Love on Location: Adventures for Two or Just You

Calle de la Sol: A Hidden Gem in Old San Juan’s Layers of History

Keli returns to Puerto Rico and this time takes a slower week exploring Old San Juan solo using AI as her main travel assistant and tour guide.


It’s funny how a place can be both peaceful and alive at the same time. That’s exactly how I’d describe my colonial apartment on Calle de la Sol. The street itself feels like stepping into history—colorful walls that have seen centuries of stories, from Spanish colonists to modern-day woman crying after getting pulled over for some kind of traffic infraction five feet from my front door. The apartment is tucked behind an large wooden door that creaks in a way that makes you wonder how many people have peeped their heads through those iron gate doors.

Inside, the thick stone walls do their job, keeping the space cool even when the Caribbean sun outside is relentless. I turned off the AC to let my skin soak in the humidity. Exposed wooden beams cross the high ceiling, and just beyond the small kitchen, an interior courtyard opens up like a private little sanctuary. There’s something timeless about sitting there, surrounded by tropical plants and the sound of rustling leaves, knowing that this exact setup has been part of daily life here for generations.

Old San Juan is one of the most walkable neighborhoods I have stayed in with multiple grocery store options and restaurants within in a 5 minute walk. Be sure to shop the local bodegas and no-name stores. I had an extra immersive experience at one while pulling plantain from a branch of them in the store. I also love to cook and try new local ingredients so a Bnb option was a better choice for me than a hotel. My walking pace is adjusting to the humidity, heat and the city streets with a 30% incline.

While eating lunch in my plant filled courtyard I had a conversation of exchanging "meows" with a neigborhood cat who remained hidden. I spent my time listening to the faint hum of life outside—trying to translate conversations of the school kids playing at the elementary school across the street, the shuffle of shoes on cobblestones, and the passing cars blasting Bad Bunny beats - clearly THE PR soundtrack.

What I love about Calle de la Sol, and Old San Juan in general, is how seamlessly the present blends with the past. The apartments along this street, built in the 18th and 19th centuries, are a reflection of Spanish colonial design: thick walls to keep out the tropical heat, tall windows to catch the ocean breeze, and iron balconies that offer the perfect spot to people-watch or shout down to a neighbor. The original cobblestones lining the street, known as adoquine, were once ship ballast brought over from Spain in the 1700s. Now, they shimmer in shades of blue, especially after a good rain.

I got caught in it after an afternoon walk—rain transforms Calle de la Sol. The adoquine cobblestones become mirrors, reflecting the colors of the buildings and the cloudy sky above. I crouched down, my clothes already drenched, and snapped photos of the puddles creating perfect reflections of pinks, yellows, and turquoise walls.


Ok so let's now go behind the scenes on my trip planning...we love a good backstage tour around here! ;)

Budgeting Breakdown for Wed/Thursday

Meals in JFK airport: $76 (Farmers Fridge salad, snack mix, clam chowder and crab cakes)

Air BnBnB Stay: $882.85 (covered by travel group I'm working for along with the $323 Delta flight)

Grocery Trip: $70 for celsius drink, coffee creamer, eggs, milk, bread, cheese, sour cream, shrimp, adobo seasoning, bacon, plantains, beans, rice, tostones, sofrito, onion, avocado, reusable shopping bags

Notes on colonial apartment in Old San Juan: The colonial apartments have low ceilings in the loft area. I'm 5'8" so I was fine but my 6" friend would have felt like they were in a hobbit sized space. The electric is kind of suss in buildings hundreds of years old. I brought a small portable solar charger with built in flashlight and work-light because the people of PR deal with cruddy infrastructure issues. Be kind and resourceful if the water pressure is low or the electric goes out for a few hours. Most of the hotels have generators.


And for the digital nerdy breakdown...

Where AI has been most useful, and most un-helpful so far:

  • Chat GTP is brilliant at re-formulating a travel schedule when flights are delayed and telling you about ways to spend time in various airports. When my layover switched to JFK it did a great job at recommending things to do like visiting the TWA hotel. It also reformulated my first day into a lighter schedule after arriving into San Juan later than expected and not having a chance to prepare for the week that evening. As someone who will generally start to riff when things go awry, this is a good way to keep me focused and on assignment.


  • The Delta airlines app with the airport maps is so very useful. Especially when you have a gate change. Also love that Delta, like us believe that diversity, equity are inclusion are positive values.


  • Chat GTP did a great job at looking at all of the items in the Air Bnb kitchen cabinet and making a suggested grocery list of local inexpensive ingredients to use for meals and made a suggested menu to make with those foods. I took a picture, told it I wanted to spend around $100 for basics and it told me what to buy and gave me a menu.


Unhelpful suggestions:

  • ChatGTP recommended an evening walk in the La Perla neighborhood after I arrived and well, basic research can tell you why that may not be the best idea.


How to get the most out of your Virtual Travel Assistant:

  • Be specific: When asking for a menu give your location and dietary restrictions, or things you do and don't like. It's a computer -it wont judge you.
  • Ask and ask again. If you get some silly result ask again using a lightly different prompt or ask it to approach the problem from a different perspective. "Pretend you are the top travel expert in the world, but you are extremely snobby about wine. What restaurants would you recommend within a 10 minute walk with outside seating, and great ocean views." or "What is the best location to watch a sunset on 2/12 in Old San Juan while getting silhouettes of palm trees and architecture in the picture frame?" - The best part is that it wont get annoyed when you tell it to try over multiple times. (You also start to get better at communicating specific directions to all people in your life.)
  • I arrange all of my travel questions and trip details in one project file in Chat GTP. This way that travel information is cross referenced with past questions and suggestions. It remembers I like to cook, I like to paint with watercolors late at night and I prefer historical or historical areas more than commercial spots in cities.


Stay tuned for part two featuring...Resort Days, Street Food and Wandering.


Cobblestone street in Old San Juan Puerto Rico descending towards the ocean with historic colonial buildings and street lights.
A cobblestone street lined with colorful colonial buildings and glowing lanterns at dusk in Old San Juan, Puerto Rico.
Historic stone guard tower overlooks the ocean from fortified wall at sunset in Old San Juan, Puerto Rico.
Historic stone guard tower with domed roof overlooks the ocean from ancient fortress walls in Puerto Rico.
View of ocean waves and cloudy horizon through a narrow window frame along a coastal viewpoint.
Weathered wall texture with rustic red, black and beige tones showing distressed paint and mold patterns.
Ancient stone archway entrance with weathered orange walls at a historic fortress under cloudy skies in Puerto Rico.
Moody sunset sky over old weathered stone building with ornate architectural details and rusting metal facade.
Silhouettes of people walking on wet cobblestones near building, captured in black and white with shallow depth of field.
Reflective puddle on cobblestone street shows mirror image of historic buildings and trees in urban setting.
Close-up view of a cobblestone street with grey and blue stones arranged in a diagonal pattern.
A street lamp illuminates a rainy seaside promenade with palm trees and stormy clouds over the ocean.
Green leaves and hanging branches of a seagrape tree against an overcast sky.
A scenic colonial street with palm trees and pastel buildings in Old San Juan, Puerto Rico, featuring parked cars on a rainy day.
Wet cobblestone street in Old San Juan Puerto Rico lined with colorful colonial buildings and parked cars on a rainy day.
A narrow cobblestone street in Old San Juan, Puerto Rico with colonial architecture and power lines overhead.
A narrow cobblestone street in Old San Juan with historic colonial architecture and ornate building facades.
Colorful colonial buildings line a historic street in Old San Juan, Puerto Rico with string lights hanging overhead.
Vintage street view in Old San Juan Puerto Rico with colorful colonial buildings and ornate lamp posts.
Ornate vintage street lamps mounted on a pink building facade with a church silhouette visible in the background.
Historic cobblestone street with colonial architecture and parked cars in Old San Juan, Puerto Rico.
Art deco style building facade in Ols San Juan features blue and cream colors with ornate wooden trim and balconies.
Colorful historic buildings line a narrow cobblestone street in Old San Juan, Puerto Rico on a cloudy afternoon.
Weathered blue cobblestones arranged in a geometric pattern create an old-world street texture with cracked surfaces.
Ornate black wrought iron security door with decorative scrollwork against a blue and white colonial building exterior.
Palm fronds and lush plants frame a charming cobblestone street with colonial architecture in Old San Juan, Puerto Rico.
Turquoise colonial building facade with arched wooden doors and windows featuring ornate white trim and brass balconies.
Two cats lounging on a checkered tile floor, one calico and one black and white cat resting near a doorway.
A cozy outdoor patio corner with terracotta tiles, wooden folding furniture, and a tall potted indoor plant against white walls. Colonial
Sliced avocado with pit on wooden cutting board shows creamy green flesh and green stem.
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