Here is a quick step by step in order of importance. Select your preffered place to stay. Boutique hotel or a private rental home. (for bigger groups, we recommend getting a house or two that are close to each other). Accomodations Book your accomodations first. Book your golf cart and rental boat if needed. This is highly recommended but they do book up MONTHS in advance. (if your rental home does not come with a dock slip- you'll need to book a spot at one of the marinas). Golf Carts - Boat Rentals Book your flights. There is the major airlines but there's also the smaller ones that tend to be easier with groups. Airlines Book your dinner reservations especially if you're with a big group and if you're coming during a busy time of year. (busiest during US and international holidays) Restaurants Book any fishing charters, boat trips/excursions, private chefs, baby sitters etc. Fishing Charters Touch base with the resort or the Property Manager for the house you're staying at. Let them know what time you plan to arrive and on what ferry. Be sure to keep them updated on any travel delays so they know when to meet you. Also- keep the golf cart company posted on any delays so they can meet you when you arrive.