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.
Getting there
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.
Key Largo
Stay
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.
Eat
Harriette’s for breakfast. Diner style. MM 95.7
Avoid Snapper’s. Food is only mediocre, and prices don’t
make up for it.
Do
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
walking around.
Islamorada
Stay
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
Eat
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
Do
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 Key West
and experience the Marine Sanctuary.
Marathon
Eat
Cabot’s has a wonderful reputation, but I’ve never eaten
there. Phone: 305-743-6442, 725
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.
Key West
Stay
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.
Eat
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.
Do
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.
