Don-Littlefield-Headshot

Don

Littlefield

12 years of experience
Portland, Maine
United States of America (USA)

Contact Options

Nobody wins unless everybody wins.

About

I have lived in Portland, Maine, my entire life, and I know first-hand that it wasn’t always as popular as it is today. 

After being named on prominent lists that helped people discover the city, hundreds of thousands of travelers were now arriving in the largest city in Maine. They were mostly looking for adventures based on our culinary and beverage scene. 

I started working as a craft beverage guide for a local start-up tour company a dozen years ago. I helped the founder grow the business and I moved into an oversight role within the company as the first General Manager.

Since 2012, I have worked to hone my skills as an adult tour guide, leading thousands of half-day tours around Maine and parts of New England, giving thirsty guests opportunities to learn more about the incredible craft alcohol industry. 

I also was asked to lead multi-day tours around New England for foreign travelers. Shortly after that, I helped organize and lead several European trips for American travelers who wanted to explore the craft beer scene in Belgium, Germany, Ireland, and Iceland. 

In 2022, I participated in the TripSchool East Coast Megatraining. This training, specifically for multi-day tour directors, helped me understand more about the multi-day tour business for students and adults. I quickly realized that I would enjoy this style of leading tours for one group over multiple days. 

I immediately connected with a company that needed a tour manager for a student group coming out of Maine and headed to New York City. I quickly became a licensed tour guide in New York City and Washington, D.C. By the end of my first half-year as a tour director, I managed six different student and adult trips to NYC and Washington, D.C. 

Adult trips come to my home area of New England for summer activities and foliage displays in the fall. I happily serve as a lead Tour Manager for many departures traveling up and down the Coast of Maine and around New England. 

My varied background in retail and restaurant management, data collection and reporting, technology sales, real estate, and non-profit leadership helped me grow as a tour director. It allows me to develop a real connection with the travelers and to find ways to amaze and delight them with the overall experience.

I also am a tour operator. I own a majority share of Brews Cruise, Inc., a tour company founded in 2006 with diverse culinary and beverage operations in over a dozen locations around the United States. This position offers me much flexibility with my schedule and allows me to develop new professional skills as a tour director. 

Every year, I take additional training to continue learning to manage and guide even more tours beyond the East Coast. Recently, that training has given me the confidence to lead tours to most National Parks in Western states and cities in the South known for their music heritage.

Tours Offered & Destination Knowledge

Bus ToursDriver GuideFood & Drink ToursGeneral Walking ToursLarge Group ToursLocal GuideMulti-Day Tour Director/LeaderPrivate ToursStudent Tour DirectorTour Business Owner/Operator
  • Extensive experience leading student and adult tours in Boston, Gettysburg, New York City, Niagara Falls, Pittsburgh, and Washington, D.C. 
  • Multi-day tours for foliage, history, and craft beer throughout New England.
  • Culinary and Craft Beverage Tours in Maine, Boston, and Providence, RI
  • History-focused walking tours in Portland, Maine, Portsmouth, NH, and Boston, MA
  • Led group trips to European destinations of Ireland, Belgium, and Iceland.
Fun Fact!
I am also a licensed amateur radio operator (commonly called ham radio) at the highest level, Extra Class.
Hobbies & Interests
I love exploring Maine and New England but also learning more about the rest of the country and world. I am an avid bicyclist and I am getting to be a decent bread baker.

Virtual Tour Experience

In March 2020, I led the efforts to create virtual tours as interviews with owners to showcase how the breweries, distilleries, and restaurants had changed their service models in Maine to deliver their products to the public in new ways. In the span of a few weeks, we recorded 26 episodes. I arranged for all of the guests, served as the on-camera host, and edited the video to offer for free on our website.

Testimonials

Thank you for giving us a great holiday time in NYC. Sometimes it's the things that don't go as planned that produce the best of memories! Mary S., December 2023

Thank You Don. It's been a pleasure. You are good. Great Job! Alice W., December 2023

Don, thank you for a great fun-filled week of travels! Diana and Wayne B., August 2023

Great Tour! Enjoyed your add-ons to give us the history and local knowledge. Peg and Jim A., June 2023

Thank you for sharing your expertise of Maine, both past and present. We appreciated your attention to detail and the printed documents you provided. Gene and MaryAnn S., June 2023

Your vast knowledge and upbeat attitude really made the trip. As mentioned, your use of technology on the tour...was the the best I have seen. Thank you for sharing your state with us. We had a wonderful tour! Christine F., June 2023

Thank you for making my first (group) tour a success! I so appreciated your kindness and patience!! I also appreciate your sense of humor. Everyday was a fun adventure. You made everyone feel so at ease. You have great people skills. I also enjoyed your sharing little buts of your personal life! You even gave me the desire to visit Maine! Cindy O., April 2023

Thanks so much for all your hard work on our Heritage tour. It was awesome!! Your knowledge and expertise was greatly appreciated. Your sense of humor and calm demeanor were bonuses! Sharon T., April 2023

Thank you for a great "taste" of Washington, DC. It was a very enjoyable trip! Barb R. and Judy A., April 2023

Thanks Don, we enjoyed meeting you and your expertise and knowledge was icing on the cake. Thanks for the introduction to the (people) on the trip. Each one was extremely competent, knowledgeable and enjoyable. We couldn’t have picked a better trip to introduce us to (group) tours. Hope to see you on the trail. John S., September 2022

Just a quick note to say what a great time we had on your tour. You were awesome in leading our great group of travel partners around a section of the country we've never experienced before. So many great memories we took home. All the best to you as you travel the world. Alan K., September 2022

You are a fantastic Tour Manager - knowledgeable, humorous, detailed, great at keeping us "in line" in a good way. Always happy, friendly, very thorough in details, great voice and tone, and extremely knowledgable. It was amazing how you timed out our stops so that the hosts were ready & waiting to happily greet us! We learned so much at each place! Kathy M., September 2022

Thank you for sharing your knowledge and patience with us. Our time with you was delightful! Ruth D., September 2022

Details

Gateway Airport(s)

PWM, BOS

Licenses

Washington, D.C., New York City (NYC)

Training

TripSchool: East Coast Megatraining Feb 2022, Southwest National Parks Aug 2023, NOLA Destination Training Nov 2023, Chicago Masterclass 2024

Language(s)

English

Additional Education

  • Licensed New York City Sightseeing Guide (2106073-DCA | Expiration 3/31/2024)
  • Licensed Washington D.C. Tour Guide (TGL40000204 | Expiration 12/31/2025)
  • Licensed tour guide for Portland, Maine
  • Portland History Docent 2018
  • TV Host and Producer, "Cheers from Maine" produced by Maine Life Media
  • I hold a valid Commercial Driver's License with Passenger endorsement
  • Experienced bicycle tour guide
  • Former Board Member: Craft Beverage Tour Operators Association, Visit Portland, and the Maine Motorcoach Network
  • Cicerone Certified Beer Server
  • Civil Air Patrol Carl A. Spaatz Award #1088, earned in 1991

General Availability

I promote tourism and lead tours as a full-time job. But I actually do have a lot of flexibility and could arrange to work for others to lead tours with enough notice.

Photo Album

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