Annapolis punches well above its weight for a port city of 40,000 people. It’s America’s sailing capital, a Revolutionary War hotspot, and home to the U.S. Naval Academy — all within easy walking distance of the dock. Give it half a day and it’ll be one of your favourite stops on the East Coast itinerary.
Arriving by Ship
Most cruise and riverboat vessels dock at the City Dock, right in the heart of downtown Annapolis. You’re practically in the action the moment you step ashore — the Maryland State House dome is visible from the gangway.
Tender operations are rare here, as the dock handles ships comfortably in calm Chesapeake Bay waters. From the dock to the main historic district is a flat, five-minute walk, so no taxis or shuttles are needed unless you’re heading further afield.
Things to Do
Annapolis is compact but genuinely rich — you can walk its entire historic core in a morning while still fitting in a museum, a waterfront crab lunch, and a browse through the Naval Academy grounds. Here’s where to focus your time.
History & Architecture
- Maryland State House — The oldest state capitol still in continuous legislative use in the U.S.; free entry, open daily 9am–5pm, and the interior dome is breathtaking up close.
- U.S. Naval Academy — Tour the grounds and the Naval Academy Museum for just $15 per adult; the Chapel crypt holds the remains of John Paul Jones.
- William Paca House & Garden — A stunning 18th-century Georgian mansion with a two-acre terraced garden; entry is around $10 and it’s one of the best-preserved colonial homes on the East Coast.
- Historic Annapolis Walking Tour — Explore the red-brick streets and blue harbour views on a self-guided scavenger hunt that turns sightseeing into a game 🎟 Book: Awesome Scavenger Hunt: Annapolis Red Bricks & Blue Views; alternatively, try the Amazing Annapolis Scavenger Hunt for a two-hour adventure from just $20 🎟 Book: Amazing Annapolis Scavenger Hunt.
On the Water
- Waterfront Boat Tours — Chesapeake Bay sailing excursions depart from City Dock throughout the day; prices start around $35 for a 90-minute sail aboard a classic wooden schooner.
- Kayak Rentals — Paddle the harbour independently from Annapolis Canoe & Kayak, with single kayak rentals from approximately $20/hour.
Families
- Kunta Kinte–Alex Haley Memorial — A powerful, moving landmark at City Dock marking the arrival of the enslaved ancestor depicted in Roots; free and deeply educational for older children.
- Annapolis Maritime Museum — Hands-on exhibits about Chesapeake Bay ecology and boatbuilding history; entry is $7 for adults, $3 for kids.
What to Eat
Annapolis is Chesapeake Bay crab country, and you’d be doing yourself a disservice not to eat seafood here. The waterfront streets are lined with restaurants that have been perfecting blue crab recipes for generations.
- Maryland Blue Crab (steamed) — The definitive local dish; head to Cantler’s Riverside Inn for a bucket of Old Bay-seasoned crabs, expect to pay $40–$60 per dozen depending on season.
- Crab Cake Sandwich — Thick, lump-meat patties with minimal filler; Chick & Ruth’s Delly on Maryland Avenue does a legendary version for around $18.
- Clam Chowder — Try the Maryland-style version (tomato-based, not cream) at Dock Street Bar & Grill right on the waterfront, around $10 a bowl.
- Oysters on the Half Shell — Fresh local oysters at Preserve restaurant, with a rotating selection from nearby Bay producers; around $3–$4 per oyster.
- Berger Cookies — A Baltimore-born obsession but widely sold in Annapolis; these chocolate-frosted shortbread rounds are sold at most bakeries for around $2 each and make brilliant edible souvenirs.
Shopping
City Dock and the streets radiating off it — particularly Maryland Avenue and Main Street — are lined with independent shops rather than chains. You’ll find nautical decor, local artwork, and maritime antiques that actually feel worth bringing home.
Look for hand-painted crab-themed pottery, Chesapeake Bay–themed prints by local artists, and quality sailing gear at West Marine (handy if you’re also a sailor). Avoid the souvenir T-shirt shops near the dock — the quality drops sharply and the prices don’t.
Practical Tips
- Currency — USD only; most places accept cards, but carry some cash for smaller food stalls and market vendors.
- Tipping — Standard 18–20% at restaurants; cab drivers expect 15%.
- Getting around — The entire historic district is walkable; for the Naval Academy or outlying areas, ride-shares (Uber/Lyft) are plentiful and cheap.
- Best time to go ashore — Head out early (by 9am) to beat heat and crowds, especially in summer.
- How long you need — Three to four hours covers the highlights comfortably; six hours lets you linger over lunch and catch a boat tour.
- Safety — Annapolis is very safe for visitors; stick to the waterfront and historic core and you’ll have zero issues.
- Dress code — Smart casual works everywhere; comfortable walking shoes are essential on the cobblestone streets.
- Sun protection — The waterfront offers little shade; bring sunscreen and a hat, particularly May through September.
Annapolis rewards curious travellers — so slow down, crack some crabs, and let this beautifully preserved colonial city remind you why the American East Coast never gets old.
🎟️ Things to Book in Advance
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📍 Getting to Annapolis MD, Maryland
Use the interactive map below to explore the port area and plan your route from the terminal.
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