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
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.
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.
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Depending on the weather and time of year, we may have time for a swim or water activity, so bring your swimsuit. If it’s later in the year, beyond summer, a light jacket is always nice to have. Most important, bring sunscreen and a hat to protect from the sun, even on cloudy days.
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Rubber soled deck shoes (non-black) are the safest shoes for boats.
For our charters, we ask you to remove your shoes before boarding the yacht and we will keep them dry and out of the way for the trip. -
Sailing is always weather and wind dependent. Captain Chris is a master at reading the winds and positioning the vessel to catch the wind if there is wind to catch! Your time on the water will be just as wonderful either way – we can motor-sail and it’s just as beautiful!
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The motion of our sailboat is very easy, and we are never far from land. The design of Southerly is very stable, and “heeling” (tipping) you may have experienced on other sailboats is minimal and controllable. If you’re in doubt, we have ginger chews on board, as well as ginger ale that has been said to help. If you are someone who is prone to seasickness, we have Sea Bands pressure point wristbands available for purchase.
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Not to worry, we won’t be going out in heavy rains, thick fog, high winds or threatening weather conditions.
We do sail in cloudy, cool or overcast conditions, and on and off sprinkles.
Unfortunately we can't guarantee you a postcard picture-perfect sunset and we won't cancel a "sunset sail" just because it's overcast.
If the weather looks questionable, we'll check the radar before we leave and if it looks like it's going to start pouring and rain for most of the sail, we will cancel. If it looks like there might be an occasional light sprinkle, we'll go!
Weather can change quickly and dramatically here. Some days it may be pouring in the morning and then be beautiful in the afternoon, or pour all day only to stop just before our sunset sail. And there have been days where the chance of rain is 80% and then it never rains. Therefore, we don't call off our trips when we see a five day forecast that calls for "a chance of thundershowers."
The timing and path of thunderstorms is very hard to predict, therefore a decision to cancel a sail because of a thunderstorm watch is typically only made 30 minutes before departure.
If we cancel your sail due to adverse weather conditions, you will receive a 100% refund, can elect to reschedule, or receive a gift certificate for a future trip.
The final decision to sail resides with us. If you've booked a charter and decide not to show up because of the weather and we are able to sail, your charter will not be refundable.
We have had many enjoyable trips in less than spectacular conditions. We think this policy is fair and appreciate your cooperation.
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As with any vacation experience, a gratuity is never expected, but always appreciated!
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Yes, there are electric outlets on board.
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Yes, we have our own playlist, or you can connect your device to our Bluetooth speakers if you have music you would like to have on during your sail. We do, however, ask that all music is off if we are managing lines and sails.
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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
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Safety is always our top priority. In the rare event of a mechanical issue, we’ll either delay while we get it sorted, bring in a comparable boat to keep your trip on track, or reschedule if there’s no safe option that day. If we’re able to get you out on the water with a substitute vessel, that’s considered a completed charter. Because of the logistics and costs involved, we can’t offer refunds or credits for delays or vessel changes, and any pre-arranged items like food, drinks, or a photographer are non-refundable.
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Our yacht is meticulously maintained with exceptional attention to detail, ensuring every charter feels like stepping aboard a private luxury vessel. The bottom is cleaned regularly for smooth, effortless sailing, while the deck and hull are professionally detailed to maintain their gleaming finish. After each trip, the interior is thoroughly cleaned and sanitized so every guest is welcomed into a pristine, fresh, and beautifully cared-for space.
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. By purchasing a charter with STB, you acknowledge that you have read, understood, and fully agreed to these TERMS AND CONDITIONS.
Number of Guests & Children On Board
Seas the Bay Sailing Charters is licensed to carry a maximum of 6 paying guests.
Maritime law counts children of all ages as passengers; a ticket is required for each child regardless of age.
Children under 10 years of age MUST be accompanied by an adult at all times. This adult must be a member of your party, not a crew member. This is for the child’s safety, as sailboats have open decks and are subject to unpredictable movements.
A minimum of two guests is required for any charter.
Life Vest Policy
Life vests are provided for each passenger.
Federal law requires children under 13 years of age to wear a lifejacket at all times when on deck and the vessel is underway (except when below deck).
Cancelling Reservations and Charters
Charters are valid only for the date and time purchased.
Cancel at least 5 days in advance: 100% refund.
Cancel less than 5 days in advance: 75% refund.
Cancel less than 24 hours in advance: No refund.
Weather Policy
If STB cancels your sail due to adverse weather, you may receive a 100% refund, reschedule your trip, or receive a gift certificate for a future charter.
The Captain has the sole authority to decide if conditions are safe to sail.
If you choose not to attend because of weather but the Captain has deemed it safe to sail, your charter fee is non-refundable.
Mechanical Issues, Delays & Vessel Substitution
The safety of our guests and crew is our highest priority. By booking a charter, you acknowledge and agree to the following in the event of unforeseen mechanical or safety issues:
STB reserves the right to:
Delay departure until the issue is resolved,
Provide an alternate vessel (motor or sail) to complete the charter experience, or
Cancel the charter entirely if no safe alternative is available.
If an alternate vessel is provided and the charter proceeds, the trip is considered fulfilled in full. No refunds, credits, or discounts will be given for delays related to securing a safe vessel or for differences between vessels provided. Coordinating an alternate vessel involves significant expense and logistical work; guests agree such accommodations are a service, not grounds for reimbursement or credit.
If the charter must be cancelled prior to departure and no safe alternative is available, guests will receive a 100% refund or may choose to reschedule.
Costs already incurred to provide the charter experience (including catering, beverages, or professional photography) are non-refundable regardless of vessel substitution or delays.
Photographs
Representatives of STB may photograph your charter. Unless agreed otherwise prior to departure, STB reserves the right to publish such photographs without further consent.
Each guest releases STB and its representatives from liability in connection with the use of such photographs.
If you do not want photos used from your charter, you must notify STB prior to the start of the trip.
Personal Responsibility
All guests agree to follow the Captain’s directions and safety instructions at all times.
Each guest is entirely responsible for their own safety, health, and well-being during the charter.
Guests prone to motion sickness are responsible for their own preventative measures.
All guests release STB from liability for injuries or damages resulting from reckless behavior or failure to follow crew instructions.
The Captain reserves the right to disembark any guest whose behavior poses a danger to themselves or others.
STB does not provide health or travel insurance; guests are encouraged to arrange their own coverage if desired.