A Surprise Weekend in Boston

I had no idea where we were going.
My husband (then boyfriend) told me to pack for a weekend away — and that was all I got. No hints, no clues, just a playlist and a car full of anticipation. A few hours later, we were pulling into Boston, and that’s when I realized this wasn’t just a weekend away — it was a full-on surprise trip he’d planned entirely himself.

Friday: Rooftop Views & A Hidden Plan

We checked into the Revere Hotel Boston Common, and it immediately set the tone for the weekend — modern, stylish, and walking distance to everything. Up at Rooftop@Revere, we shared a flatbread, guacamole, and a pitcher of grapefruit margaritas with the skyline stretching in every direction. It felt like the city had been waiting for us.

That night, the surprise continued with the Boston Signature Dinner Cruise aboard the Odyssey, departing from Commonwealth Pier (200 Seaport Blvd, Boston, MA). The ship boards right in the Seaport District — one of my favorite areas in the city — with discounted weekday parking at the nearby Seaport Hotel Garage (1 Seaport Lane).

Once onboard, we were greeted with a cocktail and led to our reserved table by the window, offering a perfect view of the Boston skyline as the boat set sail. The atmosphere was elegant but relaxed — live DJ music, dancing, candlelight tables, and the glow of the harbor lights bouncing off the water.

Dinner was served buffet-style, with a surprisingly upscale spread that felt more like a curated restaurant menu than a buffet line. We started with a Greek salad and roasted vegetable grain mix, followed by a mix of mains — the sesame-glazed Atlantic salmon and hand-carved tri-tip steak were the clear standouts. My husband loved the caribbean jerk braised pork, while I couldn’t stop picking at the baked orecchiette pasta. Everything was paired with a glass of crisp white wine and the hum of soft jazz from the DJ.

We ended the night with desserts from their signature dessert station — a little bit of everything from baked apple crisp to chocolate mousse cups and seasonal fruit. Between the city lights, the view of the Zakim Bridge, and the calm sway of the boat, it felt like the perfect way to kick off the weekend.
💡 Tickets typically start around $129 per person and include a 2–3 hour cruise, full dinner buffet, DJ entertainment, and unbeatable skyline views.

Saturday: Old Streets & A Familiar Favorite

Saturday started with a city tour, the perfect way to experience Boston’s blend of old and new. What made it special was how interactive it was — our guide wasn’t just sharing facts, he was telling stories that made the history come alive.

We wandered through cobblestone streets, passed the Old State House, and stopped at spots along the Freedom Trail where you could almost feel the weight of the past in the air. The highlight? Throwing tea into the harbor at the Boston Tea Party Ships & Museum — a surprisingly fun and hands-on way to relive one of the city’s most famous moments. It’s one thing to read about it, but another to actually stand on the ship and toss the “tea” overboard yourself.

After the tour wrapped up, we grabbed a table at Bell in Hand Tavern, one of the oldest taverns in the U.S. The place has that perfect old-meets-modern Boston vibe — creaky floors, great drinks, and the kind of energy that makes you want to stay for another round. We ordered fresh oysters and buffalo chicken nachos, the perfect reward after miles of walking (and maybe a little too much history geeking out).

That evening, we dressed up for dinner at The Capital Grille, a restaurant that’s quietly become our tradition — we try to visit one in every city we travel to.

We always start the same way:
a dirty martini with blue cheese olives for me, an old fashioned for him, and a shared order of their seafood tower and thick-cut bacon — easily one of our favorite pairings on any menu.

For appetizers, I can never resist their French onion soup, perfectly rich and cheesy, while he always goes for the New England clam chowder.

Then come the mains — my go-to South African lobster tail, buttery and melt-in-your-mouth, and his New York strip (or sometimes the ribeye, depending on the mood).

It’s always flawless, but what makes it special isn’t just the food — it’s the ritual. No matter what city we’re in, this dinner always feels like home.

Sunday: Southie & Full Circles

On Sunday, we drove over to South Boston to meet a few of my husband’s college friends for brunch at a cozy spot near Bolton Street and Third Street. It was the kind of sunny, easy morning that wraps a trip together — the kind where the coffee’s good, the conversation’s better, and you already know you’ll be talking about this weekend for years.

Wander Weekly Tips ✨

🏨 Stay: Revere Hotel Boston Common — rooftop views, modern rooms, and perfect central location.
🚢 Dinner Cruise: Odyssey Boston Harbor Cruise — a must for sunset dining and skyline views.
🍸 Drink with a View: Rooftop@Revere — laid-back and colorful, perfect for afternoon cocktails.
🦪 Historic Bite: Bell in Hand Tavern — oysters, nachos, and 200 years of Boston charm.
🥩 Classic Dinner: The Capital Grille — order the lobster tail, seafood tower, and a martini, and thank me later.
☀️ Sunday Brunch: South Boston (Bolton & Third) — relaxed, local, and the perfect end to a surprise-filled weekend.