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Frequently Asked Questions

Walking Tours || Yacht Charters || Sightseeing Cruises || Field Trips || Groups

Where do the tours start and end?

Our tours start and end at several locations. Visit our Tours page for a listing of our public tours and their locations.

How long are the tours?

Our public guided walking tours are led by guides in Colonial attire and last between 90 minutes and 2.25 hours. Visit our Tours page for a listing of our public walking tours and their durations. Private walking tours may be arranged for groups of any size. For more information visit our Groups page.

Do the tours stop anywhere?

Your guide will stop frequently during the tour to provide information to you. When the group stops, there are not typically places to sit.

Where should I park?

There are several parking options in Annapolis including parking garages and street parking. Visit our Directions and Parking page for information on how to get to Annapolis and where to park when you get here.

What will we see on the tour?

We offer a variety of tours that provide a unique perspective of Annapolis. Our Three Centuries Walking Tour includes the historic district of downtown Annapolis Maryland and the grounds of the U.S. Naval Academy. Visit our Tours page for a complete listing of our public walking tours.

Will we go inside any buildings?

Our Three Centuries Walking Tour includes the interiors of the Maryland State House, the U.S. Naval Academy Chapel and the Crypt of John Paul Jones. Tours of interiors are subject to availability and may be closed without notice to Watermark.

Will I need to bring anything with me?

You will need to bring photo identification with you. Everyone 16 years of age and older will need to present photo identification when entering the Maryland State House and the U.S. Naval Academy (penknives are not permitted in the Maryland State House). We suggest your dress comfortably. We offer tours year round, so dress appropriately for the weather.

What happens if it rains?

Our tours take place rain or shine. Plan and dress accordingly.

Are the tours handicapped accessible?

Yes. Most of your tour will take place outside. However, any building(s) that you enter are handicapped accessible. Please contact the Watermark Sales Office at 410.268.7601 or contact us online to discuss any special needs or requests.

How do I pay for and get tour tickets?

Tickets for most of our public tours are sold on a walk-up basis only (no advanced reservations). Tickets may be purchased from your tour guide 15 minutes prior to the tour start time. Payment may be made by cash, check, traveler’s check, or money order (and for tours that require reservations, tickets may be purchased by credit card in advance).

Annapolis Yacht Charters

What time does the charter begin?

Your charter start time and duration is customized to meet your needs. Your Watermark Event Planner will work with you to create a custom event that can vary in start time and duration. Event specific information will be outlined on your contract.

Where do we board the boat?

Boarding and departure locations vary based on your needs (and other factors such as size of the boat, water depth, etc.). A Watermark Event Planner will work with you to find the best location for your group. Once the location has been finalized the Event Planner will provide you with directions and parking information.

Where does the boat go?

A Watermark Event Planner will work with you to determine the cruise route that best meets your vision of your event. The cruise route may be altered during your event if you so choose or as weather dictates. Ask a Watermark Event Planner about Destination Charters and Themed Events.

What do we do during the charter?

A Watermark Event Planner will assist you with additional activities that can help create a memorable event for your group. For a unique experience, package your event with a Walking Tour with our colonial tour guides. Ask a Watermark Event Planner about Destination Charters and Themed Events.

How big is the boat and what does it look like?

Watermark proudly owns a fleet of 11 boats that vary in size and style and has access to many other U.S. Coast Guard Certified vessels. A Watermark Event Planner will work with you to find the perfect boat for your event. Visit Our Fleet page to see pictures and descriptions of our boats.

What happens if it rains?

Our events take place rain or shine. Most of our vessels have indoor space that is climate controlled. A Watermark Event Planner will help you choose a boat that will allow your group to have a perfect event, even if it rains.

Do charter guests get seasick?

Our charter guests rarely get seasick. Most of our charter events take place on the Severn River, a waterway that is calm in most weather conditions. Some guests may still choose to take precautions if they are prone to motion sickness.

Do I have to wear a life jacket?

No. Guests who wish to wear a lifejacket during the cruise are welcome to bring one. All Watermark vessels are U.S. Coast Guard inspected and certified; they have emergency equipment including lifejackets in the unlikely event they are needed.

Can I bring my own food and beverages?

Guests are welcome to bring their own food for a per person fee that varies by boat. We recommend using one of our preferred caterers who are all very experienced in providing top-notch meals aboard our boats. Beverage service is offered through Watermark. All boats have liquor licenses and our Event Planners will help you customize catering and beverage service options based on your budget and your vision of the event.

Who do I talk to if I have questions during the event?

Questions during an event may be directed to an Event Planner or Watermark captain. Watermark’s captains are all licensed by the U.S. Coast Guard and are trained to provide a safe and fun environment for your guests.

Are the boats handicapped accessible?

Please contact our sales office at (410) 268-7601, ext. 100 or contact us online to discuss any special needs or requests.

Sightseeing Cruises in Annapolis Maryland

Where do the cruises start and end?

Our public cruises depart from Annapolis City Dock. Boarding time is 15 minutes prior to the start time of the cruise. Visit our Directions and Parking page for information on how to get to Annapolis City Dock.

How long is the cruise?

Our cruises vary in duration from 40 minutes up to 8 hours. Visit our Cruises page for a listing of all cruises and their durations.

Where should I park?

Can I bring food and drinks onto the boat?

Guests are welcome to bring a snack onto the boat. However, beverages are not permitted. Light snacks, beverages and cocktails may be purchased on all of our cruises.

What if it rains?

Our cruises will take place rain or shine. All cruises are subject to cancellation due to severe weather, lack of participation, or mechanical breakdown.

Do I have to wear a life jacket?

How do I pay for and get cruise tickets?

Advanced ticket reservations are available for many of our tours and cruises either through online reservations or by calling the Sales office at 410.268.7601, Monday – Friday from 8:30 AM – 5:00PM. For cruises that are walk-up only, tickets may be purchased on the day of the cruise. Acceptable payment methods are credit card (Visa, MasterCard, American Express, Discover), cash, check, traveler’s cheque, and money order.

May I bring my dog?

Yes! Watermark welcomes dogs on leashes and their responsible owners aboard our tour boats.

May I bring a stroller?

Yes. Strollers are welcome aboard our tour boats.

Are the cruises handicapped accessible?

Please contact our sales office at (410) 268-7601, ext. 104 or contact us online to discuss any special needs or requests.

Annapolis Maryland Field Trips

What if it rains on the day of our field trip?

Our field trips take place rain or shine. You should advise your students to dress appropriately for the weather.

What time will our field trip start?

Our field trips are customized to meet the needs of your group. We offer several tours and cruises per day, so there is flexibility that allows us to work with your time schedule. Our Field Trip Planners will work with you to find a schedule that will work for your group. Visit our Field Trips page for some field trip ideas.

Are we required to have parent chaperones?

We do not require a specific number of chaperones. However, we request that there be an appropriate number of adults present to manage the group. Keeping a low ratio of students to adults allows us to provide you with the most informative and fun field trip possible.

Where does our field trip start and how do we get there?

The start location of your field trip may vary depending on your itinerary. Our Field Trip Planners will make sure you have directions, a map, and parking information.

Where can we eat lunch?

Many school groups choose to eat lunch at Susan Campbell Park located at Annapolis City Dock. It is an outdoor area with limited seating. Our Field Trip Planners will be able to provide you with other options including purchasing box lunches, eating aboard a boat, or eating in a local restaurant. Visit our Field Trip Meal Options page for details.

Is there anything we need to bring?

If you are taking a walking tour, everyone 16 years of age and older will need to present photo identification when entering the Maryland State House and the U.S. Naval Academy (penknives are not permitted in the Maryland State House). In addition, any required payments must be made prior to the beginning of your field trip. Your Field Trip Planner will notify you if there is any outstanding balance.

How much paperwork is involved in booking a field trip?

Our Field Trip Planners will be happy to provide you with a written proposal that you can discuss with your team. Once an itinerary has been agreed upon, a contract will be sent to you. A signed copy of the contract must be returned to Watermark in order to guarantee your trip. Along with your contract you will receive directions, parking information, a map, a field trip guide, and other appropriate paperwork (menus, other instructions, etc.). You will be given a receipt for any payment you make to Watermark.

Are the field trips handicapped accessible?

Please contact our sales office at (410) 268-7601, ext. 104 or contact us online to discuss any special needs or requests.

Groups Explore Annapolis Maryland by Land and Water

What if it rains on the day of our trip?

Our group trips take place rain or shine. You should advise your group members to dress appropriately for the weather.

What time will our trip start?

Our trips are customized to meet the needs of your group. We offer several tours and cruises per day, so there is flexibility that allows us to work with your time schedule. Our Group Tour Planners will work with you to find a schedule that will work for your group. Visit our Groups page for some group tour ideas.

Where do we start our tour or cruise and how do we get there?

The start location of your trip may vary depending on your itinerary. Our Group Tour Planners will provide directions, a map, and parking information.

Where can we eat lunch or dinner?

Our Group Tour Planners will assist you with any decisions about where or what your group would like to eat. For added convenience, we will make your group meal arrangements for you. Visit our Group Meals page for some meal options.

Is there anything we need to bring?

If you are taking a walking tour, everyone 16 years of age and older will need to present photo identification when entering the Maryland State House and the U.S. Naval Academy (penknives are not permitted in the Maryland State House). In addition, any required payments must be made prior to the beginning of your trip. Your Group Tour Planner will notify you if there is any outstanding balance.

How much paperwork is involved in booking a group trip?

Our Group Tour Planners will be happy to provide you with a written proposal for your consideration. Once an itinerary has been agreed upon, a contract will be sent to you. A signed copy of the contract must be returned to Watermark in order to guarantee your trip. Along with your contract you will receive directions, parking information, a map, and other appropriate paperwork (menus, other instructions, etc.). You will be given a receipt for any payment you make to Watermark.

Are the group trips handicapped accessible?

Please contact our sales office at (410) 268-7601, ext. 104 or contact us online to discuss any special needs or requests.