Annapolis guide
Best Walking Tours in Annapolis
Here's our pick of the best Walking Tours in Annapolis, ranked by traveler rating. No sponsored spots, just what's actually worth booking.
Honest prices and ratings, never a sponsored spot
Checked against live availability and pricing, last updated September 28, 2026.
How we build thisThis guide includes real bookable activities from our booking partners. Travinora may earn a commission if you book through a link here, at no extra cost to you.
Our top pick for a walking tour in Annapolis is Tipsy History Tour: 300+ Years of Annapolis Drinking History. Travelers rate it 5.0★, and it's the highest-rated option right now. Watching your budget? Colonial Annapolis and Maryland State House Walking Tour is a lovely, well-rated option from just $26. Want it just for your group? Annapolis Historic Walking Tour: Harbor and Colonial Downtown is a private tour, so you can go at your own pace.
Our picks
Best overall
Best value
Best small-group
Best privateWhat to check before you book
- Shared or private
- Private tours cost more but move at your own pace.
- Duration
- Check the real time commitment against the rest of your day.
- Group size
- Smaller groups generally mean more personal attention.
- What's included
- Confirm entry fees, transport, and food are covered where relevant.
- Cancellation policy
- Free cancellation gives you flexibility if plans change.
Compare every option
| Tour | Rating | Duration | Format | Price from |
|---|---|---|---|---|
| ★ 5.0 | 2 hr | Shared | $39 | |
| ★ 5.0 | 1.8 hr | Private | $235 | |
| ★ 5.0 | 1.5 hr | Shared | $26 | |
| ★ 5.0 | 1.5 hr | Private | $235 | |
| ★ 5.0 | 1.3 hr | Shared | $28 | |
| ★ 5.0 | 1.5 hr | Shared | $32 | |
| ★ 5.0 | 1.5 hr | Shared | $40 | |
Historic Annapolis Walking Tour - Small Group Guided TourBest small-group | ★ 4.9 | 1.8 hr | Small group | $35 |
| ★ 4.8 | 1.5 hr | Shared | $52 | |
| ★ 4.7 | 3.5 hr | Shared | $80 |
What you'll pay
Budget
$31
average · 17 options
Mid-range
$66
average · 2 options
Premium
$381
average · 4 options
Practical advice
- Some of these offer free cancellation, which is worth checking before you commit to one that doesn't.
- A few of these tend to sell out fast, so if your dates are set, it's worth booking a few days ahead.
- Plan for anywhere from 1 hr to 3.5 hr, depending which one you pick, and factor that into the rest of your day.
See every real, bookable experience in Annapolis in one place.
Browse Annapolis experiencesFrequently asked questions
What's the best walking tour in Annapolis?
Tipsy History Tour: 300+ Years of Annapolis Drinking History is our top pick. Travelers love it, rating it 5.0★.
How much does a walking tour cost in Annapolis?
Prices here range from $8 to $579 per person, depending on the operator and what's included. You'll see the exact total when you book.
Are there more Walking Tours in Annapolis than just these?
Yep, we found 23 in Annapolis in total. We're showing you our top 23, ranked by traveler rating.