Hotels:
Cheeca Lodge- a luxury hotel on the island. The views are stunning, and the main lobby has three restaurant concepts: Italian, sushi, and steak. When you walk through the main lobby onto the beach- the scenery is fantastic! There are fire pits and string lights, lounge furniture, a stunning dock… There was/is live music at nights. The hotel also has a small golf course (think 3-4 mini holes), watersports, spa, fitness center. You name it, Cheeca probably has it.
Post Card Inn- A family-friendly hotel located off of highway one. If you stay here, be sure to request a room with beach access. Buildings 1 & 2 have great ocean views and are a step from the beach. This hotel has a great tiki bar that locals (according to our fishing mate) like to grab drinks after work. Post Card Inn also has a marina attached, making fishing excursions easy to book and be on time for in the early morning. In terms of activities, any game you can think of this place has. Evan and I stayed here with his family & created our family Olympics- Post Card Inn has kayaks, horseshoe, volleyball, bags, ladders, ping-pong, frisbee golf, paddleboards, and a water trampoline. This resort is family-friendly and has lots of little ones running around. They have an Italian restaurant on-site , Ciao Hound; as well as the Tiki Bar & Raw Bar. We went for Christmas dinner, and we were not impressed by the food. However, it is very convenient if you have a family you need to feed for dinner. This hotel does not have a fitness center. Instead, guests get access to the fitness center at the sister hotel- Amara Cay. It is a small hotel gym and about 4 miles from Post Card Inn. Lastly, I will add that the hotel has a Starbucks on-site. So getting coffee in the mornings is a breeze.
Amara Cay- As mentioned earlier, this is the sister hotel to Post Card Inn. They advertise this hotel as the more pet friendly of the two. I thought this hotel was "more adult" as well. Fewer kids were running around & it was quieter than Post Card Inn. There are great ocean views but no beach access. It still has sand and is on the ocean, but you have to lower yourself using the pool ladders into the sea. The pool and patio design are very chic and relaxing. Evan and I would walk from Post Card Inn to workout at Amara Cay, so we could see the lobby & outdoors; however, we did not get a peek at the rooms here.
 
Eat:
Ziggie & Mad Dogs- a fun local spot said to be a typical restaurant for Al Capone to play poker in the back. You can see the history of the restaurant online. I would recommend steak or fish oscar style here. They had soft shell crab here- would not recommend. However, the other food was excellent.
Nikai Sushi- sushi spot at the Cheeca Lodge. Request to sit on the patio. It is much better than the restaurant's interior—very spicy rolls with lots of tempura fish. I stuck with the sashimi- the tuna, salmon, and sea bass were incredible. They also have two unique sashimi appetizers that are great- Wahoo Tataki & Hamachi Mariachi.
Bad Boy Burrito - my favorite spot on the island. Evan and I stumbled upon this walking from our hotel to Amara Cay. It is tucked away in an area called the trading post. The trading post has a few tiny boutiques and a coffee shop, but bad boy burrito is a must. They have a very funky menu with sushi, tacos, burritos, poke bowls, salads… you name it! Great vibes, fun outdoor seating. I can't say enough about the grilled fish salad… I had it two days in a row. Evan got the shrimp tacos and then the fish tacos the second day. He says the fish was incredible. He also tried the poke bowl and thought that was fab too. If you like limeade, this is a must-order!
Chef Michaels- in my opinion, the best restaurant on the island. Note this place only has wine and beer. Hogfish is their specialty. The slogan is Peace. Love. Hogfish. They have a dish that's called the trio- Fish cooked in all three of their styles! A must. Also, order the ceviche it's served in a fresh coconut! 
Lazy Days - I did not check this spot out but saw it off the road. Very casual place with beach access. If you happen to be a lucky fisherman or woman, you can bring your catch, and they will cook it up for you.
Marker 88 - great lunch spot on mile marker 88. Right on the water, fun bar, and good lunch food. The margaritas were fantastic here. They had a great healthy lunch option, too- zucchini noodles with shrimp!
Hog Heaven- total sports bar that Evan and I walked to for a drink and football. It was popping. People were docking at the restaurant and coming in for barbeque! We did not try the food, but it smelled great.
Midway Café-  They sell Mama & Isa's key lime pie here. A good café for breakfast or lunch. Lots of homemade pastries here too! They even had vegan and gluten-free options.
Green Turtle Inn - This spot had everything, a sports bar, restaurant, and bbq food truck outside, plus a boutique that has Patagonia, Orvis, and Vineyard Vines
Florida Keys Brewery- brewery, fun outdoor patio with live music. Lots of unique beers on tap, but go for the classic-iguana bait!
Islamorada beer company - This beer was sold all over the keys. Similar to Iguana Bait but has a larger outdoor patio.