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Annapolis by Invitation creates personal visits to one of America’s most storied small cities: settled in 1649, Maryland’s capital since 1694, and still alive with brick lanes, colonial homes, the Naval Academy, and a harbor at its heart. From the moment you book your flight to your last evening in town, we arrange your travel, your lodging, your table, and the experiences worth the trip, drawing on more than 30 years of local friendships and a town we know by heart.
Three ways to be our guest in Annapolis
The Calling Card
For guests who want the essentials handled beautifully. We arrange your flights, transfers to and from the airport, and lodging at one of Annapolis’s most charming inns or hotels.
The Sojourn
A bespoke Annapolis visit for anniversaries, girls’ weekends, family celebrations, and Naval Academy occasions. Everything in The Calling Card, plus dinner reservations, private experiences, and a thoughtfully paced itinerary designed together, priced as one total.
In Residence
Our most personal service. Everything in The Sojourn, with your host on call throughout your stay, smoothing every detail in the spirit of the great English country houses.
We believe the best visits are never overbooked.
Each itinerary pairs a few well-chosen moments with unhurried time to wander the brick lanes, browse Main Street, and linger by the harbor.
Discover a side of Annapolis few visitors see, gather around the right table, and renew yourself in the rhythm of a waterfront town.
Request your invitation
Complimentary planning consultation
Curated by Wild Air Journeys · Live the Story