Best experience going to the trophy!!! The drinks are amazing! Garnett is amazing!! And Sofys food is great! I tried the pizzas are amazing! I will definitely be back!!!
Atmosphere: 5
Food: 5
Service: 5
Petr Valenta
Calm place, good food, good beer. Highly recommended.
Atmosphere: 5
Food: 5
Service: 5
FELIX MARADIAGA
Great service. Went with my daughter and wife we all enjoyes the service thanks to Sofia:)
Atmosphere: 5
Food: 5
Service: 5
silvia deras
Service was good and very attentive. Food was excellent and quick. Sofia was great
Atmosphere: 5
Food: 5
Service: 5
Alexandra Deras
Food was delicious, I love it! Will be coming back. Sophia assisted me and was super nice thank you!
Atmosphere: 5
Food: 5
Service: 5
Jennifer Tose
Went on Friday night. Place was packed. Music was great. Pizza was delicious and wine was flowing. Bartenders were fabulous! Will come again
Atmosphere: 5
Food: 5
Service: 5
Alexa Lamberti
Had a great time!! Bar tender Garnett was a pleasure. amazing atmosphere and great drinks.
Atmosphere: 5
Food: 5
Service: 5
CJ J
Jonathan is that guy! The only bartender and waiter for the entire restaurant—and somehow, he’s holding it down like a pro. From the moment I walked in, he was gracious, attentive, and moving with purpose, making sure everyone felt seen, served, and taken care of.
Despite being a one-man show, drinks came out strong, food was hot, and vibes were high. He was juggling tables, mixing cocktails, taking orders, and still had time to be warm, funny, and completely unflustered.
It’s rare to see that level of professionalism and grace under pressure. Give this man a raise, a bonus, and a full team—he deserves it all.
If you’re lucky enough to catch Jonathan when you visit Trophy Room, know you’re in great hands.
From the moment we arrived at Staypineapple in Boston, we were welcomed like old friends. The front desk team greeted us with the warmest smiles, and everyone seemed genuinely happy to have us there. The lobby was cozy yet modern, filled with quirky pineapple-themed decor that set a fun, welcoming tone right away. One of the most unexpected highlights? The hotel dog! A friendly, fluffy companion named Goffy came trotting over to greet us, tail wagging and eyes sparkling. He even did a little tail-wagging dance when we scratched behind his ears—such a sweet welcome. Just his presence alone added so much charm and made us feel right at home. That night, we ordered dinner from the hotel restaurant—pizza and nachos—and let me tell you, both were knock-your-socks-off good. The pizza had a crisp, buttery crust with gooey cheese that stretched perfectly with every bite. And the nachos? Piled high with toppings and just the right kick of spice. But what truly stood out were the drinks—handcrafted cocktails that packed a punch without being overwhelming. My margarita was fresh, minty, and ice-cold, while my wife had a passionfruit margarita that tasted like vacation in a glass. Every interaction with the staff added to the experience. Housekeeping always left fun little notes alongside perfectly folded towels. The beds were cloud-soft and the robes—those signature Staypineapple yellow-striped robes—were ridiculously comfortable. We even found complimentary snacks waiting in our room when we returned from sightseeing. What really sealed it was the hospitality from the manager. She stopped by during check-in just to say hello and gave us a list of lesser-known Boston activities curated perfectly to our interests—from hidden bookstores to charming harbor cruises and rooftop art museums. It felt personal, not like just another tourist tip. I don’t say this lightly: we’ll absolutely be coming back. Between the cheerful staff, fantastic food and drinks, and that uniquely playful Staypineapple vibe, it felt more like staying with good friends than just a hotel. Can’t wait to return.
Atmosphere: 5
Food: 5
Service: 5
Valeria Trevino Cortes
From the moment we arrived at Staypineapple in Boston, we were blown away by the entire experience. This boutique hotel is the perfect combination of charm, comfort, and class, and it quickly became one of our favorite stays ever.
First, the staff was incredibly warm and welcoming. Every interaction we had—from check-in to casual hallway greetings—felt genuine and friendly. They truly go above and beyond to make you feel at home. Whether it was offering local tips, helping with directions, or just being great conversationalists, their customer service was top-notch.
The room was stylish, spotless, and filled with quirky, thoughtful touches that made it stand out. The bed was insanely comfortable, and we loved the signature pineapple plush robes and cozy duvets (yes, they give you two!). You can tell they’ve put a lot of thought into the guest experience, down to the smallest detail.
We also really enjoyed the Trophy Room, the hotel’s restaurant and bar. The drinks were phenomenal — creative, perfectly balanced, and beautifully presented. It’s not often you stay somewhere where the food and drinks rival standalone restaurants, but this place nails it. The bartenders were not only skilled but also super friendly and made the experience even more fun.
Another standout? The location. Right in the heart of Boston, Staypineapple is walking distance to so many of the city’s must-see sights, great coffee shops, and vibrant neighborhoods. It made exploring easy and enjoyable without ever feeling too far from home base.
To sum it up: Staypineapple Boston is an absolute must if you’re visiting the city. Whether you’re traveling solo, with friends, or for a romantic getaway, it checks every box. Amazing staff, delicious drinks, a cozy and modern vibe, and the kind of personalized service you don’t often find these days.
We’ll definitely be back — and we’ll be recommending Staypineapple to everyone we know. Thank you for a truly memorable stay!
Atmosphere: 5
Food: 5
Service: 5
Elton Palencia
Garnett is hands down one of the best bartenders I’ve ever come across. Garnett is fast, friendly, and actually makes you feel welcome the second you sit down. He knows his drinks, has great energy, and somehow keeps the vibe going even when the place gets packed.
Whether you want a classic cocktail or something creative, he nails it every time. You can tell he takes pride in what he does—and it shows. If you’re coming here, hope Garnett’s behind the bar. He’s a big part of what makes this spot worth coming back to.
Atmosphere: 5
Food: 5
Service: 5
Matthew Rafferty
Dakota is Trophy Room's best employee who always brings a positive attitude and uplifts the spirits of those around him. He goes above and beyond in entertaining guests andbeven cleans up the floor at the end of the night! His owner Isaac is a great team player as well and pours a nice drink when behind the bar, though he sometimes misses the mark when tossing his napkins.
My favorite place! Jonathan is my favorite!
Atmosphere: 5
Food: 5
Service: 5
Very bad
Atmosphere: 1
Food: 1
Service: 1
Best experience going to the trophy!!! The drinks are amazing! Garnett is amazing!! And Sofys food is great! I tried the pizzas are amazing! I will definitely be back!!!
Atmosphere: 5
Food: 5
Service: 5
Calm place, good food, good beer.
Highly recommended.
Atmosphere: 5
Food: 5
Service: 5
Great service. Went with my daughter and wife we all enjoyes the service thanks to Sofia:)
Atmosphere: 5
Food: 5
Service: 5
Service was good and very attentive. Food was excellent and quick. Sofia was great
Atmosphere: 5
Food: 5
Service: 5
Food was delicious, I love it! Will be coming back. Sophia assisted me and was super nice thank you!
Atmosphere: 5
Food: 5
Service: 5
Went on Friday night. Place was packed. Music was great. Pizza was delicious and wine was flowing. Bartenders were fabulous! Will come again
Atmosphere: 5
Food: 5
Service: 5
Had a great time!! Bar tender Garnett was a pleasure. amazing atmosphere and great drinks.
Atmosphere: 5
Food: 5
Service: 5
Jonathan is that guy! The only bartender and waiter for the entire restaurant—and somehow, he’s holding it down like a pro. From the moment I walked in, he was gracious, attentive, and moving with purpose, making sure everyone felt seen, served, and taken care of.
Despite being a one-man show, drinks came out strong, food was hot, and vibes were high. He was juggling tables, mixing cocktails, taking orders, and still had time to be warm, funny, and completely unflustered.
It’s rare to see that level of professionalism and grace under pressure. Give this man a raise, a bonus, and a full team—he deserves it all.
If you’re lucky enough to catch Jonathan when you visit Trophy Room, know you’re in great hands.
Atmosphere: 5
Food: 5
Service: 5
Restaurantji Recommends
From the moment we arrived at Staypineapple in Boston, we were welcomed like old friends. The front desk team greeted us with the warmest smiles, and everyone seemed genuinely happy to have us there. The lobby was cozy yet modern, filled with quirky pineapple-themed decor that set a fun, welcoming tone right away.
One of the most unexpected highlights? The hotel dog! A friendly, fluffy companion named Goffy came trotting over to greet us, tail wagging and eyes sparkling. He even did a little tail-wagging dance when we scratched behind his ears—such a sweet welcome. Just his presence alone added so much charm and made us feel right at home.
That night, we ordered dinner from the hotel restaurant—pizza and nachos—and let me tell you, both were knock-your-socks-off good. The pizza had a crisp, buttery crust with gooey cheese that stretched perfectly with every bite. And the nachos? Piled high with toppings and just the right kick of spice. But what truly stood out were the drinks—handcrafted cocktails that packed a punch without being overwhelming. My margarita was fresh, minty, and ice-cold, while my wife had a passionfruit margarita that tasted like vacation in a glass.
Every interaction with the staff added to the experience. Housekeeping always left fun little notes alongside perfectly folded towels. The beds were cloud-soft and the robes—those signature Staypineapple yellow-striped robes—were ridiculously comfortable. We even found complimentary snacks waiting in our room when we returned from sightseeing.
What really sealed it was the hospitality from the manager. She stopped by during check-in just to say hello and gave us a list of lesser-known Boston activities curated perfectly to our interests—from hidden bookstores to charming harbor cruises and rooftop art museums. It felt personal, not like just another tourist tip.
I don’t say this lightly: we’ll absolutely be coming back. Between the cheerful staff, fantastic food and drinks, and that uniquely playful Staypineapple vibe, it felt more like staying with good friends than just a hotel. Can’t wait to return.
Atmosphere: 5
Food: 5
Service: 5
From the moment we arrived at Staypineapple in Boston, we were blown away by the entire experience. This boutique hotel is the perfect combination of charm, comfort, and class, and it quickly became one of our favorite stays ever.
First, the staff was incredibly warm and welcoming. Every interaction we had—from check-in to casual hallway greetings—felt genuine and friendly. They truly go above and beyond to make you feel at home. Whether it was offering local tips, helping with directions, or just being great conversationalists, their customer service was top-notch.
The room was stylish, spotless, and filled with quirky, thoughtful touches that made it stand out. The bed was insanely comfortable, and we loved the signature pineapple plush robes and cozy duvets (yes, they give you two!). You can tell they’ve put a lot of thought into the guest experience, down to the smallest detail.
We also really enjoyed the Trophy Room, the hotel’s restaurant and bar. The drinks were phenomenal — creative, perfectly balanced, and beautifully presented. It’s not often you stay somewhere where the food and drinks rival standalone restaurants, but this place nails it. The bartenders were not only skilled but also super friendly and made the experience even more fun.
Another standout? The location. Right in the heart of Boston, Staypineapple is walking distance to so many of the city’s must-see sights, great coffee shops, and vibrant neighborhoods. It made exploring easy and enjoyable without ever feeling too far from home base.
To sum it up: Staypineapple Boston is an absolute must if you’re visiting the city. Whether you’re traveling solo, with friends, or for a romantic getaway, it checks every box. Amazing staff, delicious drinks, a cozy and modern vibe, and the kind of personalized service you don’t often find these days.
We’ll definitely be back — and we’ll be recommending Staypineapple to everyone we know. Thank you for a truly memorable stay!
Atmosphere: 5
Food: 5
Service: 5
Garnett is hands down one of the best bartenders I’ve ever come across. Garnett is fast, friendly, and actually makes you feel welcome the second you sit down. He knows his drinks, has great energy, and somehow keeps the vibe going even when the place gets packed.
Whether you want a classic cocktail or something creative, he nails it every time. You can tell he takes pride in what he does—and it shows. If you’re coming here, hope Garnett’s behind the bar. He’s a big part of what makes this spot worth coming back to.
Atmosphere: 5
Food: 5
Service: 5
Dakota is Trophy Room's best employee who always brings a positive attitude and uplifts the spirits of those around him. He goes above and beyond in entertaining guests andbeven cleans up the floor at the end of the night! His owner Isaac is a great team player as well and pours a nice drink when behind the bar, though he sometimes misses the mark when tossing his napkins.
Atmosphere: 5
Food: 4
Service: 5
Sophia is amazing!! The food was delicious!!
Atmosphere: 5
Food: 5
Service: 5
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