Roaming Boston: Your Expert Travel Advisor

Discover Boston

Traveling to Boston is like stepping into a living history book filled with vibrant neighborhoods, iconic landmarks, and a rich cultural tapestry. As you wander through the cobblestone streets of Beacon Hill or stroll along the bustling waterfront at the Seaport District, you’ll find yourself immersed in the city’s unique blend of old-world charm and modern innovation. From the historic Freedom Trail, where every step echoes with the footsteps of revolutionaries, to the cutting-edge museums and galleries of the Innovation District, Boston offers something for every traveler. Whether you’re exploring the historic sites of the North End, catching a game at Fenway Park, or simply soaking in the atmosphere at Quincy Market, traveling to Boston is an unforgettable experience that will leave you enchanted and inspired.


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Best places to visit

Three Fun Facts About Boston


North America’s First Subway System

Boston boasts the first subway system in North America! Begun in 1897, this underground marvel kickstarted the city’s public transport love affair, and it’s been keeping Bostonians moving ever since. Next time you hop on the “T,” just think of the history humming along with you.



Did you know that much of Boston was underwater? That’s right! Before the 1800s, modern Boston’s footprint was actually part of the bay. Landfill projects transformed it into the bustling city you see today. Imagine that – parts of the city where you’re searching for vacation rentals once had seagulls flying over waves instead of pigeons over pavements!


Boston Cream Pie

This delicious dessert originated in Boston and is the official dessert of Massachusetts. Despite its name, it’s actually a cake filled with custard or cream and topped with chocolate icing.


Must See Attractions

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Freedom Trail

Nature & Parks

This 2.5 mile long trail takes visitors on a journey through Boston’s revolutionary past, passing by 16 historical sites including Faneuil Hall, Paul Revere’s House, and the Old North Church.

Fenway Park


Home to the Boston Red Sox baseball team, Fenway Park is the oldest ballpark in Major League Baseball and a must-visit for sports fans.

Faneuil Hall Marketplace


A bustling shopping and dining destination since 1742, Faneuil Hall Marketplace is filled with shops, restaurants, and street performers. Don’t miss the historic Faneuil Hall and Quincy Market buildings.

Isabella Stewart Gardner Museum

Speciality Museums

This unique museum features an eclectic collection of art and artifacts displayed in a stunning Venetian-style palazzo. And the indoor garden is not to be missed!

Boston Common and Public Garden

Nature & parks

These adjacent green spaces offer a peaceful retreat in the heart of the city. Boston Common is America’s oldest public park, while the Public Garden features lush gardens, iconic statues, and the famous Swan Boats.

Harvard Square and Harvard University

Education & Institutions

Located in nearby Cambridge, Harvard Square is a lively hub of shops, cafes, and street performers. Take a stroll through Harvard Yard and explore the prestigious Harvard University campus.

Lakes Near Boston

Have you ever dreamed of serene waters just a stone’s throw from the hustle and bustle of city life? Boston, MA, can fulfill that dream with its stunning lakeside spots perfect for a quick escape. Did you know that all these beautiful lakes are so conveniently located near the city? You can get back to your urban adventures or meetings in no time after a day spent by the lake. Or maybe you’ll decide that one day isn’t enough; I wouldn’t blame you! Whether it’s a weekend getaway or a pleasant day trip, lakes near Boston have a little something for everyone.

Walden Pond

915 Walden St., Concord, Massachusetts 01742

First up, Walden Pond, a gem that’s not just a lake, it’s a slice of literary history! Remember reading “Walden” by Henry David Thoreau? This is where he penned those famous lines. Today, you can swim, hike, or simply enjoy the scenery—it’s only about 20 miles west of Boston!

Distance from Boston: 19 miles
Kayaking, swimming, picnicking, hiking

Spot Pond

4 Woodland Rd, Stoneham, Massachusetts 

Heading north of Boston, you’ll arrive at Spot Pond. It’s a fantastic place for you and your family to rent a boat and spend the day on the water. Wrapped by the lush Middlesex Fells Reservation, this tranquil pond is a haven for both wildlife and outdoor enthusiasts.

Distance from Boston: 8 miles
Activities: Swimming, hiking, stand-up paddling

Crystal Lake

30 Rogers Street Newton Highlands, Massachusetts 02459

Now, let’s talk about Crystal Lake. It’s not just a name; the water here really does sparkle! Nestled in the heart of Newton, just a few miles from Boston, this little lake is ideal for a refreshing swim or just chilling on the shore. Could there be a better way to spend a sunny afternoon?

Distance from Boston: 28 miles
Activities: Swimming, hiking, picnicking

Secret Fishing Spots Near Boston

Hey there, fellow angler! Looking for some hidden fishing spots around Boston where you can enjoy a quiet day with just you and the fish? I’ve got you covered! Before you pack your rods and reels, remember that anyone over the age of 15 needs a fishing license for both saltwater and freshwater in Massachusetts. Got that? Alright, get out there and enjoy these secret spots! Just remember, they’re our little secret. Good luck!

Charles River

Charles River, Massachusetts

Ever heard whispers about the Charles River? You should. It’s not just rowers and sailboats here; the Charles offers some sweet fishing spots. Just find a quiet riverside nook—bring your tackle!

Fishing: Shoreline
Species: Bass, shad, perch, sunfish

Mystic River

Mystic River, Massachusetts

The Mystic River Reservation is a bit of an open secret. With its diverse fishing near Boston, it’s perfect for those who love a serene environment by the water.

Fishing: Shoreline 
Species: Bass, flounder, bluegill, perch, mummichog

Jamaica Pond

Jamaica Pond, Boston, Massachusetts

Are you ready for some action? Jamaica Pond isn’t just any pond. This historic kettle pond is loaded and it’s in the heart of the city. You might be surprised by how good the fishing is just a stone’s throw from downtown!

Fishing: Shoreline, kayak
Species: Bass, crappie, bluegill

Best Hiking Trails 1 Hour Away From Boston

Hey there, nature lover! Are you in Boston and craving some leafy retreats just an hour away? Let’s zip through a few trails where you can stretch your legs, fill your lungs with fresh air, and maybe even play “I spy with my little eye” with some local wildlife.

Skyline Outer Reservoir Loop

24 S Border Rd, Medford, Massachusettes 02155

This scenic trail traverses through dense forests, meandering along the outer edges of the picturesque Houghton’s Pond and neighboring bodies of water. As hikers embark on the loop, they are treated to panoramic vistas of the Boston skyline and the tranquil waters below, creating a captivating backdrop for exploration.

Distance: 7.7 miles
Type: Loop
Difficulty: Moderate
Elevation Gain: 287 m
Time to Complete: 3.5 hours

Blue Hills Skyline Trail: Route 138 to Willard Street

2991 Washington St Parking, 2991 Washington St, Canton, Massachusetts 02021

As adventurers embark on this trail, they are greeted by a diverse terrain of lush forests, rocky outcrops, and rolling hills, providing both challenge and reward along the way. The trail follows the ridgeline of the Blue Hills, offering panoramic vistas of the surrounding countryside and distant city skyline, creating a breathtaking backdrop for exploration.

Distance: 6.7 miles
Type: Point to point
Difficulty: Moderate
Elevation Gain: 450 m
Time to Complete: 4 hours

Wachusett Mountain Loop

Mount Wachusett Visitor Center & Trailhead, Bicentennial Trail, Princeton, Massachusetts 01541

How about a little summit action? Wachusett Mountain’s inviting trails beckon you to its peak for some sweet vistas. Just less than an hour’s drive and you’ll find yourself at an elevation of 2,006 feet!

Distance: 6 miles
Type: Loop
Difficulty: Moderate
Elevation Gain: 550 m
Time to Complete: 3.5 hours

Best Golf Courses Around Boston

Playing golf in Boston, MA? You’re in for a treat! While Boston might not always come first to mind when you think of golf havens, let me assure you, it’s a hidden gem for the sport. Here’s a quick guide to some of the top courses where you can enjoy a round or two. Remember, golf is more than just hitting a tiny ball—it’s about the experience! Each of these courses offers something unique, whether you’re looking for history, accessibility, or just a stunning place to play. Now, go ahead, choose your course, book your tee time, and enjoy the greenery!

George Wright Golf Course

420 West St, Hyde Park, Massachusettes 02136

Lush fairways, strategic bunkering, and meticulously maintained greens characterize the course, providing a picturesque backdrop for a round of golf. As players navigate through the rolling terrain and mature trees, they are treated to panoramic views of the Boston skyline, adding to the allure of the experience. With its historic charm, challenging layout, and convenient location, George Wright Golf Course remains a beloved destination for golf enthusiasts seeking a memorable day on the links in the heart of Boston.

Holes: 18
Designer: Donald Ross
Highlight: Challenging, scenic, rich in history

Visit their website for more information

Franklin Park Golf Course

1 Circuit Dr, Dorchester, Massachusettes 02121

The course features rolling fairways, strategically placed bunkers, and fast greens, providing a memorable experience for players of all skill levels. As golfers navigate the course, they are treated to stunning views of the park’s majestic trees, tranquil ponds, and historic landmarks, creating a serene and immersive golfing environment.

Holes: 18
Designer: Donald Ross
Highlight: Friendly atmosphere, not overly difficult

Visit their website for more information

Granite Links

100 Quarry Hills Dr, Quincy, Massachusettes 02169

With stunning views of the city skyline, this 27-hole layout not only provides a good golfing challenge but also panoramas that will make your friends green with envy (pun intended).

Holes: 27
Designer: John Sanford
Highlight: Upscale, prestigious, well-maintained

Visit their website for more information

Tips On Renting A Vacation Property In Boston


Conduct thorough research on rental properties available in Boston using reputable websites and platforms. Read reviews from previous guests to gain insights into the quality of accommodations and the experiences of past renters.


Determine your budget for accommodation and look for rental properties that fit within your financial constraints. Keep in mind additional costs such as cleaning fees, security deposits, and taxes when calculating the total cost of your stay.

Check for Special Offers

Look for special offers, discounts, and promotions on vacation rental websites or through rental agencies. Booking during off-peak seasons or for longer durations may also result in cost savings.

Book Early

Boston is a popular tourist destination, especially during peak travel seasons. To secure the best rental properties and rates, book your accommodations well in advance of your travel dates.

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Jet Skiing

When you’re scouring the net for that perfect Boston getaway, wouldn’t you want some insider tips to make the hunt a breeze? Here’s a little cheat sheet just for you – think of it as your vacation rental GPS!

Get An Early Start

Procrastinators, beware! Popular spots in Boston fill up faster than a Red Sox game. So, what’s the game plan? Start your search early, especially if you’re eyeing peak seasons. The early bird not only gets the worm but also the best vacation rentals!

Pick The Right Platform

With so many options like Airbnb, VRBO, and the like, how do you choose? Go for platforms with sterling reputations that offer:

– User reviews
– Detailed descriptions (clear pictures score bonus points!)

Location, Location, Location

Boston is a quilt of neighborhoods, each with a unique vibe. Fancy a historic backdrop? Charlestown’s your bet. Crave the downtown buzz? Back Bay awaits. Whether it’s being near the Longwood Medical Area or having quick access to the “T” (Boston’s subway), pick a location that suits your plans.

What’s On The Inside Counts

It’s the little things that make a house feel like home. Keep an eye out for:

– Cleanliness
– Essential amenities like A/C, Wi-Fi, and a well-equipped kitchen
– Extras that sweeten the deal (Think private decks or a yard)

Read The Fine Print

Some rentals offer freebies like parking or say no to cleaning fees—a serious win for your wallet. But, don’t let the excitement blind you to the rules. Skim through the rental agreement to avoid any surprises.

Match The Rental To Your Style

Are you a solo traveler looking for a cozy studio, or does a spacious apartment better suit your family? Maybe a brownstone with Victorian flair ticks your boxes? Choose a rental that feels right—because you deserve to stay in style, don’t you think?

Happy hunting, and here’s to finding your home away from home in Boston!

Discover Boston, Massachusetts

Have you ever strolled through the cobblestone streets of Boston’s historic neighborhoods, soaking in the rich tapestry of American history and vibrant contemporary culture? Boston, the capital of Massachusetts, is a treasure trove for anyone looking to experience the authentic New England charm. Let’s walk through what makes Boston a top pick for travelers.

Walkabout in History

Have you ever strolled through the historic streets of Boston and felt the charm of its centuries-old architecture? Well, you’re walking in a city that’s been around since 1630! Boston is one of America’s oldest cities, and it’s rich with history that’s just begging to be explored. Follow the iconic Freedom Trail, a 2.5-mile path that introduces you to 16 historically significant sites. Imagine hearing the echoes of revolutionary speeches as you pass by the Massachusetts State House and Paul Revere’s House in the North End.

Cultural Cornucopia
The Museum of Fine Arts (MFA) houses an exquisite collection, or you might catch a game at the legendary Fenway Park, home of the Boston Red Sox. Have you ever sung Sweet Caroline amidst a sea of fans? It’s an electric Bostonian rite of passage!

Education and Innovation
Take a quick ride on the “T” to Cambridge and explore the prestigious halls of Harvard University. Fancy a bit of trivia? Harvard is the oldest institution of higher education in the United States, founded in 1636!

Natural Delights
Breathe in the serenity of Boston Common, the oldest city park in the country, before taking a leisurely stroll along the Charles River. Also, don’t forget to wave hello to the seals at the New England Aquarium.

In Back Bay, you’ll marvel at iconic Boston Brownstones and find some of the best shopping opportunities at Newbury Street and Copley Place. Crave a bite? Dive into the culinary delights at Quincy Market. As for accommodations, you’ll find a plethora of vacation rentals that let you live like a true Bostonian, whether you’re looking for a beachfront spot in South Boston or a cozy nook near Beacon Hill.

Every corner of Boston has a story. With its array of sights like TD Garden, Boston Harbor, and landmarks reflecting its storied past and dynamic present, isn’t it time you made your own Boston story?

So there you have it! Whether you’re here for the prestigious universities, the blend of historic and modern, or just the sheer vibe of the place, Boston’s got trivia and charm in spades. Ready to find that perfect vacation rental and experience it all for yourself?

Frequently Asked Questions about Boston

Book early, especially during peak seasons! Boston is a bustling city with events year-round, so securing your spot ahead of time is wise. Also, read recent reviews for the property to get the freshest take on what to expect. Keep an eye out for rentals with high ratings and exceptional reviews, and remember to consider proximity to the sights you’re eager to see.

If you want to save some greens while visiting the Green Monster at Fenway Park, opt for sites like Lake, Airbnb, and Rent By Owner™. You’ll often find competitively priced condos and rooms, especially if you adjust the filters to your budget range.

Check filters on sites like Lake and Tripadvisor for the “pet-friendly” option. With these tools, you won’t have to part from your furry friends, ensuring they’re as welcome as you are.

For a personal touch, platforms like Lake connect you directly with homeowners offering their spaces in Boston. This way, you’re more likely to find a spot that’s got that homey feel, along with helpful insider tips from the owners themselves.

Sure can! On platforms like Lake, look for properties with a “Pool” in the amenity list. Some unique finds include houseboats docked in Boston Harbor, which offer a floating escape complete with a pool to relax in.

When you’re after luxury accommodations, check out Lake for their selection of high-end villas and homes. With these platforms, you can filter for top-tier amenities that raise the bar on comfort and elegance.

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