KW has been a favorite vacation spot of mine for decades! This is some of the info I give friends who want to visit:
My first recommendation is to stay in Old Town, staying in new town (on or near Roosevelt Road) looks to be cheaper at first, but there is nothing to do out there, so you will be spending money and valuable vacation time driving into Old Town (20-40 minutes depending on where you are staying), finding and paying for parking or paying cabs/ubers. Just not worth it and not really saving anything. If you stay in Old Town you will not need your car, it's very walkable. I love to stay in the waterfront hotels in Old Town. The Pier House is probably my favorite, Ocean Key, Opal Key, Hyatt Centric and slightly off the water is the Marker, all nice. There is the historic Casa Marina and The Reach on the other end of Duval but there again you'll have a hike to most attractions on the other end of Duval. Other lodging options to consider are the Gardens (romantic) (not to be confused with garden house), Curry Mansion Inn, Ambrosia, Marrero’s Guest House (haunted), Tropical Inn, Island City House, Orchid Key Inn, and Marquesa. That should get you started, TripAdvisor has pretty up-to-date advice in the KW forum. Staying in the guest homes gives you a better feel for the Island while the hotels have more amenities (room service, etc.). Do not rent from airb&b, lots of scams in KW!
You can get a condo if you are Sat to Sat in Truman Annex, a very comfortable option located next to Truman’s Little White House, or try for The Galleon timeshare (check redbook.com), it's nice to have a kitchen if you don’t want to eat out every meal.
One rule we have while there, drink in the bars, eat in the restaurants. With a few exceptions, the food in the bars is sub-par. There are so many great restaurants in Key West, why take a risk on crummy bar food? A couple of exceptions is Jack Flats sports bar (good fish sammies and burgers and killer a/c) and Smokin' Tuna (my favorite place for music). If you aren't in the mood for a full dinner the Happy Hours at the bight (waterfront) are great options with food and drink specials. TripAdvisor had a sticky list of all the HH times and deals.
Here are some restaurants we like, in no particular order:
Blue Heaven (very Key Westy, get the yellowtail snapper at dinner, we crave it) B/L/D, must go here, no reservations, go early
Bagatelle (ask for a balcony seat),
Cafe' Sole',
Santiago's Bodega (tapas)(HH 3-6 pm with half-price menu and sangria), but anytime is good
Garbo's food truck at Hanks (nice setting, great food, self-serve),
Blue Rams Head Southenrmost, B/L/D,
Louie's Backyard (on the water) L/HH/D, nice happy hour food menu
Sarabeths (B/L),
915 for dinner (sit on porch),
Prime for steak,
A&B Lobster at the marina, dinner only (ask for a balcony table) must do,
Banana Cafe' (B/L),
Azur (dinner),
Harpoon Harry’s for hearty basic cheap breakfast,
Moondog Cafe' and bakery (B/L),
Antonia’s, inside seating only, excellent Italian (L/D)
Sunset Pier for casual on the water, beautiful views
Salute’ on the water, Blue Heaven's sister, free parking,
And for a unique dessert-only experience, Better than Sex! is so delicious!
We make reservations everywhere we go, especially during high season. Sometimes we don’t need them, but we don’t like wandering around trying to find a place when we are starving.
I highly recommend Latitudes for lunch or dinner. It’s beautiful and relaxed with great food. You take a little shuttle boat to get to the island (5 minutes) and have dinner on the beach. Get a reservation TODAY! because they book out weeks and sometimes months in advance. If you go for dinner make the reservation so that you arrive before sunset and ask them for a table on the sand. If you can’t get in there for dinner, my other go-to is A&B Lobster, again wonderful food and service, ask to sit on the balcony overlooking the marina, we always go when they open at 6 to make sure we can get on the balcony. If you get there early you see all the boats going out for the sunset and back again afterward.
Make sure to visit Mallory Square one night for sunset. It happens 1 hour before and 1 hour after sunset. Bring lots of singles for tips as this is how the artists make their living (they have to pay the city to perform). The guy with the ‘green thing’ cart has the best mojitos anywhere, he is usually by the Opal Key Resort. (may be different with COVID)
Get out on the water!!! Wind and Wine is a great wine-tasting sunset cruise, highly recommend it.
Commotion on the Ocean for unlimited beer & wine and live music, usually a younger crowd.
We love the tall sail ships, so peaceful. Jolly Rover is a good one. Family-friendly, it’s less $$, and bring your own drinks (they supply ice, cups, and bottled water).
A good snorkeling trip is Island ‘Ting, which combines kayak and snorkel.
We also like the dolphin watch/sunset combo, great fun finding and seeing the dolphin pods. You can’t go to Key West and stay on the land! So many water activities to pick from and most offer the best deals online.
If you are there for a few days, visit the Dry Tortugas National park. It’s a full day trip by boat and a ½ day trip by air, must get reservations in advance.
Have a blast, I'm jealous and wish I could be there!
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