Monday began with the transfer of clothing and other things from our suitcases to the saddlebags and touring bag we’d need while we were in Key West. It’s amazing just how much stuff you can pack into saddlebags and motorcycle luggage!
As I packed our touring bag I wondered how many Harley owners abide by the 25lb max weight limit imposed on the luggage racks on most Harley-Davidson non-touring bikes. In addition to filling both of my saddlebags, our touring bag was filled and then topped with a smaller roll-bag contained our rain gear and all-told I’m sure we abided by the max weight limits! Fully loaded the bike handled it all quite well and I was hard pressed to know I had that much luggage on the bike. In addition to the rain gear I’d also included my leather jacket and our two jacket liners “just in case” so that clearly had us hauling some extra volume that may or may not have been truly needed. However, I’ve always found it’s better to have a few things you “may need” vs. not having them: after all, I was a Boy Scout!
Since our trip wasn’t technically going to take us out onto any freeways I decided to leave the windscreen and lower air deflectors at home and ride old school for our trip down the ocean highway. I nearly regretted that decision on our first leg to Key Largo as I found us travelling at 65 mph with a 15-20 mph headwind which really tested Debbie’s and my tolerance for wind blast… noting I wear ear plugs to deal with the wind noise not our pipes! Thankfully, the rest of the trip was on roads with 45 or 55 mph speed limits and we had a tailwind as well. I also coaxed Debbie into some better eyewear with full coverage and repositioned her helmet to make it more comfortable. So, for the rest of the trip all was good.
The ride across the bridges that connected the various keys was spectacular. The turquoise blue waters of the Gulf to our right and Atlantic Ocean on our left were amazing.
The rides across the islands were less visually interesting, but the weather was great and traffic light so all was good. We made a point of searching out the “No Name Pub” on “No Name Road” on “No Name Key” when we arrived at Big Pine Key and what a treasure that was! It’s one of those places anyone making the trip to or from Key West should visit at least once, as descriptions don’t begin to do it justice. Just check out the photos of the interior we’ve included below: yes, those are dollar bills covering just about every square inch of wall, support columns and ceiling. Our friends David & Deb even added a dollar bill to commemorate our visit.
We rolled into the DoubleTree on Key West around 3:00 P.M.. Much to our surprise, we discovered David covered our room for all three days of our visit with his travel points! So, our vacation became far less costly than we had planned for. Moreover, our front desk host — Angel from Manhattan, New York — apparently upgraded us both to some very nice two-room suites so our accommodations were VERY comfortable for our 3 nights on the island.
After getting settled-in to our rooms we made our first of many 3.4 mile trips down into the heart of Key West: the Mallory Square and Duval Street areas. Along the way we got our first glipse of the numerous “gypsy roosters and hens” that roam freely around Key West. Although didn’t do the Duval Pub Crawl, we visited many of the marque venues including Sloppy Joe’s and the original Sloppy Joe’s now called Capt. Tony’s — featured prominently at the start of Jimmy Buffett’s “Last Mango in Paris” — and where Hemingway spent many of his evenings.
Before our evening-out we opted to ride back to the DoubleTree and trade out the motorcycles for the shuttle bus so we’d not have to worry about the ride home at the end of the evening. While back at the hotel and in between our showers and the 7:00 P.M. shuttle departure we visited the DoubleTree’s poolside bar where we always found some interesting folks with whom we visited for a while.
We also received some recommendations on where to dine, so for our first dinner on the island we went to the Conch Republic, one of three large and well-regarded dock-side restaurants.
After dinner we explored several of the bars and shops along Duval Street before catching the 11:20 P.M. shuttle back to our hotel. Being a Monday night instead of a weekend night it’s fair to say Duval Street was relatively quiet and many of the night spots were sparsely filled: Coyote Ugly was downright depressing given it needs patron participation to “work its magic”. But, we had a good time and didn’t over indulge so that made for a nice night out.
If I had the chance to back up the clock and do our visit to Key West all over again, the first thing I would have done when we arrived on the Island and checked-in would have been to ask the DoubleTree’s concierge to book us on either a ferry-boat or seaplane trip out to Fort Jefferson and Dry Tortugas National Park for Tuesday and a glass bottom boat tour on Wednesday. I feel we really missed an opportunity to make the most out of our trip by not doing some better pre-planning and research before arriving in Key West… something we’ll do when we visit again. But, that’s not to say we didn’t have a great time and make good use of our time on the island.
Tuesday started off with the two Debbie’s heading out to the pool to soak up the sun, noting very few of the hotels have beach front access like we enjoy at Panama City Beach. David and I headed out on the Harley’s to run a few errands and check out places to eat for lunch and dinner. We found the Mallory Square and old town areas of Key West were a bit busier when we arrived on Tuesday morning as two Carnival Cruise Line ships had arrived earlier in the day: clearly, the cruise ships that drive the Key West economy during the week. But, with one of the ships leaving at 11:00 A.M. and the other at 4:00 P.M., we weren’t overwhelmed by the cruise ship guests.
After riding back to the DoubleTree and collecting the two Debbies, we headed back into old town shortly and headed to El Meson de Pepe’s, a Cuban restaurant next to Mallory Square that we’d scoped out for lunch. Deb had indicated she wanted some Cuban food while we were in the Keys and Pepe’s seemed to fit the bill. Our server Alex turned out to be the highlight of our visit. He was hilarious, quick, witty and snarky all at the same time. Lunch was a hoot! After lunch we checked out some of the historic tours, noting Debbie and I had some VIP passes we received after sharing our less than favorable review of the Ghosts & Gravestone Tour that we took the night before New Year’s Eve in Savannah, Georgia. Given it was well into the afternoon the folks at the tour sites recommended we consider doing our tour on Wednesday so that we’d have enough time to fit it in while some of the attractions they visited were still open. So, we took their recommendation and I invited everyone to join me for a tour of the Little White House, just off the square.
When we arrived it wasn’t exactly what I expected so I asked the gal at the ticket counter if the tour was worth it – somewhat rhetorically. Her response was, “We’ll, I’ll you what. Go ahead and take the tour and if you think it was worth it you can pay at the end” as she handed us four passes and directed us to the tour group that had just formed near the entrance to the house. We had a great tour guide and as you’d expect, it was well worth the $15 per person cost, especially since the group that maintains the building is a non-profit foundation. Of course, what really made it so good was the tour guide and short history lesson he provided regarding President Truman, whose frequent visits to Key West are what gave The Little White House its historic pedigree.
Our second stop on Tuesday was The Southernmost Marker at the end of Whitehead Street where we all took the ubiquitous portraits of each other next to the marker. Our timing was impeccable as there wasn’t much of a line when we arrived vs. earlier in the day when David & I saw what had to be at least a 30-minute long line of folks queued up from the cruise ship tours. After the photo stop went back to Front & Duval Streets so we could visit a few more shops that were of interest.
A couple of hours later we had a bit of a near crisis when David’s Harley wouldn’t start as we saddled up to head back to the hotel. The bike was dead as a door-nail and it wasn’t clear why. I eventually headed off to a local auto parts store to see if they might have a battery that would work, while David continued troubleshooting the bike. About the time I arrived at the Advance Auto Parts store David discovered a short in his accessory wiring was the source of the problem. So, with a big sigh of relief, we were back on the road and then back to the hotel for our afternoon clean-up and visit to the poolside bar. Around 7:00 P.M. we boarded the shuttle down to Mallory Square for sunset and then dinner and the Red Fish Blue Fish restaurant.
Sunset at Mallory Square was quite an event, as the place is packed with visitors, vendors and performers. Homegrown acrobats on 7’ high unicycles juggling with fire, sabers and axes seems to be popular as there were two gentlemen doing the same act at either end of the square, with a variety of different other street musicians, performers and vendors stuffed in between.
We ended up buying a souvenir photo and almost had a wire-art tandem bicycle made, but quickly realized we might have a bit of a challenge getting these things home on the motorcycle. In fact, I ended up taking our photo and a few others down to the post office and stuffing them into a Priority Mail “if it fits it ships” box on Thursday just to play it safe vs trying to stuff it into our touring bag.
Dinner at the Red Fish Blue Fish restaurant was another great dining experience, made all that much more enjoyable by a great waiter. After dinner we visited a few pubs and grabbed the 11:20 P.M. shuttle back to the hotel after a really nice evening.
Our last full day on the island began with another very nice breakfast on the deck next to the DoubleTree’s pool. We also make a point of getting out with the two Debbie’s by 10:00 A.M. so we could tour the Hemingway House before it got too hot or too crowded and that was a good call. As we learned during our tour, Hemingway’s 2nd wife Pauline — a journalist and socialite — had all of the ceiling fans removed in the home and replaced with chandeliers so the house would quickly become far too hot later in the day to be enjoyable, which was as true today as it was back in the 30’s and 40’s. In fact, even more so since the lush landscape and shade-providing trees surrounding the home today did not exist in Hemingway’s day since there wasn’t any running water on the island!
As with the Little White House, the Hemingway House tour was made special by our tour host and his wonderful way of sharing what he learned about Hemingway’s life and history. From a visual standpoint he was the spitting image of Popeye’s pappy, Poopeye: sun-baked, sailor’s hat, white beard, ships anchor earing and skinny as a rail. But his stories were excellent and sprinkled with humor, mostly at the expense of Hemingway’s 2nd wife.
Seeing the 45 some-odd cats roaming around the property was quite interesting, all of them purportedly related to Hemingway’s first cat at Key West, Snowball. And, like Snowball, about ½ of them were polydactyl, i.e., having 6 toes on each front paw instead of 5 and in one case seven paws. The full perimeter porches and studio over the carriage house are things I’d love to incorporate into a home! Some day…
For lunch we found the Boat House bar & grill on the ground floor of the Commodore restaurant with a pier-side view of the marina and a lovely breeze blowing through the dark wood-lined interior. It was really a spectacular place and the food turned out to be excellent as well.
After lunch David & Deb decided to head back to the hotel and relax while Debbie and I headed back into town to take a Conch Train Tour of Key West. Again, we had some VIP passes so the price was certainly right, but we really had a great time and learned a lot about Key West history and personalities. It would have been well worth the $29 cost and would be a great deal for the $51 per person tour that included entry fees for the Hemingway House and the Little White House tours. Again, short of having read a very comprehensive tour guide like Fromers before coming to Key West (something I now wish I’d done) it helped us discover all kinds of hidden treasures like Key West’s first house, the original one-room school-house, several significant residences, the history of the economy, the various transfers of island ownership, it’s one-time wealth, Henry Flagler’s influence, its fall into receivership, and the like.
After our tour we made our way back to the hotel to clean up for dinner and a visit to the poolside bar before heading back down to Mallory Square for our second sunset celebration. This time we tried to improve our position a bit better so we could see the sun setting into the real horizon instead of the island on the other side of the marina. Hopefully iPhoto will help me clean up some of the exposure issues with those photos.
Debbie attempted to find a vendor who had some t-shirts she thought about buying the day before but sure enough he was a no-show on Wednesday night. We had it in mind to walk down to the Commodore or A&B restaurants for dinner, but Deb decided a second visit to Red Fish Blue Fish would be preferable since it was right at Mallory Square. So, while we didn’t get to enjoy a different place the meal we had for dinner was excellent.
After dinner our friends decided to see if they could catch the 9:20 P.M. shuttle back to the hotel as both of them had their fill of walking for the day. We decided to stay on Duval Street for our last evening in Key West and bid adieu to David & Deb. We then proceeded to walk from the Gulf of Mexico to the Atlantic Ocean, or put another way the 1-mile from one end of Duval Street to the other and then back for total of 2 miles. It was amazing what we discovered as we made our way along the store fronts, including a wide variety of different restaurants, art galleries, drag bars, drug stores, cigar & wine bars and you name it. It was great to see what was actually there as you can only do on foot. We stopped in to a couple different pubs in search of one that had a dance floor with (a) dance music and (b) people dancing. Again, since it was a week night instead of a weekend night those were in short supply. We found one place where we were able to get our boogie on for a short while and kept our eye on the clock as we knew we’d need to be at the shuttle pick-up point promptly at 11:20 P.M. otherwise we’d be left to find our own way back to the hotel. I’d thought about taking the 10:20 P.M. shuttle and then riding back downtown on the Harley, but a good friend had suggested that riding a Harley at night on Key West would almost always invite a traffic stop by Key West’s finest. I didn’t want to tempt fate even though I rarely drink much when riding.
Sadly, 11:10 P.M. came far too quickly so we high-tailed it to the shuttle stop, returned to our hotel and were both out like a light once we were back in our room.