3 days in Annapolis
A day-by-day itinerary covering the must-sees of Annapolis plus one day trip — perfect for a long weekend or short vacation.
Skip the search — let a CheapoTrav expert do it for you.
Phone-only fares for Annapolis, 24/7.
Call 1 (815) 473-8090Key facts
- Recommended hotel: 3 nights in a central, walkable area
- Day 1: Top sights and neighborhood orientation
- Day 2: Museums, food, and a sunset viewpoint
- Day 3: Day trip or slower neighborhood exploration
- Total budget: $800–$1,400 per person excluding flights
Three days in Annapolis is the sweet spot — enough to see the highlights, eat well, and slot in a day trip without feeling rushed. Sailing capital with the Naval Academy and historic State House.
This itinerary is designed around staying in one central hotel for all three nights, with each day organized by neighborhood to minimize transit time. Day 3 is a day-trip day; swap it for a slower city day if you'd rather not leave Annapolis.
In this guide
- Day 1: arrival and orientation
- Day 2: top sights and food
- Day 3: day trip or slow day
- Where to stay
- Cost breakdown
Frequently asked questions
- Is 3 days enough to see Annapolis?
- Yes — 3 days covers the must-sees of Annapolis with time for a day trip. 4–5 days lets you slow down or explore deeper.
- What's the best month for a 3-day trip to Annapolis?
- Shoulder season offers the best mix of weather and price. See our best-time-to-visit guide for the month-by-month breakdown. Call 1 (815) 473-8090 for phone-only fares
- Where should I stay for 3 days in Annapolis?
- One central hotel for all 3 nights minimizes hassle. See our where-to-stay neighborhood guide for picks.
- Should I rent a car for 3 days in Annapolis?
- Only if you're planning a day trip outside the city. Inside Annapolis, walking and rideshare are usually faster and cheaper. Call 1 (815) 473-8090 for phone-only fares
- How much should I budget for 3 days in Annapolis?
- $800–$1,400 per person covers hotel, food, activities, and local transit. Flights vary by origin.
- Can CheapoTrav book the full 3-day trip?
- Yes — our travel desk can quote flights, hotel, rental car, and activities as one bundled trip, often 10–20% under booking separately. Call 1 (815) 473-8090 for phone-only fares
More for travelers visiting Annapolis
Nearby destinations
- 3 days in: Baltimore
Inner Harbor crabs, the National Aquarium, and quirky museums.
- 3 days in: Washington, D.C.
Free Smithsonian museums and the seat of US government.
- 3 days in: Philadelphia
Liberty Bell, cheesesteaks, and walkable historic streets.