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Road trip from Jacksonville to Boston
All Category
Shopping
Nightlife
Food & Drink
Nature & Parks
Sights & Landmarks
Museums
Concerts & ShowsShow more (4+)
All Category
ShoppingNightlifeFood & DrinkNature & ParksSights & LandmarksMuseumsConcerts & Shows
Fun & Games
Classes & Workshops
Outdoor ActivitiesReset
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ITINERARY
22h 4m1,144 miles30 stops
1
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.
2
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.
3
Fort Ward Museum & Historic Site
4
Barracuda's Locust Point Tavern
5
Vagabond Players, Inc.
The organization has operated continuously for over 100 years making Vagabond Players the oldest continuously operating community theater in the United States. Founded in the early 1900’s as a part of the vanguard of America’s “Little Theater” movement, the organization has called its current location, the Vagabond Theatre, home for over 40 years. We have been an important part of the rich history of Fells Point and Baltimore City’s cultural landscape.
6
Howard Peters Rawlings Conservatory and Botanic Gardens of Baltimore
7
Bennett’s Curse Haunted House
We are a small family owned and operated business born and raised in Baltimore, Maryland and proud to always be the first to introduce you to the most innovative halloween attractions for the past 18 years. Bennett’s Curse Haunted Attraction in Baltimore county, Maryland, with it’s close proximity to Washington DC and southern Pennsylvania continues to dominate the Mid-Atlantic region.
8
Cylburn Arboretum
9
Bengies Drive-In Theatre
10
iFLY Indoor Skydiving - Baltimore
Ever dream of flying? Now you can at iFLY Indoor Skydiving in Baltimore. Experience the thrill of skydiving without having to jump from a perfectly good airplane - no falling, no parachutes, just you floating on a smooth cushion of air with our professional instructor right next to you. No special skills are needed, just a sense of adventure. iFLY is safe for kids 3 and up, fun for the entire family, and perfect for birthday parties or groups. iFLY is the experience of a lifetime.
11
All In Adventures Escape Rooms
Your ultimate escape destination Bring your family, friends, and coworkers in for a fun filled experience. Explore together to find the hidden objects, decipher the clues, and unravel the puzzles to win. But you must move fast– 50 minutes goes by quickly! Perfect for date night, hanging out with friends, birthday parties, or as corporate team building activity. Book your adventure today!
12
Quicktransfer - Philadelphia
As QuickTransfer we have been passionately realizing services for the travel industry since 2009. We are dedicated professionals providing high-class transport services on all continents. Extensive international experience makes us a trustworthy choice for everyone in need of reliable, safe and punctual transfer service.
13
Benjamin Rush Garden
14
Old City Hall
15
Philadelphia Distilling
16
Staten Island Children's Museum
The Staten Island Children’s Museum features 10 indoor and 2 outdoor exhibits, a dedicated art workshop and a performance space. Visitors can explore different climates, examine bugs and other arthropods, learn about construction, build with blocks, hop on board a fire truck and play games throughout the interactive exhibits. The 4-acre East Meadow offers a perfect outdoor setting to run, play and picnic. The Children's Museum is engaging, affordable and focused on STEAM learning. In addition to the exhibits, it hosts a variety of programs throughout the year, including cultural performances & celebrations, summertime "Boogie Woogie Wednesday" dance performances, as well as mini-camps during the summer and during NYC public school breaks.
17
BrainXcape
18
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.
19
The Blue Bar, Algonquin Hotel
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
20
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.
21
Bronx Documentary Center
The Bronx Documentary Center (BDC) is a non-profit gallery and educational space. Our mission is to share photography, film and new media with underserved Bronx communities and the cultural community at large. We show the work of internationally renowned and emerging photographers and filmmakers who are dealing with issues surrounding justice, education and social progress.
22
Crotona Park
23
Edgar Allan Poe Cottage
24
New Haven Railroad Station
25
Owl Shop Cigar Lounge
26
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.
27
DCU Center
28
Commonwealth Avenue Mall
29
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.
30
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.
Customize this Trip
OVERVIEW
Get ready for an epic adventure as we embark on an unforgettable road trip from the vibrant city of Jacksonville to the charming streets of Boston. Along the way, we'll discover hidden gems, immerse ourselves in captivating history, and create memories that will last a lifetime.
Our journey will span across diverse landscapes, from the sun-kissed beaches of the Atlantic coast to the rolling hills of New England. We'll navigate bustling metropolises and quaint small towns, each with its unique stories and flavors. As we traverse this cross-country adventure, we'll encounter friendly locals, witness awe-inspiring natural wonders, and delve into the rich tapestry of American culture.
Prepare to be amazed by the vibrant energy of Jacksonville, where the St. Johns River meanders through the city's heart. Boston, on the other hand, will captivate us with its historic charm, world-class universities, and lively neighborhoods. The journey itself will be as captivating as the destinations, offering a chance to explore the hidden treasures that lie in between. So, buckle up and let's embark on an adventure filled with endless discoveries and unforgettable experiences.
1
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.
2
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.
3
Start:Fort Ward Museum & Historic Site
Alexandria, Virginia·
4.0
(71) review
4301 W Braddock Rd, Alexandria, VA 22304-1007
4
Start:Barracuda's Locust Point Tavern
Baltimore, Maryland·
4.0
(9) review
1230 E Fort Ave, Baltimore, MD 21230-5105
5
Start:Vagabond Players, Inc.
Baltimore, Maryland·
5.0
(9) review
The organization has operated continuously for over 100 years making Vagabond Players the oldest continuously operating community theater in the United States. Founded in the early 1900’s as a part of the vanguard of America’s “Little Theater” movement, the organization has called its current location, the Vagabond Theatre, home for over 40 years. We have been an important part of the rich history of Fells Point and Baltimore City’s cultural landscape.
6
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
7
Start:Bennett’s Curse Haunted House
Baltimore, Maryland·
4.5
(8) review
We are a small family owned and operated business born and raised in Baltimore, Maryland and proud to always be the first to introduce you to the most innovative halloween attractions for the past 18 years. Bennett’s Curse Haunted Attraction in Baltimore county, Maryland, with it’s close proximity to Washington DC and southern Pennsylvania continues to dominate the Mid-Atlantic region.
8
Start:Cylburn Arboretum
Baltimore, Maryland·
4.5
(91) review
4915 Greenspring Ave, Baltimore, MD 21209-4698
9
Start:Bengies Drive-In Theatre
Baltimore, Maryland·
3.5
(65) review
3417 Eastern Blvd, Baltimore, MD 21220-2122
10
Start:iFLY Indoor Skydiving - Baltimore
Baltimore, Maryland·
4.5
(238) review
Ever dream of flying? Now you can at iFLY Indoor Skydiving in Baltimore. Experience the thrill of skydiving without having to jump from a perfectly good airplane - no falling, no parachutes, just you floating on a smooth cushion of air with our professional instructor right next to you. No special skills are needed, just a sense of adventure. iFLY is safe for kids 3 and up, fun for the entire family, and perfect for birthday parties or groups. iFLY is the experience of a lifetime.
11
Start:All In Adventures Escape Rooms
Baltimore, Maryland·
3.5
(9) review
Your ultimate escape destination Bring your family, friends, and coworkers in for a fun filled experience. Explore together to find the hidden objects, decipher the clues, and unravel the puzzles to win. But you must move fast– 50 minutes goes by quickly! Perfect for date night, hanging out with friends, birthday parties, or as corporate team building activity. Book your adventure today!
12
Start:Quicktransfer - Philadelphia
Philadelphia, Pennsylvania·
(0) review
As QuickTransfer we have been passionately realizing services for the travel industry since 2009. We are dedicated professionals providing high-class transport services on all continents. Extensive international experience makes us a trustworthy choice for everyone in need of reliable, safe and punctual transfer service.
13
Start:Benjamin Rush Garden
Philadelphia, Pennsylvania·
4.0
(2) review
Corner of 3rd & Walnut Streets, Philadelphia, PA 19106
14
Start:Old City Hall
Philadelphia, Pennsylvania·
4.5
(99) review
Independence Mall, Philadelphia, PA 19106
15
Start:Philadelphia Distilling
Philadelphia, Pennsylvania·
5.0
(98) review
25 E Allen St, Philadelphia, PA 19123-1753
16
Start:Staten Island Children's Museum
Staten Island, New York·
4.5
(92) review
The Staten Island Children’s Museum features 10 indoor and 2 outdoor exhibits, a dedicated art workshop and a performance space. Visitors can explore different climates, examine bugs and other arthropods, learn about construction, build with blocks, hop on board a fire truck and play games throughout the interactive exhibits. The 4-acre East Meadow offers a perfect outdoor setting to run, play and picnic. The Children's Museum is engaging, affordable and focused on STEAM learning. In addition to the exhibits, it hosts a variety of programs throughout the year, including cultural performances & celebrations, summertime "Boogie Woogie Wednesday" dance performances, as well as mini-camps during the summer and during NYC public school breaks.
17
Start:BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
18
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.
19
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.
20
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.
21
Start:Bronx Documentary Center
Bronx, New York·
5.0
(9) review
The Bronx Documentary Center (BDC) is a non-profit gallery and educational space. Our mission is to share photography, film and new media with underserved Bronx communities and the cultural community at large. We show the work of internationally renowned and emerging photographers and filmmakers who are dealing with issues surrounding justice, education and social progress.
22
Start:Crotona Park
Bronx, New York·
4.0
(9) review
Crotona Ave, Bronx, NY 10460
23
Start:Edgar Allan Poe Cottage
Bronx, New York·
4.5
(98) review
Poe Park Grand Concourse at Kingsbridge Rd, Bronx, NY 10458
24
Start:New Haven Railroad Station
New Haven, Connecticut·
4.0
(97) review
50 Union Ave, New Haven, CT 06519-1754
25
Start:Owl Shop Cigar Lounge
New Haven, Connecticut·
4.5
(9) review
268 College St, New Haven, CT 06510-2404
26
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.
27
Start:DCU Center
Worcester, Massachusetts·
3.5
(93) review
50 Foster Street, Worcester, MA 01608-1305
28
Start:Commonwealth Avenue Mall
Boston, Massachusetts·
4.5
(94) review
484 Commonwealth Ave, Boston, MA 02215-2737
29
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.
30
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.
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
HASHTAGS
#travel#transportation#cities#east coast#united states#road trip#planning#itinerary#car rental#flights#trains#buses#budget#accommodation#hotels#motels#hostels#food#restaurants#attractions#sightseeing#activities#museums#history#culture#shopping#nightlife#entertainment#safety#weather#climate#packing#tips
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Frequently Asked Questions
What's the driving distance between Jacksonville and Boston?
The distance is 1,144 miles
What's the travel time between Jacksonville and Boston?
The driving time can vary depending on traffic conditions, but it is typically 22h 4m mins in normal traffic
What are some of the best cities to visit between Jacksonville 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 Jacksonville?
We have a lot of great trip options for Jacksonville! See the links below for all the itineraries we created for you
