30-Aug 7:15pm Hotel Check-in Westin Key West Resort
30-Aug 8:45pm Dinner Lattitudes (Boat Dock Westin)
31-Aug 7:00am Breakfast Harpoon Harry's -832 Caroline Street
31-Aug 8:00am Dolphin Charter Tour (T) Wild About Dolphins
31-Aug 12:00am Dolphin Charter Tour (T) Lunch Provided
31-Aug 2:30pm Couples Massage (90 Minutes) Prana Spa
31-Aug 6:30pm Charter Sunset Cruise 201 Williams Street/Key West Historic Seaport
1-Sep 8:00am Breakfast La Creperie - 300 Petronia Street
1-Sep 9:00am Bike Tour (2.5 Hours) Key Lime Bike Tours - Corner of Simonton and Greene Street
1-Sep 1:15pm Lunch Paseo Restaurant - 1000 Eaton Street
1-Sep 3:15pm Key West Aquarium/Walkabout Tour Hemingway House Possible
1-Sep 7:30pm Dinner/Dessert Better than Sex
2-Sep 8:30am Breakfast Cuban Coffee Queen - 284 Margaret Street
I’m going to recap in the lazy way because...well...I’m lazy. That, and I realize your attention span is probably as short as mine and you don’t really need a dissertation of each day- but many of you were asking for recommendations on things to do, and I’ll share with you what I experienced and what I heard from locals/other travelers.
Day 1: Check in and dinner at Lattitudes
We stayed at the Westin Key West Resort, which is about as close to the ocean as you can get. We had a beautiful ocean view and my sweetie even had champagne and strawberries waiting for us when we got there. Our room faced the marina where the big cruise ships come to port, so on our last day, we got to see one up close. Those things are massive!
Westin Key West Resort
Pros: The Westin is, of course, really nice and as a guest you have access to purchase a day pass to the private beach at Sunset Key- which is where all the fancy pants people stay and live. (Seriously...how could anyone stomach a 6.5K HOA fee monthly?! Who are these people?!) We didn’t have a chance to go to the beach because we made some last minute changes to the plan, but we did pass it and it is very nice and would be a nice perk as a guest.
The location is great! You’re right next to Mallory Square- where you can catch the sunset and see all the street performers and vendors at night, next to the old customs house which is now a museum, next to the shipwreck museum and the Key West Aquarium, and walking distance to the Seaport and Duval street- which is the Bourbon Street of Key West.
Cons: If you are just looking for a place to lay your head, this is a bit pricey. However, on our bike tour, our guide Chris and the two girls we met from Miami said Albury Court Hotel was nice and affordable and we passed Lighthouse Court- which was right across from Hemmingway’s house and looked pretty dang cool. I may look into that for next time.
Lattitudes
Pros: Holy yumtastic fat kid food, Batman- this place was AMAZING. The ambiance is incredible- we sat outside under the torches in the most romantic vision ever. I was so impressed by everything- from the architecture of the building itself to the light up menu. Seriously, I totally geeked out. We didn’t make it for sunset, so we missed the gorgeous view of the sun setting over the Gulf of Mexico, but that didn’t matter at all. The food is phenomenal. I need to know where I can acquire a vat of jalapeno mango butter...I want to put it on everything. The cocktails were delicious too. We had prosciutto wrapped shrimp as an appetizer, and I had Parmesan crusted scallops over mushroom risotto. And a key lime martini. Yeah, clearly my diet went out the window as soon as we landed...no prob Bob it was WELL worth it.
Cons: You need a reservation, so plan ahead. Also, the ferry picks you up for your reservation, so be sure you arrive on time. And try not to die from shock when you get the bill. This is the adult version of YOLO, so just eat it!
Day 2: Dolphins and dreadlocks
We were supposed to get up and go to Harpoon Harry’s for breakfast, but man...morning came early. Side note: I didn’t sleep past 7 any day of my vacation. I’m pretty sure that’s a sign that I’m getting old. We forewent sleeping in to do all the things! So instead, we ordered room service (EEK, can we add the price of that to the “con” list, please?!) so that we could catch a cab over to the dolphin adventure.
Wild About Dolphins- Key West Harbor Marina
Pros: This is a really small tour group- I think their maximum is 8 passengers. Our guide, George, was an adorable Cuban man who was super chill and really knowledgeable. You meet at the harbor and jump in the boat, where they take you around and tell you all about the resident dolphin pod Key West is home to. We were avoiding some storm cells and did our snorkeling first, before we went in search of dolphins. Snorkeling was something I’d never done before, so it took me a minute to get acclimated to that. I kept holding my breath and clenching my teeth like a crazy lady. Once I finally relaxed I was able to start enjoying the swim. We saw lots of fish, a few sting rays (including one HUGE one under the sand) and a bunch of coral and sponges. It was a little overcast, so we were thankful that the water was really calm, because it helped our visibility. After the swim, we got back onto the boat to a snack of pitas, hummus, and veggies (thanks to George) and got underway to go in search of dolphins. We were lucky enough to see 2 dolphins breach and 2 came right up to the boat! Fun fact: dolphins turn off half their brain while they sleep and the other half remains on. Many of the dolphins we saw were actually sleeping. How friggin cool is that!? Although we didn’t take advantage of it, Wild about Dolphins offer a private day pass for our guests to the super exclusive club and bar. NO TIME! THERE’S NEVER ANY TIME!
Cons: It’s hard to predict wild dolphins, and I think I was expecting to see more than we actually saw. 20 out of 200 ain’t bad though!
Prana Spa- Couples Massage
All pros, no cons! Such a cute spa, kind of tucked away. I mean, when is a massage NOT great? On our way over to the spa, we passed a vendor for FURY sports who yelled, “10% off for Texans!” (Patrick was wearing a Rangers shirt). We found out he was originally from Ft. Worth, and he talked us into changing our plans to go to the Aquarium to a 4 hour catamaran, kayak, and snorkeling adventure. We had originally just wanted to go on the kayak eco-tour, but it was sold out. But we were excited just the same. Double win! Don’t just pass the booths- take a look! You might find an adventure you want to go on.
Sunset Cruise
Pros: While waiting at the harbor to board, we saw a water spout! Let me just say, that is pretty epic! I mean, seriously- what are the odds? The cruise included a buffet and booze, so it’s a pretty good deal. There was also a pretty cool steel drum player who gave us some...interesting renditions of theme songs, Michael Jackson, and even Led Zepplin.
Cons: This was a huge boat and a ton of people, so it felt really “tourist-y”. I’m also not a huge fan of a buffet line. It’s my inner snob, or maybe the fact that we had peaked at Lattitudes the night before. I don’t like crowds, and I really liked the small feel of the earlier dolphin tour. I’m spoiled, really.
Day 3: Tampon Commercial Activities day
I mean, truly- we were SO busy on day 3. Poor P was exhausted, but we got up at the crack of dawn again and headed over to Harpoon Harry’s for breakfast.
Harpoon Harry’s
Pros: Affordable, quick, and adorable environment.
Cons: It’s a bit of a walk from the resort, but it was close to where we were meeting for the bike tour
Key Lime Bike Tours
Pros: SO. MUCH. FUN. I was kind of skeptical about a bike tour, but I’m SO glad we did this. Once again, our group was really small- it was just us and 2 girls from Miami and Chris- our largely entertaining guide. Chris was nursing his hangover from Brewfest the day before and a night of karaoke, but he was ready to go. This guide is not really on a strict pace, so we were able to go a few blocks and then get an in depth history from Chris on the location we stopped at. He might have been making half of it up (kidding!), but I don’t even care. He was a great guide and this felt just like chillin’ with a local and getting a behind the scenes look at Key West. I learned a lot on the tour, and I had a great time. If we come back, I would likely rent a bike- that’s a great way to get around!
Cons: We had to rush off to get ready for our next adventure, but I would have liked to stay and hang with Chris and the girls as they went over to Kermit’s for a key lime pie slice. P and I got one later (dipped in chocolate on a stick...um, yeah that happened), but I really enjoyed the company. This is a 4 hour trip too, so if you are packing a ton of things in your day, you might skip this one.
Javacat Eco Tours
Pros: Again, this was an intimate group. The max is 6 out on the boat, so it feels so much less tourist-y. Our guide, John was a total hippie and he was cracking me up. People in Key West really live the “No shoes, no shirt, no problems” lifestyle. There’s a lot of semi-retired folks with ponytails and a completely laid-back style. John was no exception, and coincidentally...Patrick does a dead on impression now. We went out to the Gulf waters to kayak and snorkel. Kayaking was the best. We went along the mangroves and saw all the budding sea life. As soon as we got there, hippie John pulls up a horseshoe crab and lets us all hold it. Google that thing- it’s insane! We got to kayak inside the mangrove and see all the cool creatures inside the roots. It felt like I was in an episode of Planet Earth. I learned SO much, yet again. On the back half of the kayak trip, we even saw a bald eagle and a brown pelican- both of which were returning for fall. A bald. Eagle. ‘MERICA! We went snorkeling after this and John got in the water and pointed out a moray eel and a spiny lobster for us. I was much more comfortable snorkeling this time around and was able to enjoy the long stretch of just floating along. When we got back on the boat, John had made snacks for us- pineapple, curried chicken salad, pasta salad, cucumbers- all part of the tour.
Cons: I wish I had taken a camera so I could have documented this trip better. What the heck is wrong with me? Say it together...waterproof camera! ANNND go!This is a 4 hour trip, like the bikes- but like the bikes, it’s well worth it.
Dinner- Turtle Kraal’s
Pros: Chris (Key Lime) had told us this place had a good happy hour, so P and I stopped in for appetizers and drinks...even though we had just had snacks on the boat not long before. But c’mon...happy hour! I love mojitos and mojitos in Key West are DURRICIOUS! We each got 2 drinks, some pumpkin potato skins, ribs, 50 cent oysters, and conch fritters (fat kid alert!) all for less than we had paid for breakfast the day before at the resort. Plus, we got to watch our waiter troll a snotty table next to us. WINNING.
Cons: I ate like a super fat kid. Even though I knew we were going to Better Than Sex later that night. Fail.
Mallory Square
We stopped into Mallory Square to watch the sunset and see the street performers and vendors. Each performer has to audition for the city and draws straws to secure their place on the square. The vendors are all local and most hand-craft their items. The guy with no teeth who weaves the coconut baskets is super talented, albeit weird. The sunset was gorgeous as expected and the performers were great. I could have spent even more time here, but clearly- we had more to do. I mean, could we possibly cram any more into a single day?
Pros: Red Velvet Cheesecake with cream cheese frosting, and strawberry ale in a chocolate rimmed glass. Yes, it is better than sex. I normally can’t taste what makes red velvet different, but this cheesecake had just the right hint of berry to make that distinction for me. Patrick had an apple cider in a caramel rimmed glass and a cookie nookie pie- which was a gooey warm chocolate chip cookie, chocolate pieces and pecans wrapped up in pie crust and served with a vanilla bean ice cream. It’s super dark in there, so we got light up menus again, and there were some risqué conversation starter questions at each table to help stimulate conversation.
Cons: Obviously, if you’re offended by dessert names like Tongue Bath Truffle or drinks like Matty’s Money Shot, then you should probably not go. But if you aren’t all uptight and prude and you want to eat a bunch of delectable goodies, make a reservation and go. Make a reservation! Urban Spoon it or Open Table. Do NOT show up without a reservation. We watched like 13 groups get told there was more than a 2 hour wait at 9:15. And they close at midnight. So plan ahead, and then go!
Day 4: Finally sleeping in
We didn’t get up and go to Cuban Coffee Queen in the morning like we said we were going to. We were beat by then! But definitely go to Cuban Coffee Queen (Chris’ (the Key Lime Bike guy) wife Michelle manages it). Get a photo op with the big Key West post card on the side of the building.
Other places I’ve heard are good and/or am putting on my bucket list of places to go:
Eateries
La Creperie- breakfast - is in the black bohemian neighborhood (which is super cool) and I want to eat all the things
Cuban Coffee Queen- breakfast – great photo op with post card
Blue Haven – breakfast- Kenny Chesney favorite/iconic
Seven Fish- Hear it’s delish!
Debauchery
Rick’s
Garden of Eden – apparent “clothing optional” bar on Duval
Sloppy Joe’s – every time we passed, this place was hoppin!
Irish Kevin’s
Adventure
Kayak eco tour
Dry Tortugas (all day event- Ft. Jefferson)
Jet ski tour
Parasailing
