Elfreth's Alley in Old City Philadelphia

I love exploring old cities – the architecture is gorgeous, the museums are fantastic, the restaurants often iconic, and there are usually a ton of free things to do. While many people think they need to book an expensive flight, there are plenty of interesting destinations in our own backyard. 2024 marks the 248th birthday of America. The National Historic Preservation Act of 1966 designated historic sites of interest as worthy of preservation. More than 80,000 buildings, districts, and objects important in American history have been designated National Historic sites.

New York comes in #1 with 275 national historic landmarks, while Massachusetts comes in number 2 with 191. From touring Independence Hall (where the nation’s most historic documents were signed), to seeing the beautiful White House in person, there’s so much culture, beautiful architecture, interesting museums, landmark monuments, and charming neighborhoods to explore from coast to coast.

Featured below are some of my favorite historical cities to add to your bucket list.

1. Boston, MA

Boston Common skyline views

Founding date: September 7, 1630

Most notable attraction: The Freedom Trail

Boston, aka “The Cradle of Liberty,” is the site of many notable events during the American Revolution. Downtown Boston is the perfect destination for history buffs as there is so much to explore in a small region. From Boston Common (America’s oldest public park), to the Bunker Hill Monument (built to commemorate the first battle in the American Revolution), to Old North Church (the first stop on Paul Revere’s “Midnight Ride”), prominent sites of historical significance are easy to come across. A self-guided walk along the 2.5 mile long brick-lined Freedom Trail will take you on a journey to 16 of the city’s most notable historical landmarks.

Fall season at Boston Common
America’s oldest park
Bunker Hill monument in Boston
Bunker Hill monument
Faneuil Hall in Boston, Massachusetts
Faneuil Hall, est. 1742 as a meeting space
Old North Church on Boston's Freedom Trail
Old North Church, est. 1723 is the 2nd oldest church

Other interesting historic sites to explore include: Harvard University (tours available), Boston Public Library, Bell in Hand (the oldest tavern in the US), and The Boston Tea Party Ships & Museum

Harvard Statue of 3 Lies
Harvard’s Famous Statue of 3 Lies
America's oldest tavern
America’s oldest tavern opened in 1795!
Widener library at Harvard University
Harvard’s gorgeous Widener library was dedicated by Eleanor Widener to her son Harry after his death in the sinking of the Titanic in 1912.

Where to stay: Stay at the Omni Parker House, a gorgeous property which is actually the oldest continuously operating hotel in the country. It is also the first American site where Charles Dickens read “A Christmas Carol.” Every President since Ulysses Grant has stayed here.

2. Savannah, GA

Haunted Wright square in Savannah, Georgia

Founding Date: February 12, 1733

Most notable attraction: Savannah Historic District

This charming city, located 20 min from the Georgia coast, is one of my favorites due to the easy walkability and beautiful public squares. The historic district easily takes a place amongst the most beautiful in the country. With cobblestone streets, antebellum architecture, beautiful Spanish moss trees, and 22 leafy public squares, it’s a dream destination for photographers and history lovers alike. They city is easy to explore due to its’ grid layout, and thus, is considered “America’s first planned city.”

Savannah riverfront

I recommend anyone interested in learning more about the city to sign up for a walking tour. Various tours offered – whether your interests lie in architecture, the paranormal, or history. I highly recommend the wonderful Noble Jones tour – you will learn so much and the guides are so detailed and passionate! Trolley tours are a perfect alternative for anyone not interested in working up a sweat. Ghosts and Gravestones (pic below) offers spooky haunted rides.

Savannah, GA trolley tour

Do take some time to explore the beauty of the public squares. The most iconic, Forsyth Park, features a dazzling water fountain – it’s a picture-perfect postcard worthy scene. Various movies including Midnight in the Garden of Good and Evil and Forrest Gump filmed here. Chippewa Square is most famous for the iconic Forrest Gump bench scene. The oldest, Johnson, was founded in 1733.

Chippewa Square in Savannah, Georgia
Chippewa Square
Beautiful Oglethorpe Square in Savannah, Georgia
Oglethorpe Square
Beautiful Forsyth Park fountain in Savannah, Georgia
Forsyth Park

Other historic sites to add to your bucket list include: Bonaventure Cemetery (tours available), Cathedral of St. John the Baptist, Historic River Street, Olde Pink House (18th century mansion)

Cathedral of St. John the Baptist in Savannah, Georgia
Cathedral of St. John the Baptist

Where to stay: Perhaps the best part about visiting Savannah is staying in a gorgeous historic old property. TheEast Bay Inn is centrally located, gorgeous, and even has a bit of paranormal history. I couldn’t sleep for 2 nights as I felt the ghostly presence in the room – you can read more about my experience in the blog link above. This beautiful property, built in 1852, is one of The Historic Inns of Savannah.

The historic East Bay Inn in the Savannah historic District

3. St. Augustine, FL

Ponce de Leon statue in historic St. Augustine, Florida

Founding Date: September 8, 1565

Most notable attraction: Fountain of Youth Archeological Park

As the most historic city in Florida, St. Augustine is a great roadtrip pick from pretty much anywhere in the Sunshine state. While much of Florida is new and flashy, St. Augustine is the nation’s oldest city. It was founded in 1565 by Don Pedro Menendez de Aviles of Spain. There is much history to explore here, especially on St. George Street which runs through the heart of the city. Lots of interesting architecture to feast your eyes upon, in addition to shops, restaurants, and historic museums to explore. Do enjoy lunch at Columbia – the oldest restaurant in Florida and also the world’s largest Spanish restaurant. Great Cuban food and a wonderful ambiance.

St. George Street in St. Augustine, Florida
St. George Street
Lightner Museum in St. Augustine, Florida
The Lightner Museum

For the military buffs, Castillo San de Marcos National Monument and Fort Matanzas are must-sees. One of the most notable tourist attractions is The Fountain of Youth Park. You can drink water from the legendary springs (over 30 minerals present), watch canon and firearms demons, explore ancient Timucuan villages, & much more. This park is the alleged site where Ponce de Leon discovered the magical healing waters in 1513.

Castillo National Monument
Castillo de San Marcos
Canon firing demo at Fountain of Youth park in St. Augustine, FL
Canon firing demo
Drinking from the Fountain of Youth in St. Augustine
Drinking from the legendary Fountain of Youth

Other historic sites to add to your bucket list: St. Augustine Lighthouse & Maritime Museum, Old Jail Museum, Potter’s Wax Museum (America’s 1st wax museum), Cathedral Basilica of St. Augustine

American Presidents at Potter's Wax Museum in St. Augustine
The 1st wax museum

Where to stay: St. Augustine is home to many charming inns and B&Bs. The Old Powder House Inn, consistently ranked one of the best B&Bs in America, is centrally located to most historic attractions.

4. Charleston, SC

Charleston Rainbow Row

Founding Date: April 1670

Most notable attraction: Historic district carriage tours

This charming Southern city is located pretty close to Savannah, and thus, makes for a great daytrip destination so you don’t have to spend more money on a separate trip. Of course, there is much to do and explore here, so if you are really interested in history, you may want to spend the night in a historic inn. Plantation Oaks Inn is one of many gorgeous choices.

Serene nature setting at Plantation Oaks Inn in Mt Pleasant, South Carolina

The largest and oldest city in South Carolina became a bustling trade center and was at one point the wealthiest city south of Philadelphia. You will learn this and more on any tour through the historic district. Consider taking a romantic horse drawn carriage ride. This is a great way to learn more about the area while also taking in the beautiful 18th century architecture.

American Theater Notebook filming location in Charleston, South Carolina
The American Theater
Beautiful Battery area of Charleston, SC
Million dollar homes lining the Battery.
Charleston historic church
One of many grand churches in “The Holy City”
Pineapple fountain in Charleston, SC
Pineapple Fountain

The most beautiful and photographed place in the historic district is Rainbow Row – a street named after its’ 13 colorful townhouses. Tours of Fort Sumter are popular with military buffs. Touring extravagant mansions is also popular with tourist and history buffs – check out the best house tours.

Horse drawn carriage making its' way down historic Rainbow Row in Charleston, South Carolina
A carriage ride is a must!

Other historical attractions to check out: Haunted Jail Tour, The Battery, Charleston City Market

Historic haunted jail in downtown Charleston, SC
This jail housed many notorious criminals including Lavinia Fisher.

Where to stay: Plantation Oaks Inn is a beautiful property with many great amenities. The breakfast is delicious, the views are gorgeous, and the countryside location perfect for relaxing after a busy day exploring.

Read more about the history of Charleston

5. Plymouth, MA

The beautiful Plymouth waterfront

Founding Date: December 16, 1620

Most notable attraction: Plymouth Rock

This historical coastal city is located just an hour south of Boston, making it easily accessible to locals. Fortunately, I lived a half hour away for many years and enjoy regular weekend trips. Plymouth was settled in 1620 by the Pilgrims, thus making it the oldest town in Massachusetts. Most notably, it is home to Pilgrim Memorial State Park – one of the country’s most visited parks. The waterfront park is home to many historical sites including a Mayflower replica and Plymouth rock. The views are fabulouis and there are many great seafood restaurants and waterfront dining options. Whale watching is also a must – Plymouth is the best place in the state to take a cruise.

Plymouth Rock in Massachusetts
Plymouth Rock
Mayflower replica in Plymouth, MA
Mayflower replica
Whale watching in Plymouth, Massachusetts
I absolutely loved Captain John’s whale watching cruise!

There’s much history to explore away from the waterfront as well. First off, you need to tour Burial Hill – the final resting home of many Mayflower passengers. If you are at all interested in the paranormal do sign up for the Plymouth Night Tour. This ghost tour is so entertaining and we did capture a lot of evidence with our EMF meters! A self-guided tour of historic sites is also a must-do – the National Monument to Our Forefathers (the world’s largest solid granite monument) is just one impressive sight you will come across.

Historic Burial Hill in Plymouth MA
Historic Burial Hill
Edward Gray gravestone at Burial Hill in Plymouth, MA
The oldest legible gravestone
National Monument to our Forefathers in Boston, Massachusetts
The world’s tallest solid granite monument (81 ft)

Other historical attractions to explore: Mayflower Society House, Leyden St. (the oldest in the US), Pilgrim Hall Museum

First Parish Church in Plymouth, MA
First Parish Church, est in 1620, is located on Leyden St.

Where to stay: As for lodging, there are many historic inns to consider. The John Carver Inn is a historic gem offering modern amenities.

6. Philadelphia, PA

The famous Love sculpture in Philadelphia

Founding Date: October 27, 1682

Most notable attraction: Independence Hall

“The Birthplace of America” is a fitting nickname for the city home to “America’s most historic square mile.” In Old City Philadelphia, you will be able to tour Independence Hall where both the US Constitution and Declaration of Independence were signed. But the history doesn’t stop there! Fantastic museums dominante the area including: The Museum of the American Revolution, Benjamin Franklin Museum, and The Weitzman National Museum of Jewish History.

Independence Hall in Old City Philadelphia
Free tours of Independence Hall available year-round

Take a walk down Elfreth’s Alley (est. 1703) – one of the oldest continuously inhabited streets in America. View beautiful art at The Second Bank Portrait Gallery which houses a collection of 150+ portraits of prominent figures from the 18th and 19th century. And, of course, a visit to “The City of Brotherly Love,” would not be complete without seeing the famous Liberty Bell, an iconic symbol of freedom.

Elfreth's Alley in Old City Philadelphia
A walk down the oldest street
Historic portraits at the Second Bank Portrait Gallery in Philadelphia
Second Bank Portrait Gallery – a must-see by art & history buffs
Liberty Bell in Old City Philadelphia
“Proclaim Liberty Throughout All the Land Unto All the Inhabitants thereof”

The Benjamin Franklin Parkway was nicknamed “Museum Row” thanks to the many world-class museums. The Philadelphia Museum of Art (run up the Rocky steps and take your pic by the famous Rocky III statue!) is amongst the top in the country. The Rodin Museum collection includes 150+ masterpieces from the French sculptor. Dinosaur lovers will want to check out The Academy of Natural Sciences of Drexel University – the oldest natural history museum. Beautiful historic buildings to tour include the Free Library of Philadelphia and Cathedral Basilica of Saints Peter and Paul.

Claude Monet at the Philadelphia Museum of Art
Beautiful artwork by Claude Monet
Scenic view from Philadelphia Museum of Art
The iconic viewpoint from the Museum of Art
Rocky Statue in Philly
The famous Rocky statue at the Philly Art Museum
The Thinker statue at The Rodin Museum in Philadelphia
The iconic Thinker sculpture

Other historical attractions to check out: Eastern State Penitentiary, Edgar Allan Poe National Historic site

Edgar Allan Poe house in Philadelphia
Take a free self-guided tours of the house Edgar Allan poe once resided in

Where to stay: The beautiful Kimpton Hotel Monaco is a historic boutique hotel within walking distance of Old City attractions.

7. Washington, D.C.

United States Capitol building in D.C.

Founding Date: July 16, 1790

Most notable attraction: The National Mall

The Nation’s Capital is one of the best vacation destinations for history buffs. It’s also a great budget friendly destination as most activities are free including tours of the U.S. Capitol Building (reservations recommended) and The White House (advance requests required), self-guided tours of The National Mall, and all the wonderful Smithsonian institutions. The 2 mile National Mall walk is the must-do here. Along this beautiful journey of America’s past, you will come across some of the country’s most notable landmarks. Highlights include the Lincoln Memorial, the U.S. Capitol, and the Washington Monument.

Beautiful mural at the US Capitol in D.C.
One of many incredible murals at the U.S. Capitol
The White House in DC
The 55,000 square foot White House is home to 132 rooms amd 35 bathrooms!
Winter in Washington D.C.

Although the line is often very long, a visit to The National Archives is another must for first time visitors. Here you will be able to see the Declaration of Independence, the Bill of Rights, and The Constitution. Perhaps the highlight of visiting D.C. is enjoying all the free museums. There are 17 Smithsonian museums and galleries (including the zoo) to enjoy. The Museum of Natural History, The National Portrait Gallery, and The National Gallery of Art are my personal favorites.

African bush elephant at the Smithsonian Natural History Museum in DC
Museum of Natural History
JFK portrait at the Smithsonian Portrait Gallery in DC
JFK, 35th President portrait
Grand interior of The National Gallery of Art in Washington D.C.
The National Gallery of Art

Other historical sites to add to your bucket list: The Library of Congress, National World War II Memorial, Jefferson Memorial, Ford’s Theater, Georgetown historic district (definitely plan for dinner at Il Canale and visit the Crumbs and Whiskers Cat Cafe!).

Great view of the Jefferson memorial from Tidal Basin Park in DC
Tidal Point Park offers a prime view of the Jefferson memorial.
Amazing architecture in Georgetown
Georgetown – a great daytrip with lots of local cafes and shops to explore.
The beautiful Library of Congress in DC
The gorgeous Library of Congress is open for self tours

Where to stay: The Capitol Hill Hotel is a wonderful moderately priced option offering many amenities. It is located within walking distance of almost all attractions.

Capitol Hill hotel in Washington DC