Key West, Florida, lies at the southernmost point in the United States, and over time the area has played home to Native Americans, pirates, smugglers, fishermen, famous writers, and even a U.S. president. In 1912 businessman Henry Flagler completed his Overseas Railroad from Miami to Key West, and the result was an engineering marvel. To reach the city by car was impossible, as no road existed. That changed in 1927, when a highway was completed between Florida City and Lower Matecumbe Key. Another highway was finished at the same time, running from Key West to No Name Key. This left a 41-mile gap between the two locations, one that required a four-hour ferry trip to cover. Tragically, a devastating hurricane hit in 1935, killing more than 600 people and destroying a major section of the Overseas Railroad. The railroad was permanently closed, but the right-of-way was used to finish the road to Key West. It opened in 1938 and was named the Florida Keys Overseas Highway. This scenic route was recently named an All-American Road by the National Scenic Byways program.
Driving a Corvette to Key West is a perfect road trip for the adventure-minded owner. Divided by the Gulf of Mexico and the Atlantic, the 127.5-mile highway offers an incredible panorama of ocean vistas and crosses over many islands worth exploring. If you like water activities, great nightlife, and sunshine, a visit to the Keys is hard to beat.
We decided to grab a Corvette and take it on this scenic adventure-and not just any Corvette, but a 606hp supercharged Callaway Grand Sport coupe (www.callawaycars.com). The car, lent to us by Callaway program manager Chris Chessnoe, was the company's development vehicle, so taking it for an extended highway drive made sense from a durability-testing standpoint. We happily made arrangements to pick up this "Powerfully Engineered" beauty for our drive.
We started our trip from the VETTE editorial offices in Tampa after talking editor Heath out of the key fob. We filled up the tank, loaded our stuff, and headed south to our first stop at Rick Treworgy's Muscle Car City (www.muscle carcity.net) in Punta Gorda. Treworgy has amassed one of the nation's largest collections of GM muscle machines, with more than 200 cars and trucks housed in a 99,000-square-foot former Wal-Mart building. Incredibly, Treworgy has Corvettes on display from model years 1954 through 2010.
Our next stop was Naples, located on the Gulf Coast. On the way we hit a heavy rainstorm, but the Callaway, shod with Michelin PS2 ZP tires, handled it like a pro. Upon arrival at the Bayfront Inn 5th Ave (www.bayfront innnaples.com), we learned that guests are provided covered parking. As a bonus, we parked next to a water hose that allowed us to wash the grime off our ride. Next to our hotel was an exclusive shopping-and-dining area that was perfect for a quick photo shoot.
After breakfast we pointed the Callaway south to Homestead to link up with U.S. 1, also known as the Overseas Highway. After a quick two-hour drive, we merged onto U.S. 1, crossed the Barnes Sound Bridge, entered Key Largo, and headed south toward Key West. We passed the John Pennekamp Coral Reef State Park (www.pennekamppark.com) at mile marker (MM) 102, which was the first of many state parks we saw on this trip. John Pennekamp is a great place to snorkel and check out the coral reefs in beautiful, crystal-clear water.
Next, we stopped in Islamorada (MM 82) to top off the Callaway with fuel. (It's worth noting that fuel prices increased steadily the closer we got to Key West.) Pressing on, we quickly arrived at the island of Marathon, known as the "Heart of the Keys" because it is the midpoint of the island chain. We explored the Grassy Key Dolphin Research Center (www.dolphins.org), where injured dolphins, whales, and turtles are nursed back to health. It was only a short drive to the Tranquility Bay Beach House Resort, where we had a relaxing lunch by the ocean.
Back on the road, we soon arrived at the Pigeon Key Gift shop at MM 46. The shop is housed in a 1912 railroad car similar to the type used by the Flagler railroad, and is located at the entrance of the famed Seven Mile Bridge. Tickets may be purchased at the shop for a two-mile tram ride to the tiny historic island of Pigeon Key. This key is where workers lived during construction of the Flagler line, with trains stopping there periodically to replenish their supplies. The railroad line was converted to a roadway in 1938 and was closed to vehicular traffic in 1982.
We arrived at Key West and checked into the beautiful Parrot Key Resort (www.parrot keyresort.com). The next morning, we cleaned up the Callaway and drove into the heart of downtown. Our first stop was the southernmost point of the United States, followed by a visit to the red-brick Custom House and to Mallory Square for some photos.
Later, we took a cab downtown to experience the nightlife. Singer Jimmy Buffett has captured the essence of Key West with his popular songs, and every year thousands of his fans-known as Parrot Heads-hold a huge party to honor his contributions here. During the rest of the year, street performers gather at Mallory Square before sunset and put on free performances. It's a huge daily celebration that's not be missed. And when that party is over, nightlife begins in earnest on Duval Street. It's an excellent place to dine and people watch. After a fun night we headed back to our hotel for some much-needed rest.
The next day we pointed the Callaway north to Islamorada for our final overnight stay in the Keys, at the Chesapeake Beach Resort (www.chesapeakebeachresortspa.com). The resort serves as a perfect spot for relaxing and simply enjoying the natural beauty of this unspoiled area.
Writer Thelma Strabel summed up Key West when she noted, "There is nothing for restless people to do. It is quiet, careless, and charming." We couldn't agree more. The combination a breathtaking scenic drive-and an outstanding automobile in which to take it-all added up to a once-in-a-lifetime experience.

01 The Key West Overseas...

01 The Key West Overseas Highway provides a perfect backdrop for the carbon clad Callaway Grand Sport. The black chrome OZ wheels received a lot of comments during our trip.

02 Our first stop was Rick...

02 Our first stop was Rick Treworgy’s Muscle Car City, located in Punta Gorda. The museum is a former Wal-Mart that has been converted to display more than 200 Chevrolets, including every year of Corvette.

03 Our first overnight stop...

03 Our first overnight stop was at the picturesque Bayfront Inn 5th Ave in Naples. The city offers a host of excellent restaurants, white-sand beaches, and lots of sunshine. We parked the Callaway at a shopping complex next to our hotel.

04 After breakfasting in...

04 After breakfasting in Naples, we drove two hours southwest to the entrance of the Florida Keys Scenic Highway (U.S. 1) in Homestead. Our first stop was the John Pennekamp Coral Reef State Park at MM 102.

05 The Keys became part of...

05 The Keys became part of the American territory in 1821; at the time, boats were the only way to travel between islands. In 1912 Henry Morrison Flagler completed his Overseas Railroad to Key West, but part of the line was destroyed by a hurricane in 1935 and never rebuilt. This 1912 railcar is typical of those used on Flagler’s railroad.

06 In 1944, the Overseas...

06 In 1944, the Overseas Highway opened a new route that was 17 miles shorter. This was done to help speed war supplies to the Key West Naval Station. This 20-foot wide bridge was built in 1943 as part of that project. Its replacement (at right) opened 39 years later.

07 The highway stretches...

07 The highway stretches 127.5 miles and ends in Key West at the southernmost point in the United States. This typical view of the road was taken at MM 78, as we entered the island of Islamorada.

08 We stopped at Tranquility...

08 We stopped at Tranquility Bay Beach Houses and Resorts (Marathon Key, MM 48.5) to have lunch at TJ’s Tiki Bar, where food is served at canopied tables located next to the water. After lunch we headed to the Pa

09 More than 40 bridges were...

09 More than 40 bridges were constructed to complete U.S. 1 to key West. The highway opened on March 29, 1938, and many of the former railroad bridges were converted to road use.

10 Gorgeous sunsets like...

10 Gorgeous sunsets like this one bring to a close the daily street-performer’s celebration in Mallory Square.

11 We arose at daybreak the...

11 We arose at daybreak the next day and drove the Callaway to the southernmost point in the country, which lies just 90 miles north of Cuba. Early mornings are the best time to avoid the crowds that gather around this popular spot.

12 The Key West Custom House...

12 The Key West Custom House opened in 1891, and over the years that followed, it served as a government center, a post office, and a courthouse. It was abandoned and boarded up during the Depression, but it has since been restored and now houses the Key West Art & Historical Society.

13 The Grassy Key Dolphin...

13 The Grassy Key Dolphin Research Center is located at MM 59 and is a not-for-profit education-and-research facility. The center—which rehabilitates injured dolphins and other sea creatures—is open to the public.

14 After sunset we headed...

14 After sunset we headed over to Duval Street to have dinner and walk along this famous Key West roadway. Sloppy Joe’s is one of the town’s more famous watering holes.

15 Window-shopping and people-watching...

15 Window-shopping and people-watching on Duval Street will keep you occupied for a long time. This is a must-do Key West experience.

16 Paradise found! After...

16 Paradise found! After an enjoyable stay in Key West, we headed back toward Homestead and stayed at the Chesapeake Beach Resort, located in Islamorada at MM 83.

17 Next to Chesapeake Resort...

17 Next to Chesapeake Resort is a large, deep-water fishing marina restaurant complex. We were able to give the Callaway a rest and take a short stroll to dinner.

18 As Key West got smaller...

18 As Key West got smaller in our Callaway's rearview mirror we pondered when we could schedule another trip to paradise.