The 15 best things to do in Annapolis (November 2026)

The ranked list

1. 

   1. Tipsy History Tour: 300+ Years of Annapolis Drinking History

   Outty Ranking83

   Explore Annapolis' vibrant past on this unique historical pub crawl. Over two hours, discover how drinking influenced the city and the nation while enjoying recommended drinks at each stop. From rebels to rum-runners, ea. Exceptional at 83/100, 5.0/5 from 52 traveler reviews, 2h from $39, free cancellation.

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2. 

   2. Annapolis Historic Walking Tour: Harbor and Colonial Downtown

   Outty Ranking74

   Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor and US Naval Academy. We'll see the Georgian mansions, the iconic Maryland State House, and much more as y. Strongly Recommended at 74/100, 5.0/5 from 51 traveler reviews, 1.8h from $235, free cancellation.

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3. 

   3. Historic Annapolis Walking Tour - Small Group Guided Tour

   Outty Ranking72

   Annapolis Walking Tours provides entertaining and informative tours throughout historic Annapolis. This tour is wonderful for people of all ages and involves approximately 2 miles of walking at a relaxed pace with freque. Strongly Recommended at 72/100, 4.9/5 from 23 traveler reviews, 1.5h from $35, free cancellation.

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4. 

   4. Historic Annapolis Food Tour

   Outty Ranking72

   During The Historic Annapolis Food Tour, you will enjoy a series of dishes from restaurants in downtown Annapolis while weaving through historic sites. The tour lasts approximately 3.5 hours. Strongly Recommended at 72/100, 4.7/5 from 51 traveler reviews, 3.5h from $80, free cancellation.

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5. 

   5. Best of Annapolis Tour: Colonial, State House, Naval Academy

   Outty Ranking71

   Uncover the rich history of Annapolis on this engaging tour, showcasing Colonial Annapolis, the Maryland State House, and the U.S. Naval Academy. Guided by a knowledgeable colonial-costumed expert, wander through the his. Strongly Recommended at 71/100, 4.7/5 from 19 traveler reviews, 2.3h from $34, free cancellation.

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6. 

   6. The Original Walking Ghost Tour by Annapolis Ghost Tours

   Outty Ranking70

   The original 90-min Annapolis Ghost Tours are the only tours created by our owner, noted local Maryland historian, and author of "Haunted Annapolis". Don't be fooled by national chains pretending to be locally owned and. Solid Choice at 70/100, 4.4/5 from 49 traveler reviews, 1.5h from $26, free cancellation.

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7. 

   7. Ashes and Apparitions of Annapolis Ghost Tour

   Outty Ranking68

   Embark on this Annapolis ghost tour and step back in time as you stroll through the historic district. Your guide will share chilling tales of hauntings at iconic buildings. Discover the restless spirits said to haunt Mi. Solid Choice at 68/100, 4.3/5 from 93 traveler reviews, 1h from $26, free cancellation.

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8. 

   8. The Original Haunted Pub Crawl by Annapolis Ghost Tours

   Outty Ranking67

   The only Haunted Pub Crawls permitted inside the oldest and most haunted pubs in Historic Downtown Annapolis. Enjoy a 2-hour guided adventure on our haunted pub crawl. Drink in the history, but try not to crawl out the d. Solid Choice at 67/100, 4.4/5 from 25 traveler reviews, 2h from $31, free cancellation.

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9. 

   9. Annapolis Harbor and U.S. Naval Academy Cruise

   Outty Ranking65

   Cruise through history on the Annapolis Harbor & USNA Cruise. This narrated cruise offers insights into the U.S. Naval Academy and Annapolis' rich maritime heritage while enjoying stunning views of the Chesapeake Bay Bri. Solid Choice at 65/100, 4.8/5 from 26 traveler reviews, 0.7h from $34, free cancellation.

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10. 

    10. Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

    Outty Ranking64

    Come on to our Haunted Pub Crawl Tour in Annapolis! Enjoy some liquid courage while hearing ghostly tales of Annapolis' most historic haunts and drinking hotspots. Take a Boo's and Booze Haunted Pub Crawl for genuine st. Solid Choice at 64/100, 4.4/5 from 18 traveler reviews, 2h from $29, free cancellation.

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11. 

    11. Colonial Annapolis and Maryland State House Walking Tour

    Outty Ranking64

    Step into Annapolis's rich colonial past on a guided walking tour through the Historic District, led by a guide dressed in authentic colonial attire. Discover the history and heritage of the Maryland State House, the old. Solid Choice at 64/100, 5.0/5 from 6 traveler reviews, 1.5h from $26, free cancellation.

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12. 

    12. Amazing Annapolis Scavenger Hunt

    Outty Ranking61

    Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Aust. Solid Choice at 61/100, 4.1/5 from 8 traveler reviews, 2h from $19, free cancellation.

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13. 

    13. Day on the Bay Cruise from Annapolis to St Michaels

    Outty Ranking60

    Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, boutique shops, and historic sites. Guests enjoy a complim. Solid Choice at 60/100, 4.5/5 from 8 traveler reviews, 8h from $157, free cancellation.

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14. 

    14. Annapolis Thomas Point Lighthouse Cruise

    Outty Ranking59

    The Thomas Point Lighthouse is the most iconic lighthouse in Maryland. View this National Historic Landmark on a narrated cruise into the Chesapeake Bay. Not just for lighthouse enthusiasts, everyone loves it during this. Worth a Look at 59/100, 4.8/5 from 8 traveler reviews, 1.5h from $46, free cancellation.

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15. 

    15. Annapolis Chesapeake Bay Bridge Cruise

    Outty Ranking59

    Step aboard a classic vessel for a scenic Chesapeake Bay Bridge cruise. As you depart the dock in downtown Annapolis, you will pass along the seawall of the United States Naval Academy and out into open water. As you app. Worth a Look at 59/100, 5.0/5 from 5 traveler reviews, 1.5h from $46, free cancellation.

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Traveler ratings are provided by Viator and Tripadvisor. The Outty Ranking is our own independent evaluation. How the ranking works.

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