Where to Take Out-of-Town Guests for a Night They’ll Never Forget

Hosting friends or family from out of town? You’ve probably already mapped out the Freedom Trail, grabbed lunch at Quincy Market, and maybe even caught a Red Sox game. But what about after dark?

Boston has no shortage of classic attractions, but if you really want to show your guests a night they’ll never forget, it’s all about curating the right vibe; from dinner and drinks to an unexpected after-hours twist they’ll be talking about long after they leave.

Here’s your no-fail guide to hosting out-of-town guests like a local with a few bonus ideas to make the night one to remember.

1. Start With Dinner That Sets the Tone

Begin the evening with a restaurant that makes a statement. Whether it’s seafood at Legal Harborside, handmade pasta in the North End, or elevated pub fare at The Beehive, Boston offers plenty of options that blend local flavor with great atmosphere.

Pro tip: Choose somewhere close to your next stop, so you don’t waste time in traffic.

2. Hit a Rooftop Bar or Hidden Speakeasy

After dinner, take things up a notch with a cocktail experience that feels special. Boston has some incredible rooftop bars like Lookout at The Envoy or Contessa at The Newbury. If your guests prefer something more intimate, go for a hidden speakeasy vibe at Backbar in Somerville or Blossom Bar in Brookline.

It’s not just about the drinks; it’s about showing your guests something they wouldn’t find on a basic tourist list.

3. Cap It Off With Something Unexpected: Glass Slipper

When it’s time to really wow your guests, don’t settle for another crowded bar. Head downtown and walk them into Glass Slipper – Boston’s iconic gentlemen’s club just steps from Boston Common.

Why it works:

• World-class entertainers in a high-energy setting. 💃
• Fully stocked bar with no two-drink minimum. 
• Welcoming vibe for couples, groups, and newcomers alike. 
• Open 7 nights a week – even on holidays and long weekends. 
• 📞 Bonus: You can call the club ahead to ask about seating or events

Glass Slipper has become a local favorite not just because of its legacy, but because it offers a truly fun, unexpected, and unforgettable way to close out a night in Boston. Guests from across the country leave saying, “That was the most fun we’ve had all trip.”

And isn’t that the goal?

4. Create a Memory, Not Just an Itinerary

When you’re hosting people in your city, the best thing you can do is show them what you love about Boston, not just what TripAdvisor recommends. The freedom to wander, laugh, discover, and maybe take a few risks is what turns a good night into a great one.

So mix classic Boston with bold choices. Let them try something they wouldn’t back home. Glass Slipper is the kind of spot that surprises people in the best way.

Final Thoughts

When you’re figuring out where to take out-of-town guests in Boston, think beyond the guidebook. Show them a side of the city that blends flavor, style, and fun. From iconic bites and rooftop views to unforgettable adult entertainment at Glass Slipper.

Because the best nights aren’t always planned down to the minute… they just hit right.

📍 Glass Slipper Boston, 22 LaGrange St, Boston, MA
📞 Call the club to reserve your table or ask about group experiences: +1 (617) 338-2290