Unique Microwedding Venues in Annapolis, MD
- isabellakalmoore
- Feb 23
- 4 min read
Woodwind Sailing Cruise
Description: Embark on a memorable sailing experience aboard the Schooner Woodwind, a 74-foot wooden schooner departing from downtown Annapolis. Ideal for intimate weddings, rehearsal dinners, and celebratory gatherings, the Woodwind offers a unique maritime venue with the stunning backdrop of the Chesapeake Bay.
Website: https://schoonerwoodwind.com/private-sailing-charters/weddings-rehearsal-dinners-and-more/
Price Range: Specific pricing details are not publicly listed. For accurate and personalized information regarding event packages and availability, it's recommended to contact the Woodwind team directly at info@schoonerwoodwind.com or call 410.263.7837.
Region: Downtown Annapolis & the Chesapeake Bay
Venue Type: Sailboat
Ambiance: Breezy & serene

Gibson’s Inn at Gate One
Description: A historic inn located just steps away from the U.S. Naval Academy, Gibson's Inn is an ideal location for unforgettable occasions in downtown Annapolis. The venue offers beautifully appointed event spaces and accommodations suitable for various party sizes.
Website: gibsonsinn.com
Price Range: Pricing details are not publicly available; please contact the venue directly for rates and availability.
Region: Downtown Annapolis
Venue Type: Historic Inn with indoor event spaces
Ambiance: Timeless & intimate
86 State Circle
Description: Opening in March 2025, 86 State Circle is set to become one of Annapolis's most luxurious boutique hotels. This landmark residence has been carefully redesigned to reinvigorate Annapolis hospitality, offering unparalleled accommodations in a one-of-a-kind location.
Website: 86statecircle.com
Price Range: Pricing details will be available closer to the opening date; please contact the venue for more information.
Region: Downtown Annapolis
Venue Type: Boutique Hotel with indoor spaces
Ambiance: Historic significance & modern sophistication
Flag House Inn
Description: Situated in the heart of historic Annapolis, Flag House Inn offers a unique blend of historic architecture and modern amenities. The inn provides a charming setting for intimate gatherings, with beautifully designed rooms and common areas.
Website: flaghouseinn.com
Price Range: Pricing details are not publicly available; please contact the venue directly for more information.
Region: Downtown Annapolis
Venue Type: Historic Inn with indoor spaces
Ambiance: Warm & inviting
Harry Browne’s
Description: Located directly across from the Maryland State House, Harry Browne's Restaurant invites guests to experience fine dining and award-winning cuisine in an elegant setting. The venue offers private dining rooms suitable for intimate ceremonies and receptions.
Website: harrybrownes.com
Price Range: Pricing details are not publicly available; please contact the restaurant directly for event packages.
Region: Downtown Annapolis
Venue Type: Restaurant with private dining spaces
Ambiance: Classic & refined
The Choptank
Description: Situated on "Ego Alley" at downtown Annapolis' famous City Dock, The Choptank is a classic seafood restaurant offering a spacious interior, waterfront patio, and expansive rooftop. These versatile spaces make it an excellent choice for hosting intimate gatherings and celebrations.
Website: thechoptankrestaurant.com
Price Range: Pricing details are not publicly available; please contact the restaurant directly for group dining options.
Region: Downtown Annapolis
Venue Type: Restaurant with indoor and outdoor spaces
Ambiance: Festive & vibrant
Cascia Vineyards & Winery
Description: Nestled on Kent Island, Cascia Vineyard s and Winery is a waterfront venue with stunning views of the Chesapeake Bay, a beautiful vineyard, and outdoor dining options.
Price Range: Specific pricing details are not publicly available. For personalized quotes and availability, it's recommended to contact the winery directly at 410-604-2127 or via email at kjcascia@casciavineyards.com.
Region: Kent Island
Venue Type: Waterfront Vineyard and Winery
Ambiance: Serene & romantic
William Paca House and Garden
Description: Located in the heart of historic downtown Annapolis, the William Paca House and Garden is a meticulously restored 18th-century Georgian mansion surrounded by two acres of beautifully landscaped gardens. This National Historic Landmark offers a unique and historic setting for weddings and special events, featuring formal parterres, a wilderness garden, and a charming summerhouse overlooking a fish-shaped pond.
Website: annapolis.org
Price Range: Ceremony-only packages start at $2,500, which includes a two-hour garden ceremony for up to 40 guests, available Tuesday through Thursday. For comprehensive packages and current pricing, it's advisable to contact the Events Department at weddings@annapolis.org or call 410.990.4538.
Region: Downtown Annapolis, MD
Venue Type: Historic Manor and Garden
Ambiance: Lush & romantic

1313 West Hotel
Description: A luxurious boutique hotel in Annapolis, MD, 1313 West offers a modern farmhouse aesthetic just minutes from downtown and the Chesapeake Bay. This intimate venue features contemporary design within a historic setting, providing a unique backdrop for your special day.
Website: 1313west.com
Price Range: Pricing details are not publicly available; please contact the venue directly for a personalized quote.
Region: West Street – 5 minutes from Downtown Annapolis
Venue Type: Boutique Hotel with indoor and outdoor spaces
Ambiance: Elegant yet cozy
134 Prince Boutique Hotel
Description: Nestled in historic downtown Annapolis, 134 Prince is a luxury boutique hotel offering both indoor and outdoor accommodations for intimate ceremonies and receptions. Its premier location and illustrious grandeur make it an unbeatable venue for special events.
Website: 134prince.com
Price Range: Weddings range from $2,950 to $3,950.
Region: Downtown Annapolis
Venue Type: Boutique Hotel with indoor and outdoor spaces
Ambiance: Historic charm & modern luxury
These venues each offer unique settings and experiences to make your special event in Annapolis truly memorable.
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