A Luxury Weekend in Annapolis, Maryland

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A Luxury Weekend in Annapolis, Maryland

Home / CITY GUIDE / WEEKEND ITINERARY / A Luxury Weekend in Annapolis, Maryland
Yachts, Paddle Boarding, and #CarefreeVibes
“The food was epic, the drinks were flowing..." -Annapolis Weekender

Annapolis, Maryland is known for crabs, sailing, and lavish waterfront homes. The city is a fascinating combination of a historic town and modern vacation spot. To boot, the area boasts delicious food, exciting nightlife, and plenty of things to do during the day.

Looking to host a crawfish boil, yacht party, or just lay out on the water with your crew? Annapolis is the go-to spot for escaping the stresses of ever-expanding cities like Washington, DC, New York, and Philly. Situated between Baltimore and DC, Annapolis is the perfect location for a weekend getaway or local staycation.

Here’s how to host your next carefree weekend or staycation in style in Annapolis:

Sail the Bay in Style

Annapolis is known as the sailing capital of the world, so what better place to relax than aboard one of two 74-foot sailboats docked in the Annapolis Harbor?

The Schooner Woodwind and Woodwind II each can sail 48 guests around the Chesapeake Bay for private cruises. You may recognize the Woodwind II as the sailboat used in the movie “Wedding Crashers.”

Both Woodwind schooners have catering and bar options, so you and your guests can eat and drink off of a custom menu while sailing the Chesapeake Bay.

Boat docked in Annapolis Harbor

Cruise Around on a Chartered Yacht

If sailing doesn’t give you the same thrill as a boat with an engine, then the Watermark Yacht Charters may be a better fit for your day at the Bay.

Watermark has a fleet of 13 yachts in a range of sizes, accommodating up to 200+ people. They include tables, chairs, and linens in the package for your event and they work with several local caterers to create food menus fit for the occasion.

Check out Ken’s Creative Kitchen for menu items like seared lemon-basil salmon with asparagus bundles for dinner or crème Brulee French toast for brunch.

“I have never seen anything run so smoothly,” said Grace S., who had her wedding catered by Ken’s. “The food was epic, the drinks were flowing, and the service was unparalleled.” If the views from the top floor of the yacht don’t impress your guests, the food definitely will.

Plus, each yacht has a climate-controlled, indoor space, so you won’t have to stress about unpredictable weather or scheduling your event during the summer months.

Party at the Historic Paca House

Want to party like the founding fathers did? Leave the boats behind and plan a celebration at the historic William Paca House and Garden.

The house was once home to lawyer, politician, and signer of the Declaration of Independence, William Paca. Over the years it was home to many wealthy families. Today has been restored to its original glory and is owned by Historic Annapolis.

The two-acre gardens in the back are beautiful– featuring parterres with geometric designs and a latticework bridge leading guests over the pond. The summerhouse, also restored to its original colonial design, serves as a focal point of the garden and can also host smaller, more intimate dinner parties.

Rent a Standout Home on AIRBNB

Airbnb has a few stand out options in the Annapolis area, from a chic one-bedroom apartment on Main Street to lavish waterfront houses, like this 3-Bedroom Waterfront home and this 5-bedroom home.

Decide if you want to be on the water, close to Downtown, or somewhere with complete privacy.

Check out SunriseSup for stand up paddle boarding in Annapolis.

No matter the occasion, the season, or the group of people, Annapolis is the perfect choice for a weekend getaway. For more information and ideas on how to spend your time in Maryland’s capital city, click here.

Photography via Flickr and Susan Yin

about the author

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Lisa Dammeyer
Lisa Dammeyer is an Editorial Intern at CAPITOL STANDARD and a senior English major at the University of Maryland, College Park. As a member of the English Honors Program, Lisa is currently working on her senior thesis and completing a minor in Creative Writing.