1. Eat at Lorelai's. This place was the epitome of vacation fun. There's a giant fiberglass mermaid in the parking lot. The kids ran free. The drinks flowed. There was a band, an amazing sunset on the bay, and many, many laughs.  

2. Visit Theater of the Sea and swim with dolphins, rays and sea lions.

3. Head to Anne's Beach for some solitude and hermit crab chasing. 

4. Rent a boat. We brought our own lunch and all of us, including the kids, were able to snorkel and fish. Just tooling around on the boat, and taking in the beautiful vistas was wonderful. Prices vary from marina to marina, but it's approximately $225 for two hours with a captain.

5. Check out Founder's Park for all types of water and land fun. 

6. Take a boat out to Indian Key for a hike, picnic, or change of scenery. 

7. Shop local and browse the shelves at Hooked on Books. There's a nice children's section if your kids read through what they packed.

8. Drive to Key West, rent a bike, and look for six-toed cats. About 2 hours from Islamorada.

9. Take a ranger-guided tour of Lignumvitae Key Botanical State Park. 

10. Feed the Tarpon at Robbie's Marina. These giant fish will eat right out of your hands, although they are disarmingly large. We did this twice and the kids loved it. The pelicans and herons also enjoy getting in on the action. It's adjacent to the Hungry Tarpon restaurant, which had great conch stew, fish tacos, and outdoor seating bayside. There's also a tchotchke market, good for shell anklets, which make 7-yo girls happy.

11. Boat out to San Pedro Underwater Archaeological Preserve State Park and see a shipwreck from 1733.

12. Rent a kayak and check out the mangroves. 

13. Visit the 65-by-20 foot hurricane monument, constructed of locally quarried limestone, in memory of the over 420 people that died in the 1935 hurricane. 

14. Stop by the History of Diving Museum to see a collection of vintage diving equipment and learn the story of undersea explorations and advancements.

15. DO bring sun hats, rash guards, and very powerful sun block. Some people's children (ahem) got very sunburned.

Where to stay: We stayed at the Postcard Inn at Holiday Isle. It wasn't perfect. The front desk staff was completely clueless, there was no breakfast and the food was average. The rooms are quite pretty, particularly if you have an oceanfront room — we did not. They recently changed management companies, and are transitioning the hotel to a family friendly destination, so hopefully it will improve. The pool and ocean views were beautiful though, so we were happy.

Cheeca Lodge is the most famous resort on Islamorada, and priced accordingly. You can also rent  a condo, if you don't want the expense of meals.

Photo Credit: Adam Saynuk