Ultimate Florida Keys Road Trip // Key West Dive Trip

Our “Ultimate Florida Keys Road Trip // Key West Dive Trip” was the best diving adventure, with several reef and wreck dives, a smattering of culinary experiences, and plenty of sightseeing and exploring.

We headed out on a Wednesday evening to drive to Stuart, stay overnight and get a good start so we could really enjoy the drive down US1 in the daylight. Along the way, we made plenty of stops! This is an account of the not-diving part of the trip; the diving will be covered more deeply in another article!

Denny’s Latin Cafe

Our first official stop in the Florida Keys was at Denny’s Latin Cafe for the best flan on Earth, and Cuban coffee. It’s on Key Largo, across from Diver’s Direct and that huge dive flag. You can’t miss it.

Denny’s is also next door to a coffee chain – but why go there when you have authenticity right there! We prefer to eat “off the chain” when possible. The excitement to try something new and different, and the opportunity to meet locals and hear their stories interests us more than cookie cutter franchises.

History of Diving Museum

We stopped at History of Diving Museum next. While that sounded a bit boring, I think I read every single plaque, description, and photo caption. The place is absolutely stuffed full of fascinating equipment and details.

Their invitation to “Immerse Yourself in Diving History” is so accurate – the entire story of mankind’s attempt to survive underwater is presented in chronological order.

We couldn’t get enough of the knowledge – SCUBA and free diving are featured. We had some fun attempting to lift a heavy silver bar, and holding our breath.

A couple days later, we saw on social media that the museum had it’s biggest day ever with the most visitors ever recorded – it was a rainy day. I can’t think of a better way to spend a couple hours in the Keys if you get rained out or your dive gets postponed. You will learn a lot!

Island Fish Co.

Next was a stop for lunch at the Island Fish Co. on Marathon. We were working on a plastic-free vacation, and had a few hiccups here, but enjoyed the food. Conch salad, fish tacos, a mojito, rum punch, and fried Key Lime pie!

Traditionally, conch salad has conch, tomato, onion, and green pepper. This one was served with tortilla chips and lemon.

Fish tacos with lime, black beans and rice. Mmmmm! Sitting waterside, watching the birds and boats come and go; we felt officially “in the Keys” and like our vacation had begun.

Fried Key Lime Pie – oh, wow! I had never heard of this culinary delight. Well, anything fried has to be good, right?

NAS Key West Naval Base

One of our next stops was at the commissary on the Navy Base at Sigsbee Point Annex. We stocked up on a grocery cart full of healthy choices for the next week’s meals. After our splurge lunch on Marathon, we realized we could create our own elaborate menu for the entire week for the price of eating out two lunches.

On the long drive from NE FL down to Stuart, I had made a rough sketch of our meals for the week, simply rotating easy-to-prepare basic main dishes, vegetables, and sides. As I shopped, I checked items off, and made a few substitutions to take advantage of fresh offerings.

I circled the completed meals as we used the foods so I knew those items had been consumed. That way, I could swap the remaining meals around if the weather and our plans changed.

With the fridge packed nearly full, and the meals for the week now planned; our next stop was to check in at the dive shop.

Dive Key West – The Shop

We checked in at Dive Key West the day before my first dive to confirm dive locations, weather conditions, boat loading times, and get a new battery installed in my Suunto dive computer.

It’s always nice to meet everyone when you’re not in a rush, look around in case there’s anything you forgot, and pick up a couple shirts to take back to your local dive club for the next meeting!

Dive Key West – The Boat

With our amenities passes in hand, we headed over to the Florida Marina Club Key West to check out the boat. We wanted to get an idea of how long a drive it would be in the morning to make it for the check-in.

Also, when possible, it’s nice to take a look at the boat and familiarize yourself, from the dock, with all the visible safety gear and features.

Because we were diving through Dive Key West, we received day passes to their gym, shower facilities, small beach, and pool, as well as club and restaurant. What a great perk to diving with Dive Key West!

If you were staying somewhere without a pool; this is a great added bonus for your post-dive socializing! Plenty of space to relax and unwind.

Navy Base, Sigsbee Point Annex Recon

Thinking about future dive trips to Key West, we chose to spend some of our surface time researching the Navy Getaways offerings on Sigsbee Point Annex.

From our research, we knew there were mobile homes, townhouses, and a Navy Lodge.

We spent a couple days touring, photographing, and collecting information on the various available lodging as well as amenities and facilities.

The discounted rates are absolutely incredible – they are all included here at How to Sleep 4 in Key West on $75 a Night // NAS Key West Trumbo Point Annex // Navy Getaways Accommodations at MWR. Be sure to scroll to the bottom of that article to see the land, sea, and fishing rates!

Sigsbee Lounge at Sigsbee Point

For the best sunsets, we headed over to the Sunset Lounge at Sigsbee Point. While friends battled the crowds and paid top drink prices at a downtown Key West famous destination, we enjoyed sharing the sunset with a couple other couples. No lines, no noise, no overpriced menus.

Well, I wasn’t crazy about the plastic cups, but they do recycle. The prices were beyond reasonable, and the service fast and efficient.

Our “Cheeseburgers in Paradise” came with a million-dollar view and never any more than 12 other visitors at the Sunset Lounge. No waiting in a line for a bathroom, no waiting in a line for a drink or a snack. Plus, no crowds.

Downtown Key West

We managed to avoid Downtown Key West nearly entirely; passing through only a time or two on the way to check out a dive shop or base amenities. A stop at Diver’s Direct Key West for the sheer size of it was planned.

On our last trip through Key West, we also had stopped here just sightseeing and walking around checking out the downtown dive shops to gather dive trip schedules and information on the Florida Keys National Marine Sanctuary Shipwreck Trail.

Schooner Wharf

On one downtown jaunt, we stopped to check all the activity down at Schooner Wharf. I had worked on the Schooner Appledore in the past, so we paid a quick visit.

All the old standbys were still there- Half Shell Raw Bar, the dinghy docks, the Fury Catamaran and a couple other fishing and sailing charter boats.

Cute little venues are to be found tucked into every square foot of property on Key West. This casual spot is at the Schooner Wharf, right across from the Schooner Appledore.

Cuban Chugs at Key West Tropical Forest and Botanical Garden

Right around the corner from where we were staying on the Key West Golf Course was the Key West Tropical Forest and Botanical Garden. It’s one of those “hidden secrets” sightseeing guides like to promote.

While the gps app did not take us to the right entrance, we found it eventually, and went to explore the gardens and especially the Cuban Chugs.

The gardens not only features a quiet oasis in the middle of urban island living, they also have the largest known collection of Cuban Chugs; the boats Cubans built and trusted to carry them from Cuba to Florida.

Lunch at Kennedy’s – a Military Fave

One day, while touring lodging on the base at Sigsbee Point, we asked if there was anywhere close by for a quick lunch post-dive.

We were directed to Kennedy’s, conveniently located near a coin-operated laundry. Their menu is a mixture of Russian and a bit of Mediterranean. Portions were generous and tasty, and you could see the prevalence of service people in and out of uniform filling the restaurant at lunchtime.

While we know there’s nearly no reason to ask anyone about “where the locals eat” in such a touristy spot as Key West, this actually was a bit of a hidden gem. Friends directed us toward about three other “locals only” hangouts, but looking at their menus online, they seemed very pricey.

Beaches!

On our next trip to Key West, we definitely need to rent beach cruisers and just cruise all over the island – better parking, nice breezes, a bit of exercise, and more eco-friendly mode of transportation. It was great to see how many people were out walking, running, roller blading, and cycling!

South Beach and Smathers Beach yielded great views of the dive sites; we could see out to the exact marker from the previous days’ dives!

Baby’s Coffee – Cyclists’ Destination

A vacation on Key West simply could not be complete without a visit to Baby’s Coffee.

Baby’s sports an entire rack of spare tires, tubes, and other cycling needs right a the front door, and several cyclists stopped by while we were there. It seems to be a good destination, an easy 10-mile ride from Key West.

We enjoyed enormous bagel sandwiches, and coffee and espresso with the company of the ever-present chickens.

The hydroponic garden at Baby’s, which has a second location and roasting facility in Breaux Bridge, Louisiana.

West Marine, Key West

Boaters always seem to find the “jewelry store,” even if it’s hidden on the next island. We made a pit stop at West Marine to purchase some signal flares.

Besides, anywhere you go, it’s best to drop in at a grocery, a hardware, the dump, a marine store, and the boat ramp if you want to really get to know the area.

Florida Keys Eco-Discovery Center

I can’t say enough about the exhibits and the work being done at the Florida Keys Eco-Discovery Center in over 6,000 square feet of interactive and dynamic exhibits.

How long it takes for coral to grow – I’m standing by a core sample from 5oo years ago! Fascinating facts, information, education.

My dive partner’s broken humerus meant this was as close to diving as he would get on this trip. The exhibits were so educational and interesting. What a great place to visit on a rainy day, or a seriously hot day.

When NOAA posts information, you know it’s accurate! We had fun comparing hurricane activity, looking at reef maps, and watching all the sea creatures in the various aquariums.

The facility is manned by many volunteers. When you are looking for it; this is the very small, easy-to-miss sign. Turn right into their parking lot.

African Queen

Recently, I had watched the movie with Katharine Hepburn and Humphrey Bogart, so I was excited to get to tour the boat used in The African Queen!

It was difficult to believe I was standing in the same spot as those famous stars were while filming the movie, which, by the way, is full of fun machismo and exaggerated danger.

The African Queen still runs daily charters now – and is located in Key Largo. It’s docked at the Marina Del Mar marina, part of the Holiday Inn Complex at mile marker 100. You can take daily canal cruises, or dinner cruises.

Fort Zachary Taylor Historic State Park

Fort Zachary Taylor Historic State Park was on our list of places to visit. It is well worth the small entrance fee. There’s loads of historic information.

Having just finished some pretty simple siding that comes together at 90 degree angles, we were astounded by the multiple angles meeting in brick, and counted no less than 12 discrete angles joining in this area.

Iguanas were all around the mangroves and mote around the fort; one jumped in the water and startled me greatly. I forgot they swim quite well! I peeked over a ledge, it surprised me, I surprised it, and splash! It jumped into the moat and swam away!

Part of the grounds past the fort are beaches for snorkling and diving. Yes, you actually can shore dive from Key West! ** Best Kept Secret!!!**

Historic Homes

There are streets and streets filled with historic homes and enough historic markers to keep your most ardent historian occupied for hours and hours.

Mallory Square // Truman Waterfront

Plenty of people- and boat-watching is found just South of Mallory Square, on the base at the Truman Waterfront on the western edge of Key West.

Cruise ships come and go from the pier at Mallory Square. It’s always entertaining to watch the big boys maneuver in tight quarters and set off for the sunset.

All the Rest of the Fun in Key West!

For the balance of our stay, either I was diving, cooking, eating, cleaning gear, watching the sunset, or writing articles and processing photos. We did take this Boston Whaler for a short spin down the canal.

With crowds everywhere, we also spent a bit of time driving by some of the attractions – I jumped out and quickly snapped this shot when we went by the Hemingway House and the lighthouse.

Some other fun things we did were spending a bit of time dog walking, rebuilding a computer, lounging by the pool, and reading. This book, Longitude by Dava Sorvel was a fascinating account of building a reliable timepiece so ships could travel safely. I also read a good bit of Advanced First Aid Afloat by Peter Eastman.

In my lounge kit above, you can see my Stream2Sea tinted sunscreen. It performs two duties – first, it’s my daily sunscreen. This sunscreen is light, not greasy, and creates a protective layer instead of soaking into your skin.

Second, it serves as my foundation. Skin tone differences are evened out, and my skin is prepared to receive a dusting of powder and a swipe of mascara. It comes in spf 20 and 30 as well, and they make a great sting relief and a leave-in conditioner. You can use my code “KimW” for 10% off these products, too!

Also, my Hydrapak Stash Water Bottle is shown above. It collapses down to a hockey-puck sized disc!

Thanks for reading about our adventures – I’ll leave links below as I post more in-depth articles about each adventure, so be sure to subscribe!

What to Read Next:

The discounted rates we found for activities on base in Key West are absolutely incredible – they are all included here at How to Sleep 4 in Key West on $75 a Night // NAS Key West Trumbo Point Annex // Navy Getaways Accommodations at MWR. Be sure to scroll to the bottom of that article to see the land, sea, and fishing rates!

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Updated June 20, 2019