Everything - the ferries, the food, the flights, the strollers, the car seats, the beach chairs, the bicycles, the sun block, when you put it all together, especially for a whole family, especially when you’ve got to bring it all on one ride, those are all things you have to plan for. I would say that requires more than an administrative turn of mind. It requires experience. And if you haven't done it before I would say it requires genius. So talk to your realtor or homeowner. You will need the all information that they can provide.
Here is an interesting App from "Real Simple". It provides you with a list of things to bring to a beach vacation.
Here is a source for grocery lists.
If you're renting a home, pillows and blankets will be provided. Check with your realtor or homeowner about sheets, and bath and beach towels.
Bring medications, especially those that are required daily or on an emergency basis, like blood pressure medicine, sea-sickness pills and epi-pens. Most medications, by the way, can be filled on the mainland and flown over on New England Airlines from the CVS or McQuade's in Westerly, but they won't come at night or in the fog. There are two CVSs in Westerly so be sure you have the right one. Here is the correct number: 401-596-8182. And here is the number for McQuade's: 401-596-0277. Be sure to tell either pharmacy that your medications have to go over on the plane. Medications that contained highly controlled ingredients, like opiates, for example, will not be able to be filled this way. The New England Airlines number is 800-243-2460.
If you're walking on to the ferry, anything that rolls will be a good thing, especially if the wheels are a little more substantial, designed for uneven, sandy parking lots. If you're bringing anything perishable, use a nice big cooler with lots of ice, as it will be a few hours until you hit refrigeration under the best of circumstances. If you're taking the traditional ferry from Pt. Judith, it will be fine to leave a cooler on the car deck on the big wooden shelves on the right and left sides when you first walk on. The other ferries are set up a little differently, but there will still be a place for large suitcases and coolers. If you're coming in by plane, tell New England Airlines what you plan to bring, including dogs. They'll tell you if there are extra charges or if you'll have to have some things come over on a later flight.
You know that all night pharmacy, gas station or grocery store on Block Island? You don’t? Well that’s right because we don't have any of these on the island. So be prepared with plenty of gas and whatever you will need until morning.
Your homeowner or realtor can help you make arrangements to rent linens and baby furniture. They can also tell you about bicycles, kayaks, surfboards, fishing equipment and all the things you might not want to haul all the way to the island and then haul all the way back home. The Block Island Chamber of Commerce can help you as well.
You can also buy groceries, dairy products, fresh seafood, fresh produce, farmer's market items, gasoline, and liquor on the island. All those things will cost more than they do the mainland. I never go into the grocery store in the summer for example, without hearing someone muttering about it.
I get it. I really do, but I want to give you a little background. The food comes over in special trucks, requiring a large ferry charge as well as a full day for a driver. It costs five times as much as it does on the mainland to keep the freezers and refrigerators running. The Block Island Grocery store (the BIG) hires and often houses an entire staff of people. They have few economies of scale. In spite of this, their produce and meat is fresh and good, and they maintain a wide selection. They stay open through the winter, despite the fact they have to keep all their departments and specialized staff employed while serving less than 10% of the population they serve in the summer. That's meaningful, year 'round employment for full-time residents of the island. So I hope that makes you feel a little better about it. Lots of people, islanders too, buy as much as they can on the mainland. But the grocery store is there when we need it, God bless them and keep them open.