Annapolis offers three very different ways to spend a few hours: a classic history walk, a pub-focused history crawl, or a more detailed colonial-and-maritime walking tour. Each one emphasizes a different pace, route style, and level of included access.
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This comparison is designed for travelers researching things to do in Annapolis. For related planning, see our TourPickGuide experience comparisons and USA tours and experiences.
Compare the 3 Tour Options
Use this comparison to match the itinerary, traveler feedback, duration, and key features to your preferred travel day.
| Tour | Best for | Rating | Reviews | Duration | Key point | Link |
|---|---|---|---|---|---|---|
 Harbor history walk | travelers who want a broad first look at Annapolis on foot | ★ 5.0/5 | 47 reviews | Approx. 1 hr 45 min | Includes both the waterfront and colonial downtown area. | View on Viator |
 Pub crawl history | travelers who want history with a relaxed pub-crawl format | ★ 5.0/5 | 39 reviews | Approx. 2 hr | Uses a pub-crawl format rather than a standard sightseeing walk. | View on Viator |
 Colonial deep dive | travelers who want a focused colonial-history walk with an included entry | ★ 5.0/5 | 6 reviews | Approx. 2 hr | Includes entry to the Maryland State House. | View on Viator |
Explore Each Tour in Detail
Each option includes its own photo gallery, overview, key features, traveler profile, and direct Viator link.
Compare the harbor and downtown route
Annapolis Historic Walking Tour: Harbor and Colonial Downtown
Best for: travelers who want a broad first look at Annapolis on foot
This option is a straightforward guided walk through Annapolis that blends harbor views with colonial-era landmarks. It covers the city dock, the waterfront, and the area around the U.S. Naval Academy while also touching on major historic sites such as the Maryland State House and St. John’s College. The tour description emphasizes storytelling, including family stories from the guide, and it is set up for questions and special interests. It is a good fit if you want a general introduction to the city in a relatively short time and prefer a classic walking format rather than a food- or drink-centered outing.
Harbor and Colonial Downtown walking tour
- Includes both the waterfront and colonial downtown area.
- No tickets are required for the listed stops.
- Guide can take photos for your group at scenic locations.
Compare the pub-crawl format
Tipsy History Tour: 300+ Years of Annapolis Drinking History
Best for: travelers who want history with a relaxed pub-crawl format
This is the most social and most casual of the three options. Instead of focusing on monuments or museum-style sightseeing, it explores Annapolis through a historical pub crawl that connects drinking culture with the city’s past. The route stays downtown and involves limited walking, with roughly 30 minutes at each pub as noted in the itinerary. It is a strong choice if you prefer an evening outing with a relaxed pace and do not mind that drinks are recommended but not included. Compared with the two walking tours, this one is less about landmark coverage and more about theme, atmosphere, and conversation.
Tipsy History Tour
- Uses a pub-crawl format rather than a standard sightseeing walk.
- Recommended drinks are part of the concept, while the tour price covers the guided experience.
- Limited walking makes it a lower-effort way to explore downtown.
Compare the colonial district route
Annapolis Colonial and Maritime History Walking Tour
Best for: travelers who want a focused colonial-history walk with an included entry
This guided walk is the most focused of the three on colonial-era Annapolis and related maritime history. It includes the Maryland State House and several historic landmarks in the Historic District, along with interior access to a colonial kitchen and dining room inside a Georgian mansion. The itinerary also mentions St. Anne’s Church, the Hammond-Harwood House, the Paca House, and the Annapolis City Dock, while the guide explains everyday life in colonial Maryland. Because the route covers less than a mile, it suits travelers who want a concise but information-rich experience. A private version is also listed for guests who want a more personalized visit.
Colonial and Maritime History walking tour
- Includes entry to the Maryland State House.
- Covers less than a mile on foot.
- Also has a private option for travelers who want more flexibility.
Choosing an Annapolis itinerary style
If you want a broad first impression of the city, the harbor-and-downtown walk gives you the widest overview in a compact format. If you prefer a more social evening, choose the pub crawl; if you want the most concentrated colonial-history focus, pick the tour with included State House entry.
Walking tour with harbor and downtown stops
This route is an on-foot city tour focused on waterfront views, central landmarks, and exterior sightseeing, with no tickets needed for the listed stops.
Downtown pub crawl with historical storytelling
This route is a guided crawl through downtown pubs with short stops and limited walking, designed around drinking history rather than landmark-heavy sightseeing.
Short walking route with included State House entry
This route stays within the Historic District, keeps the walking distance short, and includes entry to the Maryland State House.
Travel planning tip
Check the live product page before booking. Departure details, activity order, inclusions, and available options can change.
Booking notes
- Check the listed age and ID requirements before booking if you plan to enter secured or restricted sites.
- If you choose the pub crawl, remember that recommended drinks are not included in the tour price.
- The private option on the colonial and maritime tour may suit travelers who want a more flexible pace or custom requests.
Frequently Asked Questions
Which tour is best if I want the broadest introduction to Annapolis?
The harbor and colonial downtown walking tour is the broadest of the three, since it combines waterfront views, major landmarks, and a general historical overview.
Which option is most focused on walking time and landmark access?
The colonial and maritime history walking tour is the most compact on foot and is the only one here that explicitly includes entry to the Maryland State House.
Which experience is better for travelers who want a more relaxed evening outing?
The tipsy history tour is the most relaxed and social option, since it uses a downtown pub-crawl format with limited walking.