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Critique My Itinerary

Waxhaw, North...
Level Contributor
16 posts
8 reviews
Critique My Itinerary

My wife and I are in our 30s. We will be traveling from Miami to Key West, then back to Miami from Wednesday, June 27 to Tuesday, July 3. We've never been to the Keys, but we've come up with a rough itinerary, and I would love to hear suggestions and feedback that any of you may have that are more familiar with the area. Money isn't really an issue. We enjoy fine dining, but we also love dive's. We're vacationing to have fun. We have no interest in historical buildings, forts, 6 toed cats, or anything like that. Mainly, we want to do the most fun and exciting things unique to the Keys. The hotel is already booked, so changing up the number of days at various places isn't an option. So here goes:

Wednesday, 6/27 - fly into Miami. Rent a convertible and have dinner and drinks at the Stubborn Seed.

Thursday, 6/28 - Drive to Blonde Giraffe at 10:00 a.m. for pie and Coffee (breakfast of champions). Next head to Islamorada. I plan on hitting Marker 88, Lorelei's, Morada Bay, and/or Lazy Day for food, drinks, and hopefully some good music. Then we'll swing by Robbie's to feed the Tarpons. I'm hoping to hit the road again by around 2:45 p.m.. Next stop will be Sunset Grill and Raw Bar in Marathon. We plan on hanging out there until around 5:00 p.m.. We'll then drive to our hotel, H2O Suites, in Key West. We have dinner reservations that night at 8:30 at the Flaming Buoy.

Friday, 6/29 - Lunch at Garbo's Grill and dinner at 6:00 pm at Loui's Grill. This may be wishful thinking, but we're hoping to make it over to Mallory Square before the sunset. The sunset should be around 7:50. We plan on spending the rest of the day at our hotel pool, bar hopping and looking for good music, and exploring the island on bikes.

Saturday, 6/30 - Lunch at Bien around noon, Key Lime Pie festival Sip n' Stroll around 2:00, and dinner at Martin's at 6:00. Again, hoping to make it to Mallory Square after dinner, and then bar hop until we're ready to crash.

Sunday, 7/1 - We may rent jet skis in the morning, and do Fisherman's Cafe for lunch, For dinner, we have 6:45 reservations at Latitude. This should put us finishing up around sunset.

Monday, 7/2 - Blue Heaven for Brunch, and Hot Tin Roof at 9:00 pm.

Some things we plan on trying to do in Key West in our free time include spear fishing, Key Lime Pie Festival, Better than Sex dessert, Sunset Pier for sunset, Michael McCloud for live music, Dante's, Schooner's Wharf, Green Parrot, Sloppy Joe's, Hog's Breath, Captain Tony's. Any other suggestions?

Tuesday, 7/3 - Get up early and drive and check out Blue Hole, then drive to Faro Blanco Resort for an early lunch. Next, drive to Key Largo and check out Sharky's, Pilot House, Backyard Cafe, and/or Jimmy Johnson. Again, we're just going to bar hop until we find the place that's the most fun. To us that usually means good live music. Next we'll drive to Alabama Jack's for an early dinner. Then we'll head to the airport for a 9:00 pm flight.

18 replies to this topic
Key West, Florida
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1,710 posts
6 reviews
1. Re: Critique My Itinerary

Wow, you’ve packed it in. Way too much for relaxing, IMO. You have hit on some of the highlights. My only suggestion is to staying at Louie’s through sunset. Don’t rush dinner, it’s a beautiful waterfront setting and you’ll catch some of the gorgeous sunset colors from there. We love what happens to the sky after the sunsets and often watch from there. It’s not just watching the sun sink directly into the water. Latitudes will have the perfect view for that, Mallory square not so much.

Key West
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for Key West
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166 reviews
2. Re: Critique My Itinerary

I agree with the prior post’s advise. Don’t rush Louie’s. While you may not see the sun drop into the water there, the sky and setting are georgeous during sunset. You have a lot of good choices, but for me, Key West is a kind of go with the flow, see where the day takes you kind of place. Don’t be too regimented with every hour planned so you can just wander around Old Town and see what you find.

Saint James City...
Destination Expert
for San Pedro
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16,561 posts
10 reviews
3. Re: Critique My Itinerary

Just a personal opinion, but, I’d give Sunset Grill a pass, and, just continue on to Key West. You’re quite a bit younger than me, but, I felt like we had landed in the middle of a frat party.

Marathon, Florida
Destination Expert
for Marathon, Islamorada
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16,664 posts
36 reviews
4. Re: Critique My Itinerary

That time of year in a convertible means you will likely only have the top down after dark.

I too would skip Sunset Grill. Not our most proud establishment. Plenty of other great places in marathon to visit.

For me its too much planning. Have an idea of places you would like to try and toss the regimented itinerary out the roof of your convertible. The Keys aren't that type of atmosphere.

United States
Level Contributor
1,490 posts
27 reviews
5. Re: Critique My Itinerary

agree with above .. skip sunset grill .. there is nothing special about the place. its fine .. just not worth a place on an itinerary and you have so little time .

Better than sex ... you could have a pretty long wait without reservations . its worth doing but i'd try to call ahead. they are open pretty late.

If you can fit in a sunset sail ... depending what you prefer, the danger's wind and wine is often recommended and on the other end of the spectrum, we had great fun on the floating tiki bar :D

if you can slip in a snack on Duval ... DJ's clam shack is worth your time ... and Bagatelle's happy hour menu is also very good

Key West, Florida
Level Contributor
2,295 posts
5 reviews
6. Re: Critique My Itinerary

You have certainly done your research!! A few thoughts for your consideration....

Arrival day and morning of day 2 look good to me. I always Ike to have something definitive in mind when I get to a new place, when so many choices can be overwhelming.

After that, other than your reservation at Latitudes (and possibly your dinner reservations at Flaming Buoy and Hot Tin Roof), ditch the entire itinerary! Seriously. The LAST thing you want to do is tie yourself to a schedule like this, complete with already identified food stops and timelines when you are in the Keys. In fact, it is exactly the opposite of what they Keys has to offer. If you follow this, you will miss the entire point of being here.

In no way do I intend to sound harsh, but in the spirit of critique, that’s my reaction. The glorious gift that the Keys offers is a laid back, take it as it comes, wandering around, adventure of discovery that is all your own. The day you thought you had planned, that becomes a once-in-a-lifetime experience that you never could have imagined, doesn’t have time to reveal itself with a schedule like this.

Some suggestions — Keep your list of places you might like to go as reference points. Go to some of them when the mood strikes, preferably if you happen to be driving, riding or walking by when you’re hungry or thirsty.

Relax, stop by a spot where the music sounds good to you. Have a drink. Chat with the bartender. Say hi to the person sitting next to you. Don’t look at your watch or your phone for hours on end. Gaze at the ocean. Breathe deeply. Marvel at the flowers blooming everywhere and notice the little bits of artistic charm that are on every street you walk. Do something (maybe several somethings) not on this list. Surprise yourself!

And, while my thoughts are rather general overall, one specific suggestion: please do skip Sunset Grill. There are endlessly more interesting and fun places to spend a couple of hours than here.

Hope you find this helpful!!

Charlotte, North...
Destination Expert
for North Carolina
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3,077 posts
31 reviews
7. Re: Critique My Itinerary

Agree with Steps!! We don't check time, or do reservations(with a very few exceptions) while in the Keys. We love the laid-back slow pace and on our Florida Keys/KW trips, while we do have some objectives, our days pretty much occur organically...so wonderful and different from other vacation spots. If you are coing to the Keys mainly for fine dining, you are going to be disappointed, better off staying home and hitting some of Charlotte's best, driving 2 hours to Blowing Rock, or take a 3 hours drive to Charleston, SC.

If it were me, I'd keep the Louie's reservation, maybe Latitudes too (even those, more for the atmosphere/experience than the food), and cancel the rest, with all those reservations/eating plans, you're going to miss out on Key West. It's not a matter of money, it's a matter of truly experiencing KW. Yes have your lists of things/places you'd like to see/do/eat, and yes, absolutely do Blue Heaven for breakfast/brunch one morning(again, the experience), but don't break your neck trying to do all/eat all in one trip, IMHO you've got about 5 trips worth of eating planned! LOL! It's very hot/humid that time(and most times of the year) of year, it really cuts the appetite. For us a day of KW eats often go similar to this: half a breakfast sandwich and have bloody mary's at Schooner Wharf while watching boat captains/crew start their day; for lunch, split a Sloppy Joe sandwich at Sloppy Joe's-escaping the heat, and enjoying a few drinks while listening to great live music. Afternoon snack-ride bikes by Kermit's for a slice of Key Lime pie.. After experiencing sunset celebration or a sunset cruise, ride bikes through beautiful and quiet residental streets to Mangia Mangia for great homemade pasta,-split an entree & bottle of wine, or El Siboney for great cuban food(although often we skip dinner-proper, instead grazing at great happy hours' offerings throughout KW)..afterwards just ride bikes by favorite bars listening for what we decide is our favorite music for the night. I urge you to really experience Key West, don't live on a schedule or by reservations for the latest/greatest restaurants. In 30 years of loving and experiencing the Keys/KW, and for the most part, restaurants come and go, but the heart and soul of KW always remains. Take a Conch Train Tour to get your bearings and learn a little about Key West. Ride bikes back in the beautiful historic neighborhoods, say hi to locals, roosters and 6-toed cats. Get out on the water, and not on a jet ski, go kayaking around the island, experiencing some of the mangrove tunnels near Stock Island. Like live music?, take a sunset cruise and enjoy! https:/…sunset-sailing-music (you can fine dine in Charlotte, but you can't experience Commotion on the Ocean!) What about a snorkel tour? there's "only in the Keys' beauty under the waters! Yes experience Sunset celebration, but don't tightly schedule time for it, arrive as street performers are setting up and just let it happen for as long as it does, later grab a cuban sandwich at Sandy's, Fritas, or Cuban dinner at El Siboney, perhaps a taco or two from Garbo's or Amigos'..maybe ride bikes down the street, smell something great and stop in to eat there...again have your lists to refer to, but just let it happen, don't schedule/plan.

As for your plans coming and leaving KW, if live music is the primary reason for all those stops, you'd better check firsthand with those places, many, if not all, don't have live music before late afternoon/early evening, and some only have live music on weekends. I know for sure that Sunset Grille in Marathon won't have live music until dinner(-average food at best)....great water views though.

Lastly, ..sorry, continuing to rip on your itinerary....you are going to Miami Beach, one of the most cultural rich/diverse places in the entire country, and you want to eat American Fusion? Really??? Expand your horizons! There's amazing foods from all over the world in Miami, save American Fusion for a weekend night in Charlotte. Ditch the car and walk the sidewalks of South Beach, check out the many sidewalk cafes' menus, and/or find the wonderful ethnic "holes in the wall".

Whatever you do, I hope you have fun! To each his/her own, but personally, I'd throw out that itinerary!

Hilton Head, South...
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368 posts
60 reviews
8. Re: Critique My Itinerary

Are you bringing a stop watch and a clip board with you so can keep on schedule?

Relax and go with the flow as suggested above.

United States
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1,490 posts
27 reviews
9. Re: Critique My Itinerary

Wise words above !

Waxhaw, North...
Level Contributor
16 posts
8 reviews
10. Re: Critique My Itinerary

I sincerely appreciate all of the feedback. We will definitely let things happen organically. Other than the hotel reservation, dinner reservations, and the Sip n' Stroll, we haven't scheduled anything, so we're pretty flexible. If the dinner reservations aren't working for us, we can always cancel.

As for the drive down and back, I listed a lot of places, but I don't plan on stopping at all of them. Basically, we just plan on bar hopping in Islamorada on the way down and Key Largo on the way back. The bars listed are places I thought we might try until we find a place we want to stop. We had just a couple of other stops just to break up the drive. After Islamorada, I planned on stopping in Sunset Grille in Marathon. What's the point of driving if we're not planning on stopping along the way, right? Several of you didn't think Sunset Grille was worth the stop. Is there somewhere else better to stop between Islamorada and Key West?

UNCMickey, I definitely didn't expect the restaurants to be as high end as some of the places we've been to around Charlotte. That's why I wasn't really interested in places like Prime Steakhouse, Tavern N Town, Antonia's, etc.. Those places looked similar but inferior to a lot of places near by. I was trying to pick places that would be on the nicer side, but with a more Caribbean/Key West style menu that I can't get back home? Does that make sense? Are those restaurants good choices, if that's what we're looking for? If not, I'd definitely bag those places in favor of dives that are more unique to Key West. I've got to eat somewhere though. I don't really understand what you mean by having five trips worth of eating planned. We've just planned to eat two meals a day - lunch and dinner.

As for the dinner cruise, I envisioned tourist trap food and the "get your iPhone out of your fanny pack for a selfie" crowd - like a Medievaltimes or a Space Needle experience? I despise those kinds of places. Are the dinner cruises not like that?

A couple of you suggested that we go to Louie's and watch the sunset from there. Given the time of year, I made the reservation for inside. Should I switch it to outside and maybe make a later reservation?

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