The Ultimate 14D USA East Coast Itinerary for First Timers!

This is our ultimate 14 Day USA East Coast Itinerary for first timers! It will be helpful if you want to explore the East Coast in around two weeks. For the unfamiliar, the “East Coast” refers to the eastern USA states that borders the North Atlantic Ocean.

This USA East Coast itinerary is a culmination of 20 months of research! Previously, I focused mainly on writing travel guides for the individual USA states. This article is a combination of all the individual guides into one ultimate itinerary. The itinerary also includes a few Canadian cities near the East Coast. We enjoyed our USA holiday very much and I hope you will have as much fun as we did!

Day 1: Singapore to New York
Day 2: Boston
Day 3: Boston
Day 4: Quebec City
Day 5: Quebec City
Day 6: Montreal
Day 7: Toronto
Day 8: Toronto
Day 9: Washington
Day 10: Philadelphia
Day 11: New York
Day 12: New York
Day 13: New York
Day 14: New York to Singapore

Day 1 Singapore to New York

We arrived at Changi Airport excited to begin our USA East Coast adventure! For our trip this time, we managed to book the fabled Singapore Airlines Suites Class seats. Therefore, we went to the airport early to chill out first at The Private Room, an exclusive lounge for SQ Suites / First Class passengers. After enjoying the lounge for a few hours, we proceeded to the boarding area for our long flight to New York City.

Day 2 Boston

Quincy Market

After the flight of our lives, we arrived in the morning at New York’s JFK Airport. We waited at the airport for a short while before catching an afternoon flight to Boston. We arrived at Boston in the evening and checked in at The Bostonian Boston, a charming boutique hotel located in North End.

After washing up, we went for a late dinner at Quincy Market, a food hall that is quite popular with tourists. After dinner, we went back to the hotel and crashed in our comfy beds.

Day 3 Boston

“Equestrian Statue of George Washington” in Boston Public Garden 

We woke up the next morning ready to explore Boston! This quaint city has many well-known historical landmarks and beautiful historic buildings. There is an intellectual vibe to it too because it is near top universities like Harvard and MIT.

For breakfast, we went to Café Luna, a cozy cafe that serves a variety of comfort food such as waffles, panini, sandwiches and salads.

After breakfast, we made our way to Harvard University. It felt surreal to stroll around the compounds of this elite university. We went to nearby Harvard Square (a public plaza) to grab a quick lunch.

Following that, we made our way back to Newbury Street, a mile-long thoroughfare with many restaurants and shops housed in beautiful historic brownstone buildings. Over here, we saw the Church of the Covenant, a historic church built in the Gothic Revival architectural style.

We also dropped by Boston Public Library, where we checked out the famous Bates Hall with its iconic green lamps and high barrel-arched ceiling.

Next, we spent about an hour strolling in Boston Common and Public Garden, two beautiful public parks that are adjacent to each other.

After that, we explored North End, a quaint district known for its historic buildings and Italian restaurants.

For dinner, we went to The Daily Catch in the North End. This homely Italian bistro is known for its delicious “Sicilian-Style” seafood and pasta dishes. After dinner, we went to the super popular Mike’s Pastry to grab some delicious Italian cannoli.

Read more: 

• The Ultimate Boston Travel Guide for First Timers
• 10 Best Things to do in Boston for First Timers
• 12 Awesome Places to Eat in Boston for First Timers

Day 4 Quebec City

Quartier Petit Champlain

Fairmont Le Château Frontenac

My proposal at La Terrasse Saint Denis!

We woke up super early today to catch our flight to Quebec City. This was one of the most beautiful cities we have ever visited. Walking along the cobblestoned streets lined with charming old world buildings, it felt like we were in a quaint European town.

We arrived at the city in the afternoon and checked in at Le Saint Pierre Auberge Distinctive, a lovely boutique hotel located in Old Quebec.

After washing up, we went for lunch at BeaverTails in the Old Quebec district. This Canadian pastry chain is known for its delicious fried dough pastries.

Having satisfied our tummies, we began our exploration of Old Quebec. First, we went to Quartier Petit Champlain, a picture-perfect neighbourhood with beautiful European architecture and cobblestoned pavements. This vibrant district is lined with plenty of shops and restaurants.

After that, we checked out the world famous Fairmont Le Château Frontenac, a Fairmont luxury hotel built in the French Renaissance Château Style. It was gorgeous and looked like a castle from a fairy tale!

Next, we went to Terrasse Dufferin (Dufferin Terrace), a beautiful wooden walkway below Chateau Frontenac. This was a great place to take a stroll while enjoying views of the St. Lawrence River.

From the terrace, we walked uphill to the La Terrasse Saint Denis (The Saint Denis Terrace), a beautiful small terrace with breathtaking views of the Saint Lawrence River and Chateau Frontenac. This is a special place to us because it is where I proposed to Raevian!

By now, we were famished. We went for dinner at Le Chic Shack, a family-friendly restaurant that serves burgers, poutines and salads.

Day 5 Quebec City

Place Royale

Place d’Youville

We woke up early today for breakfast at the La Maison Smith Cafe in Place Royale. We sat at a table by the window to watch the falling snow while enjoying our macarons and hot chocolate.

After that, we explored Place Royale for a short while. This was the site of the first French settlement in 1608. Notre Dame des Victoires Church (Our Lady of Victories Church), the oldest stone church in North America (built in 1688), is located here.

Next, we went to the famous La Citadelle de Quebec, a historic military base at the top of Cape Diamond. There is a museum here and museum visitors get access to see the Changing of the Guard and Beating of the Retreat ceremonies. Guided tours are available too. You can check out the La Citadelle de Quebec museum opening hours and ticket prices.

From the citadel, we walked to nearby Battlefields Park. This beautiful park consists of the Plains of Abraham and Des Braves Park. It is known for being the site of the 1759 “Battle of the Plains of Abraham”, where the British forces defeated the French forces and altered the course of Canada’s history.

We went for a late lunch at Chez Aston, a Canadian fast food chain known for its delicious poutine. After that, we strolled along Grande Allée, a vibrant thoroughfare with clubs, bistros and bars.

Walking down the street, we reached the Parliament Building, home of the Quebec Parliament. We saw the Fontaine de Tourny in front of the building, which has 43 water jets along with beautiful sculpted figures.

From here, we walked for about ten minutes to Place d’Youville. This beautiful public square has a public ice skating rink and is surrounded by charming old world buildings. We visited during Christmas and the place looked magical!

For dinner, we went to il Matto, an upscale Italian restaurant located near our hotel. We enjoyed our meal here very much. The setting was classy without being pretentious, and service was quite good too.

Read more: 

• The Ultimate Quebec City Travel Guide
• 17 Awesome Things to Do in Quebec City
• 6 Awesome Places to Eat in Quebec City

Day 6 Montreal

Bonsecours Market

Basilique Notre-Dame de Montréal

Today, we caught the Via Rail morning train to Montreal, a vibrant French-speaking city in Canada. The city exudes an old world charm with its historic buildings and quaint cobblestone streets. Montreal is also famous for hosting many major festivals, such as the world-renowned Montreal Jazz Festival.

We arrived in the city at around noon and checked in at our Airbnb, the “La Dany” Luxury Old Port Boutique Apartment owned by Paige (a Montreal local).

After washing up, we headed out for lunch at Olive & Gourmando, a popular cafe known for its delicious sandwiches, pastries, and other brunch items.

After lunch, we walked along the beautiful cobblestoned Rue Saint-Paul (Saint Paul Street) to Basilique Notre-Dame de Montréal, a historic basilica with a gorgeous resplendent interior. We stood still in the church for a few minutes just to fully appreciate the captivating beauty of the church.

We left the basilica and continued walking along Saint Paul Street to Place Jacques-Cartier, a public square with many cafes, restaurants and shops.

From the square, we walked about three minutes down the street to check out Bonsecours Market. This is a beautiful historic building that was constructed in 1847 in the Palladian style. It is supposed to be a public “market” but we only saw some souvenir shops and restaurants inside.

After taking a few quick pictures, we made our way to the nearby Old Port. This historic port is located along the St-Lawrence River and is known for its many fun waterfront activities. There is even a Science Centre, an IMAX Theatre, and a ferris wheel.

We went for an early dinner at at L’Usine de Spaghetti, a quaint Italian restaurant that serves delicious Italian food in a tavern-like space. It is located along Saint Paul Street, beside Place Jacques-Cartier which we visited earlier.

Read more: 

• The Ultimate Montreal Travel Guide for First Timers
• 12 Best Things to Do in Montreal for First Time Visitors
• 4 Best Places to Eat in Montreal for First Time Visitors

Day 7 Toronto

CN Tower

Raevian doing the thrilling EdgeWalk!

Graffiti Alley

We woke up early in the morning to catch our Via Rail train to Toronto. This dynamic city is home to many world famous attractions, such as the majestic Niagara Falls, CN Tower (one of the modern Seven Wonders of the World), and others.

We arrived at around noon and checked in at the Four Seasons Hotel Toronto, a classy five-star hotel with super comfortable rooms. We then went for lunch at Sunset Grill in the Entertainment District. This is a greasy spoon that serves American-style dishes (pancakes, bacon, eggs, etc) at very affordable prices.

Next, we began our exploration of the vibrant Entertainment District, an entertainment hub that is home to many tourist attractions, restaurants, sports venues, performing arts centres and more. The most famous and iconic attraction here is the CN Tower, a concrete communications tower that stands at over 500 metres tall. Raevian even did the thrilling Edgewalk at the top of the tower during her previous trip here!

After that, we grabbed a quick bite at the Wilbur Mexicana, a Mexican restaurant known for its super delicious tacos. And since we are gluttons, we had another fried chicken burger at Porchetta & Co. just across the street.

From the sandwich joint, we walked to Queen Street West, a vibrant street with many chic boutiques, galleries, and eateries. We also took many Instagram-worthy photos at nearby Graffiti Alley, a short alley with plenty of graffiti murals on the walls.

By now it was early evening and we walked around the bustling Chinatown. We saw many Chinese herbal remedy shops, restaurants and fresh produce shops in this colourful neighbourhood. After that, we had a dim sum dinner at Rol San, a Chinese restaurant that serves all day dim sum.

Day 8 Toronto

Niagara Falls!

We woke up early today feeling really excited because we were going to visit Niagara Falls! We had signed up for a day tour package with Niagara Day Tour, and the shuttle bus picked us up at around 8am. The bus ride took about 1.5 hours.

The majestic waterfalls were everything I had imagined it to be, and more! I was blown away by the massive amount of cascading waters, which was both gorgeous and awe-inspiring at the same time. Our day tour package included a ride on the famed Hornblower Niagara Cruise, which brought us up close to the waterfalls where we REALLY got a sense of its immense power. Needless to say, we both got drenched!

We arrived back in Downtown Toronto in the evening and went for dinner at PAI, a popular Northern Thai cuisine restaurant. After a long day, it felt wonderful to indulge in a steaming bowl of Tom Yum soup.

After dinner, we went to Sweet Jesus, a popular ice cream shop just down the street. We waited for about twenty minutes before getting our hands on a delicious chocolate ice cream.

Read more: 

• The Ultimate Toronto (Canada) Travel Guide for First Timers
• 12 Best Things to Do in Toronto for First-Timers
• 12 Best Places to Eat in Toronto for First Timers

Day 9 Washington DC

Lincoln Memorial

Abraham Lincoln Statue

We caught an early morning flight to Washington DC today. We had to include this city in our East Coast itinerary because firstly, it is the capital of the United States. Secondly, it has many iconic federal buildings, monuments, and world famous Smithsonian museums.

We arrived at DC around early noon and checked in at the Kimpton George Hotel, a contemporary boutique hotel that offers stylish and modern rooms at great prices.

After washing up, we left the hotel to begin our exploration of the National Mall district. First, we went to the Supreme Court of the United States, which houses the judicial branch of the US government, which is responsible for interpreting US laws. Next, we checked out the United States Capitol which is just across the street. This neoclassical structure houses the US Congress and legislative branch, which is responsible for creating US laws. We also visited the nearby Library of Congress ,which is the US national library.

From the Library of Congress, we made our way to the National Air and Space Museum, a super cool Smithsonian museum with an extensive exhibition of original production (or original backup) spacecrafts and aircrafts. We also went to the National Museum of Natural History, a Smithsonian museum with a massive collection (126 million) of natural history specimens. However, I was most excited to check out the giant dinosaur skeletons.

Leaving the museum, we went to have a quick bite at the Old Ebbitt Grill, a popular DC restaurant that serves a variety of Western meals in a tavern-like space.

After the meal, we went to the White House, home of the US President. This building also houses the US government’s executive branch, responsible for enforcing laws (its power is vested in the President). It felt surreal to finally see this iconic US building in real life!

Next, we walked to the Washington Monument, a huge obelisk that stands at about 170 metres tall. It was built to commemorates George Washington, the first US President.

From the monument, we walked about 15 minutes to the Lincoln Memorial. This majestic monument was built in honour of Abraham Lincoln, the 16th US President. Built in the style of a Greek Doric temple, it looked really beautiful when we visited it in the evening. I was equally impressed by the large Abraham Lincoln statue inside, which was imposing and awe-inspiring at the same time.

By now, it was getting late so we took a Lyft ride to the Jefferson Memorial. This beautiful monument commemorate Thomas Jefferson, an American Founding Father who was the principal author of the Declaration of Independence and also third US President.

Read more: 

• The Ultimate Washington DC Travel Guide for First Timers
• 11 Best Things to Do in Washington DC for First-Time Visitors

Day 10 Philadelphia

Liberty Bell

Evan and Rocky Statue

Fairmount Water Works

Pat’s King of Steaks

We caught the morning Amtrak train to Philadelphia today. Philly is a city that is rich in culture and historical heritage. We saw plenty of national landmarks and famous art museums here.

We arrived in the late morning and checked in at the Hotel Sofitel Philadelphia, a semi-luxury hotel with very comfortable rooms.

After washing up quickly, we set out to explore the Historic District. First, we went to the Independence Hall, commonly known as the birthplace of the US. We also bought tickets for an interesting guided tour of the building. Next, we went to the Liberty Bell Center, home to the famous Liberty Bell. Legend has it that the bell was rung on 4th July 1776 to announce the signing of the Declaration of Independence (though this story is disputed).

After that, we went to grab a cheesesteak at the famous Pat’s King of Steaks in South Street. This famous cheesesteak joint is known for its rivalry with opposite Geno’s Steaks. We only tried the one at Pat’s which was quite delicious.

From South Street, we took a Lyft ride to Rittenhouse Square, a small public park surrounded by chic restaurants and elegant boutiques. After exploring the park for a short while, we had an al fresco meal at Parc, a casual french-style bistro.

After the satisfying meal, we took another Lyft ride to the Philadelphia Museum of Art, a large museum with over 240,000 art pieces. However, the main reason we came here was to see the famous Rocky Statue and Rocky Steps! I posed with the Rocky sculpture for several photos, with both my arms held up in victory (like Rocky).

From here, we walked about ten minutes to the beautiful Fairmount Water Works. This neoclassical structure was once Philadelphia’s public water supply center but has ceased operation since 1909. We saw many people strolling and jogging in the surrounding park area.

For dinner, we went back to Pietro’s Coal Oven Pizzeria, a classy pizza joint located near Rittenhouse Square.

Read more: 

• The Ultimate Philadelphia Travel Guide for First Timers
• 15 Best Things to Do in Philadelphia for First Time Visitors
• 9 Best Places to Eat in Philly for First Time Visitors

Day 11 New York (Times Square and Downtown Manhattan)

Times Square!

Charging Bull Sculpture

Fearless Girl Sculpture

Staten Island Ferry

We caught an early Amtrak train today to New York City. We fell in love with the Big Apple after our first visit because this is an exciting city bustling with irrepressible energy. This city has a captivating allure that is hard to put in words.

We arrived at New York in the morning and checked in at Bryant Park Hotel, a luxury boutique hotel with awesome rooms, great service and a fantastic location.

After washing up quickly, we went to the world famous Times Square in Midtown Manhattan. It felt surreal to finally visit this iconic attraction of New York! We were dazzled by the many bright billboards and neon lights here.

After that, we dropped by the popular Burger & Lobster (Bryant Park) for lunch. This popular New York bistro serves just three items: Burgers, Lobsters, and Lobster Rolls.

From Bryant Park, we took the subway to Wall Street in Downtown Manhattan. This is probably the most famous financial district in the world!

We began our exploration of Wall Street by alighting at the Cortlandt Street Station. We exited the station to visit the National September 11 Memorial & Museum, which commemorates the victims of the 911 attacks. We saw the victims’ names inscribed on the parapets around the two majestic man-made waterfalls. These are built directly on the former sites of the former World Trade Twin Towers.

Next, we walked to the Trinity Church. This is a special church because it served as a place of refuge and rest for the rescue force during the 911 attacks aftermath. The interior is spectacular and designed in the Gothic Revival style.

From the church, we walked for a short while to the renowned New York Stock Exchange, which is the world’s largest stock exchange. I managed to take a photo with the building’s impressive facade of six imposing marble Corinthian columns.

Next, we went to check out the famous Charging Bull Statue, which was installed following the 1987 stock market crash to symbolise the resilience of the American people. This was one of the attractions that we were most looking forward to seeing!

We also took photos with the very popular Fearless Girl Statue, which stands directly opposite the Charging bull, “staring defiantly” at it.

After that, we went to nearby Battery Park. This urban park has many memorials, and is home to the stately Castle Clinton, a military fort built in the early 19th century.

By now, it was nearing sunset and we quickly went to catch the Staten Island Ferry. This is a free ferry ride between Manhattan and Staten Island that takes about 25 minutes each way. From the ferry, we got awesome views of the Statue of Liberty and Manhattan skyline.

After getting off the ferry, we walk for five minutes to the Stone Street Historic District, an area lined with historic brick buildings housing popular restaurants and bars. This place has an untouched vintage charm due to deliberate urban planning.

By now, we were famished and quickly went for dinner at Luke Lobster FiDi (located in the Stone Street area). The lobster rolls here were delicious!

Day 12 New York (Woodbury Commons and Koreatown)

Shopping at Woodbury Common Premium Outlets!

Today was a happy day for Raevian because we were going to spend an entire day at Woodbury Common Premium Outlets! This is a huge retail hub near New York City with over 200 outlet stores.

This is a super convenient place to shop because all the brands are located literally next to each other. And best of all, the outlets offer massive discounts. It is not surprising to find discounts of up to 50% compared to normal retail stores.The discounts can be even more during festive periods like New Year or Christmas.

After an entire day of shopping, we returned to our hotel tired but happy with our loot (two luggage worth). For dinner, we went to Kang Ho Dong Baekjeong in the vibrant Koreatown for a sumptuous Korean BBQ meal.

Day 13 New York (Midtown Manhattan, Central Park)

View from Top of The Rock

Taken at Top of The Rock

Central Park’s “Sheep Meadow”

Central Park’s “The Lake”

We woke up early today for breakfast at Le Pain Quotidien, an international bakery-restaurant chain. We went to the Bryant Park outlet which was very near our hotel.

The reason we woke up so early today was because we were going to Top of The Rock (TOTR), an observatory perched atop 30 Rockefeller Plaza, and we wanted to avoid the crowd. From up here, we got amazing views of the Manhattan skyline, Central Park, and the Empire State Building! You can click here to get tickets.

After coming down from the observatory, we began our exploration of Midtown Manhattan! We checked out the famous Rockefeller Center for a short while. This huge complex consists of 19 buildings owned by the powerful Rockefeller family. The centrepiece of the complex is the 30 Rockefeller Plaza. We took many photos of this iconic building as well as the Prometheus statue in front of it. As we visited during the Christmas period, we got to see The Rockefeller Center Christmas Tree and the seasonal ice skating rink.

We also came across the famous Radio City Music Hall, home of the precision dance group The Rockettes. Unfortunately, we did not manage to get tickets for The Radio City Christmas Spectacular, an annual Christmas performance by the Rockettes. This was one of the regrets of our trip.

From Rockefeller Centre, we walked down Fifth Avenue, a famous shopping street with many mid-market brands and luxury boutiques.

We took a short break at the Momofuku Milk Bar, known for its unique cereal-flavour treats. We ordered a delicious Cereal Milk Soft Serve. It is just down the street from the famous Trump Tower.

After that, we did some quick window shopping at Madison Avenue, a high end shopping district with many luxury boutiques.

Next, we spent about two hours strolling in the scenic Central Park. This gorgeous urban park is located right in the middle of Manhattan. It is filled with lush greenery, tranquil lakes, running tracks, ice-skating rinks, and many popular attractions.

For lunch, we went to Friedmans, a bistro that serves American comfort food. This Theater District outlet is located inside Hotel Edison. We came here mainly because of the famous Fried Chicken & Cheddar Waffle.

After the very satisfying meal, we went to check out the beautiful Grand Central Terminal, a railroad terminal that is intricately designed both externally and internally. It is designated as a U.S. National Historic Landmark.

From the terminal, we walked a little further down the street to get a good photo of the Chrysler Building, an iconic skyscraper built in the Art Deco style.

After that, we went to check out the most famous building in New York, the world renowned Empire State Building! This art deco building was the tallest in the world between 1931 and 1970. It was surreal to finally see this iconic New York building.

We walked further down the street to check out the Flatiron Building, a historic building known for its unique triangular shape.

We had an early dinner at Chelsea Market, a large indoor food market popular with both locals and tourists. Over here, we indulged in the scrumptious 1.5 pound lobster from The Lobster Place!

After dinner, we quickly went back to Times Square to catch The Phantom of the Opera, a classic Broadway musical that I’ve wanted to watch since young. You can click here to get tickets. The musical had really high production value and I enjoyed it thoroughly!

Day 14 New York to Singapore (Brooklyn)

Brooklyn Bridge Park

Brooklyn Bridge

Clinton Street Baking Co. & Restaurant

We woke up feeling glum today because it was the last day of our USA trip! We went to Lady M (Bryant Park) to have some delicious Mille Crepes for breakfast.

After that, we took the subway to Brooklyn, which is one of the boroughs of New York City. The ride took just 20 minutes.

Our first stop was the Brooklyn Bridge Park, a beautiful waterfront park. We spent around an hour relaxing on the lush green field at this serene park, admiring the awesome Manhattan skyline view across the river. The park is also home to Jane’s Carousel, a glittering merry-go-round that attracts plenty of children every day.

After that, we quickly went to Juliana’s, a pizzeria famous for its super delicious coal-fired brick oven pizzas. We went early before it opened but there was already a long queue outside the restaurant!

Juliana’s is embroiled in a famous pizza feud with nearby pizza joint Grimaldi’s. We have tried both restaurants’ pizzas and our vote definitely goes to Juliana’s.

After indulging in the delicious pizza, we strolled around the surrounding trendy neighbourhood of DUMBO, which stands for “Down Under the Manhattan Bridge Overpass”. We saw many old warehouses, boutiques, eateries, and galleries.

We also took the iconic photo of Manhattan Bridge from Washington Street, which is the same vantage point used by countless other tourists and photographers.

And course, we had to walk across the iconic Brooklyn Bridge, a suspension bridge linking Brooklyn and Manhattan. From the bridge, we took many great photos of the beautiful bridge as well as the Manhattan skyline.

After the long walk, we were a little hungry and went to Dominisque Bakery, a renowned high-end pastry shop. It is known for being the creator of the delicious Cronut!

After eating the delicious desserts, Raevian went to do some last minute shopping in the surrounding SoHo neighbourhood. This is a popular shopping district with retail stores nestled in historic cast-iron buildings.

For dinner, we indulged in the BEST pancakes in the world at Clinton Street Baking Co. & Restaurant. We ordered the Blueberry Pancakes with Warm Maple Butter and it was seriously AMAZING. I had never tasted such delicious pancakes in my life!

Well-satiated, we went back to our hotel to collect our luggage before sadly going to the airport to catch our flight back to Singapore.

Read more: 

• The Ultimate New York City Travel Guide for First Timers
• 12 Best Things to Do in New York for First Timers
• 12 Best Places to Eat in New York for First Timers

Our USA East Coast Itinerary Map

Conclusion

Thank you for reading our 14 Day USA East Coast itinerary! We had fun in all the USA states, but our favourite was definitely New York City. We were completely charmed by the captivating allure of this vibrant city!

Unfortunately, I didn’t manage to fit Queens (a borough in New York) in the above itinerary because it is already quite tight. However, if you are able to spend one more day in New York, make sure you check out this diverse and colourful district too.

And that’s it! I spent a lot of effort and time on this article, and I sincerely hope you will find it useful in planning your own USA East Coast itinerary. Please feel free to ask any questions in the comments section below.