Listing is for planning only. Some locations may have restricted vehicle access or require advance reservations. Naval Academy requires photo ID for entry.
Click + Add to Route on any landmark to start building your tour.
Tip: Most groups visit 8-12 landmarks in a half-day tour.
121 Blake Rd, Annapolis, MD 21402
⚓ Wander the historic yard of a school that's been forging Navy and Marine officers since 1845, all crisp uniforms, waterfront views, and midshipman tradition.
United States Naval Academy, Annapolis, MD 21402
🏛️ Home to every single Naval Academy midshipman under one roof, Bancroft Hall is one of the largest dorms on the planet — see where future officers actually live and train.
United States Naval Academy, Annapolis, MD 21402
⛪ The Yard's iconic domed chapel anchors Naval Academy life, blending soaring architecture with the crypt of John Paul Jones resting quietly below.
118 Maryland Ave, Annapolis, MD 21402
⚓ Two floors of naval history packed into Preble Hall, from ship models to the stories of the sailors and marines who shaped America's seapower - a shore-leave stop worth the detour.
52 King George St, Annapolis, MD 21402
⚓ Step onto the Naval Academy grounds with a certified guide and see where future officers are made, all through the Armel-Leftwich Visitor Center's walking tours.
United States Naval Academy, Annapolis, MD 21402
⚓ Grease Herndon Monument's greasy obelisk with your bare hands? No thanks - just admire where plebes scramble each spring to swap their dixie cup for an officer's cover, right in the heart of Tecumseh Court.
100 State Cir, Annapolis, MD 21401
🏛️ Swing by the oldest state capitol still in legislative use, where Congress once met and George Washington resigned his commission - history buffs, this one's for you.
110 State Cir, Annapolis, MD 21401
🏛️ Government House sits right on State Circle, the working home of Maryland's governor and a front-row seat to the state's history in the making.
100 State Cir, Annapolis, MD 21401
⚖️ Stand where Thurgood Marshall once argued civil rights cases, right on the spot of the old Court of Appeals building, now home to his bronze likeness at Lawyers' Mall.
186 Prince George St, Annapolis, MD 21401
🌷 Wander the restored 18th-century garden of a Founding Father's mansion, where colonial Annapolis still feels wonderfully alive between the boxwoods and terraces.
19 Maryland Ave, Annapolis, MD 21401
🏛️ Step into 1774 at the Hammond-Harwood House, William Buckland's final architectural masterpiece, complete with a carved doorway and rooms full of period paintings and decorative arts worth gawking at.
107 Duke of Gloucester St, Annapolis, MD 21401
🏛️ Home to Charles Carroll of Carrollton, the only Catholic signer of the Declaration of Independence, this Annapolis house and garden has stood witness to three generations of history along the Chesapeake.
199 Duke of Gloucester St, Annapolis, MD 21401
⛪ Right in the heart of Annapolis's historic circle, this stately church has anchored the city's spiritual and social life for generations - pop in for a peek at its graceful, storied sanctuary.
58 State Cir, Annapolis, MD 21401
🏛️ Three 18th-century inns tucked right into Annapolis's historic circle, blending Colonial charm with Chesapeake Bay views just steps from the water.
60 College Ave, Annapolis, MD 21401
📚 Wander the tree-lined campus of one of America's oldest colleges, where students still debate Aristotle and Einstein under the Great Books program - history and big ideas at every turn.
1 Dock St, Annapolis, MD 21401
⚓ Nicknamed Ego Alley for the boat parade of showoffs cruising in to see and be seen, Annapolis's historic harbor is prime real estate for people-watching and salty sea air.
25 Market Space, Annapolis, MD 21401
🦪 Right on the Annapolis waterfront, this historic hall dishes up fresh-shucked oysters, seafood, and live music under one roof - grab a board to share and call it lunch.
1 Dock St, Annapolis, MD 21401
⚓ Grab a bench at Susan Campbell Park and soak up the harbor views right where Annapolis's boats, breezes, and downtown charm all meet at the water's edge.
1 Compromise St, Annapolis, MD 21401
🕊️ Standing at the harbor's edge, this powerful memorial marks the actual arrival spot of Kunta Kinte, honoring Alex Haley's Roots and the resilience it symbolizes.
723 Second St, Annapolis, MD 21403
⚓ Dip into Chesapeake Bay lore at this waterfront museum and park, with exhibits on local maritime heritage and even sailboat cruises straight from the harbor.
80 Compromise St, Annapolis, MD 21401
⛵ Hop aboard a 74-foot wooden schooner and actually help hoist the sails or take the wheel on the Chesapeake Bay, right in America's Sailing Capital.
801 Chase St, Annapolis, MD 21401
🎭 Annapolis' creative heartbeat, Maryland Hall packs performances, exhibitions, and resident arts companies under one roof - pop in and see what's on stage or on the walls.
84 Franklin St, Annapolis, MD 21401
🖼️ Maryland's official museum of African American heritage, Banneker-Douglass-Tubman weaves rotating exhibits, archives, and living history into one powerful Annapolis stop worth slowing down for.
60 College Ave, Annapolis, MD 21401
🎨 Tucked on St. John's College's campus, this little museum turns big questions about freedom and human experience into thought-provoking exhibitions worth a wander.
839 Londontown Rd, Edgewater, MD 21037
🏛️ Wander the "lost" colonial streets of London Town, then drift into riverside gardens along the South River—history and blooms in one leashed-pet-friendly stroll.
600 Quiet Waters Park Rd, Annapolis, MD 21403
🌳 Trade the party bus for tree-lined trails at Quiet Waters Park, where paved paths, gardens, and creekside views give your crew a breather between Annapolis stops.
2001 Baltimore Annapolis Blvd, Annapolis, MD 21409
🌊 Perched where the B&A Trail meets the Severn River, this riverside park serves up a sandy launch beach, a 288-foot fishing pier, and prime picnic-and-breathe views.
273 Hilltop Ln, Annapolis, MD 21403
🌳 Trade the tour bus for tree cover at Truxtun Park, a leafy Annapolis escape with room to roam, play, and just breathe for a bit before the next stop.
1100 E College Pkwy, Annapolis, MD 21409
🏖️ Sandy shores, big bay views: this 786-acre park along the Chesapeake has been the go-to Annapolis beach escape since 1952, perfect for a breezy waterside wander between stops.
25 Silopanna Rd, Annapolis, MD 21403
🧒 Let the little ones loose in a playground built for curious hands and big imaginations, with hands-on exhibits made for splashing, building, and discovering.
33 West St, Annapolis, MD 21401
🎸 Annapolis' storied listening room — national acts in an intimate, seated club on West Street, with dinner and drinks served right to your table.
37 West St, Annapolis, MD 21401
🎶 West Street's easygoing saloon — live bands most nights, cold beer always, and zero attitude in between.
132 Dock St, Annapolis, MD 21401
🪩 City Dock's party corner — live music and DJs upstairs, bar-food comfort downstairs, two blocks from Ego Alley.
49 West St, Annapolis, MD 21401
🎷 A coffeehouse, wine bar and gallery in one — jazz and acoustic sets in a brick-walled room that feels like Annapolis' living room.
8 Market Space, Annapolis, MD 21401
🦪 The City Dock saloon since 1975 — raw bar, house lager, and the after-race sailing crowd telling lies about the wind.
2 Market Space, Annapolis, MD 21401
🏛️ Pouring since 1750 — Washington and Jefferson drank here; today it's oyster shooters, nightly music, and history by the pint at City Dock.
63 Maryland Ave, Annapolis, MD 21401
🍀 Maryland Avenue's proper Irish pub — patient Guinness, imported comfort food, and a warmth that outlasts the walk from the State House.
400 Fourth St, Annapolis, MD 21403
⛵ Eastport's sailing HQ — dark 'n' stormies, crab cakes, and burgees on every wall; if a boat crew isn't celebrating here, the race hasn't finished yet.
400 Chester Ave, Annapolis, MD 21403
🍺 Eastport's neighborhood classic — crab pretzels and cheap drafts on the corner where locals have been solving the world's problems for decades.
196 West St, Annapolis, MD 21401
🦪 West Street's coolest small room — raw oysters, tinned fish and inventive cocktails, all done with a wink.
193B Main St, Annapolis, MD 21401
🥃 A Prohibition-style whiskey den on Main Street — 100+ bourbons, craft cocktails, and comfort food from a kitchen that runs late.
175 West St, Annapolis, MD 21401
🌆 West Street's dinner-to-DJ spot — and the rooftop deck is the closest thing Annapolis has to a skyline bar.
110 Compromise St, Annapolis, MD 21401
🦀 Crabs and cocktails on the harbor at Compromise Street — big waterfront energy steps from Ego Alley, with deck seats built for golden hour.
Discover America's sailing capital in luxury. From the Naval Academy to the historic waterfront, skip the parking and let us handle the driving while you enjoy every landmark. 🚢✨ Family day or big night out — every seat's covered.
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