Trophy Room — Restaurant in Boston

Best South End Sunday Brunch in Boston Boston restaurants are numerous, on nearly every corner and intersection. In the South End, residents and visitors have copious choices, so we would like to point out a very pleasant experience we had this past weekend: Sunday brunch at The Trophy Room on Chandler Street (inside the Chandler Inn Hotel) at Berkeley Street. First impressions are important, and we received positive feedback as soon as we opened the door to the restaurant. The staff all greeted us so warmly that we couldn’t help but feel welcome! The host, with a big smile and a warm greeting offered us a window table, but we declined, preferring to sit at the 12-seat bar instead. The lounge has plenty of window tables, probably seating 40 or so. The comfortable-looking dining room is all banquettes, seating about 24. Fred, the bartender, smiled and immediately said “Hell-o” and when asked, recommended the very first item on the brunch menu: Eggs Caribe. The Eggs Caribe is a “Melt-In-Your-Mouth” delicious breakfast: grilled English muffin topped with lump crabmeat, poached eggs and topped with a chef-made creamy hollandaise sauce, served with leafy spinach and “breakfast potatoes”. These potatoes were not your usual home fries, but hot, crispy and yummy tidbits – and didn’t have that “Left-On-The-Grill-Forever” taste. The menu description for this dish did not do it justice - it was superb! We also highly recommend the steak and eggs dish: a 6-oz. portion of Boston strip steak cooked perfectly – moist, succulent and scrumptious. It comes complete with eggs and choice of toasted breads. Beverages are an important part of any Sunday brunch – and The Trophy Room didn’t disappoint here: the Berkeley Bellini had a nice twist, using grapefruit juice instead of the traditional OJ, with Mathilde Peche liqueur and sparkling Rose – luscious! The traditional Bloody Mary, made with bartender Patrick’s own recipe was not overly spicy, but delivered a nice kick – recommended. Coffee was hot, fresh and good – what else could you ask for, to start your day. The rest of the menu featured 6 breakfast dishes, 3 salads, 3 soups, 4 sandwiches and 5 luncheon items. We look forward to returning to The Trophy Room to investigate the rest of the Sunday brunch menu. For Sunday brunch in the South End of Boston, we give The Trophy...

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...

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...