Road trip from Leesburg to Boston
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Sights & Landmarks
Water & Amusement Parks
Outdoor Activities
Concerts & Shows
Fun & Games
Nature & Parks
Nightlife
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ITINERARY
24h 59m1,283 miles37 stops
1
Marion Theatre
2
Island H2O Water Park
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
3
The Legends Walk Course
4
Teatro Martini
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
5
1001 Transportation
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
6
Ocala Palms Golf & Country Club
7
Corpus Christi Catholic Church
8
Young's Paso Fino Ranch
9
Depot Park
Depot Park is a signature city park in downtown Gainesville providing a space for unique public outdoor enjoyment. Depot features a children's adventure play area with a custom splash pad of waterfalls, water soakers, and ground jets. A water's edge promenade hosts special events like food truck rallies, art festivals, and musical performances. The park is fully staffed and free of charge.
10
Underbelly
Located in the heart of Downtown, in Jacksonville's "Elbow District", Underbelly isn't just a building and a stage where people come to enjoy music. It's much bigger than that. It's not the paint on the walls. It's not the brick, wood, and nails that hold it all together. It's not the lights or the electricity that define it. Underbelly is a garden. A place for people, regardless of who you are or what you do, to just leave it all at the door for a small while. It's a place for humans. People wanting to be just that. Surrounded by others that feel the same to come together for however long it may be, to be here and now - no more, no less. It's a place where the best musicians unite to create moments that exist nowhere else. Isn't that what it is all about? Finding those moments of magic that will stay with you forever? Well, that's what we sell. We sell magic in all sizes. So come with many, come with none, it doesn't matter. Because when you're here, you're home.
11
Downtown Cigar Lounge
Location in the heart of downtown Jacksonville in a 101 year-old historic building. We are home to a diverse selection of premium hand-rolled cigars from various regions and a variety of wines, beers and specialty drinks . DCL is not only about cigars we are also a gallery displaying the artwork of local artists.
12
Regal River City Marketplace Stadium 14
13
Cathedral of St. John the Baptist
The oldest Roman Catholic church in Georgia.
14
Edmondston-Alston House
Constructed nearly 200 years ago, circa 1825, the Edmondston-Alston House presents a unique history of the people, both free and enslaved, who lived and labored on this property. Its collection of furniture, silver and decorative arts, largely original to those who owned the house, constitutes a rich, complex history of Charleston in the 19th century. Commanding a magnificent view of Charleston Harbor, the Edmondston-Alston House has witnessed many historic moments in the port city’s history. One of the oldest houses along the High Battery, it withstood the American Civil War, the Earthquake of 1886, and numerous hurricanes; it has survived to share a piece of Charleston history.
15
The Black Fedora Comedy Mystery Theatre
Live theatre featuring clean comic whodunit shows, volunteer audience participation, a la carte appetizers, homemade desserts, and drinks -- at the downtown City Market. “Uproarious entertainment” - Thrillist.com
16
Rockwood Park
17
St. Paul's Episcopal Church
18
Howard Peters Rawlings Conservatory and Botanic Gardens of Baltimore
19
Baltimore Spirits Company
Be the master blender for the day! Blend your own bottle of Epoch Maryland Rye, Baltimore's first Maryland Rye to be produced in the city since the 1970s. In this unforgettable experience, your tour and blending experience will take between 1.5 and 2 hours. The highlight of the afternoon will be to taste and evaluate four of our barrel-finished Maryland Rye whiskeys, and then to create your own custom blended bottle of the spirits. Epoch Rye won Double-Gold Medals at both the 2018 and 2020 San Francisco World Spirits Competition. We take care of you from the time you walk in the door to ensure your perfect date, afternoon with friends, or a great gift for a whiskey fan. In addition to creating your own custom blend of our award-winning Pot-Distilled Maryland Rye, attendees also receive: • One delicious welcome cocktail • A compelling history lesson of Maryland Rye (15 minutes) • An up-close and personal distillery tour of our production facility and 650+ barrel rickhouse.
20
Cylburn Arboretum
21
Baltimore Clayworks
22
John Heinz National Wildlife Refuge at Tinicum
Visit John Heinz National Wildlife Refuge at Tinicum! Come enjoy 10 miles of walking trails through wooded forests, an impoundment pond, and 300 acres of the largest remaining freshwater tidal marsh in PA. Visitors can also experience the marsh on the water through 4.5 mile of Darby Creek by canoe or kayak. Stop by the front desk to borrow binoculars or fishing rods. Refuge trails are open every day from sunrise to sunset, free of charge. The Visitor Center is open daily from 8:30 AM to 4:00 PM. The visitor center building is closed for all Federal holidays however the trails remain open. Darby Creek is tidal and navigable only within 2 hours before and after high tide. Boat Launch is located at the trailhead of Dike Trail. Visitors must provide their own canoe/kayak and life vests. John Heinz NWR offers year-round free recreational and educational programs.
23
Arthur Ross Gallery
24
Old City Hall
25
Dave & Buster's - Arcade
At Dave & Buster's you can play hundreds of the hottest new arcade games in our Million Dollar Midway and win tickets for epic prizes. Try our mouth-watering, chef-crafted creations in our American restaurant. From wings to steaks, we've got whatever suits your appetite. Our premium sports bar features innovative cocktails, impressive wine selection, and 20+ beers to assure we're stocked to satisfy! Watch your team on one of our massive HDTVs with epic stadium sound that surrounds you from every direction in the sports bar that crushes the competition. Invite all your friends or coworkers for an unforgettable party or event! We work with every size and budget to make planning easy so you can focus on the FUN!
26
BrainXcape
27
Daniel Roy's Parlour Of Deceptions
Join magician Daniel Roy at the exclusive Salmagundi Club of New York City for an evening of sleight-of-hand, misdirection, and magic. Limited to just 40 guests, this is an intimate experience of wonder. While this is not a kids show and the magic is geared towards adults, the performance is entirely “clean” and appropriate for audience members age 13 years and older.
28
The Blue Bar, Algonquin Hotel
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
29
Precision NY Chauffeur & Airport Transportation Services
Here at Precision NY Chauffeur & Airport Transportation Service, we offer limousine service and point to point transportation NYC. You can always depend on us for reliable transportation New York, New Jersey, Westchester, Connecticut, Washington DC, Pennsylvania, and Boston. Along with equitable rates and attentive service, we offer transfer services anywhere within the country. For your convenience, you may reserve any vehicle from our fleet vehicles up to 24 hours in advance, including the Lincoln MKT, Lincoln Town Car and Cadillac XTS. For larger parties or a more comfortable ride, we have Cadillac™ Escalades, Lincoln™ Navigators, and Chevy™ Suburbans. We also carry New 2023 and 2024 Mercedes S560s.
30
New Haven Railroad Station
31
Owl Shop Cigar Lounge
32
Yale University Art Gallery
Yale University Art Gallery is the oldest college art museum in America. The Gallery’s encyclopedic holdings of more than 250,000 objects range from ancient times to the present day and represent civilizations from around the globe. Spanning a block and a half of the city of New Haven, Connecticut, the Gallery comprises three architecturally distinct buildings, including a masterpiece of modern architecture from 1953 designed by Louis Kahn through which visitors enter. The museum is free and open to the public.
33
David S. Ingalls Rink
34
DCU Center
35
Boston Public Garden
This Frederick Law Olmsted-designed park, famous for its Swan Boats, has over 600 varieties of trees and an ever-changing array of flowers. It is America's first public garden.
36
Boston Children's Museum
Highlights of this interactive museum include the "Science Playground," featuring giant soap bubble-making tools and the "New Balance Climb," which teaches kids the laws of physics while navigating through a two-story-high maze.
37
Hex: Old World Witchery
Salem Warlock Christian Day presents magical merchandise for both the curious and Witch alike. Whether you want a candle to bless your home, herbs and roots to make your own magic, a potion to attract love, the perfect ritual tool, a Voodoo doll made by a real practitioner, or to cast a spell at our authentic Witches' Altar, Hex is for those who believe in magic and those whose hearts beat with its fire.Be sure to visit our Witches' Altar of the Dead that stands at the Western wall of the shop. Here, countless visitors through the years have left messages, photos, and mementos in honor of departed loved ones in the spirit world. We welcome you to contribute to the magic!And, while there, have an authentic psychic reading with one of Salem's most talented Witches: Leanne Marrama, Laura Broderick, and Kyri Spencer!
Customize this Trip
OVERVIEW
Leesburg to Boston
1
Start:Marion Theatre
Ocala, Florida·
4.5
(90) review
50 S Magnolia Ave, Ocala, FL 34471-1153
2
Start:Island H2O Water Park
Kissimmee, Florida·
3.5
(96) review
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
3
Start:The Legends Walk Course
Kissimmee, Florida·
4.0
(96) review
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
4
Start:Teatro Martini
Orlando, Florida·
4.5
(960) review
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
5
Start:1001 Transportation
Orlando, Florida·
5.0
(98) review
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
6
Start:Ocala Palms Golf & Country Club
Ocala, Florida·
4.5
(9) review
5174 NW 26th St, Ocala, FL 34482-3250
7
Start:Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
8
Start:Young's Paso Fino Ranch
Ocala, Florida·
4.0
(9) review
7950 NW 80th Ave, Ocala, FL 34482-1112
9
Start:Depot Park
Gainesville, Florida·
5.0
(94) review
Depot Park is a signature city park in downtown Gainesville providing a space for unique public outdoor enjoyment. Depot features a children's adventure play area with a custom splash pad of waterfalls, water soakers, and ground jets. A water's edge promenade hosts special events like food truck rallies, art festivals, and musical performances. The park is fully staffed and free of charge.
10
Start:Underbelly
Jacksonville, Florida·
3.5
(9) review
Located in the heart of Downtown, in Jacksonville's "Elbow District", Underbelly isn't just a building and a stage where people come to enjoy music. It's much bigger than that. It's not the paint on the walls. It's not the brick, wood, and nails that hold it all together. It's not the lights or the electricity that define it. Underbelly is a garden. A place for people, regardless of who you are or what you do, to just leave it all at the door for a small while. It's a place for humans. People wanting to be just that. Surrounded by others that feel the same to come together for however long it may be, to be here and now - no more, no less. It's a place where the best musicians unite to create moments that exist nowhere else. Isn't that what it is all about? Finding those moments of magic that will stay with you forever? Well, that's what we sell. We sell magic in all sizes. So come with many, come with none, it doesn't matter. Because when you're here, you're home.
11
Start:Downtown Cigar Lounge
Jacksonville, Florida·
4.5
(9) review
Location in the heart of downtown Jacksonville in a 101 year-old historic building. We are home to a diverse selection of premium hand-rolled cigars from various regions and a variety of wines, beers and specialty drinks . DCL is not only about cigars we are also a gallery displaying the artwork of local artists.
12
Start:Regal River City Marketplace Stadium 14
Jacksonville, Florida·
4.5
(9) review
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
13
Start:Cathedral of St. John the Baptist
Savannah, Georgia·
5.0
(9819) review
The oldest Roman Catholic church in Georgia.
14
Start:Edmondston-Alston House
Charleston, South Carolina·
4.5
(992) review
Constructed nearly 200 years ago, circa 1825, the Edmondston-Alston House presents a unique history of the people, both free and enslaved, who lived and labored on this property. Its collection of furniture, silver and decorative arts, largely original to those who owned the house, constitutes a rich, complex history of Charleston in the 19th century. Commanding a magnificent view of Charleston Harbor, the Edmondston-Alston House has witnessed many historic moments in the port city’s history. One of the oldest houses along the High Battery, it withstood the American Civil War, the Earthquake of 1886, and numerous hurricanes; it has survived to share a piece of Charleston history.
15
Start:The Black Fedora Comedy Mystery Theatre
Charleston, South Carolina·
4.5
(993) review
Live theatre featuring clean comic whodunit shows, volunteer audience participation, a la carte appetizers, homemade desserts, and drinks -- at the downtown City Market. “Uproarious entertainment” - Thrillist.com
16
Start:Rockwood Park
Richmond, Virginia·
5.0
(9) review
3401 Courthouse Rd, Richmond, VA 23236-1438
17
Start:St. Paul's Episcopal Church
Richmond, Virginia·
4.5
(94) review
815 E Grace St, Richmond, VA 23219-3409
18
Start:Howard Peters Rawlings Conservatory and Botanic Gardens of Baltimore
Baltimore, Maryland·
4.5
(99) review
3100 Swann Dr Druid Hill Park, Baltimore, MD 21217
19
Start:Baltimore Spirits Company
Baltimore, Maryland·
5.0
(9) review
Be the master blender for the day! Blend your own bottle of Epoch Maryland Rye, Baltimore's first Maryland Rye to be produced in the city since the 1970s. In this unforgettable experience, your tour and blending experience will take between 1.5 and 2 hours. The highlight of the afternoon will be to taste and evaluate four of our barrel-finished Maryland Rye whiskeys, and then to create your own custom blended bottle of the spirits. Epoch Rye won Double-Gold Medals at both the 2018 and 2020 San Francisco World Spirits Competition. We take care of you from the time you walk in the door to ensure your perfect date, afternoon with friends, or a great gift for a whiskey fan. In addition to creating your own custom blend of our award-winning Pot-Distilled Maryland Rye, attendees also receive: • One delicious welcome cocktail • A compelling history lesson of Maryland Rye (15 minutes) • An up-close and personal distillery tour of our production facility and 650+ barrel rickhouse.
20
Start:Cylburn Arboretum
Baltimore, Maryland·
4.5
(91) review
4915 Greenspring Ave, Baltimore, MD 21209-4698
21
Start:Baltimore Clayworks
Baltimore, Maryland·
4.5
(9) review
5706 Smith Ave, Baltimore, MD 21209-3663
22
Start:John Heinz National Wildlife Refuge at Tinicum
Philadelphia, Pennsylvania·
4.5
(93) review
Visit John Heinz National Wildlife Refuge at Tinicum! Come enjoy 10 miles of walking trails through wooded forests, an impoundment pond, and 300 acres of the largest remaining freshwater tidal marsh in PA. Visitors can also experience the marsh on the water through 4.5 mile of Darby Creek by canoe or kayak. Stop by the front desk to borrow binoculars or fishing rods. Refuge trails are open every day from sunrise to sunset, free of charge. The Visitor Center is open daily from 8:30 AM to 4:00 PM. The visitor center building is closed for all Federal holidays however the trails remain open. Darby Creek is tidal and navigable only within 2 hours before and after high tide. Boat Launch is located at the trailhead of Dike Trail. Visitors must provide their own canoe/kayak and life vests. John Heinz NWR offers year-round free recreational and educational programs.
23
Start:Arthur Ross Gallery
Philadelphia, Pennsylvania·
4.0
(9) review
In the Fisher Fine Arts Library 220 South 34th Street, Philadelphia, PA 19104
24
Start:Old City Hall
Philadelphia, Pennsylvania·
4.5
(99) review
Independence Mall, Philadelphia, PA 19106
25
Start:Dave & Buster's - Arcade
Philadelphia, Pennsylvania·
3.0
(98) review
At Dave & Buster's you can play hundreds of the hottest new arcade games in our Million Dollar Midway and win tickets for epic prizes. Try our mouth-watering, chef-crafted creations in our American restaurant. From wings to steaks, we've got whatever suits your appetite. Our premium sports bar features innovative cocktails, impressive wine selection, and 20+ beers to assure we're stocked to satisfy! Watch your team on one of our massive HDTVs with epic stadium sound that surrounds you from every direction in the sports bar that crushes the competition. Invite all your friends or coworkers for an unforgettable party or event! We work with every size and budget to make planning easy so you can focus on the FUN!
26
Start:BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
27
Start:Daniel Roy's Parlour Of Deceptions
New York City, New York·
5.0
(99) review
Join magician Daniel Roy at the exclusive Salmagundi Club of New York City for an evening of sleight-of-hand, misdirection, and magic. Limited to just 40 guests, this is an intimate experience of wonder. While this is not a kids show and the magic is geared towards adults, the performance is entirely “clean” and appropriate for audience members age 13 years and older.
28
Start:The Blue Bar, Algonquin Hotel
New York City, New York·
4.0
(99) review
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
29
Start:Precision NY Chauffeur & Airport Transportation Services
New York City, New York·
5.0
(99) review
Here at Precision NY Chauffeur & Airport Transportation Service, we offer limousine service and point to point transportation NYC. You can always depend on us for reliable transportation New York, New Jersey, Westchester, Connecticut, Washington DC, Pennsylvania, and Boston. Along with equitable rates and attentive service, we offer transfer services anywhere within the country. For your convenience, you may reserve any vehicle from our fleet vehicles up to 24 hours in advance, including the Lincoln MKT, Lincoln Town Car and Cadillac XTS. For larger parties or a more comfortable ride, we have Cadillac™ Escalades, Lincoln™ Navigators, and Chevy™ Suburbans. We also carry New 2023 and 2024 Mercedes S560s.
30
Start:New Haven Railroad Station
New Haven, Connecticut·
4.0
(97) review
50 Union Ave, New Haven, CT 06519-1754
31
Start:Owl Shop Cigar Lounge
New Haven, Connecticut·
4.5
(9) review
268 College St, New Haven, CT 06510-2404
32
Start:Yale University Art Gallery
New Haven, Connecticut·
5.0
(984) review
Yale University Art Gallery is the oldest college art museum in America. The Gallery’s encyclopedic holdings of more than 250,000 objects range from ancient times to the present day and represent civilizations from around the globe. Spanning a block and a half of the city of New Haven, Connecticut, the Gallery comprises three architecturally distinct buildings, including a masterpiece of modern architecture from 1953 designed by Louis Kahn through which visitors enter. The museum is free and open to the public.
33
Start:David S. Ingalls Rink
New Haven, Connecticut·
4.5
(9) review
73 Sachem St, New Haven, CT 06511-3518
34
Start:DCU Center
Worcester, Massachusetts·
3.5
(93) review
50 Foster Street, Worcester, MA 01608-1305
35
Start:Boston Public Garden
Boston, Massachusetts·
4.5
(9979) review
This Frederick Law Olmsted-designed park, famous for its Swan Boats, has over 600 varieties of trees and an ever-changing array of flowers. It is America's first public garden.
36
Start:Boston Children's Museum
Boston, Massachusetts·
4.5
(994) review
Highlights of this interactive museum include the "Science Playground," featuring giant soap bubble-making tools and the "New Balance Climb," which teaches kids the laws of physics while navigating through a two-story-high maze.
37
Start:Hex: Old World Witchery
Salem, Massachusetts·
5.0
(1000) review
Salem Warlock Christian Day presents magical merchandise for both the curious and Witch alike. Whether you want a candle to bless your home, herbs and roots to make your own magic, a potion to attract love, the perfect ritual tool, a Voodoo doll made by a real practitioner, or to cast a spell at our authentic Witches' Altar, Hex is for those who believe in magic and those whose hearts beat with its fire.Be sure to visit our Witches' Altar of the Dead that stands at the Western wall of the shop. Here, countless visitors through the years have left messages, photos, and mementos in honor of departed loved ones in the spirit world. We welcome you to contribute to the magic!And, while there, have an authentic psychic reading with one of Salem's most talented Witches: Leanne Marrama, Laura Broderick, and Kyri Spencer!
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FAQ
Frequently Asked Questions
What's the driving distance between Leesburg and Boston?
The distance is 1,283 miles
What's the travel time between Leesburg and Boston?
The driving time can vary depending on traffic conditions, but it is typically 24h 59m mins in normal traffic
What are some of the best cities to visit between Leesburg and Boston?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Boston?
There are plenty! Here are some stops you shouldn’t miss on your way to Boston
What’s the weather like in Boston?
The weather in Boston is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Boston in January
Weather in Boston in February
Weather in Boston in March
Weather in Boston in April
Weather in Boston in May
Weather in Boston in June
Weather in Boston in July
Weather in Boston in August
Weather in Boston in September
Weather in Boston in October
Weather in Boston in November
Weather in Boston in December
Interested in a detailed plan for your time in Boston?
Plan your dream Boston trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Boston
A 2-day itinerary in Boston
A 3-day itinerary in Boston
A 4-day itinerary in Boston
A 5-day itinerary in Boston
A 6-day itinerary in Boston
Where else can I travel to if I'm starting my trip in Leesburg?
We have a lot of great trip options for Leesburg! See the links below for all the itineraries we created for you