36 days in United States, Toronto & Montreal Itinerary

36 days in United States, Toronto & Montreal Itinerary

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Plan created by another user. Make it yours

Route & dates

1
Detroit, United States
— 2 nights
2
Saint Paul, United States
— 2 nights
3
Chicago, United States
— 3 nights
4
Toronto, Canada
— 3 nights
5
Nashville, United States
— 2 nights
6
New York City, United States
— 4 nights
7
Orlando, United States
— 3 nights
8
Sunrise, United States
— 1 night
9
Tampa, United States
— 1 night
10
Raleigh, United States
— 1 night
11
Pittsburgh, United States
— 2 nights
12
Cleveland, United States
— 2 nights
13
Montreal, Canada
— 3 nights
14
Uncasville, United States
— 3 nights
15
Boston, United States
— 3 nights

2
nights
Detroit, United States

Detroit ©
Founded in 1701 by a French explorer and adventurer, Detroit exerted a profound impact on the world for most of the 20th century.
Start off your visit on the 21st (Tue): explore the world behind art at Detroit Institute of Arts, thenexamine the collection at The Henry Ford, and then ponder the design of James Scott Memorial Fountain. On your second day here, pause for some serene contemplation at The Cathedral Church of St. Paul, see the interesting displays at The Ford Piquette Avenue Plant, thenexamine the collection at Greenfield Village, and finally contemplate the long history of Motown Museum.

To find photos, other places to visit, where to stay, and other tourist information, refer to the Detroit itinerary builder website.

Plattsburgh to Detroit is an approximately 9.5-hour car ride. You can also fly. Plan for a bit warmer nights when traveling from Plattsburgh in September since evenings lows in Detroit dip to °F. Finish your sightseeing early on the 22nd (Wed) so you can travel to Saint Paul.

Things to do in Detroit

Museums Historic Sites

Side Trip

Dearborn
Find places to stay Sep 20 — 22:
Highlights from your plan
The Henry Ford ©
The Henry Ford
Detroit Institute of Arts ©
Detroit Institute of Arts
Greenfield Village ©
Greenfield Village

2
nights
Saint Paul, United States

Saint Paul
The capital of Minnesota, Saint Paul represents half of the "Twin Cities" and embraces the outdoors and urban culture.
To find ratings, traveler tips, and more tourist information, you can read our Saint Paul sightseeing planning app.

Traveling by flight from Detroit to Saint Paul takes 5 hours. Alternatively, you can drive; or take a train. The time zone difference when traveling from Detroit to Saint Paul is minus 1 hour. Expect a daytime high around °F in September, and nighttime lows around °F. You will leave for Chicago on the 24th (Fri).

Things to do in Saint Paul

Parks Nightlife Outdoors
Find places to stay Sep 22 — 24:

3
nights
Chicago, United States

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, meet the residents at Shedd Aquarium, walk around Millennium Park, and have some family-friendly fun at Fox in a Box Chicago.

To find traveler tips, reviews, more things to do, and other tourist information, go to the Chicago visit planner.

Getting from Saint Paul to Chicago by flight takes about 4 hours. Other options: drive; or take a train. In September, daytime highs in Chicago are °F, while nighttime lows are °F. Wrap up your sightseeing on the 27th (Mon) early enough to travel to Toronto.

Things to do in Chicago

Parks Museums Zoos & Aquariums
Find places to stay Sep 24 — 27:
Highlights from your plan
Fox in a Box Chicago ©
Fox in a Box Chicago
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

3
nights
Toronto, Canada

Toronto ©
Possibly the world's most diverse city, Toronto houses over 80 ethnic communities speaking nearly 150 different languages or dialects.
Change things up with these side-trips from Toronto: Niagara Falls (Skylon Tower, Niagara Falls Canada, &more). The adventure continues: take in panoramic vistas at CN Tower, see the interesting displays at Royal Ontario Museum, walk around Toronto Music Garden, and contemplate in the serene atmosphere at St Michael's Cathedral Basilica.

To find other places to visit, where to stay, more things to do, and more tourist information, go to the Toronto visit planning website.

You can fly from Chicago to Toronto in 5 hours. Alternatively, you can drive; or do a combination of train and car. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Traveling from Chicago in September, expect nights in Toronto to be about the same, around °F, while days are slightly colder, around °F. Finish up your sightseeing early on the 30th (Thu) so you can travel to Nashville.

Things to do in Toronto

Parks Nature Historic Sites

Side Trip

Niagara Falls
Find places to stay Sep 27 — 30:
Highlights from your plan
Niagara Falls Canada ©
Niagara Falls Canada
CN Tower
CN Tower
The Distillery District ©
The Distillery District

2
nights
Nashville, United States

Nashville ©
Known as the capital of country music, the thriving city of Nashville combines old-world southern charm with a progressive urban flair.
Start off your visit on the 1st (Fri): take in the architecture and atmosphere at Upper Room, catch a live performance at Grand Ole Opry, thensee the interesting displays at Country Music Hall of Fame and Museum, and finally take an in-depth tour of The Johnny Cash Museum & Cafe. Here are some ideas for day two: walk around Edwin and Percy Warner Parks, witness the site of a historic battle at Lotz House Museum, and then learn the secrets of beer at a beer tour and tasting.

To find where to stay, traveler tips, photos, and more tourist information, use the Nashville travel planning website.

Getting from Toronto to Nashville by flight takes about 5.5 hours. Other options: drive; or do a combination of train, car, and bus. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. While traveling from Toronto, expect somewhat warmer days and about the same nights in Nashville, ranging from highs of °F to lows of °F. Finish your sightseeing early on the 2nd (Sat) so you can travel to New York City.

Things to do in Nashville

Museums Parks Breweries & Distilleries

Side Trip

Lotz House Museum
Find places to stay Sep 30 — Oct 2:
Highlights from your plan
Lotz House Museum ©
Lotz House Museum
Grand Ole Opry ©
Grand Ole Opry
Country Music Hall of Fame and Museum ©
Country Music Hall of Fame and Museum

4
nights
New York City, United States

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, and shopping. Your plan includes some of its best attractions: take in the pleasant sights at Central Park, pause for some photo ops at Statue of Liberty National Monument, admire the striking features of Grand Central Terminal, and take in panoramic vistas at Empire State Building.

To see photos, more things to do, other places to visit, and more tourist information, use the New York City day trip planning app.

Fly from Nashville to New York City in 6 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Nashville to New York City. When traveling from Nashville in October, plan for a bit cooler days and about the same nights in New York City: temperatures range from °F by day to °F at night. Finish up your sightseeing early on the 6th (Wed) so you can travel to Orlando.

Things to do in New York City

Parks Museums Historic Sites
Find places to stay Oct 2 — 6:
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

3
nights
Orlando, United States

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Pack the 7th (Thu) with family-friendly diversions at Universal's Islands of Adventure. Have a day of magic on the 9th (Sat) at Walt Disney World Resort. The adventure continues: find something for the whole family at Universal Orlando Resort.

Plan trip to Orlando with our itinerary maker to find out where to go and what to do.

Traveling by flight from New York City to Orlando takes 6.5 hours. Alternatively, you can drive; or take a bus. In October, Orlando is somewhat warmer than New York City - with highs of °F and lows of °F. Wrap up your sightseeing on the 9th (Sat) to allow time to drive to Sunrise.

Things to do in Orlando

Theme Parks
Find places to stay Oct 6 — 9:
Highlights from your plan
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Universal Orlando Resort ©
Universal Orlando Resort
Walt Disney World Resort ©
Walt Disney World Resort

1
night
Sunrise, United States

Sunrise ©
Sunrise is a city in central-western Broward County, Florida, United States, in the Miami metropolitan area. Kick off your visit on the 10th (Sun): let the kids burn off some steam at Welleby Park and then buy something for everyone on your list at Sawgrass Mills.

To find more things to do, maps, traveler tips, and tourist information, go to the Sunrise trip itinerary planner.

You can drive from Orlando to Sunrise in 3.5 hours. Alternatively, you can fly; or do a combination of train and bus. In October, plan for daily highs up to °F, and evening lows to °F. Wrap up your sightseeing on the 10th (Sun) early enough to drive to Tampa.

Things to do in Sunrise

Shopping Parks Fun & Games
Find places to stay Oct 9 — 10:
Highlights from your plan
Sawgrass Mills ©
Sawgrass Mills
Welleby Park ©
Welleby Park

1
night
Tampa, United States

Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
On the 11th (Mon), pause for some serene contemplation at Sacred Heart Catholic Church, thensee what you can catch with a fishing tour, and then take in the spiritual surroundings of Wat Mongkolrata Temple.

To find where to stay, other places to visit, photos, and more tourist information, read our Tampa road trip planner.

Traveling by car from Sunrise to Tampa takes 4.5 hours. Alternatively, you can fly; or do a combination of bus and train. Traveling from Sunrise in October, Tampa is little chillier at night with lows of °F. Finish up your sightseeing early on the 11th (Mon) so you can travel to Raleigh.

Things to do in Tampa

Outdoors Wildlife Tours
Find places to stay Oct 10 — 11:
Highlights from your plan
Fishing Charters & Tours
Sacred Heart Catholic Church ©
Sacred Heart Catholic Church
Wat Mongkolrata Temple ©
Wat Mongkolrata Temple

1
night
Raleigh, United States

Raleigh ©
For those not from the South, Raleigh might be one of the region's better-kept travel secrets.
On the 12th (Tue), identify plant and animal life at Fletcher Park, walk around Pullen Park, thencontemplate the waterfront views at Apex Community Park, and finally admire the majestic nature at Umstead State Park.

To find ratings, photos, traveler tips, and other tourist information, read Raleigh online travel route planner.

Fly from Tampa to Raleigh in 5 hours. Alternatively, you can drive; or take a train. In October, Raleigh is little chillier than Tampa - with highs of °F and lows of °F. Finish your sightseeing early on the 12th (Tue) so you can travel to Pittsburgh.

Things to do in Raleigh

Parks Nature Wildlife

Side Trip

Apex Community Park
Find places to stay Oct 11 — 12:
Highlights from your plan
Pullen Park ©
Pullen Park

2
nights
Pittsburgh, United States

Pittsburgh ©
Known primarily for its steel-related heritage and 446 bridges, Pittsburgh sits at the confluence of the Monongahela and Allegheny Rivers, which meet to form the Ohio River.
On the 13th (Wed), trek along Montour Trail, thentake in the spiritual surroundings of Millvale Murals of Maxo Vanka, thenexamine the collection at Bicycle Heaven, and finally pause for some photo ops at Southern Pennsylvania World War II Memorial. On the next day, get engrossed in the history at Cathedral of Learning, thentake in nature's colorful creations at Phipps Conservatory and Botanical Gardens, and then take an in-depth tour of Soldiers & Sailors Memorial Hall & Museum.

To find other places to visit, more things to do, maps, and other tourist information, read Pittsburgh trip itinerary builder website.

Getting from Raleigh to Pittsburgh by flight takes about 4.5 hours. Other options: drive; or take a bus. Traveling from Raleigh in October, expect nights in Pittsburgh to be about the same, around °F, while days are little chillier, around °F. Finish your sightseeing early on the 14th (Thu) to allow enough time to drive to Cleveland.

Things to do in Pittsburgh

Museums Parks Historic Sites

Side Trips

Montour Trail, Millvale Murals of Maxo Vanka
Find places to stay Oct 12 — 14:
Highlights from your plan
Bicycle Heaven ©
Bicycle Heaven
Phipps Conservatory and Botanical Gardens ©
Phipps Conservatory and Botanical Gardens
Soldiers & Sailors Memorial Hall & Museum ©

2
nights
Cleveland, United States

Cleveland ©
A culturally diverse city situated on the shores of Lake Erie, Cleveland boasts many places to visit, such as world-class museums, popular amusement parks, and sprawling recreational areas.
On the 15th (Fri), stroll around Rocky River Reservation, thensee the interesting displays at Rock & Roll Hall of Fame, and then admire the masterpieces at The Cleveland Museum of Art. On the next day, look for all kinds of wild species at F.A. Seiberling Nature Realm and then admire the natural beauty at Stan Hywet Hall & Gardens.

For maps, photos, and other tourist information, you can read our Cleveland visit planner.

You can drive from Pittsburgh to Cleveland in 2.5 hours. Other options are to take a train; or take a bus. In October in Cleveland, expect temperatures between °F during the day and °F at night. Cap off your sightseeing on the 16th (Sat) early enough to travel to Montreal.

Things to do in Cleveland

Parks Museums Historic Sites

Side Trip

Akron
Find places to stay Oct 14 — 16:
Highlights from your plan
The Cleveland Museum of Art ©
The Cleveland Museum of Art
Stan Hywet Hall & Gardens ©
Stan Hywet Hall & Gardens
F.A. Seiberling Nature Realm ©
F.A. Seiberling Nature Realm

3
nights
Montreal, Canada

Montreal ©
Quebec's economic and cultural capital, Montreal serves as the province's major point of entry, known for its rich history and high standard of living.
Montreal is known for historic sites, parks, and museums. Your plan includes some of its best attractions: don't miss a visit to Notre-Dame Basilica, browse the fresh offerings at Jean-Talon Market, see the interesting displays at Pointe-a-Calliere, Montreal Archaeology and History Complex, and take an in-depth tour of Chateau Ramezay Historic Site and Museum of Montreal.

For maps, ratings, reviews, and more tourist information, go to the Montreal trip planning site.

Traveling by flight from Cleveland to Montreal takes 7 hours. Alternatively, you can drive; or take a train. Plan for a bit cooler temperatures traveling from Cleveland in October, with highs in Montreal at °F and lows at °F. Finish your sightseeing early on the 19th (Tue) so you can travel to Uncasville.

Things to do in Montreal

Museums Historic Sites Parks
Find places to stay Oct 16 — 19:
Highlights from your plan
Musee des beaux-arts de Montreal ©
Musee des beaux-arts de Montreal
Notre-Dame Basilica ©
Notre-Dame Basilica
Montreal Botanical Garden ©
Montreal Botanical Garden

3
nights
Uncasville, United States

Uncasville ©
Get out of town with these interesting Uncasville side-trips: Dondero Orchards (in South Glastonbury), A Place Called Hope (in Killingworth) and Gotta's Farm and Cider Mill (in Portland).

To see traveler tips, ratings, where to stay, and other tourist information, read Uncasville online journey planner.

Explore your travel options from Montreal to Uncasville with the Route module. While traveling from Montreal, expect somewhat warmer days and about the same nights in Uncasville, ranging from highs of °F to lows of °F. Finish your sightseeing early on the 22nd (Fri) to allow enough time to drive to Boston.

Things to do in Uncasville

Parks Outdoors Trails

Side Trips

Norwich, Dondero Orchards, Vernon Rails-to-Trails, Main Street Park, Essex Village, The Lodge at Crandall Park
Find places to stay Oct 19 — 22:
Highlights from your plan
A Place Called Hope ©
A Place Called Hope
Gotta's Farm and Cider Mill ©
Gotta's Farm and Cider Mill
Dondero Orchards ©
Dondero Orchards

3
nights
Boston, United States

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Change things up with these side-trips from Boston: Sandwich (Hoxie House, Heritage Museums & Gardens, &more) and Brewster Gardens (in Plymouth). And it doesn't end there: admire the masterpieces at Museum of Fine Arts, contemplate the long history of Granary Burying Ground, walk around Boston Common, and get to know the fascinating history of Freedom Trail.

To see ratings, more things to do, traveler tips, and other tourist information, read our Boston trip tool.

Traveling by car from Uncasville to Boston takes 2 hours. Alternatively, you can do a combination of taxi and train; or do a combination of taxi and bus. October in Boston sees daily highs of °F and lows of °F at night. Finish up your sightseeing early on the 25th (Mon) so you can travel back home.

Things to do in Boston

Historic Sites Museums Parks

Side Trips

Sandwich, Mount Auburn Cemetery, Brewster Gardens
Find places to stay Oct 22 — 25:
Highlights from your plan
Mount Auburn Cemetery ©
Mount Auburn Cemetery
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum

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