Top Boston Summer Date Ideas

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Forget the typical dinner and a movie date night. Here in Boston, there are so many quirky events and sights to see that you will never be at a loss when deciding what to do with your significant other. From cheering on the Red Sox or enjoying some comedic classic Shakespeare, you will never have to go on the same date twice. With these unique date ideas, you and your special someone will make memories you’ll never forget.

Cruising the Boston Harbor

Catch amazing views of the Boston Harbor and the famous USS Constitution from the cruise.

Catch amazing views of the Boston Harbor and the famous USS Constitution from the cruise.

There are few things more romantic than standing on the deck of a boat with the breathtaking Boston skyline before you and the open night sky above. Massachusetts Bay Line offers daily cruises around the harbor. If you’re looking for a classic experience, choose between the sunset cruise or the moonlight one. If you or your loved one is a history buff, the pirate tours provide a two hour narrated tour that teaches all of the history behind “America’s Home Port” and highlights some of the most famous sights from the harbor.

Free Observatory Nights at Boston University

Maybe you like the idea of watching the stars, by the thought of doing it from a boat makes you a little sea sick. In that case, check out the open observatory nights at Boston University. Held every Wednesday night, weather permitting, this is the perfect date for a warm, clear night. Through the telescopes and binoculars, you and your date can see the night sky with amazing clarity. There are also plenty of restaurants within walking distance in Kenmore Square if you’d like to grab dinner beforehand. Learn more here.

Red Sox Game/ Night out in Fenway

Outside gate of Fenway Park

Catching a Red Sox game is a classic Boston experience you and your date can’t miss.

There is nothing more Boston than cheering on the Red Sox at Fenway. Check out their season schedule here and check this classic date off your bucket list. After the game, check out the great bars and restaurant packed around Fenway. Cask ‘N Flagon is always a popular post-game destination with good food and a large selection of beers on tap. At night, the back room turns into a dance floor and DJs blast top hits and memorable throwbacks. If you’re in the mood for a good burger, Fenway is also home to the famous Wahlburgers, just a five minute walk from the stadium.

Taza Chocolate Tour

Got a sweet tooth? Take a behind-the-scenes look at how this Boston-based company makes their stone-ground, organic Mexican-style chocolate and then sample the results. Offered to the public Monday-Sunday, these tours are also great if you’re a couple on a budget, costing only $8. Or, if you want to coordinate a group date with friends, Taza also books private group tours. Learn more here.

Gondola Tour

If you’re looking to pull out all of the stops, these gondola tours go above and beyond the dream date. Taking a tour on Boston’s only authentic Venetian gondolas sets the romantic scene as you and your date are serenaded with beautiful Italian music, sip champagne and observe the Boston and Cambridge skylines. Included in the tour package are a dozen roses, sparkling cider, chocolate, strawberries and cheese and crackers as well as a framed photograph to remember your date.

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