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is Like at this Old World Treasure

While browsing hotels in Puerto Rico, I discovered a picture of The Cannon Club inside The Gallery Inn. I was scouring the ‘net trying to determine where to stay in Old San Juan. Albeit, even from a photo on the computer screen, I was lured in by the mystique of the suave interior decor. From the moment I saw it… I knew. I had to stay at The Gallery Inn Old San Juan.

Several large balconies of the bright green building of The Gallery Inn Old San Juan
These are the rooms with an ocean view
Black, metal front door gate of The Gallery Inn Old San Juan
The front door of The Gallery Inn has secured entry – you’ll have to enter a code

What is the appeal, you ask? Besides this inn being housed in a 450 year old historical building? It was fully restored by a husband and wife duo nearly six decades ago now. Further, being steps away from numerous historical landmarks, with gorgeous views of San Juan Bay is always an incentive.

Entering The Gallery Inn Old San Juan is like entering a time capsule that transports you to old world charm. You’ll be surrounded by nearly six decades of the owners paintings, statues and sculptures in every nook of the hotel. Truly, the place is bursting with character and elegant personality.

I honestly have never stayed anywhere quite like it.

Lodging type: Unique Stay, ★★★ Boutique Hotel, Historical Hotel

Book The Gallery Inn Old San Juan: Here

Where is the Hotel Located?

The age old real estate adage of location, location, location can often ring true for travel accommodations too. In fact, one of the perks of staying at The Gallery Inn is its accessibility to so many things on foot. It’s situated on the corner of Calle Norzagaray, right off a main thoroughfare that gives you gorgeous views of the bay as you walk.

You can easily access some of the main historical sites like Castillo San Felipe del Morro and Castillo San Cristobal in just a short walk. It’s also pretty central to neighboring bars, restaurants and other points of attraction.

What to Expect & Amenities On Site

If I were to personify The Gallery Inn, I’d say she’s artistic and quirky in a sophisticated way. Her imperfections make her more interesting. It’s as if every inch of her tells some kind of story. This is an instance where structures tell stories too.

It’s my understanding that in The Gallery Inn’s glory days, the owner, Jan D’Esopo, would roam the halls making her Guests feel at home. Warmly inviting them to join her in the sun room for refreshments while they chat. Truly acting as a remarkable host.

an exotic, antique table with a coffee and tea bar on top at the Gallery Inn Old San Juan
The Inn’s coffee and tea bar – complimentary
an rustic, shabby chic open kitchen at the Gallery Inn Old San Juan
The open kitchen where all the food for the Cannon Club & hotel are made

She has four ‘exotic’ birds that roam the hotel freely, they are her personal pets. Paulina, is a colorful, rather shy ‘traditional’ parrot. There is Rembrandt, a stoic and demure African Gray Parrot. Also, Mikey, a Blue Macaw that we hardly saw the entire time.

A large parrot with blue, yellow and red feathers perched on a free stump near a muilticolored window placed on a green wall
Paulina, the resident Parrot at The Gallery Inn Old San Juan

At last, but certainly not least, is Campeche, a very sassy Cockatoo that greeted me with a warm, “Hola!” and then “Hello,” when I first entered the lobby area.

a white cockatoo perched on a statue against a yellow wall
Campeche the resident sassy Cockatoo at The Gallery Inn

There is a restaurant and bar underneath the hotel, as well as a pool that’s great for wading or a refreshing dip on a hot day.

Brunette woman sitting on a ledge inside a very eccentric pool surrounded by greenery and statues
Taking a dip in the pool upon arrival

Tip: There isn’t room service, so if you want to order food you’ll have to sit at the bar in The Cannon Club or the main dining room if there’s available seating. Also, the pool isn’t heated, so expect some frigid water (which may feel nice on a very hot day).


The Inn feels more like staying at an eccentric mansion rather than a hotel. Surely, in some ways that’s good and in other ways, maybe not so much – depending on who you’re asking. The front desk staff seems quite green to hospitality, albeit, well intended.

The hotel portion isn’t very service driven, so if that’s important to you or you enjoy more attentive personalized assistance, this may not be the stay for you. But if you don’t mind the aforementioned, this certainly will be one of the most unique stays you’ve encountered.

an off white sculpture of a plump and curvy woman sitting on a dark brown table
One of the owner’s creations -her statues and sculptures are all over the hotel

In some ways, The Gallery Inn might be a shell of its former self. In other ways, the spirit of what Jan and her late husband have created is still alive and flourishing.

I was hoping to meet Jan, but, alas, she was on a trip during my stay. It’s almost like you can feel her absence when she’s not there. Kind of like the feeling of being at a friend’s home and they have stepped out to do something, so someone else who lives their entertains you in their absence.

The Cannon Club

The Cannon Club is the bar – restaurant and intimate live music venue underneath the Inn. Now, The Cannon Club is run like a well oiled machine. We went there on a Wednesday night for dinner, drinks and live music in the main performance room. It was delightful!

There is live music every night and the performers and musicians vary.

The Cannon Club at The Gallery Inn Old San Juan - stairs leading down into the bar with a giant crystal chandelier, a man playing a guitar and Campeche, the white cockatoo sitting nearby
Campeche made a cameo at The Cannon Club

The Cannon Club is open to the public. There’s a street side entrance that goes directly into The Cannon Club for non hotel Guests. Patrons of The Cannon Club are welcomed to dine or have drinks on the hotel patio, weather permitting. They can also sit in a common room that is right amidst several hotel rooms, which was not cumbersome at all.

Tip: It will reach capacity Thursday – Sunday in the main room where the musicians perform. I highly recommend making a reservation for that specific room. I believe on the weekends there is a nominal extra fee for seating in that room.

The Room

By the time I went to book this hotel, most room types were booked. The only room that was available for all of the dates that I wanted to stay here was one of the Suites.

This is a 27 room boutique hotel and what’s really special is that no two rooms are the same. As in, each room has a different motif and decor style.

a dark brown four post bed sitting on tile against orange colored walls The Gallery Inn Old San Juan
The bedroom area of our Suite

The suite we were assigned had a city view and a little kitchenette. There are also suite(s) with ocean views, but none available when I arrived. The city view was cool though, it definitely gave my view more of an Old San Juan feel.

A bed with multiple decorative pillows on it at The Gallery Inn at Old San Juan
The bedroom area from another angle

Overall, it was a comfy stay, no complaints. It won’t feel super frilly, but it definitely gives you a homey atmosphere.

But, keep in mind, depending on where your room is located, you’ll likely hear the music from The Cannon club. If you’re very sensitive to sound, this usually ends around 10:00pm – 11:00pm.

The suites are humongous. Like, definitely huge for two people. There is also a living area with a sectional couch and steps that lead out to the enormous veranda deck with tables and chairs and a view of Old San Juan.

yellow walls surround a tiled kitchen counter in our hotel suite at The Gallery Inn Old San Juan
The kitchen area – a sink and small refrigerator

Tip: None of the rooms have phones or televisions. I personally rarely use an accommodation’s TV, but I just wanted to make you aware in case it’s important to you. The hotel does not use WhatsApp, if you need to communicate with the desk, you’ll have to do it the old fashion way… walk over.


There is secured entry at the front gate of the Inn where you need a push button code to enter. Also, they have security at the hotel all night long in the evenings.

brick flooring, hallway with ornate decor, table and chairs, yellow walls, a giant chandelier with green
One of the common rooms around the hotel for lounging

Food Situation

Our suite was right above the kitchen that provides delicious tapas to The Cannon Club. If you want to dine within the hotel, you’ll need to order at The Cannon Club bar or sit at a table. For hotel Guests, they can serve you in one of the common rooms upon request.

wooden countertop with white bowls on top - a very rustic looking kitchen with hanging lights and a red floor mat
The kitchen that makes food for The Cannon Club, was right below our room

If you dine at The Cannon Club or even sit at the bar, the service is excellent. Thoughtful and attentive. The food is pretty good.

piña colada on the rocks sitting on a table in front of a grand piano and ornately decorated room
The Cannon Club only serves Piña Coladas on the rocks, but they’re wonderful

Some of the menu was unavailable and the fare is mostly tapas. I highly recommend the tartare and the piña colada flan!

a flan adorned with a chocolate drizzle and berries
Piña Colada Flan – to die for!

Rembrandt, the African Gray Parrot made a cameo the night we sat at the bar for cocktails during the musical performance.

Rembrandt, the resident African Gray Parrot at The Gallery Inn Old San Juan

Know Before You Go

I think if you go to The Gallery Inn knowing what they offer and do well, you’ll enjoy your stay. The Gallery Inn Old San Juan is a unique stay that will appeal to those whom like boutique hotels with historical heritage.

As long as you don’t go expecting the type of stay you won’t get (high touch service, modern amenities). But, if you like a cozy ambiance with a distinct style that’s centrally located in Old San Juan with music and the arts at the heart of everything they do, you’ll love this atmosphere.

The general “high season” to visit Puerto Rico is mid December – mid April. Now, I typically don’t ever travel to destinations during its high season unless I have a good reason. But, in this instance, I found a really great flight deal through the flight service I subscribe to: Going.

So I visited in February. I found it to be bustling, but certainly not overwhelmingly crowded. The one area where it did make a difference was in my hotel rate. My nightly rates were definitely on the higher end. Always travel whenever is best for you, but consider visiting during the “low season” August – November if you’re looking to save! It is technically considered hurricane season, but it’s actually a very popular time in Puerto Rico for locals to head out to the islands of Vieques or Culebra.

If you have any questions about staying at this accommodation, please drop them in the comments!

Headed to Puerto Rico?

Things to do in Puerto Rico – an Epic Guide for First Timers

Travel Tips & Resources to Help You Plan an Epic Trip!

Going – I’ve subscribed to Going (formerly, beloved, Scott’s Cheap Flights) for awhile now and it’s an amazing resource for finding… did you guess cheap flights? Yes, you can set your preferences from airports to flight class and get destination deals right to your inbox. It’s fab! I use the Premium paid version, but they have a FREE version too. So what are you waiting for?! Let’s get Going! – the majority, if not almost all of my stays are booked on It’s a reliable site to book and manage your reservations. It’s a great way to find boutique stays and unique accommodations at the best rates! You can also easily communicate with your accommodation through the app.

Expedia – If I am looking for a flight to a specific destination for specific dates, I find myself booking many flights on Expedia. It’s user friendly and straight forward. I often find the most cost effective rates, while earning points for every flight I book (in tandem with the points I receive from the credit cards I pay with).

Viator – most of the activities, tours and excursions I book for my trips are booked through Viator. Whether you’re seeking a guide for the day, a group tour, a cooking class, Viator has you covered!

Get Your Guide – this is another great marketplace to find tours, excursions and activities to book for your upcoming trip.

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