Annapolis, MD - Join Watermark® for an unforgettable holiday season! Voted one of the "25 Best Christmas Towns in the U.S." by Travel + Leisure, Annapolis truly becomes a winter wonderland. Watermark looks forward to sharing our charming city and this special time of year with our guests. "Amidst the hustle and bustle of business, it's important to pause and celebrate our cherished holiday traditions" said Jake Iversen, Watermark President. "These timeless customs remind us of what truly matters in our lives and in our work. We look forward to yet another wonderful holiday season!"

All aboard the Jolly Express! Annapolis' favorite holiday activity makes its return for the 2023 holiday season. Miss Anne will be adorned with reindeer spirit for an intimate 45-minute "sleigh ride" including hot cocoa, holiday music, and good cheer. Captain Santa is at the helm during this festive evening cruise on Spa Creek. Blankets will be available to stay warm and cozy, and alcoholic beverages will be available for purchase. Private cruises aboard the Jolly Express are also available! This is the perfect opportunity to start a family tradition, switch up your office party, or gather your friends for the holidays. In the spirit of the season, a portion of proceeds will be donated to Historic Annapolis. Beginning November 24th, this event will take place Friday, Saturday, and Sunday evenings as well as Midnight Madness Thursdays.

Tickets are S25/adult and $13/child. For reservations, please visit watermarkjourney.com/events/jolly-express-cruise.

Our traditional 90-minute Holiday Candlelight Stroll will lead you by lantern through the streets of Historic Annapolis. Stroll around Maryland's historic State Capital trimmed in greenery, and walk with our period-attired guide, who will share holiday traditions of times past among colonial mansions, Victorian homes, and quaint shops. Bring home the holiday cheer with a goody bag of treats including George Washington's famed eggnog recipe! This event will take place Friday and Saturday evenings at 7:00pm beginning November 24th.

Tickets are $26/adult and $15/child. For reservations, please visit watermarkjourney.com/events/holiday-candlelight-stroll.

A hit in 2022, our Special Historic Holiday Tour with the Hammond Harwood House will be available on a weekly basis this year! Hear the stories from our Holiday Candlelight Stroll, and step into the Hammond Harwood House as the final stop on your tour. There, enjoy authentic, colonial, holiday decorations provided by local garden clubs, and learn about early nineteenth-century holiday traditions. Cider will be served, and the Hammond Square Gift Shop will be open for holiday shopping at the end of the tour. This event will take place every Saturday from November 25lh through December 30.

Tickets are $29/adult and $15/child. For reservations, please visit watermarkjourney.com/events/special-historic-holiday-tour.

New this season is a Holiday Sup & Stroll in partnership with the Historic Inns of Annapolis. Begin your adventure with a gourmet meal in a beautifully decorated room at the historic Maryland Inn. The three-course, prix-fixe menu will feature specially chosen seasonal selections, along with fresh artisanal breads, and non-alcoholic beverages. Alcoholic beverages will be available for purchase from the bar. During your dessert course, a period-attired guide will greet you and introduce you to a variety of holiday traditions through the ages. After a celebratory toast of eggnog or spiced cider, follow your guide on a 60-minute walk around Church Circle, the Maryland State House, and nearby vicinity. You'll learn more about how the holidays were celebrated through the ages, as well as the beginnings of many of the modern-day customs we observe today. Bring home the holiday cheer with a goody bag of treats including George Washington's famed eggnog recipe! Enjoy dinner on Wednesday, December 6th or brunch on Sunday, December 10th.

Tickets are $95 per guest, and reservations can be made at watermarkjourney.com/events/holiday-sup-stroll.

Making its debut this year is Watermark’s Lights Parade Holiday Dinner Cruise with Ken’s Creative Kitchen. Join us aboard Raven for butler-served hors d’oeuvres, dinner and dessert with an open beer and wine bar. Enjoy live jazz and holiday classics by Fred Hughes and Paul Langosch. Venture to the open-air top deck to take in the scenery and see the Eastport Yacht Club’s Lights Parade. This event will take place on Saturday, December 9th from 5:00pm to 8:00pm, and tickets are $225 per guest based on tables of two, four, and six. To reserve your table, please visit watermarkjourney.com/events/holiday-dinner-cruise-with-kens-creative-kitchen.

Also on Saturday, December 9th is Watermark’s annual Queen of All Fund Drives benefitting We Care and Friends. Join us aboard Harbor Queen all decked out for the holidays. Enjoy festive music, a beverage from the cash bar, and a front-row seat to the Eastport Yacht Club’s Lights Parade. In lieu of a ticket, guests are asked to make a $10 donation, which will go to helping We Care and Friends’ efforts this holiday season. We Care and Friends will also be accepting donations of linens, bedding, blankets, toiletries, clothing, and non-perishable food items.

Make your New Year's Eve memorable with a special celebration on the water. Climb aboard for New Year’s Eve Yacht Parties in Annapolis and Baltimore. Enjoy a DJ, dancing, desserts, a complimentary glass of bubbly, and fireworks. Both cruises take place on Sunday, December 31st from 10:00pm to 1:00am. Tickets are $130/adult (21 and over only). For reservations in Annapolis, please visit https://watermarkjourney.com/events/new-years-eve-annapolis-fireworks-cruise. For reservations in Baltimore, please visit https://watermarkjourney.com/events/new-years-eve-charm-city-cruise.

Join Watermark for an unforgettable holiday season!