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We asked AI to plan the perfect Boston day. Here’s where it took us.

A new artificial intelligence-powered website, Forgemytrip, is designed to build customized travel itineraries. So we put it to the test.

An AI-powered day through Boston
Globe business reporter Dana Gerber used a new website, Forgemytrip, to take her on a tour through the city. Here's how it went.

Since crashing the scene late last year, AI chatbots such as ChatGPT have proven themselves capable of crafting college admissions essays, producing viral images out of whole cloth, and spooking everyone from curious journalists to Silicon Valley tech execs.

But one important question remains: Can they advise me on where to find the best lobster roll in Boston?

That was my premise when I embarked on a recent expedition around the city, solely at the mercy of the generative artificial intelligence technology that has taken the world by storm (and set off experts’ alarm bells).


AI bots like ChatGPT function by analyzing mountains of text to “learn” language patterns so they can process user prompts and spit out eerily humanlike responses. Such as, say, a timestamped itinerary for a day of gallivanting around Boston.

A crop of new AI-powered websites and apps are designed for just that, letting users plug in their destination, travel dates, and specific criteria to build a customized list of must-sees. Ahead of the Memorial Day weekend, I decided to try Forgemytrip, a free website that launched a beta version earlier this month.

“The unique angle I wanted to come up with was specifically for making itineraries,” said Jaideep Patil, a travel enthusiast who helped create the service. “That’s always something I enjoy doing, but it’s something that’s very time-consuming.”

And demand for these digital concierges is on the rise: A recent survey from tourism market research firm Longwoods International found that 32 percent of respondents are either “very” or “somewhat” likely to use ChatGPT in the planning process for their next trip (27 percent, however, said they didn’t know what ChatGPT was).

So I put Forgemytrip to the test, asking it to build me a one-day itinerary for Boston with the following specifications:


  • Breakfast: An inexpensive, funky diner.
  • Lunch: A good place to get a lobster roll with outdoor seating.
  • Dinner: An Italian restaurant with a nice cocktail menu.
  • Activity 1: A secluded garden that shows off beautiful spring flowers.
  • Activity 2: A quirky museum that both kids and adults can enjoy.
  • Activity 3: A cozy bookstore.

I also requested that there be no more than a mile in walking distance between each location and that all of the locales should be “extremely off-the-beaten-path ― nothing that would be in a normal guidebook.”

In just minutes, my itinerary was ready, complete with an emoji-laden map to show me all my destinations. With my robo-curated route in hand, I set off on my journey. (If you are so inclined, you can compare AI’s itinerary with one crafted last year by the Globe’s travel columnist, Christopher Muther.)

Stop 1

“Start your day with breakfast at The Friendly Toast. This funky diner serves delicious and affordable breakfast dishes, such as pancakes, omelets, and breakfast sandwiches. Be sure to try their famous homemade jam!”

The Friendly Toast in Back Bay.Dana Gerber

My first stop is The Friendly Toast in Back Bay, a kitschy diner with an eclectic menu. I have dined there before, but I decide to defer to the AI when it comes time to place my order; it instructed me to try the “famous homemade jam,” so (after confirming with my waitress that it was, in fact, homemade) I order the churro bites — cinnamon-topped balls of fried dough with a side of the strawberry habanero jam. I’m usually spice-averse, but the flavors mingle surprisingly well. After wolfing down three of the treats, I ask for a to-go box and pay my check. So far, so good.

Stop 2

“Take a short walk to the Boston Public Garden. This secluded garden showcases beautiful spring flowers, such as tulips, daffodils, and cherry blossoms. Enjoy a peaceful stroll around the garden and take some photos for your memories.”

A Swan Boat at the Boston Public Garden.Dana Gerber

A short walk later, I am at my second stop: the Boston Public Garden. While it isn’t exactly the “secluded” locale I had requested, I’ll never turn down a sunny day watching the Swan Boats glide across the water or listening to the omnipresent bagpipers. Unfortunately, I seem to have come a bit too late in the season to take in the full beauty of the flowers — the AI failed to alert me that peak bloom season had come and gone. The technology is starting to show its limitations, but with the gentle breeze and sounds of birdsong, I’m not complaining.


Stop 3

“Enjoy a leisurely lunch at Neptune Oyster. This seafood restaurant is known for its delicious lobster rolls and outdoor seating. Sit outside and savor the flavors of New England's freshest seafood while enjoying the sunny weather.”

Pauli's, a restaurant in the North End.Dana Gerber

I board the Green Line at Arlington station to Haymarket, where my lunch destination, Neptune Oyster, is a short walk away on Salem Street. I had asked Forgemytrip for an eatery with outdoor tables, but al fresco seating is nowhere to be found. What’s more, a waiter informs me that lobster rolls cannot be taken to-go, and there’s a line out the door. So, in the interest of keeping my day moving, I defy my robot overlord and hop next door to Pauli’s, a cozy spot that touts its $27 cold lobster rolls as “best in town.” There is still no outdoor seating, so I chow down on a grassy spot along the nearby Rose Kennedy Greenway. No travel experience goes by without a little improvisation.

Stop 4

“Walk to the Isabella Stewart Gardner Museum. This quirky museum is a hidden gem that both kids and adults can enjoy. Admire the beautiful art collection and the unique architecture of the museum, which resembles a Venetian palace.”

The Courtyard at the Isabella Stewart Gardner Museum.Dana Gerber

It is a little after 3:30 p.m., and my next destination, the Isabella Stewart Gardner Museum, is closing at 5 p.m. Even though I’d asked Forgemytrip to put no more than a mile between each stop, 3.2 miles stand between me and the Fenway museum, so I hop in an Uber. More difficulty awaits me upon arrival, where a sign outside declares tickets are sold out for the day. Thankfully, when I explain my AI quest to the front desk, they agree to let me in to explore the lush Courtyard that has graced many an Instagram feed. While it’s not exactly the “quirky” spot I was aiming for, I still enjoy my time marveling at the ornate sculptures, the Venetian-style architecture, and the purple blooms.


Stop 5

“Take a short walk to Trident Booksellers & Cafe. This cozy bookstore offers a wide selection of books, magazines, and gifts, as well as delicious coffee and pastries. Browse the shelves and find your next favorite book, or simply relax and enjoy the cozy atmosphere.”

A display of books at Trident Booksellers & Cafe on Newbury Street.Dana Gerber

A short ride on the 39 bus and a half-mile walk down Newbury Street bring me to my next stop, Trident Booksellers & Cafe. I will find just about any excuse to browse a bookstore, and Trident is one of my favorite spots, so I waste no time settling into the familiar “cozy atmosphere,” as the AI put it. I browse the fiction section for Annie Ernaux titles and consider the various paint-by-numbers kits before deciding to buy a $6 bookmark shaped like a stick of butter for Father’s Day. A solid tick in the pro-AI column.

Stop 6

“End your day with dinner at Giacomo's Ristorante. This Italian restaurant serves authentic and delicious dishes, such as homemade pasta, seafood, and pizza. Don't forget to try their signature cocktails, which are a perfect match for your meal.”

Pasta at Giacomo's Ristorante in the North End.Dana Gerber

For my final stop, I hop on the Green Line back to Haymarket for dinner at Giacomo’s Ristorante, a cozy Italian spot in the North End. I encounter another line outside, but am determined not to deviate from another AI-ordained meal. Sure enough, within 15 minutes or so, I snag a table upstairs overlooking Hanover Street. There is a sign alerting patrons that this is a cash-only establishment — a caveat that the AI failed to flag. Thankfully, I have just enough cash on me to cover the $26 bowl of scallops over a bed of linguini. The pasta hit the spot, but the cocktail menu I’d requested was nonexistent — another strike against AI.


Closing thoughts

My robo-guided tour around the city was one example, but the world of travel is already leaning into the AI revolution, with booking websites like Expedia and Kayak recently announcing integrations with ChatGPT.

“Emerging technology has always been quickly adapted by the travel industry,” said Amir Eylon, the president and CEO of Longwoods, the firm that did the recent survey on travelers and chatbots.

To be sure, AI was not a flawless tour guide. It was a shoddy logistician, sending me zigzagging around the city even after I asked it to keep everything within walking distance. It failed to provide important details about Giacomo’s cash-only policy and the lack of outdoor seating at lunch.

And AI services like Forgemytrip, while a convenient way to outline an excursion, are simply not built to find you that hidden gem that only locals know — as evidenced by my entertaining but largely unoriginal itinerary.“It’s great to start the ideation process, but not end it,” said Makarand Mody, a professor at the Boston University School of Hospitality Administration.

Now, with some experts opining that generative AI will dramatically change or even supersede traditional search engines, businesses may be left scrambling to figure out how to be prioritized by AI systems. (James Hook & Co., for example, would probably be none too pleased to discover they didn’t clinch the top spot for my local lobster roll query.) Patil noted that AI apps like his could begin offering “very targeted promotions for restaurants or hotels in a very specific city,” much like a “sponsored” result appears on a Google search.

Though the locales it gave me were essentially Boston’s Greatest Hits, that may have been a blessing in disguise. It finally got me to the Gardner Museum, for example, which I had always put off visiting. The technology gave me permission to do the cliche.

And, hey, I’ve had AI-less days that have gone far worse.

Dana Gerber can be reached at Follow her @danagerber6.