On an East Coast trip in April, I enjoyed a three-night stay in Boston, Massachusetts, surely one of our most historic and interesting cities, as well as a prime destination for group tours.

It can also be one of the most confusing places to get around, since many of the streets reportedly originated as cow paths during Colonial times, and eventually were paved over as transportation technology advanced. Happily, however, I have not forgotten my way around town, learned by trial and error when I lived here for the better part of a year back in the early 1980s. 

One of the fascinating things I’ve learned about Boston in over 40 years as a tour operator is that very few domestic groups outside of those domiciled in the Northeast and Middle Atlantic States ever get here except during fall foliage season. I suppose that the rationale is something along the line of “as long as we’re going to go to New England, we might as well go when we can see the beautiful fall colors.” 

Far be it from me to discourage the annual “leaf peeping” migration, but I would like to suggest that Boston really is a destination in itself. In fact, like New York and San Francisco, it’s a great place for a four or five-day trip, and not just a big city to be seen as quickly as possible en route to Vermont and New Hampshire for autumn mountain splendor, maple sugar candy and Ben & Jerry’s Ice Cream.

Bob Hoelscher, CTC, CTP, MCC, CTIE, is a longtime travel industry executive who has sold his tour company, bought a motorhome and is traveling the highways and byways of America.  He is a former chairman of NTA, and was a founding member of Travel Alliance Partners (TAP).

Well-known in the industry as both a baseball and symphony aficionado, Bob is also one of the country’s biggest fans of our national parks, both large and small.  He has already visited more than 325 NPS sites and has several dozen yet to see.  He is currently traveling the country to visit as many of those parks as possible.  His blog, “Travels with Bob,” appears periodically on The Group Travel Leader’s blogsite, “Are We There Yet”. 

Bob is available for contractual work in the industry and may be reached at bobho52@aol.com or by calling (435) 590-1553.

Boston Public Library, Prudential Tower, Lenox Hotel and Boylston Street

Newbury Street bistros, Boston

Downtown Boston from Prudential Tower Skywalk Observatory

Instead of a typical September or October tour, I’m going to suggest that group travel planners think a little “outside of the box” and consider a trip to Boston during the spring! Why so early in the year? Let me count the ways! 

As soon as Mother Nature waves her magic wand and replaces winter’s icy blasts with gentle spring rains, magnificent flowers, budding trees and lush green pastures are sure to soon follow. April marks the arrival of two storied Boston traditions, which almost reach the level of religious fervor for some. 

First is the arrival of the Red Sox from their Fort Myers Grapefruit League home early in the month. Please note that they are known only as the “Sox” locally, as the “pale hose” of Chicago are not recognized in these parts. Few cities take their baseball as seriously as does Boston, so early in the season is the best time to score tickets for a contest at historic Fenway Park. 

Secondly, the storied Boston Marathon, held on Patriots Day in mid-April, is a really big deal, with thousands of active participants and countless more race enthusiasts who come to watch from along the route.    

Few visiting groups would want to miss the opportunity to attend a live performance by the world-renowned Boston Pops, whose brief annual season in town runs only from early May until late June. Staffed by most of the members of the world-class Boston Symphony Orchestra, who don white jackets rather than their black formal attire, the Pops perform in Symphony Hall, the acoustically magnificent concert venue built in 1900.

However, traditional concert seating is replaced by cabaret-style tables for five, food and beverages are served by a uniformed wait staff, and featured guest performers run the gamut of different popular music styles. Furthermore, hotel space in the city is much easier to come by at this time of year rather than during the “peak” fall season, room rates are substantially lower, sightseeing attractions are all open for business, and attractive “shoulder season” air fares are available between Easter and family summer vacation time.

Fenway Park, home of the Boston Red Sox

Statue of Ted Williams outside of Fenway Park, Boston

Symphony Hall, Boston

Most group travel planners are already familiar with, and are sure to include visits to the many historic attractions Boston has to offer: the Freedom Trail, Massachusetts State House, Faneuil Hall, Old North Church, Bunker Hill, the U.S.S. Constitution, etc. I’m going to suggest, however, that you plan ample time for your group to experience the “Back Bay” area surrounding the Prudential Center.

You can begin your sightseeing with splendid panoramic views of the entire city from the Skywalk Observatory atop the Prudential Tower. Downstairs you’ll find an outstanding shopping mall complete with “food court” and popular stand-alone restaurants like the Cheesecake Factory.

Right outside you can board one of 27 brightly colored “Boston Ducks” (amphibious vehicles) for a great, one-hour-and-twenty-minute orientation tour combining a trip through the streets of the city’s central core, plus a refreshing cruise on the Charles River, separating Boston from Cambridge. Boston Duck Tours is also happy to customize tours for groups with such specific interests as history, architecture, or parks and gardens. 

After you’ve familiarized yourself with the basic layout, you’ll discover that Boston is truly a great walking city. Also in the “Back Bay” neighborhood are the trendy upscale shops and cafés lining Newbury Street, the aforementioned Symphony Hall, plus an attractive variety of hotels. 

Faith-based groups and others with an interest in religion or architecture won’t want to miss a visit to the “Mother Church” of Christian Science, as well the adjacent Mary Baker Eddy Library for the Betterment of Humanity, housing the unusual “Mapparium” three-story, walk-in globe.

Fenway Park is a short drive away, or even within walking distance for more mobile groups, as are the individual community garden plots along the “Fens.” Excellent, free concerts are presented regularly by students of the New England Conservatory (classical) and the Berklee College of Music (popular, folk and jazz). Considering that you will be visiting a city that is always ready for a celebration, you may even stumble upon a parade marching down Boylston Street, as I did last month, which recognized the area’s citizens of Greek heritage.

Aboard a "Boston Duck"

Greek Heritage Parade down Boylston Street, Boston

First Church of Christ, Scientist ("The Mother Church"), Boston