things to do in Annapolis, MD

See Smithsonian icons with an art historian guide

Cruise quietly with your own food, drinks, and music

Explore 18th-century streets, landmarks, and live historical interpretations

See the Eastern Shore from an open cockpit, with room to customize your route

See Washington, D.C. landmarks by day and night with photo stops and property drop-off

Anchor in protected waters for a gentle paddleboard yoga flow

Book a one-way private DC transfer with your own pickup and drop-off plan

Cruise or fish aboard a stable 23-foot center console

Build Practical Sailing Skills With Private, Hands-On Instruction

Walk Easton's haunted past through its notorious Tragedy Triangle

Cruise in classic comfort with personalized service and scenic water views

Harbor landmarks, skyline views, and bring-your-own snacks and drinks

Explore two Smithsonian museums with an expert guide

Take to the water with two boats rented together

Explore Fredericksburg’s battlefield history with private transportation and a licensed guide

Taste your way through Annapolis history, one restaurant stop at a time

See Washington, DC’s illuminated landmarks with a guide after dark

Build paddleboarding skills with certified coaches, then paddle at your own pace

Trace the events surrounding Lincoln's final hours with an expert guide

Relax and cruise the South River on a spacious pontoon

Make your vows your own aboard a private Chesapeake Bay catamaran

Make sushi together, then share a sit-down meal

Relax and celebrate on a stylish private cruise with stewardess service

Explore aviation icons and vineyard country at your own pace