This post may contain affiliate links. I only recommend excursions, products and tours that I have personally used and purchased myself. If you click on a link and make a purchase, I may receive a very small commission at no extra cost to you. All proceeds go to running this blog and your support is truly appreciated! All opinions are my own. While browsing hotels in Puerto Rico, I came upon 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. What is the appeal, you ask? Besides the 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 hand made 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 The age old real estate adage of location, location, location often rings 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. Situated on the corner of Calle Norzagaray, right off a main thoroughfare it 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. 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. 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. 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. 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. 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. 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 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 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. 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. 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. 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. 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. 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. 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. Some of the menu was unavailable and the fare is mostly tapas. I highly recommend the tartare and the piña colada flan! Rembrandt, the African Gray Parrot made a cameo the night we sat at the bar for cocktails during the musical performance. 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! Check these out! Want to know how I travel so frequently? By booking jaw-dropping flight deals that are often so low you’d have to see ’em to believe it. The best part? They’re sent right to my inbox. You can try it out for free: here. I exclusively use this site to book all my stays. I get 20% off on all my stays plus additional perks from their loyalty program. Check it out! Get reliable travel medical insurance for your trip, for just $2 a day – here Looking for a flight on a specific date? Use this search engine and start earning rewards! 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is Like at this Old World Treasure
Where is the Hotel Located?
What to Expect & Amenities On Site
Service
The Cannon Club
The Room
Security
Food Situation
Know Before You Go
Is The Gallery Inn Old San Juan the right stay for you?
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Travel resources for YOU to plan an epic trip!
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