My first trip to Key West was in the early 90s in college, and I quickly fell in love with the quirky, sub-tropical, art and boat community. After 14 trips (as of 2016), here are some of my favorites places to stay, places to eat, and things to do.
Fly into either
Miami or Fort Lauderdale Intl (just seven
miles from Miami Intl). Sometime the difference in airfare is dramatic. The
drive is longer than you think. It can take a good three to four hours to drive
from Florida City to Key West, depending on the time of day and the day you go.
Friday through Sunday is sometimes a traffic nightmare. Problem is most keys
are single lane, and if you get behind a truck pulling a boat, there are very
few places to pass in some stretches. US-1 seems to always be under construction
as they put in a new aqueduct system down to the keys. All fresh water in the
keys is pumped down from Miami, and they construction delays can be irritating
at times through the everglades.
Ocean Pointe Suites – You stay in resort owner’s condos. Most have ample space, with full kitchen (with dishes provided) and are clean. Gated community with private beach, bar, dock and pool. In the $155-$200 per night range, depending on the season.
Harriette’s for breakfast. Diner style. MM 95.7
Avoid Snapper’s. Food is only mediocre, and prices don’t make up for it.
John Pennekamp State Park – Boat/jetski rentals, beach, nature area with glass bottom boat tours. But for eco-tours, save your time go to
Key West and
hit the Marine Sanctuary off the tip of Key
West. But Pennekamp is a nice place to spend some time
Cheeca Lounge and Spa – Close to a five-star resort, known for their spa relaxation packages. Very expensive, in the $400 - $500 per night range. MM 82
Island Grill – Dockside restaurant with decent food, but the draw is live music while sitting either on their private beach or on their deck. Local hangout and a good place to mingle with locals. MM 85.5 on the left right over the bridge.
Braza Lena – Meat fest. Churrascaria style, Brazilian restaurant. Bring a big appetite. MM 83.5 by the Whale Harbor Inn.
Hungry Tarpon – Simple sandwich place, but the neat part is out back on the dock where you can buy a bucket of fish and feed the tarpon off the docks. Hundreds of them. If you are brave enough, you can hand feed them (instead of tossing the bait in), but be prepared to bleed if your reflexes suck. MM 77.5
Theatre of the Sea – We stopped but did not enter, due to the very high price ($50 per person). To swim with the dolphins, the price is $150 per person. But if you want guaranteed contact with dolphins or rays, this is a place to go.
Robbie’s – The marina that will rent you about anything you want to do on the water, plus hosts different eco and ocean tours. Still, best money is to head to
and experience the Marine Sanctuary.
Cabot’s has a wonderful reputation, but I’ve never eaten there. Phone: 305-743-6442,
11th St., Marathon.
Big Pine Key
Bahia Honda State Park – Beautiful beaches, and in the spring during low tide you can walk out into the ocean for hundreds of yards and still be in knee to waist-high water. Showers are available for washing off the sand after hitting the ocean.
If walking is your primary mode of transportation in Key West, look for a place on Duval Street. Duval is the center of Key West activity. Finding a hotel near the west end of Duval will put you within short walking distance of most water activities, restaurants and cultural activities. Parking around Duval is very scarce, so it benefits you to be able to walk to Duval. You can drive to the beaches where there is plenty of parking. But hotels around Duval are more expensive, so the bed and breakfast and boutique places can save you money. Some hotels around Duval I have stayed …
Pier House – Expensive ($300) but you are purchasing perfect location. Found the rooms to be average (motel-like), and their beach is very tiny. Nice pool.
La Concha – Right in the middle of Duval, cheaper ($250) than Pier House. Nice hotel, great rooftop bar. The best view on the island is from their rooftop bar, which is open to the public.
The second way to get around Key West is to rent scooters for the duration of your stay. Scooter parking is much easier to find around Duval than car parking, so it allows you to stay anywhere on the island and still be connected to Duval. Most hotels can hook you up with a scooter rental company. I rent scooters every trip and never drive the car while there. Some off-Duval hotels to consider …
Casa Marina – Waldorf Astoria resort. Expensive ($300+), but the place to be pampered. Great beach and rooms. Special occasion kind of place.
Southernmost – Cheaper ($200) still on the far east end of Duval. Watch out during spring break time. This is party central for college spring breakers. Long walk to the business end of Duval.
DoubleTree Grand Key Resort – My recommendation as the best place to stay away from Duval when considering cost and amenities. Costs during off-season are around $150. Awesome pool, but no beach. Hourly shuttle service takes guests to Duval or the beaches for free. Great place to stay if you fly direct into Key West and want to avoid renting a car.
There is an endless supply of great places to eat. Some of the more popular places fill up quickly in season, so reservations are recommended in season. In order of my favorites …
Camille’s – Favorite place on the island. This is a charming locals place. Popular breakfast location (Godiva white chocolate French toast is amazing), and great chef (Joel). Owner, Denise, is chatty and pleasant. Fresh seafood and inventing preparations. Pork in gorgonzola cream sauce is a Bon Appetite award winning dish. New dinner menu every day.
Blue Heaven – My no. 2 spot on the island. Food is great, but the atmosphere is better. Indoor and outdoor seating. Outdoor has live music as little chicks run around under your feet during your meal. This is right down the street from you (down Petronia at the corner of Thomas).
Better Than Sex – A dessert restaurant. It has to be seen to be believed. Very interesting concept.
BO’s Fish Wagon – Another great lunch spot. Best fish sandwiches on the island. Looks like a dive, and it is. But cheap and great food.
Sloppy Joe’s Bar – Open air island tradition. Constant live music, and kid friendly during the day. Bar food. Nice lunch spot. Everyone buys a t-shirt here. World famous.
El Siboney – Best Cuban food on the island. The pork is amazing. Long walk from Duval.
Antonia’s – Italian on Duval. I prefer this over La Trattoria. Both have a great menu, but we had a horrible service experience at La Trat, so we tend to go to Antonia’s now.
Le Petit Paris – Relatively new place on Duval. Menu is fusion. Great salads. Expensive. Might not be worth the price unless you value organic food and unique presentations. Side dishes are the best part of the meal.
Hog’s Breath Saloon – Island biker bar. Bar food. Good burgers. Another place you want to buy a t-shirt, if you are into biker culture.
National Marine Sanctuary – This is the protected area off the tip of Key West featuring mangroves, and great snorkeling and kayaking. Water is very shallow in some areas, and you can get up close with jellies (upside down jellies are cool), dolphin, shark and rays. Reefs are struggling due to global warming, and not as bright as they used to be. But still very nice snorkeling. There is a nautical map of this area on my office wall at Rea, so if you want to come back I can show you some places. Eco tours are very educational. I recommend Danger Charters (305-304-7999) for a great trip. Lots of companies do these tours, but I like Danger. You see the same people working the boats year after year. Do the full day and you can mark off kayaking, snorkeling and sailing from your list. Watch the weather forecast, find the best looking sunny day, and book in advance.
Dry Tortugas – A full-day trip out to Fort Jefferson National Park. Tour the fort and great beaches around the fort. If you have more money than time, you can skip the long boat ride and go out by sea plane.
Sunset Cruise – Many companies will do a couple hour sunset cruise that is very nice, some featuring dinner or a cheese and wine snack.
Sunset Celebration – At the west end of Duval is Mallory Square. It comes alive every evening with street performers and craft vendors. Every evening people gather to watch the sun set. It is a tradition to applaud when the sun does set.
Hemingway House – Great guided tours of the Earnest Hemingway house. The tour guides will mix stories of Hemingway and the island. It is nice to go here early in your visit, as it will help you recognize other things as you go on through the week.
Drag shows – Several places host nightly drag shows which are hilarious. If you hear of a drag benefit, definitely go. Benefits will be hosted for a variety of charities, and the auction items at these events are awesome. We’ve paid $25 for free meals at the best restaurants, and $40 for a $200 spa package.
Beaches – Key West beaches are not nice. The nicest is the Fort Zachary Taylor Beach, which is through the Truman Annex and has an admission fee. The large public beach is Smathers beach, where you will see the bulk of the people. Since Key West is in the Gulf/Atlantic current, timing can make your beach experience good or bad. Tides will bring seaweed in with the tide during several times of the year. It can be a stinky mess until the island cleans the beaches. And during certain times of the year, Portuguese Man-of-War are swept past the Keys and you will need to be aware of them. The Keys post warning on the beaches, and they are easy to spot in the water.