Watermark Tours Charters Cruises

Watermark Tours Charters Cruises


From 1972 to 2022, Watermark Tours Charters Cruises has immersed people in the history, culture, and fun of the Chesapeake Bay area. Read the full story at: https://www.proptalk.com/watermark-celebrates-50-years
Join us for a compilation of the highlights of what the T2PTV team pointed cameras at to bring you the action, the stories, the mission of events, locations, and maritime companies on and near the water in 2021!!

Chicago Yacht Club Race To Mackinac, Clearwater Marine Aquarium, Chesapeake Bay Yacht Racing Association, Bacardi Cup Invitational Regatta, Annapolis Yacht Club Regattas, Annapolis Snipe Fleet 532, Jworld Sailing Annapolis Md, Schooner Woodwind: Annapolis Sailing Cruises, Annapolis Maritime Museum & Park, Watermark Tours Charters Cruises, boats.com, Boatyard Bar & Grill, Boat Trader, Elaine Weiner-Reed, Jeanneau, U.S. Naval Academy Alumni Association & Foundation, US Sailing, J105 Class Association, J/70 Fleet 1 - Annapolis, Maryland USA, Visit Annapolis, Hospice Cup, C. Thomas Clagett, Jr. Memorial Regatta, Corinthian Yacht Club National Women’s Invitational Team Race-Thayer Trophy, Intercollegiate Sailing Association (ICSA), Eastport Yacht Club, Eastport Yacht Club Lights Parade, Severn Sailing Association, Dave Gendell, Dobbs Davis, Scott Nixon, Bruce Nairn, Carter Cameron, Lenny Rudow, M. Ashley Love, Little Treasury Jewelers, Wilkins autos
Picture yourself sitting here having a fresh cooked breakfast, mostly scratch made, fresh locally roasted coffee (thx Ceremony Coffee Roasters )… after a great nights sleep…. Ready to explore Annapolis…. United States Naval Academy Schooner Woodwind: Annapolis Sailing Cruises Watermark Tours Charters Cruises ,,,, grazing around town …. Forward Brewing , Boatyard Bar & Grill Preserve Galway Bay Irish Restaurant and Puba ….. and so many more…..

Ok snap out of your daydreaming! Start planning your visit to Annapolis today! Links in profile….

Think warm thoughts today!

Photography by @elizabethcampbellphotography

#annapolis #visitannapolis #travel #downtownannapolis #historicannapolis #breakfast #bedandbreakfast #travellerschoice #bookdirect
Congratulations to the Iverson family and we wish all the best to Debbie Gosselin in her retirement/new adventures.
Watermark Tours Charters Cruises
Last but not least! Our final Special Shout Out to our Maryland Fun Sponsors - Experience Prince George's & Watermark Tours Charters Cruises - for the ABA Foundation American Bus Association Auction Presented by MARS & Partners to take place during the ABA Marketplace 2022 in Grapevine, Texas!

#princegeorgescounty #watermark #americanbusassociation #abamarketplace #abamarketplace2022 #grapevinetx
It’s peak season for fall foliage in #annapolis and #annearundelcounty! Watch this segment from Fox 5 DC and Watermark Tours Charters Cruises to learn more.

#fallfoliage #visitannapolis
During our trip to Baltimore, our tour guide Mistress Mary brought us into the world and early experience of young Frederick “Freddie” Douglass’! Mistress Mary brought us to major landmarks within the inner harbor and brought to life the people (good and bad) that shaped Frederick Douglass’ before his escape to the north. It was a great way to learn about a major figure of US history and see the inner harbor area of Baltimore! We certainly got our 5,000 steps in!!!
S/O to Watermark Tours Charters Cruises and Janet M. Budzyna (Mistess Mary) for a great experience!
👻 Tonight's Spooky Halloween Nights 👻

Many of us know there are graves around the St. Anne's Episcopal Church - Annapolis Maryland .

This particular one has a skull on it. Do you know what this meant?

Discover what important message the skull on this grave relays with Watermark Tours Charters Cruises
The Historic Hauntings Tours.

Hurry, the last tour of the season is tonight.

👻 Tonight's Spooky Halloween Nights 👻

Little Brice House / John Brice II House
195 Prince George Street

This is one of the oldest houses in Annapolis. Haunted? If you look long enough up into the corner window, you see something but what or who?

Learn more with Watermark Tours Charters Cruises
The Historic Hauntings Tours run this week:

More to come!

A peek at The Historic Hauntings Ghost Tour by Watermark Tours Charters Cruises with Kevin Sullivan.
The Historic Hauntings Tours run:

👻 Listening to ghost stories of Annapolis under this moon👻

A peek at The Historic Hauntings Ghost Tour by Watermark Tours Charters Cruises with Kevin Sullivan.
The Historic Hauntings Tours run:

Only the moon knows.....

Historic Hauntings Ghost Tour by Watermark Tours Charters Cruises .

The Historic Hauntings Tours run:


Watermark has immersed people in the history, culture, and fun of the Chesapeake area more completely than any other tour or charter company for over 45 years.

Whether you want to learn or just enjoy the Chesapeake Bay area, no one else offers so many ways to experience this special place, both by land and by water, in less than an hour or as long as you like. Watermark® an Annapolis-based, locally owned and operated business, has been creating authentic experiences since 1972. Offering land and sea tours, cruises and special events for individuals and groups in both Annapolis and Baltimore.

Operating as usual

Timeline photos 05/20/2022

Here's your sign to surprise your partner with a sunset date night 🥰🌅🥂

🎟️ cruisesonthebay.com/annapolis-sunset-cruise/ 🎟️

Timeline photos 05/19/2022

Trace the journey of African Americans, and explore their impact both nationally and internationally on our 2-hour walking tour, offered in partnership with the Kunte Kinte-Alex Haley Foundation and named a “Heritage Award Winner” by the Four Rivers Heritage Area ➡️ This Saturday afternoon in Annapolis

🎟️ annapolistours.com/african-american-heritage-tour/ 🎟️

📸 Wendy Hickok Photography

Timeline photos 05/18/2022

How we feel about this spring weather😄🌸😎

Timeline photos 05/14/2022

Different year, same vibe ☔🦆

Timeline photos 05/13/2022

We'll be here at the end of City Dock all weekend (and all month and all spring and summer 😉)

Timeline photos 05/12/2022

Annapolis gets very quiet on Sundays during the early-evening lull, making it the perfect time to explore the city's architectural history 🏛️🌅✨

🎟️ annapolistours.com/architrex/ 🎟️

📸 Wendy Hickok Photography

Timeline photos 05/11/2022

Enjoy summer cocktails this Thursday afternoon as you cruise along the beautiful Middle Branch of the Patapsco River in South Baltimore and hear the history and significance of Port Covington, the surrounding neighborhoods, and the Patapsco River 😎🍹☀️ Presented by Port Covington

🎟️ cruisesonthebay.com/middle-branch-water-tour/ 🎟️

Timeline photos 05/09/2022

Come hang with us Saturday night on our Annapolis Sunset Cruise with Live Music, featuring Crosby Cofod 🤩🎶🌅

🎟️ CruisesOnTheBay.com/Annapolis-Sunset-Cruise-With-Live-Music/ 🎟️

Timeline photos 05/02/2022

Is it Friday yet? Get over the mid-week slump on Wednesday's happy hour cruise: It's 5 O'Clock on Harbor Queen 🕔 Enjoy a fun music playlist, $1 off soft drinks, beer, wine, and house cocktails, and complimentary popcorn 😎🍿🍹

🎟️ cruisesonthebay.com/its-5-oclock-on-harbor-queen/ 🎟️

Timeline photos 05/01/2022

Happy Sunday! It's a beautiful day to try a Queen's Kolsch 😉🍻✨

(Only available aboard Harbor Queen 👑)

Timeline photos 04/30/2022

Beginning tomorrow, our 90-minute Colonial Annapolis Walking Tour is back, departing from the Annapolis Visitor's Center on West Street 📜🖋️🙌

🎟️ AnnapolisTours.com/Colonial-Annapolis-Walking-Tour/ 🎟️

📸 Wendy Hickok Photography

Timeline photos 04/29/2022

Who's hanging out with us in Baltimore this weekend? 🙋‍♀️

Timeline photos 04/28/2022

Dancing into Friday like 🤪💃🙌


Thank you to our caterers, vendors, sponsors, partners, and community for such a wonderful evening! Here’s to 50 more 🥂✨

Timeline photos 04/25/2022

Saturday's guests got to see the Ever Forward pass under Chesapeake Bay Bridges! 🤩

📸 Captain Alex King

Timeline photos 04/24/2022

Pssst 👀 Mother's Day is right around the corner! Treat the moms in your life to a lovely brunch cruise ☺️

🍳 Buffet omelette station by The Original Omelette Man
🍾 One complimentary Momosa for moms
🎶 Live music by Guava Jelly

🎟️ watermarkjourney.com/events/mothers-day-cruise-in-annapolis/ 🎟️

Timeline photos 04/23/2022

Mood when you see 70s on the weather forecast 😁☀️🙌

📸 Wendy Hickok Photography

Timeline photos 04/22/2022

Last night was wonderful! Thank you to everyone that came out to support Watermark and Historic Annapolis 😊✨

📸 Rick Brady

Timeline photos 04/17/2022

We have spots open on our upcoming Bay Lighthouses Cruises April 25th & 28th! 🤩

🎟️ cruisesonthebay.com/bay-lighthouses-cruise/ 🎟️

Photos from Watermark Tours Charters Cruises's post 04/16/2022

Colonials are the coolest 😎

Timeline photos 04/15/2022

Living her best life 🐶🐾☀️

📸 youberrabelieveit on Instagram


Happy birthday, Jake, from the Harbor Queen crew! 🥳🎂🎉

Timeline photos 04/10/2022

Captain in training 😎⚓🛥️

Photos from Watermark Tours Charters Cruises's post 04/09/2022

"I’m here on a boat with a Francis Scott Key impersonator and a few dozen eighteenth-century literary historians as I sip a free martini and the sun sets over the Baltimore harbor. 10/10 would recommend."


Celebrate with us! ✨🍾

Celebrate with us! HA and Watermark Tours Charters Cruises are celebrating milestone anniversaries this year, and we want you to be a part of the party. Join us on April 21 for a spring evening in the Paca Garden - enjoy a glass of bubbly and sample creative bites from 19 of the area's premier caterers - plus live music, a raffle, and a gorgeous setting!

Tickets are $100 per person and all proceeds benefit Historic Annapolis. Buy yours now: https://6324.blackbaudhosting.com/6324/Watermark-Anniversary-Gala

Timeline photos 04/05/2022

Thank you all for your votes! We are so excited to win Best of Annapolis 2022 in the Charter Boat category 😊🙌✨


Timeline photos 04/03/2022

Who are you sipping bubbly with? 🥰🥂✨

Timeline photos 04/02/2022

What's your favorite Annapolis history tidbit? 🤔

📸 Wendy Hickok Photography

Timeline photos 04/01/2022

Catch the city lights on the water this Saturday night 🌃

🎟️ CruisesOnTheBay.com 🎟️


Amphicar Tour

Newest addition to the Watermark fleet 🤩

Just kidding! 🤣 But how cool would that be? 🙌


Tomorrow is opening day in Baltimore! Join us to explore Charm City from the water 😎🌊

🎟️ CruisesOnTheBay.com 🎟️

Watermark to Celebrate 50-Years at Historic Annapolis' William Paca House on April 21 - Eye On Annapolis 03/30/2022

Watermark to Celebrate 50-Years at Historic Annapolis' William Paca House on April 21 - Eye On Annapolis

Who's celebrating with us? 😊🥂🎉

Historic Annapolis


Watermark to Celebrate 50-Years at Historic Annapolis' William Paca House on April 21 - Eye On Annapolis Since 1972, Watermark has provided unforgettable journeys to millions of people with its iconic cruises and historic walking tours. Join Watermark in celebrating 50 years with an Anniversary Garden Gala on Thursday, April 21st from […]


Annapolis Town Crier, Squire Fred, giving a proclamation for On The Road with Bob Paff 🗣️📜

Timeline photos 03/27/2022

Our Anniversary Garden Gala is coming up quickly! 🥳🥂🌸

➡️ watermarkjourney.com/celebrating-50-years/

📸 Kenneth Tom


Cheers to the weekend 🥂🍾✨

Videos (show all)

Jolly Express Cruise
Jolly Express Cruise
Annapolitan II
Rock the Harbor with Tranzfusion
Baltimore Harbor Cruise
Day on the Bay to St. Michaels
Join the Watermark team!



Cruises, Private yacht charters, and Walking tours



1 Dock St
Annapolis, MD

Other Tour Guides in Annapolis (show all)
Schooner Woodwind: Annapolis Sailing Cruises Schooner Woodwind: Annapolis Sailing Cruises
80 Compromise St
Annapolis, 21401

Sail aboard two identical, wooden 74-foot schooners that sail out of Annapolis, Maryland. Public Cruise or Private Events can be arranged. Certificate of Excellence by Trip Advisor 2014, 2015, 2016, 2017, 2018 & 2019!

Seas the Bay Sailing Seas the Bay Sailing
326 First Street
Annapolis, 21403

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.

Southern Girl Sportfishing Southern Girl Sportfishing

Recreation, Education, Conservation. Light tackle fishing on the Chesapeake Bay.

Z Flight Parasail and Watersports Z Flight Parasail and Watersports
222 Severn Ave
Annapolis, 21403

Parasailing in beautiful historic downtown Annapolis. Families, friends, coworkers and special groups can all share in this fun activity. Fly above the Naval Academy and parallel to the Chesapeake Bay Bridge. 222 Severn Ave Annapolis, MD

Non Sea Quitter LLC Non Sea Quitter LLC
7074 Bembe Beach Road, Annapolis Md 21403
Annapolis, 21403

FUNtastic sailing tours on the 38' sailboat "Non Sea Quitter" from historic Annapolis Maryland. Relax and enjoy the Chesapeake with up to six guests--less than an hour from Baltimore or DC.

Skyline Adventure Tours Skyline Adventure Tours
Annapolis, 21401

This Sport craft is a pleasure flight available from popular US beach front locations. Taking to the air is the ultimate way to appreciate the landscape.

Annapolis Eventours Annapolis Eventours
26 West St
Annapolis, 21401

Annapolis Eventours is the best way to see Annapolis! We have history, food and craft beer tours and get you around town in our electric carts. We also provide transportation for weddings, corporate events, bachelor(ette), birthdays, graduations and more.

Colonial Tours Annapolis Colonial Tours Annapolis
26 West St
Annapolis, 21401

We are walking guides and colonial entertainers, offering tours in the Historic District of Annapolis. Our goal is for you to enjoy and experience History.

Haunted Harbor Tours Haunted Harbor Tours
Annapolis, 21403

At Haunted Harbor Tours we focus on giving the most scare for your buck. Hauntedharbortours.com