏆🏅. So proud of you both! ❤️⛵️🏃‍♀️🏊‍♀️🚴‍♀️#ironman #ironmancambridge #visitannapolis #sailingcharter #weekendgetaway #familyfun #chesapeakefamily

Seas the Bay Sailing congratulates this Ironman family and Karis and Macy for their impressive completion of this incredible event in Cambridge MD. Way to go girls👏🏆🏅. So proud of you both! ❤️⛵️🏃‍♀️🏊‍♀️🚴‍♀️#ironman #ironmancambridge #visitannapolis #sailingcharter #weekendgetaway #familyfun #chesapeakefamily

It's now easier to send Seas the Bay Sailing a message. 06/17/2021

It's now easier to send Seas the Bay Sailing a message.

It's now easier to send Seas the Bay Sailing a message.

06/15/2021

Congratulations on 47 years of wedded bliss. ❤️🍾Seas the Bay Sailing is honored to be their chosen vessel for marking their date.
We always learn something from our guests! As they so wisely noted, they are in their GoGo chapter of life. Next is SLO-go, then it’s NO-go. They are fully embracing their GoGo days❤️⛵️🥰😎A truly inspiring couple. Thank you for sharing your day with us! #anniversary #anniversarygift #sailinggifts #yachtcharter #visitannapolis #annapolisdiscovered #sailannapolis #lifeonthewater #surpriseproposal #celebrateanniversary

Congratulations on 47 years of wedded bliss. ❤️🍾Seas the Bay Sailing is honored to be their chosen vessel for marking their date.
We always learn something from our guests! As they so wisely noted, they are in their GoGo chapter of life. Next is SLO-go, then it’s NO-go. They are fully embracing their GoGo days❤️⛵️🥰😎A truly inspiring couple. Thank you for sharing your day with us! #anniversary #anniversarygift #sailinggifts #yachtcharter #visitannapolis #annapolisdiscovered #sailannapolis #lifeonthewater #surpriseproposal #celebrateanniversary

06/11/2021

People may forget what you said, but not what you did! Join Susan on Seas the Bay Sailing for an unforgettable day on the #chesapeakebay. Go to https://www.seasthebaysailing.com/ to book your trip today!
#sailing #sailingcharters #sailinglife #boatinglife #annapolissailing #chespeakebaysailing

People may forget what you said, but not what you did! Join Susan on Seas the Bay Sailing for an unforgettable day on the #chesapeakebay. Go to https://www.seasthebaysailing.com/ to book your trip today!
#sailing #sailingcharters #sailinglife #boatinglife #annapolissailing #chespeakebaysailing

Sea Us in the News — Seas the Bay 06/08/2021

Sea Us in the News — Seas the Bay

Thank-you SpinSheet Magazine for the mention in the June Issue. Follow the link to read the complete article. https://www.seasthebaysailing.com/sea-us-in-the-news

Sea Us in the News — Seas the Bay

06/02/2021

Seas the Bay Private Sailing Charters

Great video and article that Visit Annapolis put together showcasing our private charters including crew interviews and onboard sailing! We still have openings for the second week of June so head on over the seasthebaysailing.com to book your private sailing charter today!
#sailing #boating #annapolis #VisitAnnapolis #sailinglife #annapolissailing #chesapeakebaysailing

06/01/2021

Seas the Bay Private Sailing Charters

What a fun day on the Bay with the team at Annapolis Discovered. Thanks so much for this great video!

05/31/2021

Seas The Bay Sailing Charters remembers and honors our brave men and women today - and every day- who have made it possible for us to freely fly our American flag with pride🇺🇸❤️⚓️⛵️#memorialday #proudamerican #memorialdayweekend #visitannapolis #naptownscoop #lifeonthewater

Seas The Bay Sailing Charters remembers and honors our brave men and women today - and every day- who have made it possible for us to freely fly our American flag with pride🇺🇸❤️⚓️⛵️#memorialday #proudamerican #memorialdayweekend #visitannapolis #naptownscoop #lifeonthewater

Seas the Bay Sailing updated their address. 05/28/2021

Seas the Bay Sailing updated their address.

Seas the Bay Sailing updated their address.

Seas the Bay Sailing updated their phone number. 05/28/2021

Seas the Bay Sailing updated their phone number.

Seas the Bay Sailing updated their phone number.

05/28/2021

See and experience Annapolis and the Chesapeake Bay on your own private charter with Seas the Bay Sailing. Go to www.seasthebaysailing.com to book your private sail today.
#sailinglife #sail #sailannapolis #visitannapolis #boating #Annapolissailing #boatlife #yacht

Seas the Bay Sailing updated their phone number. 05/28/2021

Seas the Bay Sailing updated their phone number.

Seas the Bay Sailing updated their phone number.

New Private Charter Sailboat Sets Sail in Annapolis | Eye On Annapolis 04/28/2021

New Private Charter Sailboat Sets Sail in Annapolis | Eye On Annapolis

In case you missed here is an article that Eye On Annapolis posted about us. #sailing #annapolissailing #chesapeakebay #eyeonannapolis #annapolis #boating

New Private Charter Sailboat Sets Sail in Annapolis | Eye On Annapolis Seas the Bay Sailing has announced they will be offering private sailing cruises in and around Annapolis on the 54-foot sailing yacht, Southerly . Starting June 1, 2021, Seas the Bay Sailing will be offering three-hour luxury private afternoon and sunset charters aboard the 54-foot Irwin sailing yac...

04/24/2021

Did you know we provide specialty cruises by request?
Our excursions are 3 hours and can include up to 6 people. Included are gourmet appetizers and fine wine or champagne. Perfect for anniversaries and birthdays, wedding proposals, and bachelorette parties. To book your specialty cruise email [email protected] or call 410-881-3264.
#sailing #annapolis #annapolissailing #chesapeakebay

Did you know we provide specialty cruises by request?
Our excursions are 3 hours and can include up to 6 people. Included are gourmet appetizers and fine wine or champagne. Perfect for anniversaries and birthdays, wedding proposals, and bachelorette parties. To book your specialty cruise email [email protected] or call 410-881-3264.
#sailing #annapolis #annapolissailing #chesapeakebay

04/22/2021

Meet the Crew of Seas the Bay Sailing, Captain Chris and First Mate Susan. They look forward to welcoming you aboard. Be sure to go to seasthebaysailing.com to book your private sailing charter today.

Meet the Crew of Seas the Bay Sailing, Captain Chris and First Mate Susan. They look forward to welcoming you aboard. Be sure to go to seasthebaysailing.com to book your private sailing charter today.

Seas the Bay Sailing updated their business hours. 10/21/2020

Seas the Bay Sailing updated their business hours.

Seas the Bay Sailing updated their business hours.

Seas the Bay Sailing updated their information in their About section. 10/20/2020

Seas the Bay Sailing updated their information in their About section.

Seas the Bay Sailing updated their information in their About section.

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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Location

Category

Products

Private Sailing charters on 54ft sailboat in the Chesapeake Bay

Telephone

Address


326 First Street
Annapolis, MD
21403

Opening Hours

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