AI Travel Planning

Image Credit: Canva Image Generator

 Fair warning, this is, I believe, the longest post I've ever written at over 15 pages! If you're not interested in the details of this journey, feel free to scroll to the end and just find out what I decided on.

 Have you ever wished you could sit down and chat with a travel agent who knew where you were going intimately? Do you want to ask a million questions, but don't want to be a bother? Have you ever considered using AI? I hadn't, until I read this post from Trip-It's Blog. This concept was initially a little off-putting. I enjoyed a brief stint as a travel agent and I don't much relish the idea of replacing people with AI. But what I found was that rather than replacing traditional travel agents, AI trip planners can help you visualize your dreams so that you are prepared to work with a travel agent to book them.

 As I went about learning and testing out this concept, I decided to use a free day my son and I have in Miami at the end of our cruise in September. The boat will get in early in the morning and we don't need to be at the airport till 4:30, so we had at least seven hours to kill. I didn't much relish the idea of sitting at the airport for seven hours, even if we could do it in a lounge. So this made for an excellent test case!

 The first challenge I faced was luggage. I couldn't imagine anything we could do in Miami with all our bags and my son having to push my wheelchair (I am not going to try to bring my power chair on this trip). So, something had to be done with the bags. Could I leave them at the port? Should we head to the airport first and check them in/store them before touring? It was a quandry, and one I thought made a great first search. I opened up CoPilot, because that is what I am most familiar with, and asked it what I should do. Here's what I got:

Great question, SaltyZebra — and smart thinking! Since PortMiami doesn’t offer luggage storage on-site due to security regulations, your best bet is to use a third-party service nearby. Here are some solid options:

🧳 Luggage Storage Services Near PortMiami

Service	Location	Price	Notes
LuggageHero	Multiple spots near Downtown & Brickell	From $1.49/hour or $4.90/day	Flexible pricing, insurance up to $3,000, book via app or website
Bounce	Locations like Downtown Miami (37 NE 2nd Ave) & Miami River (437 SW 2nd St)	Around $5.90/day	Easy app booking, 24/7 support, insurance included
Radical Storage	Near Bayside Marketplace & Bayfront Park	Flat $4.50/day	No size limits, insurance up to $3,000, book online

🏨 Other Options

• Hotel Concierge: If you’re staying at a hotel before or after your cruise, many will hold your bags even after checkout.
• Miami International Airport: Has storage at Central Terminal E, but it’s a bit of a trek unless you're flying later.

 This was an amazing start to my AI Trip Planning experience! First off, I love how the answers have a familiar, conversational tone, like you're chatting with a friend. Next, it had a great idea that I had never considered - luggage storage services. In all my travels, this was something I had never heard of! I was a little leery of dropping off my luggage somewhere, so I headed to Trustpilot to see what they thought of these companies. I was amazed at the wealth of reviews available, and while one company had higher reviews than the others, I actually found that I resonated with the reviews for Bounce in Miami the most. The way I found these was to look up Bounce on Trustpilot and then in the review area I searched for "Miami." This gave me reviews from lots of other people that had done exactly what I wanted to do, gotten off a cruise and dropped their luggage before touring for the day. With this awesome new tool of luggage storage in my toolbelt, I went about trying out some different AI trip planners to see what ideas they had for my day. I had very little to go on at first, I just knew that I didn't want to have to pay for ubers all over so I wanted to stick to public transit and I didn't want to drop a lot of money on attractions so I wanted to focus on free or low cost options.

 Canva's Trip Planner was at the top of my list to try, so I started there. What Canva, a graphic design company, is doing putting out a trip planner I have no idea, but I gave it a go anyways. I was so impressed with the ideas it came up with - but in hindsight after trying other options the details were seriously lacking. This was my first go at chatting with a computer though, so I'm sure there was more than a little user-error. I asked it to come up with a day plan starting at our luggage drop off and ending there using public transportation. It came up with some great suggestions that gave me a springboard that I used when chatting with other AI platforms. It's AI graphics generator is top notch though and I love the image it created for this post!

From there I tried Layla (I was drawn to this one because I have a lovely niece named Layla!). I was super disappointed when I got a ways into the chat and ran out of "free credits." This promptly ended my trip planning with Layla because I was not going to pay an AI, at least at this point when I was still trying the whole concept out. What I did get from her though was a really helpful idea that became the key to my future trip planning efforts. She told me about the MetroMover:

Ah, the Metromover—Miami’s little free gem for getting around downtown without breaking a sweat or your wallet. Here’s the scoop:

What’s the Metromover?

• It’s a free automated people mover system that zips around Downtown Miami and Brickell.
• Think of it as a mini elevated train that glides above the streets, giving you a sweet view of the city while you ride.
• Perfect for short hops between key spots like Bayside Marketplace, Brickell City Centre, Government Center, and more.

Why it’s awesome for you:

• Zero cost — free rides, no tickets, no fuss.
• Minimal walking — stations are close to major attractions and your luggage spot at 133 NE 2nd Ave.
• Frequent service — trains come every 90 seconds to a few minutes during peak times.
• Easy to use — just hop on and off at any station along the loops.

 Thanks, Layla! I'm probably never going to talk to you again (the free credits don't seem to regenerate over time), but you were helpful.

 Next up came Mindtrip. By now I had curated my starting prompt to be, "A fun day in Miami beginning at the cruise port around 10am, we'll need to take an uber to 133 NE 2nd Ave, Miami, FL 33132 to store our luggage and then return there to pick it up before heading to the airport (MIA) around 3:30pm two people, no museums, use public transportation, especially the metromover, we'd like to visit bayside marketplace, brickell, riverwalk and little havana." Mindtrip came back with a really great, conversational trip idea including places to stop for lunch and sweet treats. It's idea of a good lunch was at an oyster bar though and I can't see either my son or I slurping back oysters in Miami, so I told it, "we don't like oysters and would prefer a food truck." Now I was starting to really adjust the plans given me by the AI and we began to get somewhere! It asked me a question back to figure out what type of food truck cuisine I preferred. I told it I was looking for mexican or cuban food and it got back to me saying that there weren't consistent food truck options available but it recommended Tacology which it said was, "designed like a lively Mexican market with a variety of taco stands." That sounded great to me, so I had it add that to the itinerary. Next, we discussed transportation as I was interested in heading to Little Havana but it isn't on the Metromover route. Mindtrip suggested that I take the bus, but I started thinking about my wheelchair and how difficult that can be on a city bus, so I asked about that. It confidently assured me that the Metro Bus is very accessible and I shouldn't have a problem, but I've heard about AI and their overconfidence so I needed more information. It offered to give me a breakdown of accessibility for all my stops on the itinerary and I took it up on the offer! We chatted further about Bayfront Park and things to do there and then I was ready to firm up my plans so I asked for an updated itinerary with times. It came back and asked me a few specific questions but right about then I hit a popup saying I had run out of free time with this AI too. This offered me an option to start a free account though to continue my chat so I did that and went on. Mindtrip and I tweaked a few more details, like the timing of lunch and when I wanted to be at the airport, and I asked it for specific directions on how to get to and use the transportation for my day. It gave me a really useable itinerary that I was very excited about!

Here’s your Miami itinerary, including detailed Metromover directions between each stop:

9:30am

Store luggage at Bounce Luggage Storage - Downtown North (133 NE 2nd Ave). 

 

10:00am – 11:30am

Bayside Marketplace

How to get there:

Walk north on NE 2nd Ave and turn right (east) on NE 3rd St.

College/Bayside Metromover Station is less than a 5-minute walk.

Take the Metromover one stop east to Bayside Station (or walk 5 minutes east—Bayside Marketplace is very close). 

 

11:45am – 12:30pm

Bayfront Park

How to get there:

Exit Bayside Marketplace and walk south along Biscayne Blvd.

Bayfront Park is directly across the street (about a 5-minute walk). 

 

1:00pm – 2:00pm

Lunch at Tacology (inside Brickell City Centre)

How to get there:

Walk to Bayfront Park Metromover Station (at the north end of the park).

Board the Metromover (Brickell Loop) southbound.

Ride four stops to Brickell Station (about 10 minutes).

Enter Brickell City Centre and go to the 4th floor for Tacology. 

 

2:00pm – 3:30pm

Miami Riverwalk

How to get there:

Exit Brickell City Centre and walk west (less than 5 minutes) to the Miami Riverwalk entrances along the river (access points at S Miami Ave or SE 5th St). 

 

3:30pm

Return to Bounce Luggage Storage - Downtown North

How to get there:

Walk back to Brickell Metromover Station.

Board the Metromover northbound (Omni or Inner Loop).

Ride four stops to College/Bayside Station.

Walk west on NE 3rd St, then north on NE 2nd Ave to 133 NE 2nd Ave (about a 3-minute walk). 

 

3:45pm – 4:30pm

Uber or take transit to Miami International Airport (MIA) 

 

4:30pm

Arrive at MIA for your departure.

 This day was really coming together! But I still wanted to try out the bigger AI players that weren't dedicated trip planners. Could they do as good of a job as the little guys who were more focused?

 First up was ChatGPT. I've used this platform before, primarily for generating images like the one I used recently for my 400th blog post. I used the same prompt I had with Mindtrip, except I left off the specific locations to see if ChatGPT might give me any new ideas. Right away it came up with an exciting, well-formatted itinerary that I could totally see working. It also gave me some helpful tips like when to arrive at the luggage storage to avoid a long wait as well as a good amount of buffer time to allow for getting to the airport on time. I hadn't given up on the idea of a food truck lunch though and I thought that ChatGPT might win where Mindtrip had failed. Sure enough, it came right back with four different places that were likely to have good food truck options at lunch time! More tips followed with the most likely places to find food trucks as well as a profile on Instagram to check for that day's particular offerings. Fleshing out the itinerary a bit, I asked for specific stops and things to do on the MetroMover loops and ChatGPT did not disappoint. We made a few adjustments, added in a coffee stop, and this is what it came up with (I love the formatting and the graphics!)

🗓️ Miami Metromover Adventure – Itinerary

Date: [Fill in]
Start: ~9:15 AM after luggage drop
End: ~2:45 PM – pick up luggage & Uber to MIA

---

✅ Overview

• Transportation: FREE Metromover (Inner & Brickell Loops)

• Stops:

  1. Freedom Tower

  2. Knight Center

  3. Brickell (coffee)

  4. Bayside Marketplace (lunch)

  5. Bayfront Park

• Luggage Storage: 133 NE 2nd Ave (Bounce or similar)

• Return to MIA: ~2:45 PM by Uber

---

📍 9:00 – 9:15 AM – Luggage Drop

• Address: 133 NE 2nd Ave

• Walk to: Bayfront Park Metromover Station

---

🏛️ 9:15 – 10:15 AM – Freedom Tower Station

• Admire historic Freedom Tower

• Optional walk to Maurice A. Ferré Park (Bayfront photos)

🟢 Take Inner Loop Metromover → Knight Center Station

---

🌇 10:30 – 11:30 AM – Knight Center Station

• Walk along the Miami Riverwalk (scenic palm-lined path)

• Relax and take skyline & boat photos

🟢 Take Brickell Loop Metromover → Brickell Station

---

☕ 11:45 AM – 12:45 PM – Brickell Station (Coffee Stop)

• Coffee options:

  • Crema Gourmet Coffee Bar

  • Naughty Coffee (VW van)

  • Vice City Bean (8-min walk)

• Optional quick stroll through Brickell City Centre

🟢 Take Brickell Loop Metromover → College/Bayside Station

---

🛍️ 1:00 – 2:00 PM – Bayside Marketplace

• Grab lunch from food trucks or quick eats

• Shop souvenirs, enjoy live music

• Take photos by the marina

🚶‍♀️ Walk to Bayfront Park (5 mins)

---

🌴 2:00 – 2:45 PM – Bayfront Park

• Stroll the waterfront

• Visit Torch of Friendship, fountains, shaded benches

• Relax before airport trip

🚶‍♀️ Walk 2 mins back to luggage storage

---

🧳 2:45 PM – Pick Up Luggage

📍 Return to 133 NE 2nd Ave

---

🚗 2:45 – 3:15 PM – Uber to MIA

• Estimated arrival: ~3:15 PM

• Relax and reflect on a great Miami day!

 I didn't think it could get much better than this, but I still had a couple of platforms to try so I moved on to:

 Gemini is Google's AI personality. It's tone was less conversational and it gave me a complete new itinerary with each answer. This could be helpful, but it quickly became repetitive and cumbersome. I appreciated Mindtrip's approach of just having an ongoing pop-out itinerary on the side I could refer to as I went. I also found that any of the platforms would give me an updated itinerary at any point if I asked them, so having it in every answer was just... extra. Over the course of my VERY LONG conversation with Gemini (thanks to the constant reprint of the itinerary) I determined that trying to get out to Little Havana was going to be cumbersome and stressful, so I axed it from the plan. As I explored through our conversation the different activity ideas on the MetroMover loops, Gemini came out with a Public Art Tour idea that really resonated with me. I aske some follow up questions to flesh out what it meant and different locations and here's the final itinerary that Gemini suggested for me:

Here's your comprehensive Miami itinerary, now including details for your public art tour along the Metromover line:

Miami Day Itinerary (10:00 AM - 4:30 PM Airport Arrival)

10:00 AM - Arrive at Cruise Port & Uber to Luggage Storage

• From PortMiami: Take an Uber directly to Bounce Luggage Storage – Downtown North at 132 NE 2nd Ave. This will be the most efficient way to get your luggage stored quickly.

10:30 AM - Drop off Luggage & Head to the Metromover

• After storing your luggage, you're just a short walk from several Metromover stations.

• Closest Metromover Station: The College/Bayside Metromover Station is very close to 132 NE 2nd Ave.

10:45 AM - Metromover to Riverwalk & Explore

• From College/Bayside Metromover Station, take the Metromover (Inner Loop or Brickell Loop) to the Riverwalk Station or Knight Center Station. The Riverwalk is easily accessible from these stations.

• Activity: Miami Riverwalk (approx. 10:45 AM - 12:15 PM)

  • Enjoy a peaceful stroll along the Miami Riverwalk, a promenade offering scenic views of the Miami River and Biscayne Bay. You'll see yachts, open-air art installations, and the downtown skyline. It's a great spot for people-watching and enjoying the waterfront.

12:15 PM - Metromover to Bayside Marketplace & Lunch

• From the Riverwalk area, you can easily walk or take a short Metromover ride back to the Bayfront Park Station, which is right at Bayside Marketplace.

• Activity: Bayside Marketplace & Lunch (approx. 12:15 PM - 2:00 PM)

  • Enjoy the vibrant atmosphere of Bayside Marketplace. This open-air mall offers waterfront views, unique shops, and often live music.

  • Lunch at Bayside Marketplace: Choose from options like:

    • CRAFT Bayside: Highly rated at 4.9 stars.

    • Black Market Bayside: Rated 4.7 stars.

    • La Cañita Bayside: Rated 4.8 stars, known for Latin and Caribbean cuisine.

    • Kuba On The Bay: Rated 4.6 stars.

    • Casa Italia Cucina: Rated 4.8 stars.

  • Consider a short Island Queen Cruise from Bayside if you want to see Miami from the water (check schedules and prices directly at Bayside).

2:00 PM - Public Art Tour & Metromover Exploration

• Activity: Public Art Tour (approx. 2:00 PM - 3:15 PM)

  • Ride the Metromover to explore its various loops (Inner, Omni, and Brickell) and admire the public art installations at different stations. You can hop off at stations to get a closer look or enjoy the art from the elevated tracks.

  • Art Installations to look out for:

    • Brickell Metromover Station: "Reaching For Miami Skies" by Connie Lloveras (ceramic tiles on the ceiling).

    • Brickell Metromover Station (northbound platform) / Tenth Street Promenade: "Solar Window" and "Gate of Sentiments" by Carlos Alves.

    • Brickell City Centre Metromover Station: "La Palma" by Carlos Alves (ceramic royal palm tree mosaic).

    • Riverwalk Metromover Station: The "Red M" by Roberto Behar and Rosario Marquardt (a giant red "M" landmark).

    • Bayfront Park (near Bayfront Park Metromover Station): "Slide Mantra" by Isamu Noguchi (a marble sculpture that is also a slide), "Challenger Memorial," and "Miami's Icon" by Noel Santiesteban.

    • Government Center Station: "Rhythm of the Train" by Joan Lehman, "Seven More of Them" by Carol Brown, and "Dropped Bowl with Scattered Slices and Peels" by Claes Oldenburg and Coosje van Bruggen (in the adjacent park).

    • Freedom Tower (near Freedom Tower Metromover Station): A significant architectural landmark.

3:15 PM - Head back to Bounce Luggage Storage

• From your last Metromover stop, navigate back to a station near your luggage storage, such as College/Bayside Station.

• Pick up your luggage.

3:45 PM - Uber to Miami International Airport (MIA)

• An Uber from Bounce Luggage Storage (132 NE 2nd Ave) to Miami International Airport (MIA) is estimated to take approximately 11 minutes.

• Uber Route: Map Link

3:56 PM - Arrive at MIA

• You should arrive at MIA by approximately 3:56 PM, giving you plenty of time before your 4:30 PM desired arrival.

Enjoy your fun-filled day of art and exploration in Miami!

 Finally, I rounded out the AI Trip Planning learning where I started it when I inquired about luggage, with Microsoft's CoPilot. This is sort of a bittersweet exchange because CoPilot was the bulk of what my husband worked on at Microsoft before he was laid off in May. Still, it's the AI I am most familiar with, also because of that. Here's the final version of my search prompt, so you know what CoPilot had to go on, "A fun day in Miami beginning at the cruise port around 10am, we'll need to take an uber to Bounce Luggage Storage – Downtown North at 132 NE 2nd Ave to store our luggage and then return there to pick it up before heading to the airport (MIA) around 4:30pm two people include a self-guided metromover tour starting near the luggage drop off."

 It's first option was pretty good, and very nicely formatted. I was impressed! It only had me on the MetroMover the first half of the day though and then going out to a far flung neighborhood after lunch which was not my preference, so we tweaked it. It didn't offer any new ideas, but I really liked the formatting, so when it offered to create a downloadable PDF for me I accepted! That's where things started to break down. You see, it gave me this lovely screen:

 Looks great, so what's the problem? The link didn't work. I tried over and over again and all I got was:

 Ok, so I scrolled up to the beautiful itinerary it had given me complete with links to walking maps between each stop and copied that over to a Word document. Then I checked the links to make sure they work on the copy. Spoiler alert, they didn't. When I went back to the original and tried the links there, I had the same issue. Instead of pulling up a nice little walking map all it did was send me to Bing with a search prompt of, "walking map First Street Station to Bounce Luggage Storage Downtown North Miami," which while well-intentioned does not give you a walking map. All you get is a search page that shows you options for Bounce luggage storage and other options. Grrr... So, pretty but completely nonfunctional. 

 So which AI wins? That's a tough question. They all had things they did well and things they didn't. I can tell you two that I won't be using for trip planning again: Layla and CoPilot. You hit a hard paywall with Layla and CoPilot's pretty answers don't actually work. Canva was a neat starting ground, but unlike the other sites it doesn't save your chat history so there's no way to go back and see what you did later. For me that's a no-go. Mindtrip had a lot of cool features and furthered my trip plans a lot. What I wasn't fond of is it took multiple requests for it to actually update things in the standing itinerary on the right-side popout. So, we would discuss ideas, and I would ask it to incorporate it, and it would for a small part of the itinerary in the chat, but not in the main working itinerary. Gemini had some great ideas but was really cumbersome to use with the constantly repeated full itineraries. The winner in my book? ChatGPT! Great ideas, great tips, great interactions. Its final itinerary was well formatted with cute graphics (the way to my heart). I may go back and ask it to add specific walking directions in, or I may keep it simple and just create a Google Map. Either way, I'm pretty happy with the results! 

Here's the Thing: Travel agents shouldn't worry. While AI can do a great job at giving you ideas, the reality is they are just that, ideas. And AI is notorious for over promising and underperforming. So, what is it good for? You can chat with them to your hearts content, tweaking and adjusting your plans without worrying about "bothering" anyone. Then, once you have your ideas in hand, you can chat with a travel agent to help you book your dreams!