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.