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The 10 Best Date Ideas in Boston, Massachusetts

Asking for the date is the easy part. Now, you must plan to impress. Boston is home to many unique, fun, and creative date spots and hidden gems that can take any date from bearable to rememberable. To help you plan the best date possible, we’ve compiled a list of our favorites.

10 of the Best Date Spots in Boston, Massachusetts

1. Rooftop Cocktails

There’s nothing quite like enjoying a cocktail while taking in breathtaking views of the city skyline and bay. Many rooftop bars are open year-round and provide heating or shelter to keep you and your perfect date cozy during any kind of weather.
Plus, there are many unique spots to choose from, each with a different ambiance. For something extra fun, try out the igloos at the Envoy Outlook Kitchen & Rooftop Bar. (let’s hyperlink the Envoy as well)

2. Local Markets

Boston is also home to a plethora of homegrown goods and local products. Explore the city’s open-air and farmer’s markets to pick up a delicious local lunch. Or, have a picnic in the Commons or at the Boston Harbor. Some of our favorite markets include the Haymarket and the Boston Public Market.

3. New England Aquarium

The New England Aquarium is a great date idea, rain or shine. Plus, it’s interactive, allowing for a day of discovery and exploring together.

4. Historic Sites & Museums

Boston has a rich history, illustrated throughout its many museums. Spark creativity and learn more about Boston at a local favorite like the Museum of Science or the Paul Revere House.

5. Castle Island

Take a trip to Castle Island in South Boston. The island is a public park found right in the city, a great place to jog, take a walk, relax and explore. Plus, if the weather is warm, you can enjoy a day of swimming at Castle Island Beach.

6. Wineries & Breweries

Popular wineries and local breweries are everywhere in Boston. Enjoy a light lunch and try a few flights at local favorites such as Cisco Brewers or Hopsters, both located in the Seaport. (I believe Cisco Brewers should be www.ciscobrewers.com)

7. Famous Recreation Paths

Take a romantic stroll through some of Boston’s many famous walking paths. Some of our favorites include the Harborwalk, the Charles River Esplanade and the Commonwealth Avenue Mall.

8. Concerts & Shows

Boston features many comedy shows, concerts and plays throughout the year. Plus, many venues are free or inexpensive to attend. Some venues to check out include the Improv Asylum and the Berklee Performance Center.

9. The Boston Common

There’s always something happening at the Boston Common such as local festivals and live music. The oldest public park in America is also beautiful, perfect for an afternoon walk or picnic.

10. Romantic Marinas

This wouldn’t be a collection of perfect date spots in Boston without mentioning the many marinas. Take a romantic walk down the pier at sunset or look at the many beautiful boats surrounding marinas such as the Boston Harbor Shipyard and the Constitution Marina.

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