Five Ways to Spend a Date Night in Boston

When you stay at The Envoy Hotel, Autograph Collection, we guarantee a stay that’s miles away from the ordinary. Your date night in Boston should be the same. No matter what sort of romantic evening you’re after, we’ve curated a list of five tried-and-true date night ideas. With this guide, you’ll see Boston from a whole new perspective.

Sip & Paint at Muse PaintBar

It doesn’t matter if you consider yourself to be an artist or not at Muse PaintBar. This paint-and-sip experience is a creative destination for painters and novices alike. It is known for its inviting atmosphere, expert instructors, and wide selection of artworks to choose from. Settle in with your partner and begin creating something together while you enjoy some wine and light bites. At the end of the night, you’ll be able to take home your creations to remind you of this special time spent together in Boston.

Go to a Sofar Sounds Show

For a musical and intimate experience, head to Lookout Rooftop for a live performance. On November 21 at 8:00 p.m., Lookout is hosting a show presented by Sofar Sounds. This experience is a great way to discover local artists and dive into the heart of Boston’s music scene. The cozy setting allows you and your significant other to connect with the city and its cultural vibrancy in a truly unique way. Let the music wash over you while you take in Boston’s one-of-a-kind skyline. Sip on a glass of wine or cocktail alongside your loved one.

Stargaze at the Coit Observatory

Discover the wonders of the night sky at the Coit Observatory, located at Boston University. Every Wednesday they open their rooftop to the public for stargazing, weather permitting. Peer through binoculars and telescopes to get a closer look at the celestial beauty that covers Boston each night. While admission is free, reserving tickets in advance is recommended, as space is limited. This educational and magical experience is a date night for the books.

Enjoy a Romantic Evening at Para Maria

Take your taste buds on a flavorful journey at Para Maria. Chef Tatiana Rosana, a Cuban-American chef and two-time Chopped champion, adds a dash of sazón to New England’s classic cuisine. The breakfast and dinner menus at Para Maria are perfect for sharing—ideal for trying a variety of dishes with your partner.

From the Mexican chili crisp wings to the sweet shrimp tradito, and sweet plantain gnocchi, there’s something for every palate. Indulge in Boston’s best when you pair your stay at The Envoy with the Para Maria Experience. This special offer includes a $30 food and beverage credit per night.

Hike the Blue Hills

If you’re looking for a date option that’s a little more adventurous, consider a hike in the Blue Hills. Located in Milton, just outside the city, this natural oasis boasts a variety of trails suitable for all levels of experience. One of the local favorites is the skyline loop trail, offering spectacular views of Boston’s skyline in the distance. This moderately challenging hike takes a little over two hours to complete.

For a more leisurely stroll, opt for the Ponkapoag Pond Trail or Houghton’s Pond Trail. Both are perfect for a romantic, laid-back outing. After working up an appetite, come back to Para Maria to refuel or treat yourself to a drink at Lookout Rooftop.

We believe a stay in Boston should be elevated and inspiring, and similarly, date night should be just as exciting. From romantic concerts to adrenaline-fueled hikes, the opportunities to experience Boston with your partner are endless. We can’t wait to welcome you to The Envoy, where there’s something new to explore around every corner.