Planning a vacation to the islands? You might be thinking it is not worth bringing a checked bag since you do not need a ton of clothes — leave the long pants and jacket at home. But for our family of four, we have found that one checked bag is perfect and pays for itself. Everything on an island is more expensive, and a few items packed from home save real money. Plus, with a checked bag you can bring full-sized bottles of sunscreen, shampoo, and conditioner instead of being stuck with 3oz carry-on limits. Some links in this article are Amazon affiliate links, which means we may earn a small commission if you buy through them at no extra cost to you.
Here are the eight things we think are worth the checked bag space.
If you already know where you are going, we also have destination-specific versions for Grand Cayman, Saint Martin and Sint Maarten, Saint Thomas, and Turks and Caicos.
8. Sun hat
A packable, lightweight, breathable sun hat keeps the sun out of your eyes without making your head too hot. Simple, classic, and effective. At the price point for most of these, maybe grab two.

7. Backpack cooler
We used ours as a personal item on the flight. It works fine as a regular backpack, but on beach days we loaded it up with cold drinks, water, and ice. On some of our vacations, a single cocktail at the beach bar costs as much as this backpack. We saved a lot by packing a few cold beers and seltzers.

6. Deep Woods Off
In the evenings, there is about an hour when mosquitoes are vicious. DEET is the only substance tested to work effectively against these pests. It does not take up much space, and having a reliable insect repellent will save you from countless itchy bites. The price at home is usually less than half of what we found on the island.

5. Mask, snorkel, and travel fins
Renting snorkel gear can be costly, with daily rental fees often equaling the purchase price of your own set. The first time we visited the islands, we did not pack fins and we regretted it. There is so much to see, and fins mean you can double or triple the distance you can safely swim from shore.
We have personally tested these sets and they have lasted for years. Cheaper options often have valves in the snorkel that fall out or get ruined by sand quickly, so investing in a quality set is worth it.

4. Packable beach chair
Get out of the resort and see the island. Many of the most beautiful beaches are free to access, but there is not always a place to sit. We fit two of these in our checked luggage along with all our snorkel gear, everything on this list, and more.

3. Full-size reef-safe sunscreen
Sunscreen is a must for any beach vacation, but on the islands it can cost double or triple the mainland price. In many places now, reef-safe sunscreen is required by law, and using sunscreens with prohibited ingredients can result in confiscation at the airport or even fines.
Our recommended reef-safe sunscreen has a non-greasy feel that makes reapplying less annoying. The sun at lower latitudes is intense — even on an overcast day we sunburn quickly without protection. Protecting your skin while preserving the marine environment is a win-win.

2. Underwater camera
We have tried those plastic cases intended to keep your phone dry underwater. Touch screens just do not work well below the surface. An underwater camera is a much better option for capturing the coral reefs and marine life.
We bought ours — an older model of the same brand — three years ago and have used it on four vacations since. It still works and takes great pictures. For the price, that is fantastic.

1. Inflatable pool float hammocks
These are perfect for lounging in the calm waters off one of the many beaches or floating in the pool. Since they are inflatable, they pack small and are easy to transport. One of those items that feels like a luxury but costs almost nothing.

Bonus: clear-bottom inflatable boat for kids
If you are traveling with toddlers or kids under seven, consider packing a clear-bottom inflatable boat. It lets little ones sit comfortably beside you while you snorkel, giving them a chance to see the underwater world without getting tired. It is a great way to share the snorkeling experience and enjoy the many shallow reefs not far from shore.

Our bottom line
One checked bag for the family, packed with the right items, pays for itself on the first beach day. The goal is to spend less time buying overpriced basics on the island and more time in the water.
For a planning-first example of how this fits into a full trip, our Grand Cayman planning hacks show how the checked bag, lodging, food costs, and itinerary all work together.