Andrea M. Rotondo has traveled to 50+ countries using points and miles. She's a luxury, small-ship cruise expert and hotel maven who can share the not-to-be-missed spots in her adopted home state of Florida. She will also talk all day long about her ancestral homeland: Italy.
July 21, 2026 • 20 min read
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Editorial note: TPG accepted a complimentary hotel stay, food and beverages, and sightseeing tours to experience what’s new in Boston for America’s 250th anniversary. The editorial content and opinions expressed are entirely those of the author and were not subject to review by the city’s visitors bureau, InterContinental Boston or any other external entity.
Editorial disclaimer: Opinions expressed here are the author's alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.
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By commenting, you agree to our Community Guidelines to help create a positive space for conversation. The responses below are not provided or commissioned by the bank advertiser, our partners, or The Points Guy (“TPG”). They have not been reviewed, approved, or otherwise endorsed by any of these parties. All responses are submitted by individual contributors, and neither the bank advertiser, our partners, nor TPG are responsible for ensuring that all posts and/or questions are answered.
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Quick summary
Boston offers a compelling alternative to international summer trips, blending rich history, family-friendly activities and accessible travel options.
The city is celebrating America’s 250th anniversary with special events, exhibits and festivities running through 2026, making it an especially vibrant time to visit.
Key attractions include walking tours of historic sites, interactive museums, waterfront parks, and diverse dining options from classic seafood to international cuisine.
Accommodation options like the InterContinental Boston provide convenient access to major sites and unique local touches, appealing to solo travelers, couples and families.
What to consider
Boston is easily accessible by air or train, with many direct flights and Amtrak service to the city center.
Special events for the 250th anniversary may increase demand for hotels and tours, so advance planning is advised.
Some museums offer free entry on select weekends with eligible payment methods; check specific requirements before visiting.
What you'll miss from the article
A detailed guide to Boston’s historical tours, seasonal events, dining highlights and practical tips for maximizing your visit.
Generated by AI with support from our editorial team.
A friend recently called me in a panic about summer vacation plans. Like so many families, work schedules mean she can’t always lock plans in advance. While she had reserved hotel rooms in Dublin, Ireland, and Edinburgh, Scotland, she hadn’t yet booked the flights. Airfare, it turned out, was just too expensive and beyond her budget for a family of five. (This is why families — especially — need points and miles. You can pool everyone’s miles, and most award tickets can be canceled and the points refunded at no or little cost.)
She was frantic. Her husband and kids were looking forward to a vacation that would blend history with a healthy dose of outdoor activities. She asked if I had any ideas for an alternative destination with availability at the right price. Boston, I knew, would save her summer.
Boston's Old South Meeting House. ANDREA M. ROTONDO/ THE POINTS GUY
The historic city had everything she was looking for, and, with just a few clicks, her crew could be on their way. Full disclosure: I grew up in Boston and have always loved the city. But a recent trip back there reminded me why it’s a fabulous place to visit while also introducing me to some new things, too.
Like my friend, here’s why you should consider visiting Boston this year, alongside tips to make the most if it.
How to get there
Aerial view of Boston, Massachusetts. ANDREA M. ROTONDO/ THE POINTS GUY
It’s easy to fly to the very manageable Boston Logan International Airport (BOS) on airlines such as Alaska, Allegiant, American, Delta, Frontier, JetBlue, Southwest and United. A major international hub, you'll also find direct flights from many major cities across the globe.
Alternatively, take Amtrak to South Station (within walking distance of several hotels, including the InterContinental Boston).
South Station, Boston. ANDREA M. ROTONDO/ THE POINTS GUY
History that predates the United States
Boston is the birthplace of the American Revolution, but its history is much older. Algonquian-speaking indigenous tribes lived in the area as far back as the last Ice Age. Despite displacement over the years, organizations such as the North American Indian Center of Boston exist today to empower the descendants of the area’s original Native American community. Check the website’s events page, which often lists cultural events open to the entire community.
The 'Cradle of Liberty' and the birth of America
Paul Revere statue in Boston's North End neighborhood. ANDREA M. ROTONDO/ THE POINTS GUY
Colonial Boston was incorporated in 1630, ten years after the Mayflower landed about 40 miles south of the city at nearby Plymouth Rock. And, of course, it was where tensions stemming from taxation without representation — the famous Boston Tea Party — ignited war with Britain in the late 1770s.
In the 19th and 20th centuries, Boston became “the Ellis Island of Massachusetts”: a major port of entry for Europeans, Canadians and, later, Central and South Americans. My own family was part of that migratory path, settling in the North End and East Boston. That influx of people and ideas built the vibrant and diverse city that exists today.
North Square in Boston's Italian North End neighborhood. ANDREA M. ROTONDO/ THE POINTS GUY
A guided tour is the best way to learn more about Boston’s rich history. There are many providers, but my group worked with Hub Town Tours, which specializes in introducing the city to small groups (16 people or fewer). While we opted for a customized private tour just for our group, the company offers three group tours:
Freedom Trail History: Follow a pedestrian path through the city to hear all about what happened between 1760 and 1776.
Irish famine memorial. ANDREA M. ROTONDO/ THE POINTS GUY
Beacon Hill: Underground Railroad History Tour visits historic sites along cobblestone streets, the elite homes of Boston’s upper class and abolitionist landmarks, such as the African Meeting House.
Back Bay: Walking the Women’s Heritage Trail, with stories of the fight for women’s suffrage (Boston Common, Back Bay, Public Garden, Newbury Street and Copley Square).
Sculpture in Boston Common. ANDREA M. ROTONDO/ THE POINTS GUY
If you’ve never been to Boston before and don’t know much about the American Revolutionary period, go for the 2.5-hour Freedom Trail tour. A brick-lined path links 16 important landmarks so you could just explore on your own, but Hub Town Tours’ guides are historians and archaeologists and access to them — and their stories — brings this part of Massachusetts to life. It’s worth going with a guide.
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Old State House. ANDREA M. ROTONDO/ THE POINTS GUY
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Paul Revere House. ANDREA M. ROTONDO/ THE POINTS GUY
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North Market. ANDREA M. ROTONDO/ THE POINTS GUY
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Faneuil Hall. ANDREA M. ROTONDO/ THE POINTS GUY
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Quincy Market. ANDREA M. ROTONDO/ THE POINTS GUY
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Boston's Old City Hall. ANDREA M. ROTONDO/ THE POINTS GUY
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Park Street Church. ANDREA M. ROTONDO/ THE POINTS GUY
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King Chapel. ANDREA M. ROTONDO/ THE POINTS GUY
Among the sites you’ll visit are Boston Common, Massachusetts State House, Park Street Church, Granary Burying Ground (dating to 1660), King’s Chapel & First Burying Ground (dating to 1630), Benjamin Franklin Statue (he went to school at Boston Latin in 1635) and Old City Hall, Old South Meeting House, Old State House, the Site of the Boston Massacre, Faneuil Hall, North Square and Paul Revere’s House, Old North Church, Copp’s Hill Terrace and more.
Custom House Tower. ANDREA M. ROTONDO/ THE POINTS GUY
You can’t scroll through TikTok these days without seeing details about events around the country centered on America’s 250th anniversary. Boston actually started celebrating last year on April 18, 2025, to give a nod to the 250th anniversary of Paul Revere’s ride warning Bostonians that the British were on their way to wreak havoc. Festivities continue throughout 2026 and include the following:
Sail Boston 26, where Boston Harbor hosts an international fleet of Tall Ships from July 11–16.
Patriots of Color exhibit at the Family Heritage Experience on Newbury Street: Running until Dec. 31, 2026, this is a fascinating look at the stories of Black, Native and multiracial Bostonians who fought for independence.
America At 250 at The MFA (Museum of Fine Arts): The Art of Americas collection is on display from June 21, 2026–July 4, 2027, featuring pieces such as Paul Revere’s Sons of Liberty Bowl (1768), Gilbert Stuart’s unfinished portrait of George Washington (1796) and a work by Alan Michelson, a Mohawk member of the Six Nations of the Grand River, which proffers a modern critique of Washington, known to the Mohawk nation as “Town Destroyer.”
There are many more events, so take a look at the Boston 250 calendar for a full rundown.
Other 'can’t miss' things to do in Boston
Boston Tea Party Museum. ANDREA M. ROTONDO/ THE POINTS GUY
Beyond historic sites, there are many cool things to see in Boston — many of which are perfect for families. And there are many museums to discover. Don't forget Bank of America's Museums on Us benefit, which unlocks free entry to Boston's Museum of Fine Arts and The Institute of Contemporary Art on the first full weekend of every month. (Eligible products include any credit or debit card issued by Bank of America, Merrill or Bank of America Private Bank.)
One trip to the city won’t allow you to see it all, but here are a few staples to consider.
Kid-friendly activities: The interactive Boston Tea Party Museum is a lot of fun. You can literally throw bales of tea into the harbor from a replica 18th-century ship. Pair that with the Children’s Museum (right next door) and the New England Aquarium.
Boston Children's Museum. ANDREA M. ROTONDO/ THE POINTS GUY
Dine and shop at the Seaport (home to restaurants, breweries, waterfront parks and even an F1 arcade) and stroll along the Harborwalk (a near-continuous 43-mile path along Boston’s shoreline).
Boston's Seaport. ANDREA M. ROTONDO/ THE POINTS GUY
Catch a baseball game at historic Fenway Park or take a tour of the ballpark.
Explore Chinatown: Check out Pao Arts Center, pop into specialty markets and apothecaries, take a selfie under the Chinatown Gate, and, of course, sample excellent dim sum, noodles, Peking duck and more.
Visit the Isabella Stewart Gardner Museum in the city’s Fenway-Kenmore neighborhood. The collection is world-class, and there’s even a true crime exhibit telling the story of a famous art heist that took place there in 1990. Well worth the visit.
Walk the Rose Kennedy Greenway, stretching from Chinatown’s gate (Essex St. and Surface Rd.) to the North End (Cross and Hanover streets). Free events are held throughout the year, and it’s a wonderful place to let kids run off some steam, experience the Greenway Carousel, enjoy seasonal flowers, splash in the fountains or simply grab lunch from nearby food trucks and enjoy a picnic-style meal on the grass.
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Rose Kennedy Greenway sculptures. ANDREA M. ROTONDO/ THE POINTS GUY
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Rose Kennedy Greenway carousel. ANDREA M. ROTONDO/ THE POINTS GUY
Take a whale-watching harbor cruise or take a ferry or water taxi to one of Boston’s 34 outer islands that comprises Boston Harbor Islands National and State Park.
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View of Boston's skyline for a water taxi. ANDREA M. ROTONDO/ THE POINTS GUY
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Water taxi stop. ANDREA M. ROTONDO/ THE POINTS GUY
If walking is a challenge, there are several hop-on, hop-off trolley experiences in the city.
Boston is a multicultural city and you’ll find restaurants serving cuisine from around the globe. However, you can’t visit Beantown without sampling some of the following specialties:
New England clam chowder
Fried clam strips and bellies
Lobster rolls (Connecticut style, warm and dripping with butter, or Rhode Island style, cold and accompanied by mayo)
Oysters on the half shell
Boston baked beans
Boston cream pie
Cannoli (order from a North End bakery that fills the shell with ricotta right in front of you)
Sfogliatelle, aka a “lobster tail” (a flaky horn-shaped pastry filled with cream — pick one up in the North End)
Samuel Adams beer (the brewery’s research hub is in Jamaica Plain)
Here’s a fun way to cap off an evening in Boston. Book the Loyall Counting Room speakeasy at the InterContinental Boston. I won’t give away too many of the night’s secrets, but it’s hidden away beyond Bar Fellini in the lobby. The hotel grants limited access to this intimate space (Wednesday–Saturday, 5–10 p.m.).
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InterContinental Boston speakeasy. ANDREA M. ROTONDO/ THE POINTS GUY
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InterContinental Boston speakeasy. ANDREA M. ROTONDO/ THE POINTS GUY
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InterContinental Boston speakeasy. ANDREA M. ROTONDO/ THE POINTS GUY
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InterContinental Boston speakeasy. ANDREA M. ROTONDO/ THE POINTS GUY
Mixologist Rey Cruz led our group through some inventive cocktail choices, each with ingredients and stories tied to the American Revolution and the history of Boston. You can also order small bites. The venue qualifies for the Resy statement credit (up to $100 back quarterly), a benefit of the (enrollment required). Simply pay with your Amex Platinum at an eligible U.S. Resy restaurant; no reservation is required.
InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
When I grew up in Boston in the early 1980s, the Seaport — east of the Financial District and across from the Fort Point Channel — didn’t exist as it does today. A lot has changed over the last 20 years, as the $14.6 billion “Big Dig” transformed much of Boston. The project moved the elevated Central Artery (I-93) underground, creating the beautiful Rose Kennedy Greenway walking path and making way for a massive waterfront experience (much of it on manmade land) that’s packed with museums, activities, hotels, restaurants and bars.
From the Seaport, you can easily walk to the Financial District, Downtown Boston, Boston Common and the Public Garden, the North End and more. You can also commute by water taxi.
InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
On previous visits to the city, I’ve always stayed closer to the Boston Common or Public Garden, so I was excited to make the InterContinental Boston my home-away-from-home for my most recent trip. Often, I worry about staying in larger luxury hotels because, while they are, in fact, luxurious, they sometimes aren’t unique to the destination’s landscape. I was elated to see so many New England touches throughout the InterContinental. It truly channeled Boston’s spirit. Case in point: Order the lobster roll from the room service menu. It's exquisite.
A yummy lobster roll from InterContinental Boston's room service menu. ANDREA M. ROTONDO/ THE POINTS GUY
The facade of the building’s two towers evokes a sailing ship, which is apropos since the address at 510 Atlantic Street is right on the water. I also love that the hotel used limestone from the Big Dig as wall accents on certain floors. If you look closely, you’ll see fossils from bygone days. It’s a cool way to incorporate the massive transformation of this part of town that made way for the hotel itself.
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InterContinental Boston lobby. ANDREA M. ROTONDO/ THE POINTS GUY
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InterContinental Boston lobby. ANDREA M. ROTONDO/ THE POINTS GUY
The interior color palettes of sand, light green, sky and sea blue give the hotel a very New England feel, and every single room — whether water- or city-facing — seems to have a spectacular view. My 480-square-foot room overlooked the water and the Boston Tea Party Museum. It was fun watching visitors toss tea into the harbor every so often and to see families in rented pedal boats that looked like swans, ducks or dragons.
Boston Tea Party Museum as seen from a guest room at the InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
The room was equally equipped for vacation (a luxe king-size bed, a chaise longue, an armchair, a snuggly bathrobe and slippers, a soaking tub and a separate shower in the marble-decked bathroom) or for work (a desk with plenty of real estate to spread out, with a view of the city right out the facing window). I also made good use of the in-room coffee/tea maker and appreciated the ironing board and iron.
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InterContinental Boston ANDREA M. ROTONDO/ THE POINTS GUY
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InterContinental Boston ANDREA M. ROTONDO/ THE POINTS GUY
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InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
There’s a good-sized indoor pool, and the fitness center was fully equipped. Sadly, I didn’t get in a workout there.
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InterContinental Boston indoor pool. ANDREA M. ROTONDO/ THE POINTS GUY
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InterContinental Boston fitness center. ANDREA M. ROTONDO/ THE POINTS GUY
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InterContinental Boston fitness center. ANDREA M. ROTONDO/ THE POINTS GUY
Instead, I started and ended each day with a brisk walk from the hotel along the Harborwalk, across the Evelyn Moakley Bridge (Seaport Blvd.), through Martin’s Park along the Fort Point Channel and then back across the retractile-style Summer Street Bridge. It was a great way to get to know the hotel’s neighborhood.
Boston Seaport. ANDREA M. ROTONDO/ THE POINTS GUY
The property is very well maintained — not a nick or scratch on anything in my guest room, and the public spaces are absolutely stunning. But what really stood out was the staff. Every person I interacted with was knowledgeable about the hotel and the Greater Boston area, and they seemed excited to share their perspectives with me. I wouldn’t hesitate to recommend the InterContinental Boston for solo travelers, couples or families (there are some lovely suites and connecting rooms).
The food and beverage at the hotel's restaurants and bars exceeded my expectations. Breakfast buffets can be ho-hum, but I enjoyed the options at Matria. The friendly waiter glanced at the plate I had made for myself, piled high with fresh fruit, and then recommended the made-to-order acacia bowl. (One made-to-order entree is included in the price of the buffet.) The sunny dining room — accented with orchids and other flowers — made for a pleasant start to the day.
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Matria, InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
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Matria dining room at InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
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Matria dining room at InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
Later in the trip, I dined at the Terrace on the Waterfront for some pre-dinner Champagne and oysters (offered on special Thursdays from 4–7 p.m.). You can’t beat waterfront views, $1 oysters and Moet & Chandon.
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Oysters at InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
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Matria outdoor patio at InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
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Matria outdoor patio at InterContinental Boston. ANDREA M. ROTONDO/ THE POINTS GUY
We followed that up with an excellent meal at Matria consisting of roasted tomato focaccia ($14), farro salad ($22) and gnocchi alla Bava (fontina and Parmesan cheese with toasted hazelnuts and black pepper, $24). The meal rivaled some of the spots I’ve tried in the North End. The focaccia was a standout. I’d go back just for that.
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Matria farro salad. ANDREA M. ROTONDO/ THE POINTS GUY
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Matria gnocchi. ANDREA M. ROTONDO/ THE POINTS GUY
After dinner, we noticed several groups sitting at fire pit tables, enjoying s'mores. That looked incredibly fun, whether you're looking for a romantic evening or something to keep the kids entertained.
S'mores tables at InterContinental Boston's Matria. ANDREA M. ROTONDO/ THE POINTS GUY
The terrace's adjacent lawn area is the spot to lounge during the day, enjoy yoga or simply watch the boats go by in the channel.
The hotel also has its own water taxi launch. The concierge can help you arrange transportation to and from the airport, the North End and other destinations across the city. It’s a relaxing way to get around Boston and affords you some incredible photo ops.
InterContinental Boston's water taxi stop. ANDREA M. ROTONDO/ THE POINTS GUY
Bottom line
Boston is an ideal getaway — especially in the spring, summer and fall — for either a weeklong or weekend getaway. You can blend history, art, sports, culture and fine dining in just one trip. And it has so much extra to enjoy during the 250th. I’m already planning my next trip back, and can't wait to see what's new on my next visit.
By commenting, you agree to our Community Guidelines to help create a positive space for conversation. The responses below are not provided or commissioned by the bank advertiser, our partners, or The Points Guy (“TPG”). They have not been reviewed, approved, or otherwise endorsed by any of these parties. All responses are submitted by individual contributors, and neither the bank advertiser, our partners, nor TPG are responsible for ensuring that all posts and/or questions are answered.
