11 Holiday-Themed Anniversary Date Ideas In Boston

Author Cristina LaPenna
Date Feb 15, 2021

Between the twinkling lights and decorations, the romantic music playing, and the overall holiday spirit, it's no surprise that the holiday season is one of the most popular times of the years to get married.

Celebrate your anniversary in a way that is much more seasonal than a date idea you could do at any time of the year. Leave the brainstorming up to us, and fall in love all over again at one of these perfect anniversary date ideas for the holidays:

1. Holiday Pops & Happy Hour

Boston Anniversary Date Ideas For Holiday 2015 Holiday Pops
Photo Credit: The WGBH Blog

If you have never been before, celebrate your anniversary by seeing the Boston Pops put on their classic Holiday Pops show at the Symphony Hall. The performance is filled with your favorite holiday music and the traditional Pops sing-a-long. Add on a romantic dinner and drinks with your loved one to really make the night together special.

2. Show Them The World

Boston Anniversary Date Ideas For Holiday 2015 Commonwealth Ave. Mall
Photo Credit: The Back Bay Association

Only have a little bit of time in the city but want to see it all? Although it may sound like a cliche, typical Boston date, going on a Duck Tour is a fun way to see all of the city and learn about the history in a short amount of time. The tours start at the Prudential Center, so you can browse the shops after while making your way to Newbury Street, where you could enjoy a delicious dinner out. Make your way to the Commonwealth Avenue Mall when its dark and walk along the romantic trees set up with lights lining the entire green way. Try to plan your anniversary celebration around December 1st, the night of the lighting of the Commonwealth Ave. Mall for a special surprise for your significant other!

3. A Show & A Stroll

Boston Anniversary Date Ideas For Holiday 2015 Nutcracker Boston Ballet
Photo Credit: Blog Post by C.C. Chapman, Performance Photography by Gene Schiavone and used with permission from the Boston Ballet.

When you think of shows and events during the holiday season, The Nutcracker probably immediately comes to mind. Take your loved one to the ballet and be transported through Tchaikovsky's music to the land of toy soldiers and candy canes by the Boston Ballet. Want to mix it up a little? The Back Bay Events Center is showing Tony Williams' Urban Nutcracker, which Fuses Tchaikovsky’s classic score with Duke Ellington’s jazz interpretation and shows not only classic ballet, but urban tap, hip hop, swing, flamenco, and step dances as well. After, take a stroll around the Boston neighborhoods and check out all of the windows decorated for the holidays while you talk about the spectacular show you just saw.

4. Classic Holiday Boston Date Night

Boston Anniversary Date Ideas For Holiday 2015 Ice Skating Frog Pond
Photo Credit: Michele McDonald for The Boston Globe

Want to surprise your significant other with a traditional holiday anniversary date idea in Boston? Ice skating at Boston Common’s Frog Pond is must. When you've had your fair share of falling and getting back up, warm up with a cup of hot cocoa or a fresh Belgian waffle in their warming house, a fun alternative to going out to dinner for your anniversary celebration. After ice-skating at Frog Pond, stroll through Boston Common and take a picture in front of Boston’s Christmas tree. The Boston Common Tree Lighting is scheduled for December 4th this year, which is a fun celebration to plan your anniversary date around.

5. For The Creative Couple

Boston Anniversary Date Ideas For Holiday 2015 Paint Nite Boston
Photo Credit: Paint Nite Boston Facebook Page

If you took a cue from our blog post about proposal ideas for the creative couple, then an anniversary date that is similar for the holiday season could be more of what you were looking for. The Harvard Square Holiday Fairs is one of the most popular (and one of the oldest!) fairs in Boston, that offers a huge selection of beautiful gifts crafted by New England natives. You could also plan your anniversary date to be at a Paint Nite location where you and your significant other can paint a beautiful holiday-inspired picture by following step-by-step instructions from an artist, all while drinking cocktails and munching on food. The perfect way to celebrate your time together.

6. Wine & Dine

Boston Anniversary Date Ideas For Holiday 2015 City Wine Tours
Photo Credit: City Wine Tours

What's better than strolling through your favorite Boston neighborhood while drinking wine? Pick an area of the city that is significant to you or your partner, and spend the afternoon on a private City Wine Tour, sampling delicious wines, tasting contemporary cuisine and discovering great restaurants and wine shops nearby. Be a little spontaneous and pick a new restaurant that you see while walking by, and grab a dinner there! After, make your way to Faneuil Hall Marketplace for dessert to see their Blink! show, a light and sound extravaganza in which the lights dance to the music through every inch of the marketplace. A fun ending to the perfect day.

7. Copley Square Tree Lighting & A Cozy Room

Boston Anniversary Date Ideas For Holiday 2015 City Wine Tours
Photo Credit: Fairmont Copley Plaza Website

If you're planning on spending the day pampering yourselves and then staying the night in Boston on December 2nd, consider yourself lucky. The Copley Square Tree Lighting is a cute way to end a romantic anniversary celebration. Cozy up in a close-by romantic room with a fireplace at the Fairmont Copley Plaza, or grab a drink at MiniBar in the Copley Square Hotel after.

8. Chocolate Lovers Dream Date

Boston Anniversary Date Ideas For Holiday 2015 Boston Chocolate Tours
Photo Credit: Boston Chocolate Tours

Chocolate. Hot Chocolate. Chocolate Truffles. For the significant other who loves ooey-gooey chocolate, an anniversary date involving chocolate is the perfect way to surprise them with their second love (after you, of course!) Try a private chocolate tour through your favorite Boston neighborhood, a chocolate truffle making workshop if you are more of a hands-on couple, or a hot chocolate walking tour as a way to see Boston in all of its holiday-decorated and lit-up glory, all while being warmed from the inside out!

9. A Whole Different Kind Of Show

Boston Anniversary Date Ideas For Holiday 2015 Dinner Detective
Photo Credit: The Dinner Detective Facebook Events Page

Think dinner and movie, but a lot more hilarious and entertaining. The Dinner Detective Murder Mystery Show is America's largest interactive murder mystery dinner, so while you are enjoying a four-course plated meal at the Holiday Inn Boston Bunker Hill, you can celebrate your engagement trying to figure out who exactly the killer is. Take advantage of the area, and see the Bunker Hill Monument or the U.S.S. Constitution before the show.

10. Tour Fenway Together

Boston Anniversary Date Ideas For Holiday 2015 Tour Fenway
Photo Credit: Flickr User mgwilkins

Fenway Park is a place where "dreams are made, traditions are celebrated and baseball is forever," so why not celebrate your relationship milestone with a tour of the famous park? Tours run throughout the year and seeing the park covered with snow is certainly an enchanting sight. Afterwards, try out one of these anniversary date ideas.

11. Sweets With Your Sweet

Boston Anniversary Date Ideas For Holiday 2015 Cupcake DecoratingBoston Anniversary Date Ideas For Holiday 2015 Cupcake Decorating
Photo Credit: Oak Leaf Cakes

You probably have had your fair share of cakes together for birthdays or special occasions, and maybe your significant other has even handmade them from scratch. Let them know how sweet you think they are, and schedule a private holiday-themed cupcake decorating class for the two of you. Try Oak Leaf Cakes or Tatte Bakery & Cafe to schedule your anniversary date night treat. End the night toasting to each other with champagne and trying out your tasty treats together.

Find out what you should give for an anniversary gift and when you should give annniversary bands before you plan your anniversary date for the holiday season. Need some help? Visit any of our five retail locations throughout New England or contact us with any questions.

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