There is no better way to see Annapolis than by the water on our 54-foot sailing yacht! We will meet you at the boat with a welcome beverage to enjoy while we prepare the boat for launch. Before we take off, we will have the safety briefing and tour of the vessel.

Then leave the work to us and the fun to you!

3 Hour Charter

Our excursions are 3 hours. All beverages are included on our charters and this includes fine wine or champagne. We offer gourmet appetizers for an additional fee. For special, intimate occasions, a dinner and dessert offering is available for parties of two only. When possible, we are happy to accommodate dietary restrictions and special requests.

Our water tour begins with a cruise along the protected Annapolis shoreline dotted with beautiful homes. During the season, you may see nesting Osprey that return year after year from Central and South America to the very same nests.

We enter into the Chesapeake Bay where you will be fascinated with the water view perspective of the Bay Bridge, at one time the world's longest continuous over-water steel structure at 4.3 mi (6.9 km).

Weather permitting, we hoist the sails and immerse in the quiet peacefulness of sailing! From the Bay, we sail towards historic Annapolis, taking you along the banks of the Severn River. From this on-the-water perspective, you will have incredible views of the US Naval Academy and come to understand the allure and charm of the area.

Before our return, we will enter the famous historic Annapolis harbor area, which today is a vibrant, fun and picturesque destination not to be missed.

Cruises

Sail and Swim Sunset Charter - Our Signature (and most popular)

For this excursion we take you on a tour around the Bay and Annapolis Harbor, then complete your sail time in a beautiful anchorage spot. Take a dip to cool off, float on a multi-person raft, enjoy a beverage and cast your worries aside, while watching the sunset fill the sky with hues of red, orange and purple

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Sunset and Champagne Cruise – For the Romantics

For 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!

Specialty Cruises by Request

Our excursions are 3 hours and can include up 6 people. All beverages are included on our charters and this includes fine wine or champagne. We offer gourmet appetizers for an additional fee. For special, intimate occasions, a dinner and dessert offering is available for parties of two only for an additional charge. When possible, we are happy to accommodate dietary restrictions and special requests.

• Anniversaries and Birthdays Celebrations Cruise

• Proposal Cruise (and we will keep the surprise for you)

• Bachelorette Soiree On The Water Cruise

• USNA Family Weekend Cruise

• Corporate Outing Cruise

To book a specialty cruise email susan@seasthebaysailing.com or call 410-881-3264

Food & Beverage Options

Depending on the Experience Level you select, we can accommodate your requests as follows:

Snacks (nuts, chips, dips etc.) and non-alcoholic beverages

Appetizers (i.e.: select cheeses, breads, salamis, fruits, crudite) - $25 per person

Lunch (sandwiches or wraps) - May be brought onboard. We can give you contact info for local places that have wonderful prepared foods for you to order and bring onboard

Special occasion for Two (On Request) Special beverages and select gourmet appetizers (ie: Italian antipasti) , dinner (grilled fish or meat) cooked and served on-board) with sides– TBD( fee ranges $200-$250 per person)

Special diet arrangements within reason are available (vegan, gluten-free etc)

Gift Certificates – Not sure what to gift a loved one… Consider giving a gift certificate aboard the Southerly! To purchase a gift certificate, please contact Susan at susan@seasthebaysailing.com or text 513-604-1387.

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FAQ’s

We answer some of our most frequently asked questions here. If something remains unanswered for you, please feel free to contact us anytime.

Where do we embark and disembark?

You will board the boat at 1795 Beachfield Rd., Annapolis MD 21409. You will be dropped off at the same location, 1795 Beachfield Rd., Annapolis MD 21409. NO EXCEPTIONS


Terms & Conditions

These TERMS AND CONDITIONS outline what Seas the Bay Sailing Charters LLC ("STB") agrees to provide when you purchase a charter with STB , and what you agree to do in return. This information is very important, please read it carefully.  By purchasing a charter with STB sailing charters, you have agreed to have read, understood, and fully agreed to the foregoing TERMS AND CONDITIONS. 

Number of Guests Required and/or Allowed - Special Note about Children On Board
Seas the Bay Sailing Charters
is licensed to have a maximum of 6 paying guests. Maritime law considers children of all ages to be passengers, therefore no matter the age of the child, a ticket purchase is required. Although we allow children, children under the age of 10 MUST have an adult with them AT ALL TIMES. That adult is NOT the crew. This if for the safety of the child, as a sailboat has wide open decks and is subject to unpredictable movements. Seas the Bay Sailing Charters requires a minimum of two guests for any charter.


Life Vest Information
Life Vests are provided for each passenger on our vessel. Federal Law requires that when a vessel is underway, children under 13 years of age must wear their lifejacket at all times except when below deck.

Cancelling Reservations and Charters:
Charters are valid only for the date and time purchased. Charters may be cancelled and a 100% refund issued, if you cancel at least 5 days before your sail. If you cancel less than 5 days before departure you will be refunded 75%. No refunds for sails cancelled less than 24 hours before departure. 

Weather: 
If we cancel your sail due to adverse weather conditions, you will receive a 100% refund, can choose to reschedule, or receive a gift certificate for a future trip. See our FAQ answer above about weather.

The final decision to sail resides with us. If you've made a reservation for a charter and decide not to show up because of the weather and the boat is able to sail, your charter fee is non-refundable.

Photographs
We respect your privacy and understand if you do not want photos used from your charter.  You must let us know prior to the start of the charters.  Representatives of Seas the Bay LLC may be photographing the Charter. Unless agreed upon differently prior to the cruise, Seas the Bay Sailing Charters reserves the right to publish any such photographs without obtaining further consent from any Charter Participant. Each Charter Participant releases Seas the Bay Sailing Charters LLC and its representatives from any liability in connection with any such use of such photographs.

Personal Responsibility: 
All guests on Seas the Bay Charters agree to abide by the directions and safety instructions of the Captain at all times. Each guest is entirely responsible for their own personal safety, health, and mental, physical, emotional, and general well-being during the Charter. If a guest feels they are prone to motion sickness, they must take responsibility for their own preventative measures.  All charter guests release Seas the Bay LLC of any liability for any injuries or damages mentally or physically incurred during the charter as a result of reckless individual behavior. Captain of the vessel reserves the right to disembark any guest for reckless behavior or if posing danger to themselves or other charter guests.  Charter guests understand that no health insurance or travel insurance will be provided by the charter company, and, if they wish to be insured, they must take personal responsibility for securing their own coverage.