For the 50+ Traveler

Living in Boston may be the only way to truly experience it. There are so many options, you'd need that much time to see it all. These experiences are to make you feel half-tourist and half-local. That said, your accent, or lack of one, will give you away.

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1. The Freedom Trail

This tops everyone's list because they've literally mapped out 17 historic sites to see with a thick red line around town. The sites were an integral part of helping shape the future of America. The Freedom Trail is the easiest way to take in the city without feeling overwhelmed.

You start in Boston Common and along the way will see where John Hancock and Paul Revere are buried. You'll also see where Revere lived and the Old North Church where the lanterns were hung in 1775. The trip culminates with the world's oldest extant naval vessel "Old Ironsides." The old gal recently underwent a two-year renovation.

The Trail is 2.5 miles long, but you can stop any time and there are spots to rest and even grab lunch or dinner along the way. There are some especially good restaurants in the North End, where Paul Revere lived.

The Freedom Trail path

2. Whale Watch/Harbor Cruise

Boston is all about being on the water. On a beautiful summer day, sailboats dot the ocean and you'll wish you owned one. While you may not be able to buy a boat quickly, there are ways to get out on the water and enjoy it.

Several Whale Watch and Harbor Cruises leave from downtown Boston. The whales actually return to the area, year after year, and the crews know some of them by name.

If you prefer to go old school, take a cruise on the Liberty Fleet of Tall Ships. Beware: you may be put to work hoisting the sails, but it's still very relaxing.

Most of the boats leave from Long Wharf or Central Wharf, near the New England Aquarium. But, trips are also offered from the towns of Gloucester, Newburyport and Plymouth, as well as others farther away.

Black whale tail in the water

3. 4th of July

It may not get more American than spending July 4th in Boston. The birthplace of the Revolution puts on a very special party. The day starts with a flag raising ceremony and parade from City Hall Plaza. The parade goes past the Granary Burial Ground and then to the Old State House, where the Declaration of Independence is read, just like it was on July 18, 1776.

After that, you may want to head straight to the Esplanade. Grab a picnic and plan to spend the day saving your spot for the Boston POPS performance at the Hatch Shell and the evening Fireworks. It's spectacular and you get to sing-a-long with about a half million of your closest friends. Yes, it's really crowded. Spend the money to get a hotel nearby, so you can walk back. Squeezing onto the T or the interstate for the ride home will be the least memorable part of your trip.

If you prefer to watch the party from the water, check out the Liberty Fleet of Tall Ships, mentioned above. It's pricey, but a truly special way to experience the fireworks. If you are more interested in the concert and not the fireworks, the Boston Pops does a rehearsal performance on July 3rd at the Hatch Shell. The celebrity guests are there too, the only thing missing will be the fireworks.

Hopefully you're visiting for several days, if so, check out original copies of The Declaration of Independence and The Bill of Rights at the Commonwealth Museum. Admission to the museum is free, but it's closed on the 4th of July. The museum is located near the John F. Kennedy Presidential Library, about five miles south of downtown Boston.

4. Walden Pond

This is your escape from the big city. Walden Pond is about 20 miles northwest of Boston and is a perfect spot to spend a peaceful day, but this stop is also historic.

Author Henry David Thoreau lived in a cabin on the shore of the lake for two years. It inspired his book, Walden; or, Life in the Woods. The cabin isn't there any more, but the site is marked by several granite posts. There is a beach where locals relax on a hot day and walking trails, which are especially gorgeous in the fall when the leaves are changing.

Walden Pond lake in Concord
Walden Pond. Flickr / angela n.

5. Isabella Stewart Gardner Museum

This is a true gem, and even more impressive when you realize it was the personal collection of one woman. There are 7,500 paintings in the museum, on top of the thousands of rare books, sculptures, and objects from around the world.

Isabella Stewart Gardner's travels in the late-1800's inspired her love of art. She and her husband realized their collection was too large for their home and decided to create the museum. Her husband died, but Gardner moved forward with the plan and was key in designing the building you see today.

During her life, she lived on the fourth floor of the museum and spent her days acquiring and installing her collection. The courtyard of the building is its own work of art. You will think you traveled to Europe, as you step through the archways. Gardner stipulated in her will that everything must remain in place, nothing added, nothing sold. What you see today, is her vision.

In 1990, two robbers stole 13 items from the museum, including works by Rembrandt, Manet, Degas and Flinck. Their estimated value: $500 million. The crime remains unsolved and a $10 million reward is still offered for the safe return of the art.

Isabella Stewart Gardner Museum in the Fenway–Kenmore neighborhood of Boston
Isabella Stewart Gardner Museum. Wikimedia Commons

6. Museum of Fine Arts

This is located near the Isabella Stewart Gardner Museum and the two collections give you the opportunity for a full day of art immersion. The Museum of Fine Arts houses one of the most impressive collections in the world, including works from Rembrandt, Renoir, Monet and Manet. In 2010, a four-floor wing dedicated to The Art of the Americas opened.

One-hour guided tours are offered, but check about availability. Weekday afternoons usually give you the best opportunity.

Interior of the Museum Fine Arts Boston
Museum of Fine Arts, Boston. Flickr / BillDamon

7. Boston Public Library

This will be a brief visit, but a beautiful one. Architect Charles Follen McKim called it his "palace for the people," when it was built in 1895. It's simply gorgeous. The Barrel-Arched ceiling is enclosed by half domes on each end, murals grace the walls of the grand staircase and can be seen throughout the library, and there's an impressive fireplace made of French rouge antique marble.

Today, the McKim building houses the library's research collection and is a National Historic Landmark. Free tours are offered and last about an hour, but be sure to check the times.

The Boston Public Library was the first large, free, municipal library in the country. Boston is also where the library branch system we know today began.

8. John F. Kennedy Presidential Libraryand Museum

Presidential libraries are a fantastic way to view history. They are an immersive experience into a brief time in America's history and the person who was leading it.

The John F. Kennedy Presidential Libraryand Museum is a fantastic tribute to the life and legacy of America's 35th President. Whether it's his run for the White House, the country's journey into space or Mrs. Kennedy's fashion that interests you, it's all here, and much more. Its location on the water creates a tranquil setting, as do the grounds, which are landscaped with plants reminiscent of his life on Cape Cod.

President Kennedy had chosen a spot for his library near the Harvard Graduate School of Business Administration, before his assassination. After his death, his family decided on the site where it's located today.

John F. Kennedy Presidential Library and Museum
John F. Kennedy Presidential Library and Museum. Fr James Bradley/Flickr

9. International Museum of World War II

This is an experience unlike any in the world, and it's because of the dedication of the founder and director, Kenneth Rendell. What began as his private collection, now connects today's generations to those of World War II.

You don't just revisit World War II, you relive it. It's emotional, inspiring and unique. Unlike many museums, you're allowed to handle some of the items. The museum is filled with unique artifacts like General George Patton's war helmet, the negotiation draft of the 1938 Munich Agreement, and letters from President Roosevelt, Winston Churchill and Adolf Hitler. The range of items is staggering, and Rendell's passion for this time in world history is palpable throughout.

The museum is in Natick, which is about 20 miles west of Boston. It's in an office park, which is something to be aware of when you're looking for it. It's only open to the public on Fridays and Saturdays because they host school groups during the week. The museum does charge admission and you need your I.D. to enter. Visitors must also sign a waiver, which you can find on the website. Be sure to check out the do's and don'ts. They're different than most museums.

10. Swan Boats

The Swan Boats are a tradition dating back to 1877 in Boston and are in The Public Garden. It's a peaceful and picturesque ride around the lagoon. It doesn't take long, and it's simply fun for all ages.

Members of the same family who founded the business, still operate the boats today. The Swan Boats only operate from mid-April through early September. There is a small fee.

After your ride, you'll need to stop and see the ducks. Mrs. Mallard and her eight ducklings, from Robert McCloskey's Make Way for Ducklings, hold a permanent place in The Public Garden. You can find them near the corner of Beacon and Charles Streets.

Swan Boats, Public Garden, Boston
Swan Boats, Public Garden, Boston.Doug Kerr/Flickr

11. Fenway Park

There's a tour of Fenway and then there's experiencing a game at Fenway. If your team is visiting, even better!

The fans try wicked hard to be respectful of opposing fans. OK, not really, and by the way, wicked is Bostonian for really or very. I've found if you can take the ribbing and successfully dish it back, you're good to go. Red Sox fans have changed a bit since the curse of the bambino was lifted, but they're still the passionate, knowledgeable folks you'd expect.

Don't forget about the park itself. It's the oldest major league ballpark in the country and while the fans around you create the experience, the history of the park engulfs you. You'll especially notice it if you're sitting down the right-field line. Your neck may be a bit stiff by the end of the game because you've spent 9 innings looking to your left to see the batter. Ah, history.

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Spectators watching game at Fenway Park
Fenway Park. Peter Galvin/Flickr