WWingAwayWEEKENDSFly to lunchDestination guide 85
Maryland · Couples · Two nights

Annapolis

Sailboats, brick streets and the Naval Academy.

Annapolis is a colonial capital on the Chesapeake, with brick streets, a harbor full of sailboats and the U.S. Naval Academy at the end of town. Tour the Academy, see the State House where George Washington resigned his commission, take a sunset sail on a schooner and eat crab cakes on the water.

Sailing townColonial historyChesapeake seafood
See the weekend itineraryFlight & arrival details
The white Thomas Point Shoal Lighthouse in the blue Chesapeake Bay
Thomas Point Lighthouse, Annapolis
YOUR ROUTEKMYR to KANP
STRAIGHT-LINE DISTANCE~336 NM
ILLUSTRATIVE FLIGHT TIME~2 hr 29 min
WEEKEND STYLETwo nights · Rideshare or walk

Time illustration: direct distance at 150 KTAS plus 15 minutes for departure and arrival, matching the discovery page. Use ForeFlight for your actual flight plan.

01 / Aviation & getting around

Land at Lee Airport.

KANP, Lee Airport, is a small non-towered field in Edgewater, about 15 minutes south of downtown Annapolis.

The FBO

Lee Airport

Lee Airport, Edgewater, MD

410-956-1280

Lee Airport sells 100LL. Confirm hours, transient parking and fees before you go; rideshare is the easiest way into town. No live fuel price is shown.

Lee sits under the Washington Class B and near the DC Special Flight Rules Area. Brief the SFRA and Flight Restricted Zone boundaries carefully. About 335 nm from Myrtle Beach.

02 / Where to stay

A historic inn or a harbor hotel.

Rates and availability need travel dates. Boat-show and commissioning weeks book early.

03 / Where to eat

Crab cakes on the water.

Reserve weekend dinners.

04 / Things to do

Sails, the Academy and the State House.

Everything is close; slow down and walk.

01

U.S. Naval Academy

Guided walking tours from the visitor center; bring photo ID.

Visit USNA
02

Schooner Woodwind

A two-hour sail on the bay, best at sunset.

Sailing
03

Maryland State House

The oldest state capitol in continuous legislative use.

State House
04

Historic Annapolis

The William Paca House and Garden and walking tours.

Historic Annapolis
05

Ego Alley

Watch boats parade through the narrow harbor at dusk.

Visit Annapolis
05 / What’s happening

Sometimes the season is the reason to fly.

This prototype links to the local visitor site. It does not yet match events to your travel dates.

Concerts, festivals & local happenings

Check the local calendar when choosing a weekend, and confirm dates and tickets with the organizer.

Browse Annapolis events
06 / Suggested itinerary

Friday in. Sunday home.

A sample weekend: the harbor, the Academy and a sunset sail. No bookings or availability confirmed.

DAY 1

Arrive & the harbor

  1. Arrival

    Land at KANP, subject to weather and your actual flight plan.

  2. Afternoon

    Walk Main Street and Ego Alley.

  3. Evening

    Dinner at Carrol’s Creek.

DAY 2

Academy & a sail

  1. Morning

    A Naval Academy tour.

  2. Afternoon

    The State House and the Paca House garden.

  3. Evening

    A sunset sail on the Woodwind, then Lewnes’.

DAY 3

Breakfast & home

  1. Morning

    Breakfast at Chick & Ruth’s.

  2. Before leaving

    Allow time at the airport.

  3. Fly home

    Summer storms build in the afternoon; leave early.

07 / Good to know

Keep the weekend easy to change.

These details make the difference between an appealing list and a usable getaway.

Book in this order

Lodging first, then the sail and dinners.

Airspace

Brief the DC SFRA and FRZ; this is not a place to improvise.

Academy access

Bring government photo ID; security rules change.

Best seasons

May to October for sailing.

Reviewed · Destination 85

Reviewed November 4, 2026.

Picks and links reviewed by WingAway Weekends. Hours, prices, menus and availability change often, so confirm directly with each place before booking.

WingAway Weekends helps you discover the destination. Use ForeFlight and current official aviation information for route, performance, weather, NOTAMs and preflight decisions. Flight planning and PIC responsibility stay with the pilot.