29 days in Canada & United States Itinerary

29 days in Canada & United States Itinerary

Created using Inspirock visit planner

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Fly
1
Toronto, Canada
— 5 nights
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2
Charlottetown, Canada
— 4 nights
Fly
3
Boston, United States
— 3 nights
Fly
4
Provincetown, United States
— 4 nights
Drive
5
Falmouth, United States
— 3 nights
Fly
6
New York City, United States
— 7 nights
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Toronto, Canada

— 5 nights

New York City of Canada

Possibly the world's most diverse city, Toronto houses over 80 ethnic communities speaking nearly 150 different languages or dialects.
You'll find plenty of places to visit near Toronto: Niagara Falls (Journey Behind the Falls, Niagara Falls Canada, &more). The adventure continues: take in panoramic vistas at CN Tower, admire nature's wide array of creatures at Ripley's Aquarium of Canada, squeeze the most out of the city with Bluffs Tours, and learn about wildlife with up-close encounters at Toronto Zoo.

For where to stay, reviews, photos, and other tourist information, use the Toronto driving holiday planner.

Melbourne, Australia to Toronto is an approximately 26-hour flight. The time zone difference moving from Australian Eastern Standard Time to Eastern Standard Time is minus 15 hours. Expect a bit warmer temperatures when traveling from Melbourne in September; daily highs in Toronto reach 26°C and lows reach 16°C. Finish your sightseeing early on the 22nd (Wed) to allow enough time to fly to Charlottetown.

Things to do in Toronto

Parks · Nature · Zoos & Aquariums · Museums

Side Trip

Find places to stay Sep 17 — 22:

Charlottetown, Canada

— 4 nights

Birthplace of Confederation

The largest city on Prince Edward Island, Charlottetown remains small enough for easy exploration on foot.
Explore the numerous day-trip ideas around Charlottetown: The Links at Crowbush Cove (in Lakeside) and Cavendish Cliffs (in Cavendish). There's lots more to do: explore the striking landscape of Prince Edward Island National Park, see the interesting displays at Farmers' Bank of Rustico Museum & Doucet House, contemplate the long history of Sir Andrew Macphail Homestead, and don't miss a visit to Victoria Row.

To find reviews, where to stay, photos, and tourist information, refer to the Charlottetown itinerary planning website.

Getting from Toronto to Charlottetown by flight takes about 4 hours. Other options: drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Toronto to Charlottetown. Traveling from Toronto in September, things will get little chillier in Charlottetown: highs are around 22°C and lows about 13°C. Wrap up your sightseeing on the 26th (Sun) to allow time to fly to Boston.

Things to do in Charlottetown

Parks · Nature · Historic Sites · Outdoors

Side Trips

Find places to stay Sep 22 — 26:

Boston, United States

— 3 nights

Beantown

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.
Take a break from Boston with a short trip to Louisa May Alcott's Orchard House in Concord, about 36 minutes away. And it doesn't end there: take in nature's colorful creations at Boston Public Garden, explore the different monuments and memorials at Mount Auburn Cemetery, stroll around Boston Common, and get engrossed in the history at John F. Kennedy Presidential Museum & Library.

Before you visit Boston, use our trip planner to discover what you can do and see there.

Traveling by flight from Charlottetown to Boston takes 8 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Charlottetown to Boston. In September, Boston is a bit warmer than Charlottetown - with highs of 28°C and lows of 17°C. Finish your sightseeing early on the 29th (Wed) so you can fly to Provincetown.

Things to do in Boston

Side Trips

Find places to stay Sep 26 — 29:

Provincetown, United States

— 4 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Change things up with these side-trips from Provincetown: Atwood Museum (in Chatham) and Eastham (Nauset Light Beach, Coast Guard Beach, &more). There's still lots to do: appreciate the history behind Pilgrim Monument & Provincetown Museum, get lost in a book at Provincetown Library, take in the waterfront at MacMillan Wharf, and tour the pleasant surroundings at Marconi Beach.

To find reviews, maps, photos, and tourist information, read Provincetown trip planner.

Traveling by flight from Boston to Provincetown takes 2 hours. Alternatively, you can ride a ferry; or drive. Expect a daytime high around 25°C in September, and nighttime lows around 16°C. Finish your sightseeing early on the 3rd (Sun) to allow enough time to drive to Falmouth.

Things to do in Provincetown

Beaches · Outdoors · Parks · Museums

Side Trips

Find places to stay Sep 29 — Oct 3:

Falmouth, United States

— 3 nights
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Explore Falmouth's surroundings by going to Edgartown (Edgartown Lighthouse & Mytoi), Heritage Museums & Gardens (in Sandwich) and Cape Cod Canal (in Buzzards Bay). And it doesn't end there: grab your bike and head to Shining Sea Bikeway, relax in the rural setting at Coonamessett Farm, meet the residents at Woods Hole Science Aquarium, and play a few rounds at Farm Neck Golf Club.

To find maps, ratings, other places to visit, and other tourist information, read our Falmouth travel itinerary planner.

You can drive from Provincetown to Falmouth in 2 hours. Another option is to take a bus. In October, daily temperatures in Falmouth can reach 20°C, while at night they dip to 9°C. Wrap up your sightseeing on the 6th (Wed) early enough to fly to New York City.

Things to do in Falmouth

Museums · Parks · Outdoors · Historic Sites

Side Trips

Find places to stay Oct 3 — 6:

New York City, United States

— 7 nights

Big Apple

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 trip includes some of its best attractions: take in the pleasant sights at Central Park, don't miss a visit to Rockefeller Center, stroll around The High Line, and admire the landmark architecture of Grand Central Terminal.

To find traveler tips, other places to visit, reviews, and more tourist information, go to the New York City trip planner.

You can fly from Falmouth to New York City in 3 hours. Other options are to drive; or do a combination of bus and train. In October, New York City is somewhat warmer than Falmouth - with highs of 24°C and lows of 16°C. Wrap up your sightseeing on the 13th (Wed) early enough to fly back home.

Things to do in New York City

Find places to stay Oct 6 — 13:

Canada travel guide

4.6
Most people remember their holiday in Canada by the country's great outdoors, yet this sprawling land of hulking mountains and rocky coastlines also boasts numerous modern cities, home to some of the world's finest dining, shopping, and entertainment options. Made for leisurely road trips, North America's biggest country features vast landscapes still unspoiled by mass tourism. A tour of Canada reveals a place packed with diverse cultures, living in tolerance and enjoying one of the highest standards of living in the world. If the vastness of those natural landscapes overwhelms you at any point during your Canada vacation, head to the openhearted cities of Vancouver, Toronto, or Montreal, ideal destinations for art lovers, history buffs, shopaholics, fashionistas, and impassioned foodies.

Prince Edward Island travel guide

4.3
Historic Sites · Beaches · Theme Parks
Garden of the Gulf
Canada's only island province, Prince Edward Island earned the nickname the "Garden of the Gulf" thanks to its pastoral landscape of rolling green hills and a patchwork of cultivated fields. The country's smallest province in terms of land and population, the island boasts a long coastline marked by sandy beaches, making up in visual appeal what they lack in modern infrastructure. It's easy to get away from everyone during a vacation in Prince Edward Island, as this photogenic landmass features just a scattering of small towns housing warmhearted locals stubbornly clinging to their easygoing lifestyle. Begin your Prince Edward Island tour in Charlottetown, the quaint provincial capital with a good selection of bars and restaurants.

United States travel guide

4.5
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.