The 15 Best Annapolis Tours

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

★★★★★★★★★★4.7 · 126 reviews · 40 min · from $34Our pick

Board Watermark Journey’s 40-minute cruise at the end of Prince George Street for views of Annapolis Harbor, historic buildings, sailboats, and the U.S. Naval Academy. A recorded English narration explains the city’s maritime culture and Academy history. Drinks and light snacks are available for purchase on board. The boat and route may change.

“It was hard to hear the guide’s explanations due to engine noise.”

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2.Ashes and Apparitions of Annapolis Ghost Tour

★★★★★★★★★★4.5 · 84 reviews · 1 hour (approx.) · from $32

Starting at Federal House Bar & Grille at 8 pm, this guided walk pairs Annapolis history with ghost tales at historic homes, taverns, and inns. You’ll hear stories tied to sites including the Brice House, Maryland Inn, and Reynolds Tavern. Guides vary, with past tours led by Spirited Nan, Shelby, Tal, and Cal.

“Great historical lesson about the dark secrets of Annapolis. I was shocked and disappointed by the abuse of women and the way many of them met their end here. My heart weeps for them and their spirts.”

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3.Historic Annapolis Food Tour

★★★★★★★★★★4.5 · 44 reviews · 3 hours 30 minutes (approx.) · from $80

Spend about three and a half hours walking historic Annapolis with a guide such as Carolyn, stopping at landmarks and locally owned restaurants for a progressive meal that ends with dessert. The 1 p.m. tour starts and finishes at the Annapolis Visitor Center, takes up to 12 people, and includes food but not drinks unless specified.

“Carolyn was awesome very knowledgeable and the licks were perfect and the tour with all the history and local ears was memorable. Thank you”

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

★★★★★★★★★★4.8 · 41 reviews · 2h 15m · from $34

Follow a period-attired guide through Annapolis’s historic district, the Maryland State House, and the U.S. Naval Academy on this 135-minute walking tour. Guides such as Mistress Laura, Squire Curtis, and Squire Dave bring local stories to life. Bring a U.S. passport or U.S.-issued Real ID if you are 18 or older and want to enter the Academy.

“Naval academy-would have enjoyed more time there. We could have done single tour there but enjoyed the Maryland history”

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5.The Original Walking Ghost Tour by Annapolis Ghost Tours

★★★★★★★★★★4.5 · 41 reviews · 1 hour 30 minutes (approx.) · from $26

Spend about 90 minutes walking historic downtown Annapolis, hearing ghost stories alongside accounts of the city’s troubled past. Tours start at Church Circle and end at City Dock. Guides named on past tours include Becka, Sarah, and Ireland. Expect storytelling rather than a paranormal investigation, and dress for the weather.

“Becka was great! She is an amazing story teller. We had the best time exploring the streets of Annapolis. I know I felt much closer to the city after the tour.”

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6.Annapolis Historic Walking Tour at Harbor and Naval Academy

★★★★★★★★★★5.0 · 38 reviews · 2 hours (approx.) Top rated

Join Annapolis native Michael for a private two-hour walk from Ego Alley through the Naval Academy, its chapel, historic homes, the State House, and St. John’s College. Your group of up to 10 gets a flexible pace and local context. Bring a REAL ID or passport if you’re over 18 and plan to enter the Academy.

“Excellent tour....Michael is well informed, kept things interesting and easily adapted to our age group....and he's good company! Highly recommend.”

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7.The Original Haunted Pub Crawl by Annapolis Ghost Tours

★★★★★★★★★★4.5 · 18 reviews · 2 hours (approx.) · from $31

Start near the Maryland Inn for a two-hour walk through historic Annapolis, stopping at three pubs or taverns for drinks you buy yourself and tales of local ghosts. Guides have included Kacey, Sarah, Rebecca, Megan, and Cerise. Expect a changing route, time to order before the stories, and a possible stop in a church graveyard.

“Great way to walk around historic Annapolis while learning about the area, hearing researched ghost stories and having some drinks. We had a great time, even in the cold. Cerise, our guide, was wonderful. She is local and truly knows the history snd stories of Annapolis. We love to support great local small businesses.”

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8.Awesome Scavenger Hunt: Annapolis Red Bricks & Blue Views

★★★★★★★★★★3.5 · 17 reviews · 2 hours (approx.) · from $14Best value

Explore Annapolis with a private, self-guided scavenger hunt that starts at State Circle and visits the Kunta Kinte-Alex Haley Memorial, James Brice House, and Maryland State House. The Let’s Roam app supplies clues, trivia, and photo challenges for about two hours. You set the pace, but bring a charged phone and be ready to troubleshoot check-ins.

“Nothing really memorable. Similar to many others but not as user friendly. When we arrived at our destination it never pickup that we were there. Always had to “check in anyways”.”

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9.Ghosts of the Harbor & Old Town Tour

★★★★★★★★★★4.3 · 12 reviews · from $27

US Ghost Adventures leads a one-hour walk through Annapolis’s historic district, with stories tied to the Maryland Inn, Reynolds Tavern, Galway Bay, and the James Brice House. Your guide carries a lantern; past guides include Tal and Shelby. The tour costs $27, starts outside Federal House Bar and Grill, and runs rain or shine.

“She was incredible. I’m a tough one and she dealt with me like a champ. I had the best time!”

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10.Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

★★★★★★★★★★4.5 · 9 reviews · 2 hours (approx.) · from $36

Start at 6 pm near Market Space for a two-hour haunted pub crawl through seven Annapolis sites, from the nearly 300-year-old Middleton Tavern to Galway Bay. Your guide shares local history and ghost stories, with time to stop inside several pubs. Drinks cost extra, and the group is capped at 25. Ryan is one named guide associated with the tour.

“We had a great time with Ryan, the tour is very informative, the pubs are super cozy and quaint, Ryan is a great, patient tour guide, we would have enjoyed her company for the rest of our evening.”

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11.Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

★★★★★★★★★★4.3 · 7 reviews · 2 hours · from $30

Walk through historic Annapolis with a live English-speaking guide, hearing stories of sailors, bootleggers, tavern keepers, and prisoners. The two-hour route visits eight haunted spots and enters four bars, starting with a tale-filled stop at Middleton’s Tavern. Drinks cost extra, and you’ll need valid ID to buy alcohol. Ryan has guided a highly praised tour, though guide assignments can vary.

“It was ok. We had fun going to a few bars we hadn’t been in before. Just a few ghost stories. We also had some confusion in the beginning. We were told to be there at 5:45 but the tour guide didn’t show up until 5:55. We thought we were in the wrong place.”

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12.Amazing Annapolis Scavenger Hunt

★★★★★★★★★★4.5 · 7 reviews · 2 hours (approx.)

Set off from Brown Mustache Coffee for an approximately two-hour Annapolis scavenger hunt led by a remote host. Follow clues to places such as Blue Crab Antiques and the Maryland State House, take on playful challenges, and send photos as you go. You can walk or drive, bring a dog, and choose a morning or afternoon start.

“We really enjoyed the experience, it was so fun and we discovered a lot from the city in a very small period pf time.”

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13.Outdoor Painting Activity with a Local Artist in Annapolis

★★★★★★★★★★5.0 · 7 reviews · 1 hour 30 minutes (approx.) · from $95

Join Annapolis artist and teacher Em Campbell for a 90-minute outdoor watercolor class near the Maryland State House. She supplies the paints, mess-free waterbrush, camp chairs and premium paper, already marked with a pencil sketch. You’ll learn at your own pace and leave with your own painting.

“Such a fun activity! Em was an excellent instructor and we all enjoyed learning something new and the best part is we now have beautiful watercolor artwork to take home as souvenirs!”

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14.Maryland State House Tour

★★★★★★★★★★5.0 · 6 reviews · from $24

Meet a period-attired guide at 188 Main Street for a 75-minute tour of the Maryland State House. You’ll walk to the building, then spend most of the visit inside, hearing about George Washington’s resignation, the Treaty of Paris, and Maryland figures including Harriet Tubman and Thurgood Marshall. Guides include Beth, though the guide for your date may differ.

“Our tour guide was excellent. He was knowledgeable, informative, and an engaging story teller. I would strongly recommend this tour.”

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15.Round Trip Cruise to St. Michaels

★★★★★★★★★★4.3 · 5 reviews · 8 hours · from $157

Travel by yacht from Annapolis to St. Michaels, with a complimentary non-alcoholic drink on the outbound trip and about three hours ashore. Explore the village at your own pace and visit the Chesapeake Bay Maritime Museum before cruising back. The full outing takes about eight hours, with roughly 2 to 2.5 hours on the water each way.

“I enjoyed the trip very much. The captain explained we needed to do. I would highly recommend this trip. I would book it again.”

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