Day One:

Places to Stay:

Fairmont Copley Plaza

Well, we finally made it. After a year and a half delay due to a pandemic, Brenda & I finally made it to Boston. It was an easy flight from West Palm. We landed at Boston Logan International Airport on Jet Blue (my new favorite airline) and took an Uber to the Fairmont Copley Plaza Hotel. This is where we will set up camp for Three Days in Boston as we embark on the first leg of the Boston, Lobster, Lighthouse Tour.

Cori Copley, the canine ambassador greeted us as we checked in to the hotel. She is pretty famous around here.

Staying at the Fairmont Copley Plaza put us in the center of Boston in the heart of Back Bay. We were close to many of Boston’s top sights, like the Boston Public Library, and the Trinity Church which is just outside the door. The hotel is over 100 years old. The Fairmont Copley Plaza is a luxury downtown Boston hotel that has been a symbol of the city’s rich history and elegance since its opening in 1912.

The Lenox

Another great choice in the area is The Lenox Hotel. The Lenox is located on the Back Bay and steps from Copley Square, which makes it the ideal choice if you are looking for a boutique hotel experience. In fact, The Lenox is known as the original boutique hotel. When it opened in 1900 it was Boston’s tallest building.

The Lenox is a Boston landmark. Room Tip: Ask for number 423, where you’ll have views of Boylston Street and parts of Copley Square. It’s called the Judy Garland room because she lived there for three months in 1965.

Sam Lagrassa’s Famous Pastrami

Brenda and I got into Boston early and had some time to kill before check-in. We headed to Sam Lagrassa’s to get some lunch. This family-owned restaurant has been serving mountain high sandwiches since 1968. I had the Pastrami Reuben. Meats are prepared in-house and served fresh daily.  Sauces and dressings are made from scratch. I hope I can still walk around after this huge sandwich. If you want a great sandwich this is the place to go.

Boston Public Garden

If you visit Boston, you will want to spend some time strolling around the Boston Public Garden. It is one of the nicest outdoor things to do in Boston and a great way to start touring Boston. The Boston Public Garden is the oldest botanical garden in the United States. The park was opened to the public in 1838. Quiet and beautiful, it’s a great place to relax, take a walk, and enjoy a bit of peace in the midst of the hustle and bustle of the city.

The Make Way for Ducklings statues in the garden near Beacon and Charles Streets appeal to grownups and children. The duck family bronze sculptures are the most popular attraction in the Public Garden. Based on the children’s story by Robert McCluskey about Mr. and Mrs. Mallard and their adventures while finding a safe place to hatch and raise their ducklings in and around the Public Garden, the sculpture depicts Mrs. Mallard and her ducklings. On holidays and special occasions, folks dress up the ducklings. In October, it was trick or treat.

One of Boston’s largest and most impressive statues is at the Arlington Street entrance to the Boston Public Garden. This is where you will find George Washington on horseback. This statue was sculpted by local artist Thomas Ball and cast in bronze. With the flowers around it, the statue makes a great photo with the Boston skyline framed behind.

Address: 139 Tremont St, Boston

Boston Common Frog Pond Carousel

Boston Common is just across the street from the Public Gardens. This is the oldest city park in the United States founded in 1634. The park is a peaceful break from the busy city with ponds, walking paths, and even a carousel.

In addition to horses, there are fire-breathing dragons, zebras, cats, fish, and roosters. Tickets are only $3 a ride. The carousel is a charming addition to this city park.

Boston Public Library

The Boston Public Library was established in 1848 and was the first large free municipal library in the United States. It is now the second-largest library in the US, following the Library of Congress. 

In addition to being exquisitely beautiful, visitors can revel not only in the historic architecture of the building itself, from its oak bookcases to its majestic barrel-arched ceiling, but what it contains inside: first edition folios by William Shakespeare, the personal library of John Adams, Mozart’s original music scores, and an extensive collection of rare books, prints, maps, and manuscripts. The Reading Room is a must-see during your visit.

Trinity Church

Located in Back Bay, Trinity Church is Boston’s oldest and most beautiful church. It was built in the 1870s after the original church burned down in the Great Boston Fire of 1872. The overall style was dubbed Richardsonian Romanesque after the architect. The church has beautiful stained glass. Trinity Church is one of the most recognized buildings in America. It is an amazing piece of history that ushered in a new style of architecture. This historic church is open to all.

Dinner at Atlantic Fish Company

Since we were in Boston, the first dinner that came to my mind was seafood. Atlantic Fish Company was our choice for the evening. Atlantic Fish Company has been serving some of the best Boston seafood since 1978. For starters, I warmed up to a bowl of their award-winning clam chowder. The restaurant features a comfortable atmosphere with detailed woodwork and beautiful murals of the sea. After a day of walking the streets of Boston, it was good to sit down to dinner. I would suggest a reservation.

761 Boylston Street

Day Two:

Old Town Trolley Tour

Since we walked most of the day yesterday, today, we are going to tour Boston with the Old Town Trolley Tours. We decided that this was the best way to see the most in one day. We bought a 2-day ticket that will allow us to hop on and hop off at any location. Because we are staying at Copley Square, we will start our tour here.

Boston’s Beacon Hill & Acorn Street

Can you even say you went to Boston and did not visit Beacon Hill and Acorn Street? This is the cities most famous neighborhood. Beacon Hill is known for its redbrick row houses, cobblestone streets, and gas lamps. Make sure to visit Acorn Street, the most photographed street in the United States. The best time to visit is in the morning.

October is one of Boston’s prettiest months to visit. The crisp cool air and the beautiful buildings with bright-colored doorways decorated with pumpkins. These folks sure know how to decorate for fall! Do be respectful of the residents who live here. I can only imagine what it would be like to have a constant flow of strangers taking pictures of my doorway.

Breakfast at Tatte Bakery & Cafe

After getting our picture taken on Acorn Street, it was time to get a cup of coffee and something to eat. We headed over to Tatte Bakery on Charles Street. This is one of Boston’s most popular bakeries. We just wanted to get a quick and relaxing breakfast. Tatte has some amazing pastries, coffee, and breakfast sandwiches. They have an open kitchen so you can see the chefs hard at work. There have several locations in Boston.

Omni Parker House

While we didn’t stay here, we did want to peek inside the Omni Parker House. This is Boston’s oldest inn and the longest-running hotel in America. Stepping into this hotel was like stepping back in time to a bygone era. You are immersed in wood-carved walls and soft leather chairs. It’s classic luxury at its best.

The twinkling Waterford crystal chandeliers and the ornate hand-carved woodwork that welcome guests to Parker’s Restaurant serve as reminders of days long ago. This restaurant has seen some history. A lot of influential people have spent time in the hotel one way or another. Activist Malcolm X and future Vietnam leader Ho Chi Minh both worked at the hotel in years past. John F. Kennedy proposed to Jackie Onassis in the hotel restaurant. The Boston Cream Pie was invented here in 1856, as well as the famous buttery Parker House Dinner Rolls. The Boston Creme Pie (which is actually a cake) can be found all over the city as it is the official dessert of Massachusetts, but you should get it here where it was originated at The Omni Parker House.

The North End

If you close your eyes and smell pizza, you must have made it to the North End. There are over 80 Italian restaurants located along the beautiful North End cobblestone streets, so you’re bound to find something that appeals to your appetite.

Carmelina’s (Dinner)

We wrapped up the day in Boston with a stroll down Hanover Street and dinner at one of the best Italian Restaurants. Carmelina’s is located in the heart of Boston’s North End and serves Italian comfort food at its best.

I had the Bronx Tale which is Mimmo’s meatballs and Sulmona sausage, slow-cooked tomato sauce, tossed with rigatoni.

We sat out on the patio but the restaurant has a comfortable dining room and an open kitchen with the sounds of the chefs cooking. Dessert? Forget about it. We will have to head over to Mike’s for a cannoli.

Mike’s or Modern Bakery (Dessert)

Mike’s or Modern Pastry? Decisions Decisions. These are choices that you will have to make when you are looking for that perfect cannoli. Many locals say, don’t follow the crowds to Mike’s Pastry. You don’t need your picture taken with one of their blue boxes. Instead, head over to Modern Pastry.

Spoiler Alert! Since Mike’s was just across the street from our restaurant, we opted for Mike’s. Now, shall I get the Florentine Cannoli, the Pistachio, or the Amaretto? Decisions Decisions. I couldn’t decide so I got all three. The lines get pretty long, but they move quickly. Also, make sure you bring cash.

Giacomo’s Ristorante

Another popular choice for dinner in the North End is Giacomo’s Ristorante. There are a few things you need to know so there are no surprises. First, they do not take reservations, and there is always a line. Second, You must pay in cash. Giacomo’s has been voted Boston’s Best Italian Restaurant. The portions here are huge.

Address: 355 Hanover St, Boston

Day Three:

Shopping on Newberry Street

Boston’s most enchanting shopping street offers eight blocks filled with high-end designer shops, salons, boutiques, and fabulous dining. Newbury Street has something for everyone. Brenda spent some time shopping and making her Christmas list. Newbury Street is located in Boston’s elegant Back Bay neighborhood.

Boston’s Freedom Trail

One of the top attractions in Boston and a good way to see many historical sites in a short amount of time is to follow the Freedom Trail. This trail runs 2.5 miles through the city and is marked with a red brick path. The path leads to 16 historical sites scattered around the city. It’s an absolute must when visiting Boston for the first time. So, for our last day in Boston, we started The Freedom Trail.

Some of the attractions you will see along the trail include the Paul Revere statue at Old North Church, the Bunker Hill Monument ( where you can climb to the top), USS Constitution, Faneuil Hall (which hosted America’s first town meeting), and the Old State House. Since it is too much to include in this post, I have made a post entirely dedicated to Boston’s Freedom Trail.

New England Holocaust Memorial

Six 54-foot-tall glass towers comprise the New England Holocaust Memorial. Erected in 1995, each haunting tower is etched with numbers – the 6 million numbers represent the Holocaust’s victims, while the towers represent the six major death camps. There is also a granite path covered in quotes from survivors that leads visitors inside the towers. As you walk through the towers, you can feel the heat of the ovens coming up from the floor. Very impactful!

Dinner at The Oak Long Bar & Kitchen (Fairmont Copley Plaza)

We were so exhausted from walking the Freedom Trail that we decided that our last dinner in Boston should be at the hotel. The OAK Long Bar + Kitchen has a gorgeous 83-foot long bar, beautiful arched windows, crystal chandeliers, and oak vaulted ceilings. If you would rather eat outside, you can dine on the expanded patio with a view of Copley Square. This eatery serves up modern American cuisine made with local ingredients.

From Boston to Maine by Train – Amtrak DownEaster

We spent three days in Boston and still did not see everything we wanted to see. There is so much to do here. Do yourself a favor and make reservations where you want to eat and purchase tickets in advance of what you want to see. After spending a few hours and an Uber ride to the Isabella Stewart Gardner Museum, we arrived only to find out that it was sold out for the day. I almost lost my phone in the process after it slipped out of my pocket. Thanks to Elvis our Uber Driver for swinging back around to deliver it to us. This morning it was time to leave Boston and catch the Amtrak DownEaster for a two-hour, thirty-minute trip to Portland, Maine as we continue the Boston, Lobster, Lighthouse Tour.