Annapolis, Maryland, USA
America's sailing capital packs 300 years of colonial history, the U.S. Naval Academy, and blue-crab waterfront culture into one of the most walkable cities on the East Coast.
America's sailing capital packs 300 years of colonial history, the U.S. Naval Academy, and blue-crab waterfront culture into one of the most walkable cities on the East Coast.
Small and expedition cruise ships tie up directly at Annapolis City Dock — you step off into the historic waterfront.
💡 Pro move: The City Dock Resiliency Project (2026–early 2028) may affect some dock amenities — check with the harbormaster. Large ships (most mainstream lines) call at Baltimore's Cruise Maryland Terminal instead.
Annapolis City Dock accommodates small ships and expedition vessels; most mainstream cruise lines call at Baltimore.
| Cruise Line | Typical Berth / Arrival | Dock or Tender |
|---|---|---|
| Expedition & small-ship lines (Ponant, American Cruise Lines, etc.) | City Dock, Annapolis📍 | Docked |
| Large mainstream ships | Cruise Maryland Terminal, Baltimore (~30 mi north)📍 | Docked |
Annapolis rewards walkers and history lovers — the colonial district is compact, the Naval Academy campus is stunning, and Chesapeake Bay sailing is on your doorstep.
Guided tour (Watermark or self-guided NPS app) hits the Maryland State House — America's oldest state capitol in continuous use — plus the Kunta Kinte-Alex Haley Memorial, Hammond-Harwood House, and William Paca House & Garden.
Find Annapolis walking tours →Tour the 338-acre USNA campus: Bancroft Hall (one of the world's largest dormitories), the Naval Academy Museum, and the domed Chapel housing John Paul Jones's crypt. Bring a REAL ID or passport (required for visitors over 18).
Find USNA guided tours →Sail aboard the 74-foot wooden Schooner Woodwind — help raise the sails, take the helm, and glide past the Bay Bridge and Thomas Point Shoal Lighthouse. A quintessential Chesapeake experience.
Find schooner sailing tours →Narrated 40-minute cruise aboard the Harbor Queen (Watermark Journey) glides past the Naval Academy waterfront and historic Annapolis Harbor — great orientation before exploring on foot.
Find Annapolis harbor cruises →Annapolis is ground zero for Maryland blue crabs. Waterfront restaurants along City Dock and Ego Alley serve steamed crabs, crab cakes, and Chesapeake seafood — pull up a picnic table and dig in.
Find Annapolis seafood restaurants →Paddle Annapolis offers guided 2-hour tours from Eastport Yacht Club, weaving through marinas and past historic homes along Spa Creek — a calm, close-to-dock paddle perfect for a shore day.
Find Annapolis kayak tours →Annapolis is one of the most walkable cities in the U.S. — the entire colonial district sits within a 10-minute radius of City Dock.
From City Dock walk up Main Street past colonial storefronts, turn left on Maryland Avenue to the Maryland State House, continue to State Circle, then back down Church Circle to St. Anne's Church and return to the waterfront.
From City Dock, walk along Compromise Street to the USNA Visitor Center, tour the campus, then return past the William Paca House & Garden on Prince George Street and the Hammond-Harwood House on Maryland Avenue.
Climate normals for Annapolis, Maryland, USA (2014–2023 averages). Pack for the month you sail — highs, lows, and how many rainy days to expect.
| Month | Avg High | Avg Low | Rainy Days | Sunrise | Sunset |
|---|---|---|---|---|---|
| Jan | 42°F / 6°C | 29°F / -2°C | 10 | 7:23 AM | 5:08 PM |
| Feb | 46°F / 8°C | 31°F / -1°C | 11 | 6:57 AM | 5:43 PM |
| Mar | 53°F / 12°C | 37°F / 3°C | 11 | 7:16 AM | 7:13 PM |
| Apr | 64°F / 18°C | 47°F / 8°C | 12 | 6:29 AM | 7:43 PM |
| May | 72°F / 22°C | 57°F / 14°C | 13 | 5:53 AM | 8:11 PM |
| Jun | 81°F / 27°C | 66°F / 19°C | 13 | 5:40 AM | 8:33 PM |
| Jul | 85°F / 29°C | 71°F / 22°C | 15 | 5:53 AM | 8:30 PM |
| Aug | 83°F / 28°C | 70°F / 21°C | 14 | 6:19 AM | 8:00 PM |
| Sep | 78°F / 26°C | 65°F / 18°C | 11 | 6:47 AM | 7:13 PM |
| Oct | 68°F / 20°C | 54°F / 12°C | 10 | 7:15 AM | 6:26 PM |
| Nov | 55°F / 13°C | 42°F / 6°C | 7 | 6:49 AM | 4:51 PM |
| Dec | 48°F / 9°C | 35°F / 2°C | 10 | 7:18 AM | 4:44 PM |
Source: Open-Meteo ERA5 (10-yr daily averages)
Transport options from the pier — taxis, shuttles, transit passes, and whether ride-share apps work here.
Local taxis (Annapolis City Taxi, Annapolis Area Cab) are readily available near City Dock. Fares start around $3 plus ~$2.50–2.75/mile; most downtown rides are very short.
Both Uber and Lyft operate 24/7 in Annapolis. Ideal for reaching neighborhoods beyond the historic district or for airport runs.
Annapolis runs a free circulator connecting parking garages to City Dock and the Historic District. A free electric trolley also loops Sat–Sun 11am–5:30pm.
City of Annapolis on-demand transit app (Transigo). Book via app or phone; $1 reduced fare for seniors and disabled riders.
Watermark Water Taxi connects City Dock to Spa Creek and Back Creek destinations. Scenic and practical for reaching waterfront restaurants and attractions.
Upcoming cruises that call at Annapolis, Maryland, USA. Dates, prices, and ports of call change — always confirm with the cruise line before booking.
Itineraries and prices change — always confirm with the cruise line before booking. Some links are affiliate links that may earn us a commission at no extra cost to you.