Explore: History Miami Stiltsville Cruise

Since October I have been a traveling bandit. I've been to New York City, San Francisco, back to New York, Los Angeles, Miami and back to San Francisco. I feel tired just typing that.

Of all the aforementioned trips, the only one that was not for work was Miami. I flew home for Wednesday - Monday morning of Thanksgiving week. Because I was able to stay for so long, I had plenty of play time in addition to the festive meal on Turkey Day. 

On Sunday morning of the holiday weekend, my parents, sister, brother-in-law and I boarded a boat with History Miami. The organization was offering a boat tour of Stiltsville, which I had actually never even heard of until my mom suggested this outing (despite my parents living in Miami for 11 years). 

Stiltsville was once a community of 27 buildings that has since been transformed into seven houses in the twinkling turquoise water of Biscayne Bay. These houses were known in the 1940's, 50's and 60's as a playground for the rich and famous, including Ted Kennedy! 

Our boat was docked at Bayside, an outdoor shopping mall adjacent to Bayfront Park. They have their own parking garage, making it super easy to get to. The check-in process was very organized and each of us was handed a sticker to wear during the ride (just like at a museum). 

Our guide for the tour was Dr. Paul George. About 30 minutes into his overview, my brother-in-law decided to Google him since we were all so astounded by his depth of knowledge. The first article to come up was titled, "The Man Who Knows Everything About Miami."

As we zipped by the high rise buildings of Brickell Avenue (wear my parents live) and the neighborhood of Coconut Grove, Dr. George gave us plenty of fun facts about both areas. Once we were past Coconut Grove we went out into the open waters of Biscayne Bay. Just as our boat started to pick up speed, Dr. George said, "Sometimes we get lucky and the dolphins give us a show." Just as the words left his lips, we saw one! A beautiful, playful dolphin followed alongside our boat for a good ten minutes. People of all ages rushed to the right side of the boat and hung gleefully over the railing watching the dolphin splash in and out of the water. This was my undisputed highlight of the tour (shhh, don't tell Dr. George). 

As we approached Stiltsville I could already tell how cool these houses were going to be. 

History Miami Stiltsville Cruise

As our boat moved closer, I had my camera at the ready. 

History Miami Stiltsville CruiseHistory Miami Stiltsville Cruise

As the first house started to come into view, we could see it was painted yellow with purple trim. So Key West! 

History Miami Stiltsville Cruise

The yellow house was close to one of its Stiltsville neighbors. It was fun to imagine the guests of both houses shouting to each other from their balconies or having diving contests off their docks. 

History Miami Stiltsville CruiseHistory Miami Stiltsville Cruise

The next house was clearly uninhabited because it had become a hangout for the birds. 

History Miami Stiltsville Cruise

I feel like I should print these photos and sell them as postcards. I don't know why, but all of them perched up there cracks me up! 

History Miami Stiltsville Cruise

In all seriousness, you can see how this could be an amazingly cool vacation spot. The house has space for multiple boats and jet skiis and you couldn't ask for a more private place to swim or sun bathe. 

Our boat zipped past all seven houses. Due to the speed of the boat and the fact that I was sitting to the far right side, I wasn't able to snap all seven structures, but you can see how special Stiltsville is. With all the hurricanes Miami has endured, it's kind of a miracle they are still standing. 

As we drove away from Stiltsville and back toward the main land, we cruised by the lighthouse at Bill Baggs Park on Key Biscayne. 

History Miami Stiltsville Cruise

This is going to sound so ignorant, but I really only think of lighthouses as a New England thing. It felt out of place to me in such a tropical climate. 

History Miami Stiltsville Cruise

On the day we were out on the water, the lighthouse was set against three gradient shades of blue - the dark of the water, the gray below the clouds and the lighter hue closest to the sun. 

History Miami Stiltsville Cruise

I'd also like to personally thank the line of the birds that flew into my shot, making it such a quintessential beach scene. 

History Miami Stiltsville Cruise

Dr. George shared many interesting facts with us about Key Biscayne and the wealthy families that originally owned the land. They made all kinds of crazy deals with the city to build bridges and open up the space to the public. Much of Key Biscayne is reserved for public beaches and parks, including Crandon Park, a special spot for my family. It's one of our favorite beaches and also where my sister and brother-in-law got engaged! 

All in all, we were on the boat for close to three hours. Every single one of us learned new facts and details about Stiltsville, Key Biscayne and some of Miami's most scandalous stories. Dr. George was an excellent guide. He is a living, breathing encyclopedia of Miami history. 

The boat is super comfortable and covered on the top deck, so you don't have to worry about rain or bird poop! They sell food and drinks on board and they also have restrooms, which my mom was sure to tell me were "shockingly clean." 

If you're a 305 native or you're planning a trip this winter, Dr. George will be leading this same boat tour on Sunday, February 26, 2017 and Sunday, March 26, 2017. Both of these tours are at sunset, which I am sure will be spectacular. 

The cruise is $50 dollars for History Miami members (you can become a member here) and $60 dollars for non-members. 

At the end of the ride, we snapped a family photo, the only picture of all five of us from my entire visit! 

History Miami Stiltsville Cruise

As you can see, I am still beaming from the dolphin sighting!  


Muhammad Zeeshan's picture

What is the need for certainty regarding info on the history Miami Stittsville cruise? I never quite understood how these things were involved in fort phantom hill dock builder and amongst other things... Can anyone give me further insight?

mairakhatri khatri's picture

Excellent article. Very interesting to read. I really love to read such a nice article. Thanks! keep rocking. trips to galilee from jerusalem

Log in to comment


Molly Galler

Welcome to Pop.Bop.Shop. My name is Molly. I’m a foodie, fashionista, pop culture addict and serious travel junkie. I’m a lifelong Bostonian obsessed with frozen confections, outdoor patios, Mindy Kaling, reality television, awards shows, tropical vacations, snail mail and my birthday.

More from Molly

Pop.Bop.Shop. In the News

History Miami Stiltsville Cruise
401 Biscayne Boulevard
33132 Miami , FL
United States
Florida US