We just got home from the Keys and I want to share my Florida Keys Travel guide with everywhere we stayed, ate and what I wore. It was an absolutely incredible trip that I will never forget!! We spent a total of 9 days traveling and it was the perfect amount of time. I spent an enormous amount of time planning this trip, so this is your one stop shop for the Florida Keys Travel guide suggestions!
I will break down my Florida Keys travel guide day by day, so keep scrolling for our itinerary each day. At the end I also talk about what I would do different next time!
If you want to hear about our other Florida adventures, check out my Anna Maria Island post here.
Sizing reference: I am 5’4″ and typically XS in tops and 25 in bottoms.
The drive from Tampa to Miami wasn’t too bad until we hit the Miami traffic. We stopped half way in Naples for lunch as Osteria Tulia and it was SO good. So good, that we stopped there again on the way home from the Keys. From left to right: Shrimp caesar salad, Calamari (one of my fave calamari dishes ever), Notorious P.I.G. pizza, My Michelle pizza. The My Michelle was drizzled with honey and just divine!
We at dinner at Pane & Vino after checking into our hotel (Casa Boutique on South Beach). To be honest, I would not recommend Casa Boutique hotel because it was so noisy. We stayed at Loews in South Beach last time and I preferred that way more. Casa Boutique was alright though since we were just in and out. We happened to go to Miami during the curfew, so everyone had to be in by 8pm. I am sure it would have been way worse had there not been a curfew.
Pane & Vino makes their own pasta, and it was fabulous (you can watch them make it in the window). I got the gorgonzola gnocchi and Chad got the Cappelletti verdi Tartufati, which is handmade green cappelletti pasta stuffed with fresh ricotta and mascarpone cheese, served with butter, parmesan cheese and black truffle sauce. Mine was just okay, but his dish was to die for!!!
After dinner, we wandered around South Beach until curfew. The beach was beautiful! For the influx of travelers, we were shocked at how clean it was. I wore a super casual outfit out and it was totally fine. I sized up to a 26 in these shorts, they run small!
Outfit Details:
Tee, Shorts, Necklace (c/o), Pearl Bracelets (c/o), Woven Bracelet, H Bracelet, Hoops (c/o), Sunglasses, Sandals, Louis Vuitton Bag
We woke up Sunday morning and explored Brickell City Centre and just couldn’t get over how cool this shopping and dining space was. We ate brunch at B Bistro next door, which I highly recommend! They do not take reservations, so I am glad we arrived early. I got the crab Benedict and Chad got the spicy tuna toast and both were heavenly! I wore this super flattering sweater tank, and sized up to a small in it.
Outfit Details:
Tank, Shorts (c/o), Sunglasses, Sandals, Louis Vuitton Bag
After brunch we drove to Key West and it was the most gorgeous drive over the crystal blue ocean. Gosh, I miss it so much just writing about it! We stopped at Bahia Honda State Park on the way (you can swim there) and the water was beautiful. I went there many years ago and there used to be stretches of white sand prior to the hurricane destroying it. It was still gorgeous none the less!
Pro Tip: If you are driving from Miami to Key West, leave as early as possible to beat traffic. Traffic gets brutal in the late afternoon.
We arrived in Key West and checked into the Artist House bed and breakfast. It was such a lovely place to stay and I cannot recommend enough! It was super close to all the action, but very quiet.
After we checked in, we explored a little bit. We even got to see a manatee! Everything is super walkable. We stopped at the Fisherman’s Cafe to grab a fish taco along the way and Kermit’s for some key lime pie.
We ate a fabulous dinner at Nine One Five! I got the tortelloni de casa shaved black truffle, ricotta, pecorino cream sauce and my husband got the shrimp fettuccine. The beat salad was also wonderful! I am happy we made dinner reservations before sunset, so we could enjoy the sun going down after.
After dinner, we watched a beautiful sunset over the water. It was truly magical. Also, I have never gotten so many compliments in my life until I wore this dress! I had a ton of people asking about it!
Outfit Details:
Dress (c/o), Earrings (c/o), Louis Vuitton Bag
First stop, brunch at Blue Heaven! We got lobster Benedict and banana pancakes. They were pretty good!
After brunch, we did a lot of walking and exploring again. We saw a ton of roosters and some baby chicks!
Outfit Details:
Tank (c/o), Shorts (c/o), Necklace (c/o), Pearl Bracelets (c/o), Woven Bracelet, H Bracelet, Sunglasses, Sandals, Louis Vuitton Bag
We did a sunset sail, so had an early dinner first. We happened to go to Thirsty Mermaid for happy hour (they do not take reservations, but it was easy to get in) and it was our favorite spot we ate at in Key West (ate there twice)! The chili pineapple wings were amazing. The Mac N Cheese croquettes are probably the best thing I’ve ever put in my mouth. And holy cow, the wedge with smoked bacon was like freakin heaven. HEAVEN! I am about to cry I miss this place so much haha. If there is a must eat from my Florida Keys travel guide, this spot is it!!
The sunset sail was SO fun on the boat When and If. The story was pretty cool – this guy bought this boat in 1939 and said when we win the war, and if I survive I will sail the world. He actually died in the war and did not get to sail around the world, so the current owner is planning to after the boat is paid off. I booked it through Sunset Sail Key West and I highly recommend.
We ended the night with some late night pizza at OnlyWood. We got half pistachio and half tartufata and the pistachio was just incredible. I wish we had good pizza in Tampa like this! It’s definitely a must stop for late night or if you need a break from sea food!
Outfit Details:
Dress (c/o), Necklace (c/o), Earrings (c/o), Sunglasses, Louis Vuitton Bag
Our favorite breakfast / lunch spot we found is definitely Sara Beth’s! We ended up eating there three times! Chad got the shrimp and sausage po boy and I got the shrimp tacos and we both agreed mine were better than his!
We then did Dip & Sip, where you snorkel then drink on the boat. It was SO fun and we had a blast. We booked through Sunset Water Sports.
Pro Tip: If you aren’t the best swimmer, wear a life vest out snorkeling so you can just float there. I did that the first time because I wasn’t feeling so good and didn’t want to swim for hours.
Outfit Details:
Tee, Shorts, Swimsuit (c/o), Hat, Necklace (c/o), Pearl Bracelets (c/o), Woven Bracelet, H Bracelet, Hoops (c/o), Sunglasses, Sandals, Louis Vuitton Bag
After snorkeling, we showered and then walked around and explored. I wore this fabulous romper for the evening! We spotted some young pelicans too. The young ones have brown heads, and they turn yellow as they age. We also saw a ton of tarpon in the water along the boats trying to catch the scraps of fish from the restaurants preparing fresh caught fish.
We ate at Hot Tin Roof and it was the second best view we had for food (Latitudes is first!). The burrata salad and the lobster mac n cheese were my favorites! Make your dinner reservations here at sunset so you can enjoy the view!
Outfit Details:
Romper (c/o), Necklace (c/o), Pearl Bracelets (c/o), Woven Bracelet, H Bracelet, Earrings (c/o), Sunglasses, Sandals, Louis Vuitton Bag
We ate brunch at Sara Beth’s again before moving from Key West to Stock Island. I got the fried chicken sandwich, and Chad got the shrimp tacos. Stock Island is about 15 minutes away and we stayed at the Perry Hotel. The hotel was gorgeous and had shuttles every hour to Key West.
Outfit Details:
Tank, Shorts (c/o), Necklace (c/o), Pearl Bracelets (c/o), Woven Bracelet, H Bracelet, Hoops (c/o), Sunglasses, Sandals, Louis Vuitton Bag
Latitudes might be the most famous upscale restaurant in the Keys. It is over on Sunset Key, and a ferry takes you there. You arrive at the dock at the time of your reservation and the hostess takes your name before allowing you on to the ferry. Once you take the ferry to sunset key, you are seated for dinner. The earlier in advance you make reservations, the better chance you have at sitting outside. I made reservations two months in advance and we luckily were placed outside with a fabulous water view. All the food was fantastic, but the views were definitely the best part.
Outfit Details:
Dress (c/o), Necklace (c/o), Sunglasses, Louis Vuitton Bag
We had breakfast at Harpoon Harry’s and to be honest it was my least favorite breakfast spot, despite the great reviews. Sara Beth’s is much higher quality and fresher in my opinion.
If there is a must do activity from my Florida Keys Travel guide, it’s definitely this! We saw a ton of amazing fish, and several sharks! We did see a couple turtles on the way out to the reef coming up for air. This is definitely the best snorkeling in the Keys. The reef is about 10 miles out and we booked with Looe Key Dive Center.
Pro Tip: Bring reef safe sunscreen! And make sure you layer your back really well. Your back will get a ton of sun when snorkeling!
After snorkeling, we had the best gazpacho soup, mac n cheese croquettes and calamari. I can’t rave enough about how much I love Thirsty Mermaid!
We had one last brunch at Sara Beth’s before heading out of Key West! Chad had the best open faced tuna sandwhich (the bread is garlic bread!) and I had the grilled caesar. We took one last stroll around town before getting in the car for the drive to Islamorada. I miss Key West so much already!
Outfit Details:
Sweatshirt, Shorts, Necklace (c/o), Pearl Bracelets (c/o), Woven Bracelet, H Bracelet, Hoops (c/o), Sunglasses, Sandals, Louis Vuitton Bag
We arrived in Islamorada and stayed at the Postcard Inn. It was double the cost of the spots in Key West, and about half as nice. However, I do think it is one of the best options in Islamorada. There isn’t a whole lot out there. I think the price of this place has to do with all the amenities. There is a pool, beach, nighttime entertainment and various bars.
Outfit Details:
Tee (c/o), Shorts (c/o), Necklace (c/o), Pearl Bracelets (c/o), Woven Bracelet, H Bracelet, Hat, Gucci Headband, Sunglasses, Sandals
We got take out at Twisted Shrimp and watched the sunset and listened to live music. It was such a nice evening! Twisted Shrimp was pretty good, but if you can only go to 1 spot in Islamorada, make sure it’s What the Fish Rolls.
Outfit Details:
Jacket (c/o), Necklace, Sunglasses, Louis Vuitton Bag
Outfit Details:
Sweatshirt, Shorts (c/o), Hat, Sunglasses, Sandals, Louis Vuitton Bag
We got lunch at Lobster Shack and then headed to swim with dolphins at Dolphins Plus! It was such an incredible experience and a highlight of our trip! We got to swim with Samantha and Luna and they were incredibly sweet.
Outfit Details:
Romper (c/o), Hat, Pearl Bracelets (c/o), Sunglasses, Louis Vuitton Bag
Definitely one of our favorite meals on the trip was What the Fish Rolls!!! We got the shrimp roll, fish roll and crab cake roll. The crab cake roll was out of this world. I want to go back so so bad! After dinner we enjoyed a quiet evening of wine drinking on the beach at our resort. It was the perfect way to end the trip!
Outfit Details:
Tee (c/o), Shorts (c/o), Necklace (c/o), Hat, Sunglasses, Sandals, Louis Vuitton Bag
Thank you for reading my Florida Keys travel guide! Overall, it was one of the best trips of my life. The water was so gorgeous and that food was like none other! Next time, we will skip Islamorada. I felt the properties there were overpriced for the quality, and there wasn’t as much to do except lounge at the resort. I feel like I can find a nice resort anywhere, and it’s a far trek to the Keys to just stay at a resort, in my opinion. However, I do think Islamorada would be a great vacation for families with kids who are not interested in the food and nightlife that Key West has to offer.
That being said, me and my husband adored Key West and we would stay there the entire time next time. I loved how gorgeous the Perry Hotel was, but not being walking distance from Key West ended up not being the best decision for us. I think if the Perry had shuttles every 30 minutes instead of every hour, we would 100% stay there next time because it was such a nice hotel.
A list of restaurants we wanted to try in Key West but didn’t have time for here: Louie’s Backyard, Four Marlins, Santiago’s Bodega, Eaton Street Seafood, Firefly, Carolines, Seaside Cafe at the Mansion, La Grignote, Key Plaza Creperie, DJ’s Clam Shack
A list of restaurants we wanted to try in Islamorada but didn’t have time for: Chef Michaels, Bayside Gourmet, Square Grouper, Ziggie & Mag Dog
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View Comments
The food looks delicious! It's been forever since I've been to the Keys. Would love to go back.
Jennifer
Curated By Jennifer
Wow what a fabulous tour guide.
LOVED this post and following along on IG during your trip! Key West is one of my favorite places <3
Jen this looks like the most amazing trip ever! We have been talking a lot lately about going to the Keys and this has me completely sold on booking asap!
This sounds like so much fun! Will have to plan a trip there sometime!
Lizzie
http://Www.lizzieinlace.com
We went to Key West on our honeymoon and it was so much fun! Dinner at Latitudes was truly an experience!
Everything looked so good - the water, the food especially. I felt I could taste it and the clothes oh my - to be young again. It was nice to be able to look at the Keys again. Thank you for taking me back.
Thank you Grandma! I miss you so much!!