Aiming at the problem of transportation for heavy oil during the middle-later development stages of the Lvda oilfield, based on the self-developed design of a visual circulating flow experimental apparatus for heavy oil−water two-phase flow−the flow regime characteristics and corresponding drag properties of the two-phase flow of Lvda viscous oil, which is simulated by 500# industrial white oil and water in a horizontal pipeline are investigated experimentally. According to the Kelvin−Helmholtz instability theory, the flow pattern transition criteria from stratified flow to annular flow (AF) are proposed. The effects of 0.11−0.90 m/s oil superficial velocities, 0.06−1.49 m/s water superficial velocities, and 0.09−0.93 input water cuts on the drag reduction effect of different flow regimes are analyzed. The experimental results indicated that with the increase of mixing velocity and water volume fraction, stratified flow, AF, oil plug flow, and dispersed oil lump flow are successively observed in the horizontal heavy oil−water two-phase flow, in which AF is the main flow pattern. As the Froude number increases to 4.0, the input water volume fraction does not change any more and remains at about 10% of the total flow rate in the process of converting from stratified flow to AF. The four delivery approaches can archive the reduction of transportation resistance for heavy oil at different degrees, in which the transportation of heavy oil surrounded by a water ring has the best effect of drag reduction. At the optimal working conditions of 0.61 m/s oil superficial velocity, 0.07 m/s water superficial velocity, and 0.10 input water cut, the pressure drop of water annulus conveying for heavy oil is only 1/62.54 of that of separate transport for pure heavy oil under the same oil flow rate.