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14 Romantic (and Fun) Couples Activities to do in Boston

Spend Some Time Together In Boston

Looking to bring some romance into your life that will enhance intimacy with your partner? We know that you know how important it is for couples to spend quality time, create memories together, and strengthen your love for one another. 

Thankfully, if you live in or near Boston, you don’t need to travel too far to find romantic activities to do with your partner! Here is our list of fun and unique couples activities in Boston that will keep the intimate connection and the passion between you and your partner.

couples activities in Boston

Couples Ideas in Boston

  1. Take in the View from a Rooftop Bar
  2. Pack Picnic for the Park
  3. Go to a Farmers Markets
  4. Book Yourselves a Wine Tasting
  5. Visit a Farm
  6. Take a Walk or Hike
  7. Go to a Paint Night
  8. Enjoy Dinner and Live Music at Beehive
  9. Visit Isabella Stewart Gardner Museum
  10. SOWA Market
  11. Enjoy a Late Night Date
  12. Get a Couples Massages
  13. Attend a Burlesque Show
  14. Couples Boudoir Photography


Let’s dive into each activity!


1. Take in the View from a Rooftop Bar

Take in the impressive city views over a delicious dinner and drinks. There are several rooftop bars in Boston, including:

  • Rooftop@Revere 
  • Lookout Rooftop and Bar
  • Envoy Hotel Lookout Rooftop
  • Stratus at View Boston
  • Dorchester Brewing Company (if you are more “beer garden” people)
  • The Sinclair (for you folks north of the river!)

Recommend checking the weather first! And going early to avoid the bustle. 

Lets Picnic Boston

2. Pack Picnic for the Park

Boston is home to some of the most scenic and historic parks, so why not plan a picnic? Here are some beautiful spots in Boston to enjoy a romantic picnic.

  • Charles River Esplanade (it’s a classic for a reason!)
  • McKim Courtyard at the Boston Public Library (not a park but a gem!)
  • Boston Public Garden (thorough well traveled, there are usually spots)
  • Piers Park (amazing city views!)
  • Rose Kennedy Greenway
  • Pope John Paul Park II Reservation 
  • Jamaica Pond
  • DeCordova Sculpture Park (west of the city)
  • Castle Island

There are even great Boston picnic planners like Lets Picnic Boston to help you plan an unforgettable experience!

3. Go to a Farmers Markets

A great outdoor couples activity for the food-obsessed is to go to a local farmer’s market. There are plenty of great farmers markets in Boston and surrounding areas that occur on both weekends and weekdays. You can buy things to bring home to make or get pre-made treats to eat right there. 

  • Copley Square – Tuesdays and Fridays 11 AM-6 PM 
  • Haymarket – Dusk to Dawn, Fridays and Saturdays 
  • SoWa Open Market – Sundays 11 AM- 4 PM
  • Roslindale Village Main Street Farmers Market – Saturdays 9 AM- 1:30 PM
  • The Boston Public Market at Dewey Square on the Greenway – Tuesdays
Photo credit: Lucille Wine Shop

4. Book Yourselves a Wine Tasting

Savor some of the best wines to delight your palate. Dial in the senses and sample wine at a private tasting with your partner. Don’t forget to take a bottle, and a sense of slowing down to enjoy the whole experience home with you.

Photo credit: Lookout Farm

5. Visit a Farm

Farms offer many seasonal outdoor activities that are fun and romantic, including autumn apple and pumpkin picking. Many have food stands, petting zoos, taprooms, and live music. There are a few farms within driving distance of Boston.

  • Ward’s Berry Farm – Sharon
  • Cider Hill Farm – Amesbury
  • Nashoba Valley Winery – Bolton
  • Belkin Family Lookout Farm – Natick
  • Carlson Orchards – Harvard
  • Brooksby Farm – Peabody
  • Lookout Farm – Live music, beer garden, 

6. Take a Walk or Hike

A romantic and adventurous couples activity where you can take in scenic views. Here are some great places to hike in greater Boston:

  • Blue Hills – just 20 minutes from downtown Boston with scenic overviews, over 100 miles of trails (check out Buck Hill, Chikatawbut, and Great Blue) as well as Houghton’s Pond or Ponkapoag for easier rambles in the woods.
  • Middlesex Fells
  • Walden Pond
  • Borderland State Park
  • Nashoba Valley Winery: Apple picking, Farmstore, Winery, Brewery, and Restaurant!

7. Go to a Paint Night

A paint night can be a fun and lighthearted activity for couples to paint and laugh together. Enjoy an adult beverage as you paint if you desire. You’ll have some great paints to take home to remember your date.

Photo Credit: The Beehive

8. Enjoy Dinner and Live Music at Beehive

The Beehive, an underground Bohemian restaurant nestled in Boston’s South End, is a great date spot. Couples can enjoy a romantic dinner and cocktails while listening to live jazz music.

9. Visit Isabella Stewart Gardner Museum

One of several stunning museums in Boston, the Isabella Stewart Gardner Museum is a wonderful couples activity to add to your list of date spots. 

The museum itself is a work of art, which includes its iconic glass roof interior courtyard and lush garden. The museum holds an impressive collection of European, Asian, and American art pieces, including paintings, sculptures, and decorative arts.

Photo credit: SoWa Boston

10. SoWa Market

SoWa is home to several art studios and galleries, and hosts one of the largest artist markets in Boston.

The SoWa Winter Festival is a great activity to do as a couple, to get out of the house or apartment on those cold winter days. It features the area’s best small businesses selling everything from specialty food, art, crafts, and more.

SoWa Open Market is an artist market open May through October, and features a variety of local artists, vendors, and food trucks.

11. Enjoy a Late Night Date

Enjoy the vintage feel of Boston’s oldest cafe, Caffé Vittoria, which is open until midnight. The inside resembles an old-world cafe reminiscent of one you would find in Italy. Grab a late night cappuccino and a cannoli.

Another late night date spot is the Parish Café located right on Boylston Street and open until 2 AM on Thursday, Friday and Saturday night.

Photo credit: Serenity in the City

12. Get a Couples Massages

Treat yourselves to a romantic couples massage. Unwind and spend some time relaxing and rejuvenating together. 

There are plenty of day spas in the area:

  • Briar Barn Inn – Rowley
  • Serenity in the City – Medford
  • G2O Salon & Spa – Back Bay, Boston
  • Mandarin Oriental – Back Bay, Boston
  • Indoor Oasis – Newton, MA
  • Bella Sante Spas – Boston, Lexington, and Wellesley

13. Attend a Burlesque Show

A more risqué date idea, a burlesque show provides an intricate and exotic experience that includes captivating performances, sensuality, and artistic expression.

In addition to burlesque shows, the American Burlesque Collection in Salem is a museum dedicated to Burlesque. You can take a self-guided tour to see artifacts, costumes, personal documents, and multimedia presentations about the art of Burlesque.

14. Couples Boudoir Photography

Couples boudoir is an intimate and memorable way to celebrate your anniversary. It’s an experience that will bring you closer together, and you’ll have sexy photos that will last forever. 


What is Boudoir Photography?

Boudoir photography is a style of photography that creates intimate, sensual, and provocative images to capture a person’s beauty. Boudoir is often used as a way to grow closer with your partner.  A couples boudoir photoshoot can be a powerful experience that captures romantic moments and sensual scenes. 

You can also surprise your partner with boudoir photography as a gift – it’s a great way to spice up your relationship as a gift for an anniversary, a birthday, Valentine’s Day, or a “just because” present. 

Interested in Learning More About a Couples Boudoir Shoot for Your Anniversary?

I’m Allana, a Boston-based boudoir photographer. I’ve worked with hundreds of couples. If you’re interested in boudoir photography, I encourage you to schedule a session planning call.

In addition, here are a few resources for you to read:

And, of course, check out our couples boudoir photography page for more information.

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