On October 18, 2017, about 1545 eastern daylight time, a Cessna 402B, N900CR, was substantially damaged when it was involved in an accident near St. Petersburg, Florida. The commercial pilot and passenger and two individuals on the ground sustained minor injuries. The airplane was operated as a Title 14 Code of Federal Regulations Part 135 non-scheduled passenger flight. Federal Aviation Administration (FAA) air traffic control records indicated that the airplane departed Tampa International Airport (TPA), Tampa, Florida, at 1526. At 1539, the pilot advised air traffic control that he was “fuel critical” and requested vectors for the nearest airport. The controller provided a heading toward Albert Whitted Airport (SPG), St. Petersburg, Florida, about 7 miles away. The pilot reported that he had 20 minutes of fuel on board. At 1543, while 4 miles from the runway, the pilot was given a vector toward runway 4. The pilot reported the airport in sight, and the controller provided the pilot the SPG tower frequency. There were no further radio transmissions. The airplane landed on a residential street about 2 miles from SPG and collided with two vehicles. Examination of the airplane by an FAA inspector revealed substantial damage to both wings, the horizonal stabilizer, elevator, and nose section. Both wingtips and wingtip fuel tanks were separated from the wings. The left wing tip fuel tank exhibited minor sooting and heat damage. Both auxiliary fuel tanks were damaged and breached. The left engine fuel selector was found in the left main fuel tank position; the right engine fuel selector was in the right main fuel tank position. Examination of the engines revealed no evidence of any preimpact mechanical malfunctions or failures that would have precluded normal operation. Fuel was found in the line between the fuel flow transducer, the fuel manifold valve, and in the fuel manifold valve housing on both engines. According to operator records, the accident occurred during the third leg of a four-leg trip. The records indicated that at the start of the trip, the airplane’s hour meter read 589.0 hours. At the accident scene, it read 592.7 hours. Two of the legs were scheduled with passengers; the other two legs were positioning flights. A review of fueling records revealed that the airplane was fueled with 102.3 gallons the day before the accident. The total amount of fuel on board at the start of the trip was not listed in the company dispatch documents. The pilot did not fuel the airplane at either of the intermediate stops. According to the Pilot’s Operating Handbook, the airplane was equipped with two main wingtip tanks, each with a capacity of 50 usable gallons, and two auxiliary fuel tanks, each with a capacity of 31.5 usable gallons. With full fuel, the published endurance was between 4.8 to 5.4 hours using 73% and 65% power, respectively. The published endurance for 100 gallons of fuel (the capacity of the main fuel tanks) was 3 to 3.3 hours. Fuel consumption estimates, based on the flight’s itinerary, distances between airports, and performance tables in the Pilot’s Operating Handbook indicated that the airplane would have used about 100 gallons of fuel between the last fueling and the accident. The pilot had 38 hours in the airplane make and model, all of which were flown in the 30 days preceding the accident. The pilot completed his Part 135 checkride the day before the accident. The accident trip was his first solo revenue flight.