Carolyn Kruse

Carolyn Kruse

Carolyn Kruse

Most of us have the basic things we need, and if we don’t, we get them in our stockings for Christmas. Socks, underwear, a new toothbrush, gloves, these are a few of favorite basics to give and get. But at this time of year, we all like to feel a little spoiled. You like to know someone put thought into giving you a gift. It shows they know you, and they want you to live your best life.

Giving the gift of an experience in one of the greatest cities in the world, our F*#ing city, as Big Papi so eloquently once stated, is a special gift. It shows imagination, thought, and time-put-in. But honestly, it doesn’t actually take much time. (I won’t tell, if you won’t tell.) We all want experiences to share with people we love. And hey, if the person you gift a Boston experience wants you to be their plus-1, then…bonus!

I got this idea after playing a piece of an interview with Morgan Wallen. He told me he loves Boston for it’s history and would love to do an historic tour. I first suggested the Freedom Trail, which he seemed excited about. Then I mentioned there are historical tours with beer, or wine. And that got him fired up. Listen here:

Even those of us who live here can appreciate these experiences, and learn something along the way. Whether it’s learning about cooking, history, wine or playing games, these are the gifts your friends and loved ones will remember and appreciate. So, lets dive into 9 awesome Boston experiences to gift this holiday season.

  • 1. The Freedom Trail Walking Tour

    It’s good to be a tourist in your own town (or city)! I’ve done this tour quite a few times, and always enjoy it. Be sure to wear comfortable shoes! The Freedom Trail tours have been around a long time, and there’s a reason. But if that isn’t a fit for the person you are looking to gift and an experience, try Boston Olde Town Trolley Tour. They have many adventures to choose from. This time of year, there’s the Holiday Sights Tour, or maybe try the Boston Tea Party Tour, or the Ghosts and Graveyards Tour.

  • 2. Ye Olde Tavern Tour

    I really enjoyed this one. In fact, I loved learning about the Revolutionaries and their history with Boston’s taverns so much, I bought the book, at the end of the tour. The beers at each stop certainly helped to enhance the experience.

    Home | Ye Olde Tavern Tours | History and Beer Tours | Boston

    Ye Olde Tavern Tours offers walking tours to visit historic sites and taverns along the Freedom Trail. Led by fun and expert historians, learn about the revolutionary (and drunken) history of Boston. Beer or cocktails are included with the price!

  • 3. Indoor Golf And Lessons

    This gift works for the beginner and the enthusiast. More and more indoor golf places are popping up. Five Iron is opening soon (supposedly before the month is over), and it’s the talk of the town. But there’s also plenty of other places, like CityGolf to sharpen your skills, or just hit it around with friends.

  • 4. Boston's Politically Incorrect North End Food Tour

    Things could get interesting on this tour. Sounds like you get a saucy chararacter giving your the real deal, with your red sauce. You have to love this description, from their website:

    As the title suggests this is not your typical North End Food Tour and thank God for that. Being Boston’s “Politically Incorrect” North End Food tours , you will get the information about Little Italy with no bullshit from a true local who was born and raised here, not from some transplant who isn’t even Italian that read some stuff in a book and wants to tell you about it. I can guarantee you will laugh a lot and eat a lot of good food. So, come hungry!”

    Tour Descriptions | Boston's Politically Incorrect North End Food Tours

    Here are some of the places we will visit, Of course, we will visit famous Hanover Street where we will discover the best pasticcerias that offer the best cannoli, biscotti, and other Italian favorites. We will discuss the best of the best restaurants and coffee shops.

  • 5. A Cooking Class

    Useful, fun and in the end…delicious (hopefully). This is a great gift for the creative person in your life looking to make a little art, in the kitchen. As Julia Child once said, “This is my invariable advice to people: Learn how to cook—try new recipes, learn from your mistakes, be fearless and above all have fun.” 

    There are a few options when searching out a Boston area cooking-class to gift to a loved one. Check out Eataly in Back Bay. NBC and USA Today recommend CozyMeal for a fun culinary experience.

    Cooking Classes Boston | Cozymeal

    Find and compare the best cooking classes in Boston! In-person and online options available. Award-winning chefs. Large variety of cuisines.

  • 6. Give the Gift of a Game Night

    Leave the video games behind and have a truly sensory experience, in person, with food and bevvies! Go bowling at any of these fun places. Get out your frustrations with a little axe throwin at Urban Axes in Somerville. Or hey, check out this place- It’s called Spin. It’s new and in the Seaport District. You can rent a ping pong table for $10. Gift cards available!

    SPIN Boston | United by Ping Pong

    SPIN Boston's dynamic venue features 14 Olympic-caliber professional ping pong tables, 2 private lounges, and a full-service restaurant and bar offering the best eclectic comfort cuisine and handcrafted cocktails this side of the Fort Point Channel. Our multi-sensory interior, with sliding garage door patio space, blends graffiti, modern street art, and murals from local artists.

  • 7. Book at Night At A Boston Hotel with an indoor pool

    So many hotels. So many pools. What a fun night to give for your special someone, that you also get to enjoy. Splash around, grab a meal and sleep in luxury and quiet.

    The Best Hotels in Boston with an Indoor Pool

    The best hotels in Boston with an indoor pool as chosen by the experts at The Hotel Guru including luxury hotels, chic boutiques and waterfront stays with wonderful views. Check live availability and book online.

  • 8. Give A Personalized Message From A Boston Celebrity

    If you haven’t heard about it, Cameo is an app where you basically hire celebrities to send you a video recording. Make it sweet, make it spicy. It’s personalized, so whoever you gift a Cameo will feel super special! You can hire Boston celebrities, or anyone on the list.  Some of the local celebs for hire include the Bruins Charlie Coyle and Jeremy Swayman. Former Real Housewife and occasional Shark Tank guest Bethany Frankel is also available. She lives in Back Bay…sometimes. 

    Cameo |Personalized Video Messages | Celebrity Shoutouts | Gifts | Linktree

    Personalized Video Messages from your favorite actors, creators, comedians, athletes, and musicians. Great gifts for birthdays, holidays, motivation, and more. A wonderful way for fans to connect directly to their favorite celebrities.

  • 9. Broadway in Boston

    A live theater show can take you places, make you get up in your chair to sing and dance. It can make you laugh, and make you weap. So many great Broadway shows have hit the theater district in Boston. I just saw Six, which as fantastic. Hamilton is coming and so is Jagged Little Pill, among others. A great night out for a great friend or loved one in your life.


    The most comprehensive source for Touring Broadway Shows, Touring Broadway Tickets, Touring theater information, Tickets, Gift Certificates, Videos, News, Features, Reviews, Photos, Group Tickets.

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