+26 @Anchovy_Paste4 If I hit the big pot (like hundreds of millions), my first thought for vaca would be to charter a yacht and do like a Caribbean tour for a couple weeks. I feel like that’s the ultimate lottery jackpot trip. Yacht would have all the bells and whistles — full time staff + chefs, toys (jet skis, boats, kayaks etc). I’d bring the Fam and I’d pick like 3-4 of my closest friends who have really stuck with me. In all, it would prob set me back like 70-100k but a true once in a lifetime experience that, if you had 300mil, would be well within your reach.

+13 @DrTriage Our honeymoon cruise, some 20+ years ago, we spent a thoroughly enjoyable day in St Barts, a small Caribbean island. We'd probably rent a villa, just us. And we are both really good cooks (wife was courted by Bern's Steak House here in Tampa) though the staff would clean up.

+12 @Rochonski Im flying out to cuba and staying at one of the 5 star adult only resorts. Im hanging out there enjoying the sun, the beach and the pools for 2 weeks minimum. From there, im flying home organizing contractors and other home related matters and then flying out to los cabos mexico and spending another 2 weeks out there before i make it back home