Visiting Boston, MA - Jim Flynn's BestWeekends

Boston, MA

Boston, MA Overview

Called the most European of American cities, Boston is an exciting contemporary city steeped in history, but keeping pace with the rush of modern times. History, culture, fine dining, shopping, sports and outdoor activities combine to make this a destination worthy of any special weekend. Sleek new architecture sits side by side with Colonial era history and distinct ethnic cultures remain loyal to their past and account for many of the unique neighborhoods.

This is one of my favorite weekend destinations. Unlike some major cities, Boston is “manageable” and doesn’t overwhelm. It is easy to navigate and you can walk to most everything. It has pretty much anything a major city should have, but with a unique character all its own. It is just as much fun to just wander around as it is to have a planned itinerary. Charles Street offers art galleries, pubs and beautiful brownstones, Newberry Street is the place for great shopping, the Back Bay has great restaurants, the waterfront area has my favorite place for oysters and a cold one, the Public Garden is a beautiful urban oasis and you can enjoy the Charles River in any season.

The locals are passionate about their Boston sports teams and even if you are not a baseball fan, a day at Fenway is not something you will soon forget. Another passion? Believe it or not, ice cream, a topic many a Bostonian can wax philosophic upon, particularly in a pub. Best known for its Irish and Italian populations, Boston is also home to the 4th largest Asian community and a large African American population. Then, of course, there are the Boston Brahmins…what exactly do they look like?

As in many cities, the neighborhoods are distinct; Boston’s “Little Italy” in the North End, the Irish conclave in South End (also the waterfront district), Chinatownthe Back Bay, home to fashionable Newbury Street and the Beacon Hill areas and Cambridge across the River and the home of Harvard University are the most notable.

The many colleges and universities in and around Boston infuse the City with vibrancy and joie de vivre, making it a city for the young at heart. Patriot’s Day (Boston Marathon), opening day at Fenway, and St. Patrick’s Day are special events in the City and bring out old and young alike.

When To Go

Boston has plenty to offer for any season of the year. There is no bad time for a weekend visit, except perhaps with an impending snow storm in the dead of winter, but even then, the City is quite beautiful. The Boston Common and Boston Public Gardens are enjoyable throughout the year as is the Esplanade along the Charles River. In nicer weather you can boat on the Charles, enjoy outdoor concerts at the Hatch Shell, made famous by the legendary Boston Pops or while away a balmy day in one of the many pubs and restaurants with outdoor sidewalk seating. In the colder weather, you are greeted with a roaring fire in many pubs and restaurants, you can skate in the Commons and a walk through the Public Gardens after a snowfall can be quite magical.

Getting There

Boston is accessible by air from anywhere in the country and the Boston airport is a short cab ride or water taxi into the City. New York to Boston is a 3 hour and 45 minute drive, 4 hours and 15 minutes from Philadelphia. It can also be reached from most major cities on the East Coast by Amtrak. New York to Boston on the Accela Express is about a 3 1/2 hour trip and Washington to Boston is about 6 1/2 hours.

Getting Around

Boston is a fairly contained City with many activities within walking distance. Taxis and Uber are plentiful and the MTA is an excellent public transportation system. No car is needed and frankly, parking is an issue.

Things To Do

World class art and historical museums, wonderful jogging and walking routes, boating on the Charles River, ice skating in the Boston Commons, picnics in the Public Gardens, outdoor concerts at the Hatch Shell, sidewalk bistros, a wonderfully preserved “Little Italy”, Broadway road company theater, Colonial era historical sites (remember Paul Revere?), upscale shopping and oh yes, the best baseball park in the country are just a sampling of what Boston offers. It has everything a major city should have, but with its own unique character and flavor. Somehow Boston just seems so much more manageable than other major cities. Best of all, most major attractions are within walking distance of each other.


My favorite places are the Boston Common and Boston Public Gardens followed by the Esplanade, across Storrow Dr. along the Charles River. Beautiful in any season.

Another way to get some exercise and a bit of history is to follow the 2.5 mile Freedom Trail, marked by a red line on the sidewalk. It includes 16 historical sites of early American history.


Urban Adventours, 103 Atlantic Ave. will rent you a bike (with a prior reservation) and deliver it to your hotel.

Boat Rentals

Charles River Canoe and Kayak, Soldier’s Field Road, by the Eliot Bridge offers canoes and kayaks for rent. Also have guided tours, ask about the moonlight tours.


Freedom Trail. One of the best ways to become acquainted with Boston and its history is the 3 mile Freedom Trail. It is a walking tour (guided or self directed) that encompasses 16 historic sites and is easily followed by the red brick line painted on the pavement. The Freedom Trail Foundation offers guided tours with guides in colonial dress and other self-directed audio tours. Old Town Trolley. We’ve had good luck with this company in other destinations. Inexpensive, very complete and you can get on and off when you want.

If you are a “foodie”, Michele Topor’s North End Market Tour is a must in Boston. The informative three hour tour provides historical insights into the North End Italian community, tips on food selection, preparation and preservation, new restaurants and tastings of many authentic foods. You’ll visit a 70 year old coffee and spice shop, an Old World candy store, an authentic pastry shop, a wine store and a salumeria in search of the best olive oil, balsamic vinegar, olives, salami, cheese, prosciutto and pasta. Michele is amazingly informative and lots of fun. Do you know why Italians eat their salads at the end of the meal? Or how to select a balsamic vinegar? You will after this tour. Another good food related tour is the Beacon Hill and Back Bay Foodie Tour.

Beer fans will love the History Tour Pub Crawl of the Freedom Trail.

Another good way to see and learn about Boston and have lots of fun doing it is to take a Boston Duck Tour. Hosted by a “ConDUCKtor”, wacky characters in costume, you’ll travel in an authentic, renovated World War II amphibious landing vehicle and learn everything you need to know about Boston before the vehicle plunges into the Charles River for a view of the City like none other.

Boston Your Way. Private tours with your own guide. Plan your own itinerary or customize one of theirs. This is sightseeing in style with real knowledgeable people. $200/hr. driving, $100/hr. walking.

Walking Boston. Recently came across a wonderful book called Walking Boston, by Robert Todd Felton and published by Wilderness Press. $13.46 at Amazon. It features 34 walking tours of Boston that you can take yourself, most 2 miles and under in length. It is a great mix of history, gossip and architectural trivia with tips on cafes, bars and nightspots. This is an opportunity to really get to know the City and its history at your own pace. Choose from familiar places like Beacon Hill and the North End to less familiar spots like Bay Village and Columbia Point. I wish every city had one of these books.

Urban Adventours offers guided bike tours of Boston from their downtown bike shop.

Baseball fans will love the tour of Fenway Park, one of baseballs most cherished venues.

Professional Sports

There are few more enjoyable pastimes than taking in a Boston Red Sox game at Fenway Park, a short distance from the heart of the City. Hockey rules at the TD Garden with the Boston Bruins and 12 time NBA champ Boston Celtics also call the TD Garden home. Sundays are reserved for the beloved “Pats”, the World Champion New England Patriots, who play at Gillette Stadium, about 45 minutes from the City.


Lots of choices from traditional art museums to science, sports, beer, historical, children’s and ethnic museums. While there are numerous museums in the City and surrounding areas, there are three you shouldn’t miss if museums are your thing; Isabella Stewart Gardner Museum, designed after a 15th century Venetian palazzo and featuring European and American art. Sundays from September to April at 1:30pm, there is a chamber music concert. $17 gets you admission to the museum and the concert. The Museum of Fine Arts is right around the corner from the Gardner housing as they say, “mummies and Monets” and the JFK Library and Museum, which is even interesting to Republicans. The Museum of Science is the home to one of the world’s largest science museums, with over 700 exhibits.


Old North Church, 193 Salem Street, where Robert Newman hung the two lanterns that started the Revolutionary War. Bunker Hill Monument, Charlestown, Granary Burying Ground, Tremont Street, (you’ll recognize many of the names here), Paul Revere House,19 North Square in the North End, USS Constitution, “Old Ironsides”, Charlestown Navy Yard. You won’t want to miss Faneuil Hall Marketplace, built in 1742 or the Boston Public Garden, America’s first public botanical garden. Take a Swan Boat ride in nice weather and ice skate in the winter.


Many of the top Broadway productions work out the kinks in Boston before heading to the Great White Way. Later, virtually every road production of every major hit finds its way to Boston. It isn’t Broadway, but as close as you will get. The hilarious whodunit play ,Shear Madness, is as Boston as the Sox. Worth the trip.

The Arts

The Boston Symphony Orchestra plays from September to May and the Boston Pops from May to July 4th. Performances. Another Boston cultural favorite is the Boston Ballet.


Newberry Street is generally thought of as the place for art galleries; Krakow Witkin Gallery, 10 Newberry, International Poster Gallery, 205 Newberry, Robert Klein Gallery, 38 Newberry, Vose Galleries, 238 Newberry to name a few. However, the South End, particularly at the #450 building on Harrison Street is also coming into its own.


Outdoors concerts at the Hatch Shell on the Charles are legendary. It’s where Arthur Fiedler made the Boston Pops famous. For other concerts visit Boston Concerts.


Three primary shopping venues. Any Boston shopping list has to start with Filene’s Basement, 426 Washington Street, world renowned for upscale bargains. From there it’s on to Copley Place, a full scale urban mall, perhaps a stroll through the boutiques of Charles Street and finally to the Boston shopping mecca – Newbury Street, with its upscale shops and galleries. Some interesting shops; Pratesi fine linens, 110 Newberry, Red Wagon, unique children’s fashions, 69 Charles Street, Bromfield Pen Shop, amazing pen selection, 5 Bromfield Street, Jasmine Sola, men’s & women’s trendy clothing, 344 Newberry, Louis Boston, amazing traditional clothing for men and women, 234 Berkeley St., Flat of the Hill, 60 Charles St., interesting knickknacks.

Events & Festivals

The Boston Marathon, held in April on Patriot’s Day. Also, Harborfest, Chowderfest. Boston Arts Festival. Mid-September. Head of the Charles Regatta. Mid-October. Hundreds of thousands line the banks of the Charles for this two day rowing event which draws over 7000 athletes from around the world.

Dont Miss

  • A Sox game at Fenway
  • Boston Public Gardens
  • A stroll through Beacon Hill
  • Isabella Stewart Gardner Museum
  • Oysters, chowder and cold beer at the Union Oyster House
  • Boston Duck Tour
  • The Boston Pops at the Hatch Shell. May-July

The Best Of...

News and Resources

Smart Destinations– Discounted Sightseeing Passes. Save up to 55%.
Boston Magazine. All the “best of Boston” Winners
My Secret Boston. Uncovering the Secrets of the City.
The Boston Globe. The hometown newspaper

Food & Drink


Sonsie, 327 Newbury Street. This is a fun place, especially in the warm weather when tables spill into the street. Great music, a wonderful mahogany bar, and delicious, delicious food. Henrietta’s Table at The Charles in Cambridge has a massive all-you-can-eat buffet with just about anything you can think of to eat. Enjoy great food and live jazz at The Beehive . The Bristol at the Four Seasons offers a delightful, upscale brunch with views out over the Public Gardens. The Paramount in Beacon Hill has been serving breakfast since 1937. The Friendly Toast, Back Bay, is a local favorite.


Abe & Louie’s , 793 Boylston. Wonderful steak house. Fireplace. Sidewalk dining. Booths. Perfect place to while away an afternoon. B&G Oysters . 550 Tremont. Owned by the people of No. 9 Park. Delightful white wine list. Oysters, of course and the Lobster Roll is the best in Boston, maybe anywhere. Also try the Lobster BLT. We love Toscano’s in Beacon hill. Excellent Italian food, warm, clubby interior and sidewalk dining in nice weather. Just want some chowdah, shrimp and cold beer? Head to Union Oyster House. Great burger? Mr. Bartley’s below in Cambridge.


Mr. Bartley’s Burger Cottage , 1246 Massachusetts Ave. Cambridge. You dine on communal pine tables, it’s crowded and loud, but oh, those burgers. Absolutely worth the trip to Cambridge. 30 different types like the John Kerry, “only flipped once”, or the Ted Kennedy, “a plump and liberal burger”, or the Dick Chaney, “only a heartbeat away”. Award winning frappes and onion rings. I can’t wait to go back. Cash only.

They only make 18 per night and only serve it at the bar but the burger at Craigie on Main is a half-pound patty made with brisket, short rib, bone marrow, and suet and is to die for.

Ice Cream

Bostonians are almost as crazed about their ice cream as they are about the Sox. There’s an on-going debate as to who makes the best ice cream. Many pick Steve’s, the guy who invented adding things like heath bars and oreos to ice cream, located at Faneuil Hall. Or try Christina’s in Cambridge, specially if you are going to Mr. Bartley’s for a burger.

Oyster, Lobster Roll, Chowder and Fried Clams

When you come to Boston, these are staples. Here are the best places to enjoy them.  Union Oyster House , been around since 1826. Love sitting at the Union Bar and talking to the locals. Acclaimed chef Barbara Lynch’s B&G Oyster, puts her stamp on the favorites. Jeremy Sewall’s Island Creek Oyster Bar  serves their chowder with house-cured bacon, and buttermilk biscuit-croutons.

Wine Bar

Troquet is more of a restaurant than wine bar, but it was voted one of America’s top 100 wine restaurants. Fantastic selection. haley.henry. Boston magazine’s “Best Wine Bar”. James Beard semi-finalist “Outstanding Wine Program”. natural wines. Cat Silirie’s award-winning wine list is worth the trip to No. 9 Park. Bar Boulud is celebrity chef Daniel Boulud’s wine bar featuring an amazing selection of French Burgundy and Rhone wines.


12+ year “Best of Boston” Winner, Grill 23 & Bar ,  reigns as king of the Boston steakhouses. Their 100-day aged prime ribeye “hits all the right notes: a deftly charred salty crust, deep/rich flavor, and tender “you can cut it with a fork” meat.” A creative menu, a fireplace, outdoor seating and wonderful booths that remind me of the old Hollywood restaurants, make  Abe & Louie’s , a very close second.


Universal praise for Neptune Oyster. Love the swordfish here. Great raw bar. Legal Seafood is a chain, originated in Boston, but it garners rave reviews for its seafood. Legal Harborside is a fantastic waterfront venue. Their raw bar offers 14 kinds of oysters.


Try a chilled glass filled with cucumber organic vodka, blackberries, lemon juice and a champagne float at City Bar in the Lenox. Or, the Cucumelon Martini, a haute summer sizzler made with cucumber vodka, watermelon puree and mint at 75 Chestnut in Beacon Hill.

Top of the Hub , 800 Boylston Street, at sunset. 52 stories up with panoramic views of the City. Whew! The Living Room , Nude abstracts, comfortable sofas, fireplace stoves and good appys. The Oak Long Bar at the Copley Plaza, 138 James Avenue. Dark, cavernous, sexy and elegant. Last visit, there was a line waiting to get in on a Saturday night. The Bristol Lounge at the Four Seasons Hotel, 200 Boylston Street. Sophisticated and stylish overlooking the Public Garden. Fireplace and intimate nooks Roof Top Pool  Known locally as RTP. Colonnade Hotel. One of Boston’s “hot” spots Memorial Day-Labor Day. 11 stories up with great views of the City. Eastern Standard offers great cocktails, a very reasonably priced wine list and an excellent beer selection. Down an alley and an unmarked hallway you’ll find Backbar, one of the worst kept secrets in Boston for amazing cocktails.

Irish Pub

There are certainly more authentic Irish pubs than the Black Rose , but I’ve been stopping here for years to hoist a Guinness and listen to Irish bands. Critics claim there are too many fanny pack tourists, but let them complain.


Afternoon Delight

Union Oyster House. 41 Union Street in the Quincy Market area. America’s oldest restaurant. I love to go here in the afternoon, sit at the horseshoe shaped oyster bar, have some chowder, eat some oysters, drink a couple of cold beers and talk to the locals. The cheeses, charcuterie and pizzas are amazing at The Salty Pig.

After Dinner Fun

Lots of cultural things to do (See Things to Do) and there’s the wonderful Sheer Madness play. But if you’re not feeling “cultural” try these great spots. Dolce Vita, (North End).This is my favorite spot in the North End for dessert or a drink after dinner. It has a small but stylish bar, an amazing dessert list and its exuberant owner Franco Graceffa and two friends stroll the restaurant charming guests with wonderful songs from Italy. Regattabar at the Charles Hotel, THE hot spot, in a very cool room, for the great jazz. Big names. Sculler’s Jazz Club . Voted “Best Live Music Venue” and “Best First Date Spot”. 200 seat theater. Intimate and fun. Top of the Hub , top floor of the Prudential Building. Best view of the City. Dance to live jazz bands.

There’s dancing at Howl at the Moon, sing-along piano bar at D’s Keys and comedy at Improv Boston

Picnic Fixins

Deluca’s, 11 Charles Street. Old time neighborhood store that has just about anything you may want, including caviar! It’s fun just to walk around the store to see what they have.

Liquor/Wine Store

V. Cirace & Son, 173 North Street, North End. Quaint and charming, this has been a family business for 97 years. The best selection of Italian wines, aperitifs and digestives I have ever seen. A really fun place to shop for hard to get items.

Tourist Trap

Can there be a “best” tourist trap? If so, it’s Fanueil Hall/Quincy Market in Boston Shops, pubs, kiosks. Guess you have to stop here, but promise you’ll only go once. It’s certainly not tacky, just very touristy and overpriced. The best thing about it is you are only a block from the Union Oyster House.

Swimming Hole

Roof Top Pool. Atop the Colonnade Hotel. $25pp/day. Cocktails and lunch. Memorial Day-Labor Day. After Friday, supposed to be just for hotel guests, but it’s worth a try.

Special Things

A Picnic in the Gardens

Stop in at Deluca’s, 11 Charles Street, pick up some bread, cheese and wine or perhaps a sandwich or salad and head across the street to the Boston Public Garden. Pick a spot next to the pond and enjoy a romantic picnic in the center of a city.

A Trip To Venice

Weather permitting, a sunset ride on an authentic gondola on the Charles is the stuff of dreams. The Gondola di Venezia covers the section from the Hatch Shell to the Harvard Bridge, one of the prettiest on the river.

Skating on the Common

On a cold winter day, head over to the Frog Pond at the Boston Common and enjoy a few hours on the ice. Then walk down Charles Street to Chestnut and a wonderful little bar at 75 Chestnut for a warm drink.

A Visit to the Vineyard

If you are planning a 3 day weekend (Friday-Monday), a trip to Martha’s Vineyard would be a spectacular end to your romantic weekend. On Sunday afternoon, drive down to Woods Hole on the Cape (about an hour and a half), take the ferry to the island, it’s about an hour trip, stay at the Charlotte Inn ask for Rm #14. This will be magical evening.

Take a Trip to Salem

About 35 minutes north of Boston is the historical town of Salem, known for the infamous Salem Witch Trials of 1692. The town figured prominently in Arthur Miller’s book The Crucible. While much of what is to do here revolves around “witchcraft”, there is much history here and there is also a vibrant downtown with more than 60 restaurants.

Where To Stay

Boston Harbor Hotel

OVERVIEW of Boston Harbor Hotel

With spectacular harbor views, excellent service, an award winning restaurant and a wonderful outdoor entertainment arena, it is no wonder the Boston Harbor Hotel is a favorite of many travelers, myself included. This is not a cookie cutter chain hotel. It…

View Property Details

Eliot Hotel

OVERVIEW of the Eliot Hotel

Privately owned and operated by the Ullian family, the The Eliot Hotel,  is a stone building with green awnings and an ornate iron entry portico that suggests an exquisite European hideaway. Ideally located in the heart of the Back Bay, the hotel is only steps away from Newbury Street…

View Property Details

Lenox Hotel

OVERVIEW of The Lenox Hotel

Originally built in 1900, The Lenox Hotel, was the first "boutique" hotel in Boston and has a fascinating history. Legendary tenor Enrico Caruso arrived on his private train, Ali McGraw and Ryan O’Neal stayed here while filming Love Story and Tony…

View Property Details

Mandarin Oriental

OVERVIEW of the Mandarin Oriental

Handmade furniture, carpeting and original artwork grace the lobby while a fireplace adds warmth and coziness. Located in the Back Bay area on Boylston Street and connected to the Prudential Center, the location is ideal for both business and pleasure travelers. With…

View Property Details

The Charles Hotel, Cambridge

OVERVIEW of The Charles Hotel

For charm, history, and atmosphere, Harvard Square in Cambridge has few rivals – and it is right outside your door at The Charles Hotel. Boasting a unique collection of bookstores, museums, cafes, restaurants and boutiques, the square draws an eclectic blend of View Property Details

The Liberty Hotel

OVERVIEW of The Liberty Hotel

The Liberty Hotel, is ideally located in my favorite part of town, Beacon Hill, just steps from the cafes and boutiques of Charles Street. The 298 room hotel is the former Charles Street Jail and carries the jail theme throughout the…

View Property Details

XV Beacon


Generally the description “hip and trendy” for a hotel translates into a minimalist, ultra modern décor that has about as much warmth as, well, a glass and chrome table. XV Beacon manages to be hip and trendy without succumbing to that styling found in so many boutique hotels, particularly in…

View Property Details
Page 1 Page 2

Where To Eat

Bar Boulud

There are few chefs as accomplished as Daniel Boulud. The author of eight cookbooks and the recipient of multiple James Beard Foundation awards including “Outstanding Chef” and “Outstanding Restaurateur,” chef Boulud has also been named a Chevalier de la Légion d’Honneur by the French government. He is chef-owner of restaurants around the globe including the…

View Restaurant Details >

Gaslight Brasserie du Coin

Gaslight, Brasserie du Coin is a wonderful reproduction of a classic neighborhood Parisian brasserie. A hand crafted Parisian zinc bar, reclaimed wood floors, mosaic tiles, beamed wood ceilings and antique mirrors create a warm and comfortable setting. Guests can dine at the bar, at cafe tables, at communal tables and in booths and banquettes. When…

View Restaurant Details >

Mamma Maria

Set in an old townhouse and tucked into a corner of the North End, Mamma Maria is one of my favorite Italian restaurants, in a town of excellent Italian food. I like everything about this place; it's location on a square, its elegant decor and small, intimate dining rooms, its welcoming spirit and its wonderful…

View Restaurant Details >


Menton is that rare opportunity to experience the culinary mastery of one of America's best chefs in Barbara Lynch and the brilliance of its Wine Director, Cat Silirie. Lynch is a James Beard Award winner, has won the coveted AAA Five Diamond award and Forbes Five Star award for Menton. The Boston Globe gave the…

View Restaurant Details >

No. 9 Park

Located in a townhouse in Beacon Hill, just across from the Boston Commons, No. 9 Park is on just about everyone's list of favorites. It is a small (@16 tables) and intimate spot with wonderful food and wine and near perfect service. The restaurant and Chef/Owner Barbara Lynch have been awarded numerous accolades over the…

View Restaurant Details >

Toscano Beacon Hill

Few restaurants can offer both the feel and the food of the Tuscan countryside as well as Toscano on Beacon Hill. Century-old walnut floors, Italian stone walls, hand-carved doors, and masterfully painted chandeliers create a warm and inviting atmosphere that transport you to the hills of Tuscany. In the warmer months the restaurant spills out…

View Restaurant Details >

Troquet on South

Troquet on South combines three of my favorite things in a restaurant; ambiance, wine (an extraordinary wine program) and excellent food. Let's start with the wine because that is what sets Troquet apart from other restaurants. Troquet on South is acclaimed for offering rare and hard-to-find wines at reasonable price points. There are some 45…

View Restaurant Details >
Page 1 Page 2

Advance Search

Use our handy tool to search for the perfect weekend with all the features you prefer. Search by accomodation type, recognition, geography, amenity and more. Search now!

The Wow Factor

Join and get FREE access to The Wow Factor - 25 of the Most Spectacular Ins in America Click here to Sign Up. Aready a member? View the Book by clicking here.

Notes From the Road

Hear about our latest discoveries
before anyone else!