Leg 5: One Day, Two Destinations (The Finale)

TL;DR: Leg 5 of my JetBlue 25 for 25 challenge was a one-day sprint through five destinations. I racked up 1,280 miles, spent 5h 27m in the air, and added $371.27. Highlights included a plane full of fellow challengers on the way to Martha’s Vineyard, turning a picnic bench into an office (with a quick … Read more

Leg 4: Two Days, Three Destinations

TL;DR: Leg 4 of my JetBlue 25 for 25 challenge was packed with lounges, security loops, and a bit of déjà vu. Over two days, I hit three destinations, racked up 3,700 miles, spent 9h 59m in the air, and added $680.50. Highlights included multiple on/off plane hops, getting upgraded by my “toxic ex” American … Read more

Leg 3: Three Days, Four Destinations

TL;DR: Leg 3 of my JetBlue 25 for 25 challenge mixed planes, trains, buses, and a fair bit of confusion. Over three days I hit four destinations, racked up 4,404 miles, spent 10h 37m in the air, and added $629.75. Highlights included working remotely from airport seats in Tampa, nearly getting on the wrong bus, … Read more

Leg 2: Three Days, Seven Destinations

TL;DR: Leg 2 of my JetBlue 25 for 25 challenge was a short but eventful stretch. I hit seven destinations in three days, racked up 4,417 miles, spent 10h 57m in the air, and added $789.97 to the tally. Highlights included booking the wrong flight and somehow making it anyway, hitting my 15th destination milestone … Read more

Leg 1: Four Days, Nine Destinations

TL;DR: Leg 1 of my JetBlue 25 for 25 challenge was a blur of airports, lounges, and one very silly mistake. Over four days, I hit nine destinations, racked up 10,152 miles, spent 22h 55m in the air, and spent $1320.18. Highlights included a $29 rental car in LA, my first major delay, and accidentally … Read more

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