The Perfect Weekend in Annapolis: A 2-Day Itinerary

How to spend 48 hours in Annapolis like a local — where to eat, what to see, and what to skip

Last updated March 17, 2026 by the Recommended.app research team.

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Day 1 Morning: Starting Your Weekend Right

Start with breakfast at Chick & Ruth's Delly on Main Street and join the Pledge of Allegiance at 9:30 AM. Walk the Historic District's brick streets, exploring the Maryland State House and the William Paca Garden. Stroll down to City Dock to watch the boats in Ego Alley.

Day 1 Afternoon: Exploring the Heart of the City

Cross the Spa Creek bridge to Eastport for lunch at Carroll's Creek Cafe on the waterfront. Explore Eastport's maritime village atmosphere — boatyards, galleries, and quiet residential streets with water views. Walk back via the Naval Academy seawall.

Day 1 Evening: Dinner and Nightlife

Dinner at Galway Bay with live Irish music on Maryland Avenue, one of the most charming streets in Annapolis. After dinner, walk the harbor at night when the boats are lit up and the city is quiet.

Day 2 Morning: A Fresh Start

Brunch at Iron Rooster — don't miss the free bacon jar and the chicken and waffles. Walk through the Naval Academy Yard, visiting the Chapel and the crypt of John Paul Jones. The noon formation is worth timing your visit around.

Day 2 Afternoon: Deeper Into the City

Drive to Quiet Waters Park for a kayak paddle on Harness Creek or a walk through the formal gardens and waterfront trails. The South River Overlook is one of the best viewpoints near Annapolis.

Day 2 Evening: The Grand Finale

Close out with dinner at Vin 909 in Eastport — the garden patio on a warm evening is pure magic. Walk back along the waterfront and catch the sunset over Spa Creek from the bridge.

Neighborhoods to Know in Annapolis

Annapolis's personality lives in its neighborhoods, and understanding them is the key to a great visit. The neighborhoods to prioritize are Historic Downtown, Eastport, Maryland Avenue, West Street Arts District. Each has its own character, food scene, and energy. The best weekend trips leave time for unstructured wandering in at least one neighborhood — put away the phone, walk without a destination, and let the city reveal itself. You'll stumble into a cafe, a shop, or a park bench with a view that no itinerary could have predicted.

Pro tip: The best time to visit Annapolis: April through June and September through November for comfortable weather and sailing season. October brings spectacular fall color along the Chesapeake. Summer is warm and humid but perfect for waterfront dining.

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Recommendations from locals across 240+ US cities via Recommended.app community data.

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