My wife and I faced an empty house for the first time in 20 years after our youngest went to college for her freshman year. I mean, it’s wonderful and all — but the silence of an empty house is deafening.
By late fall, we wanted a change of scenery and a break from the overcast Northeast. Thanks to our Hilton Grand Vacation membership and some frantic tapping on a computer keyboard, we found our next getaway: McAlpin Ocean Plaza, a Hilton Grand Vacations Club in South Beach, Miami, for four days. Perfect.
But wait — neither my wife nor I had ever been to Miami.
What were we going to do?
I didn’t want to spend hours scrolling online reviews to create a vacation itinerary. Luckily, I recently learned about artificial intelligence (AI) and its capabilities from “60 Minutes.” We’re an adventurous couple and were game to allow our new digital concierge, Gemini, to plan our time in South Beach. It seemed easy enough. Provide Gemini with a prompt, and within seconds (yes, seconds), it generated three different itineraries.
Here was our prompt:
"We are a 50-year-old empty nester couple visiting South Beach for the first time. We are flying into Fort Lauderdale on [arrival date and time] and staying for four days at McAlpin Ocean Plaza, a Hilton Grand Vacations Club. We are flying home on [departure date and time]. Create a four-day itinerary with a specific interest in culture, architecture, beach and the outdoors. Keep the dining options at a reasonable cost with variety."
The three itineraries Gemini came up with were over six pages long. I know, you’re probably thinking the same thing I was: “That’s a lot of information.” But we’d never been to South Beach before and knew nothing about the area, so we picked through the itineraries to make our own.
Day 1
Armed with our luggage — and I mean seriously armed, I pack heavy — we boarded the plane and touched down in the Sunshine State.
We took an Uber from the airport to McAlpin Ocean Plaza. Since we were early, we checked our bags at the front desk, shed our outer layers of clothes and started day one with a walk along the beach. This wasn’t on our AI itineraries, but if you live somewhere land-locked and travel to the ocean, you should first and foremost dip your toes in the water.
We had lunch at La Sandwicherie, which was an AI suggestion and the perfect quick bite. Then, we explored Ocean Drive and the Art Deco Welcome Center for some shopping and admiring of the architecture. A text message from Hilton Grand Vacations said our Suite was ready, so we checked in, stocked our kitchen and took the rest of the evening to relax, shower and prepare for dinner.
We deviated from our AI itineraries (again) and went to Havana Vieja for an amazing dinner. The concierge recommended this restaurant. Sorry, Gemini. Sometimes people know best.
Day 2
We started with a Tour-de-France-style trip suggested by Gemini. Bicycle rentals were perfect for the South Beach area. Download the Citibike app for a completely automated process. We enjoyed a solid morning of biking when we ran into a problem with our AI itineraries: Joe’s Stone Crab appeared as a day-one lunch option on two itineraries. However, it was closed for lunch on day two. Oops, silly humans.
After competing against an imaginary Lance Armstrong, I started looking for a place to eat. Serendipitously, Fratelli La Bufala was nearby. Amazing salads and margherita pizza were exactly what we needed. When one door closes, another opens.
Stuffed with carbs, we went afoot. Stumbling into Miami Ink - Love Hate Tattoos, I snagged an evening flash tattoo reservation. We headed to Española Way for some shopping and gelato before returning for my spontaneous tattoo. There’s no feeling like sipping a café Cubano with an enso symbol and your daughter’s nicknames tattooed on your knuckles.
Day 3
Day three started with an Uber drive to Little Havana. We love different cultures, and Little Havana offered a different feel to the rest of South Beach. We started at La Colada Gourmet’s patio to enjoy more Cuban coffee and random roosters crowing. Caffeinated, we explored Domino Park and Calle Ocho. As a photographer, images were practically jumping into my camera.
We enjoyed visiting Cuban artists at Futurama 1637 and watching people hand-rolling cigars in cigar shops. We ventured off the AI itinerary and bought fresh churros and coconut water from street vendors before heading back to our Suite for an afternoon siesta.
My wife had a taste for Mexican food while we strolled Washington Avenue, and it was Taco Tuesday. We ate at Esquina Mexicana.
Day 4
The morning of the last day, we returned to the beach and bikes. We made our way down to South Pointe Park to boat watch while enjoying the sun and sand. Afterward, we went back to our Suite, showered, checked out and arrived at Gianni’s for our lunch reservation.
Gianni’s is possibly the best lunch in South Beach for the price — three courses for $35 per person. The food was excellent, the staff exceptional and the ambiance pleasurable.
However, Gemini hadn’t suggested this as a dining option. Perhaps it was left out because of the price. We are 100% glad we went off script again. And yes, this is a lunch suggestion if you ever ask me about restaurants in South Beach.
We spent the rest of the day at the Lincoln Road Mall before taking an Uber to the airport.
Our AI Itinerary Review
Our first-ever AI-planned trip was a success. We learned several things from the process.
- Always check business hours. I’m bummed we missed eating at Joe’s Stone Crab.
- Be flexible and willing to try something out of your comfort zone. I would’ve scoffed at renting bicycles, yet it proved an enjoyable and effective way to get around.
- We didn’t follow any of the three itineraries 100%. We cherry-picked what we liked and allowed room for exploring.
- Recognize that your input prompt can limit AI. However, it’s a useful starting point.
We had a great time at McAlpin Ocean Plaza, inside a historic art deco building. If you’re ever there, remember you’re in great hands with Tall Paul.
Since this trip, we’ve decided to head back to McAlpin Ocean Plaza with our college freshman in May. Perhaps AI can dig deeper into the matrix for our next vacation.
Read “Explore Miami’s History Through A Multicultural Food Scene” for more restaurant recommendations.