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5 Perfect Summer Dates in Boston

As summer kicks off in Massachusetts & COVID cases + restrictions die down, I know we’re all looking forward to getting out of our houses and exploring in and around this beautiful city of Boston again!

The past year totally feels like a blur, and since March 2020, date nights have been reduced to countless movies & popcorn. Even last summer in Boston was rough -with the city barely open and mask mandates- Jimmy (my boyfriend, for those who are new here) and I definitely didn’t venture into Boston or do many date nights out at places! Now, we’re excited to get back into it and start doing the things we love again, maskless and fully vaxed!

Below are 5 perfect summer date ideas for you and your partner in Boston. Hope you enjoy!

Date #1: Picnic in Boston Public Gardens

Tulips blooming in the Public Gardens

I chose this as the first date idea because it’s great for people with all levels of COVID comfortability, as I know some of y’all would still prefer to stay outdoors or avoid large groups!

The Public Gardens are surrounded by 1. public transportation & parking garages and 2. GREAT food so it’s a no-brainer that this would be a perfect picnic spot.

My suggestions for the perfect picnic?

  • Grab coffee from one of the many coffee shops on Newbury Street (Thinking Cup is a personal fav) and something small, maybe a cupcake from Georgetown Cupcakes! (Perfect for the afternoon or in between breakfast/lunch)
  • Visit Kured– a new shop in Beacon Hill that’s within walking distance from the Gardens- and get yourself a custom charcuterie board to enjoy! It will totally feel like you transported to Europe for the afternoon! (Check out their instagram )
  • Play it simple- pack a cute picnic basket with things from home!
  • Of course, don’t forget the comfortable blanket 🙂

Date #2 Night out in the North End & a comedy show

So this date night makes me laugh, because it is the EXACT date night Jimmy and I had literally days before the world shut down from COVID!

One thing I certainly have to thank COVID for is the outdoor dining options in the North End that have come about. Absolutely praying it stays like this for years to come! The North End is a perfect place to enjoy a nice bottle of wine outdoors as the sun goes down. Totally reminds me of Rome! Here are my top 3 spots to eat & drink:

  1. Lucia
  2. Trattoria il Pannino
  3. Nico Ristorante
Birthday Date Night @ Nico

Above is our most recent North End trip for my 24th birthday to Nico! We got a table next to wide open windows and enjoyed the breeze while eating cacio e pepe made from the only cheese wheel experience in Boston! I wish i got a video- it was wild & super cheesy!

Now, after dinner, walk right down to the start of Hanover Street and visit the Improv Asylum for a comedy show! Tickets are super cheap ~$20 a person, with a full bar and a very small venue (approx 50 people max!). I swear, Jimmy and I absolutely cried laughing the whole time. What’s great about this is that since the actors improv the entire thing, every single show is different!

Date #3 Boston Harbor Cruise!

Boston Harbor Cruises are super fun on a hot day! There are a ton of different types of cruises to choose from: some that go around the harbor, historical tours, whale watches, codzilla, and other boats that take you to the harbor islands.

Codzilla on the 4th

My favorites are:

  • Codzilla: You’ll get absolutely soaked & have a ton of laughs. Jimmy and I did it for 4th of July in 2019 and it was a nice way to cool down and see the harbor!
  • Ferry to George’s Island: George’s Island is around 20-30 minutes one way & totally worth it. This place is definitely for the history buffs- as Fort Warren sits on it! We took a tour of the fort and self explored one summer afternoon and it was absolutely amazing.
  • Boston Harbor Boat Tour: This is a good one if you’re looking to just sit back, relax, enjoy the breeze, and have a drink!

Date #4 Museum Day!

This one is totally my kind of date! Boston has so many amazing museums & so much history that you could spend 24+ hours exploring all of them! It’s a great way to be active, learning, and enjoying each other’s company. Oh- definitely stop for food along the way too!

A contemporary art piece at ICA

My top museums are:

  • Museum of Fine Arts
  • Institute of Contemporary Art (ICA)
  • Museum of Science
  • Aquarium
  • Isabella Stewart Gardner
  • Boston Public Library (not really a museum, but very beautiful and historic)
  • USS Constitution
  • Paul Revere House

Date #5 Ball Game & Bar Hop

A ball game at Fenway Park is an absolute MUST in Boston! A beer, a fenway frank, and singing Sweet Caroline makes for the perfect date! It’s a particularly good date if you or your partner don’t live in/are from the Boston area or have never been to a game!

Tickets to the games are generally cheap, with bleacher seats usually going for under $20. Don’t worry, they’re not actual bleachers, they’re just seats in the outfield. In my opinion, it’s a great view no matter where you sit.

If you do a weekend game or a day game, there are a ton of fun bars in the area to visit before or after to continue the fun. It’s definitely the date with the most Boston pride!

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