The Labor Weekend kept me in Boston this year.  It was a decision made from the fact that I have just not stopped work and travel wise and needed a break on my home turf.  However, every time I do this, I start to panic about what I am going to do when I get bored with my own company, which happens very quickly.  I am a people person and enjoy the connection to others.  It’s not that I can’t have a good time alone; I just prefer to be with others.  It would seem this weekend I had nothing at all to worry about as I had my weekend just quiet enough to feel relaxed with lazy mornings and busy enough with friends each day to feel like I had actually done something.  And seriously could we have asked for better weather this weekend?  I think not.  It has been perfect.


The Lookout Rooftop & Bar

So, what did I do?  Well, on Friday my office closed early so my friend, Erika picked me up and we headed to Stephanie’s on Newbury for some sidewalk, people watching dining.  Always a great time.  

Not wanting the afternoon to end we decided to head over to say hello to my friend who works at the Lookout Rooftop & Bar at the new super trendy Envoy Hotel, which opened earlier this summer.  I had been over to the Envoy a couple of times previously for cocktails after work as it is just across the street from my office.  Whether it is 5pm or late in the evening, there is always a wait, however, they very graciously take your number and call you when you can go in so you can go and grab a drink or a bite elsewhere.


5pm on Friday and busy with people enjoying the start of the Labor Weekend

It was 4pm when we arrived and the line ran from one side of the hotel to the other with patrons eagerly waiting for the bar to open.   The crowd was mixed, eclectic and interesting with locals and tourists.  The Envoy beckons everyone from the 20-something to the 60+ crowd. 

What I can say after being there a few times in the evenings is that the young “It Crowd” flocks in droves to the rooftop.  This is a place to see and be seen and truly is a scene.  For me, it is mostly a place to just observe people in their evening habitat from the young with their shorts skirts and low-cut tops and tight t-shirts and skinny jeans in the hope of meeting someone, to the couples on a date looking to the city skyline to the groups on a crazy, fun night out.  Then there is me, who probably should be trying a little harder to meet someone but it’s so much fun to just people watch sometimes.     


The sun starting to set and the crowd changes over the 20-somethings

They offer a selection of signature drinks in either a single glass or carafe for the table from the Lookout Punch with Privateer rum, fruitations, mint simple and fresh lemon to The Greenway with cucumber vodka, basil cucumber syrup and fresh lemon, which I have to say, is refreshingly delicious.  Erika enjoyed the Seaport Sangria with Pava Liquer, white wine, and berries with an interesting addition of Hennessy VS.

To be honest there is nothing really fabulous about the bar itself.  It’s a rooftop – that’s it.  It’s all about the scene, crowd, views and being outside, which Bostonians crave in the warmer weather.  For me and anyone who is like me, let’s just say of a certain age, I would suggest going early in the evening.  For all of you who are into the party, happening scene, go and have fun. 

The Outlook restaurant (far more my pace) is now open.




Lookout Rooftop & Bar Menu, Reviews, Photos, Location and Info - Zomato