49 days in United States & Canada Itinerary

49 days in United States & Canada Itinerary

Make it your trip
Fly
1
Honolulu, United States
— 4 nights
Fly
2
Koloa, United States
— 4 nights
Fly
3
Lahaina, United States
— 4 nights
Fly
4
Hilo, United States
— 2 nights
Drive
5
Kailua-Kona, United States
— 4 nights
Fly
6
Naples, United States
— 3 nights
Drive
7
Marco Island, United States
— 2 nights
Drive
8
Key Largo, United States
— 1 night
Drive
9
Islamorada, United States
— 1 night
Drive
10
Marathon, United States
— 2 nights
Drive
11
Key West, United States
— 4 nights
Fly
12
Orlando, United States
— 4 nights
Fly
13
Washington DC, United States
— 3 nights
Train
14
Philadelphia, United States
— 1 night
Fly
15
Montreal, Canada
— 3 nights
Fly
16
Boston, United States
— 1 night
Fly
17
New York City, United States
— 4 nights
Fly

S M T W T F S
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20

Honolulu, United States — 4 nights

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
You'll explore the less-touristy side of things at Shark Diving and Battleship Missouri Memorial. Go for a jaunt from Honolulu to Haleiwa to see Sunset Beach Park about 1h 5 min away. There's much more to do: see the world from above with a helicopter tour, stroll around Fort DeRussy Beach Park, trek along Koko Crater Railway Trail, and stroll through Waikiki Beach.

To see reviews, other places to visit, where to stay, and more tourist information, you can read our Honolulu tour planner.

Johannesburg, South Africa to Honolulu is an approximately 26-hour flight. The time zone difference moving from South Africa Standard Time (SAST) to Hawaii-Aleutian Standard Time (HST) is minus 12 hours. Traveling from Johannesburg in November, you can expect nighttime temperatures to be somewhat warmer in Honolulu, with lows of 26°C. Finish your sightseeing early on the 4th (Mon) so you can fly to Koloa.
more
Outdoors · Parks · Historic Sites · Trails
Side Trip

Koloa, United States — 4 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Step off the beaten path and head to Kalalau Trail and Lydgate Farms Kauai Chocolate. Change things up with these side-trips from Koloa: Waimea Canyon State Park (in Waimea), Princeville Botanical Gardens (in Princeville) and Hanalei Beach (in Hanalei). And it doesn't end there: see some colorful creatures with Holo Holo Charters, kick back and relax at Poipu Beach Park, admire the natural beauty at Allerton Garden, and tour the pleasant surroundings at Na Pali Coast State Park.

To find other places to visit, where to stay, more things to do, and more tourist information, you can read our Koloa road trip planning tool.

Getting from Honolulu to Koloa by flight takes about 2.5 hours. In December, plan for daily highs up to 30°C, and evening lows to 22°C. Cap off your sightseeing on the 8th (Fri) early enough to catch the flight to Lahaina.
more
Parks · Outdoors · Wildlife · Nature
Side Trips

Lahaina, United States — 4 nights

Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
You'll discover tucked-away gems like Parasailing & Paragliding and Haleakala Crater. Explore Lahaina's surroundings by going to Kamaole Beach Park III (in Kihei), Ho'okipa Beach Park (in Paia) and Helicopter Tours (in Kahului). There's much more to do: kick your exploration up a notch at some of the top local zipline courses and adventure parks, observe the fascinating underwater world at Maui Ocean Center, take a stroll through Lahaina Front Street, and relax in the rural setting at Maui Tropical Plantation.

To see other places to visit, maps, more things to do, and tourist information, refer to the Lahaina trip itinerary maker app.

You can fly from Koloa to Lahaina in 2.5 hours. December in Lahaina sees daily highs of 30°C and lows of 23°C at night. Cap off your sightseeing on the 12th (Tue) early enough to catch the flight to Hilo.
more
Parks · Outdoors · Beaches · Tours
Side Trips

Hilo, United States — 2 nights

One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
Kick off your visit on the 13th (Wed): explore the striking landscape at Thurston Lava Tube (Nahuku), stroll through Kipuka Puaulu (Bird Park) Trail, then examine the collection at Jagger Museum, then hike along Kilauea Iki Trailhead, and finally cruise along Devastation Trail. On the 14th (Thu), you'll have a packed day of sightseeing: take an unforgettable tour with a helicopter tour, get up close and personal with brilliant marine life at Mokupapapa Discovery Center, immerse yourself in nature at Akaka Falls State Park, then take in nature's colorful creations at Hawaii Tropical Bioreserve and Garden, then admire the natural beauty at Liliuokalani Gardens, and finally admire the sheer force of Rainbow Falls.

To find where to stay, ratings, photos, and more tourist information, use the Hilo trip planner.

Fly from Lahaina to Hilo in 2.5 hours. December in Hilo sees daily highs of 31°C and lows of 21°C at night. Wrap up your sightseeing on the 14th (Thu) to allow time to drive to Kailua-Kona.
more
Parks · Outdoors · Nature · Trails
Side Trips

Kailua-Kona, United States — 4 nights

Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Explore hidden gems such as My Kona Adventures and Hapuna Beach State Recreation Area. Take a break from Kailua-Kona with a short trip to Pu'uhonua O Honaunau National Historical Park in Honaunau, about 40 minutes away. And it doesn't end there: take a memorable drive along Saddle Road, kick back and relax at Manini'owali Beach (Kua Bay), shop like a local with Mountain Thunder Coffee Plantation, and experience rural life at Heavenly Hawaiian Kona Coffee Farm.

To see ratings, reviews, maps, and tourist information, you can read our Kailua-Kona vacation planner.

You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. In December, daily temperatures in Kailua-Kona can reach 32°C, while at night they dip to 24°C. Finish up your sightseeing early on the 18th (Mon) so you can travel to Naples.
more
Outdoors · Parks · Nature · Tours
Side Trips

Naples, United States — 3 nights

Eschew the tourist crowds and head to Naples Botanical Garden and Sanibel Causeway. Change things up with these side-trips from Naples: Sanibel Island (J.N. "Ding" Darling National Wildlife Refuge & Bowman's Beach), Edison and Ford Winter Estates (in Fort Myers) and Parasailing & Paragliding (in Fort Myers Beach).

For photos, where to stay, more things to do, and other tourist information, read Naples driving holiday planner.

Fly from Kailua-Kona to Naples in 12.5 hours. Alternatively, you can do a combination of flight and shuttle. The time zone changes from Hawaii-Aleutian Standard Time to Eastern Standard Time, which is usually a 5 hour difference. Plan for little chillier nights when traveling from Kailua-Kona in December since evenings lows in Naples dip to 20°C. Cap off your sightseeing on the 21st (Thu) early enough to go by car to Marco Island.
more
Parks · Outdoors · Scenic Drive · Wildlife
Side Trips

Marco Island, United States — 2 nights

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Start off your visit on the 22nd (Fri): get some thrills out on the water with a waterskiing or jet-skiing adventure. On the 23rd (Sat), you'll have a packed day of sightseeing: kick back and relax at South Marco Beach.

To find maps, traveler tips, reviews, and other tourist information, read Marco Island holiday builder site.

Marco Island is very close to Naples. December in Marco Island sees daily highs of 31°C and lows of 19°C at night. On the 23rd (Sat), you'll have the morning to explore before heading off to Key Largo.
more
Outdoors · Beaches · Parks · Adventure

Key Largo, United States — 1 night

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
On the 24th (Sun), stroll through Florida Keys Wild Bird Rehabilitation Center, get a dose of the wild on Capt. Sterling's Everglades Eco-Tours, then immerse yourself in nature at John Pennekamp Coral Reef State Park, and finally take a tour by water with Boat Tours & Water Sports.

For reviews, other places to visit, photos, and more tourist information, read our Key Largo trip maker.

Drive from Marco Island to Key Largo in 3 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of ferry and bus. Expect a daytime high around 30°C in December, and nighttime lows around 22°C. Finish up your sightseeing early on the 24th (Sun) so you can go by car to Islamorada.
more
Wildlife · Outdoors · Tours · Parks

Islamorada, United States — 1 night

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 25th (Mon), soothe aching muscles at Island Flow Yoga, see some colorful creatures with a scuba or snorkeling tour, and then sample the tasty concoctions at Florida Keys Brewing Company.

To see ratings, more things to do, where to stay, and other tourist information, go to the Islamorada online holiday planner.

Islamorada is just a short distance from Key Largo. December in Islamorada sees daily highs of 31°C and lows of 25°C at night. Cap off your sightseeing on the 25th (Mon) early enough to go by car to Marathon.
more
Wildlife · Outdoors · Tours · Spas

Marathon, United States — 2 nights

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Start off your visit on the 26th (Tue): see what you can catch with a fishing tour, tour the pleasant surroundings at The Turtle Hospital, then enjoy the sand and surf at Sombrero Beach, and finally take in the views from Seven Mile Bridge. Here are some ideas for day two: stroll through Dolphin Research Center, then tour the pleasant surroundings at Bahia Honda State Park, and then relax and rejuvenate at SpaTerre at Little Palm Island Resort.

To see ratings, other places to visit, where to stay, and tourist information, go to the Marathon route builder tool.

Drive from Islamorada to Marathon in an hour. Alternatively, you can take a bus. In December, plan for daily highs up to 31°C, and evening lows to 25°C. Wrap up your sightseeing on the 27th (Wed) early enough to drive to Key West.
more
Parks · Wildlife · Outdoors · Beaches
Side Trips

Key West, United States — 4 nights

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Explore hidden gems such as Dry Tortugas National Park and U.S. Coast Guard Cutter Ingham Maritime Museum. Next up on the itinerary: see what you can catch with a fishing tour, visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum, get engrossed in the history at Truman Little White House, and indulge in some personalized pampering at some of the best spas.

To see reviews, ratings, photos, and other tourist information, read our Key West route maker site.

You can drive from Marathon to Key West in 1.5 hours. Another option is to take a bus. Expect a daytime high around 30°C in December, and nighttime lows around 25°C. Finish your sightseeing early on the 31st (Sun) to allow enough time to fly to Orlando.
more
Parks · Museums · Nature · Outdoors

Orlando, United States — 4 nights

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.
Eschew the tourist crowds and head to Stetson Mansion and St. Augustine Distillery. Explore the numerous day-trip ideas around Orlando: Boat Tours & Water Sports (in Saint Cloud) and St. Augustine Lighthouse & Maritime Museum, Inc. (in St. Augustine). Have a day of magic on the 3rd (Wed) at Walt Disney World Resort. And it doesn't end there: find something for the whole family at Fun Spot America, admire the natural beauty at Harry P. Leu Gardens, and make an unforgettable trip to Magic Kingdom Park.

To find other places to visit, where to stay, and more tourist information, read our Orlando trip tool.

Fly from Key West to Orlando in 3.5 hours. Alternatively, you can drive; or take a bus. Traveling from Key West in December, expect slightly colder with lows of 17°C in Orlando. Finish your sightseeing early on the 4th (Thu) so you can fly to Washington DC.
more
Theme Parks · Historic Sites · Outdoors · Tours
Side Trips

Washington DC, United States — 3 nights

The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
You'll explore the less-touristy side of things at National Gallery of Art and Library of Congress. The adventure continues: take an in-depth tour of United States Holocaust Memorial Museum, see the interesting displays at National Air and Space Museum, pause for some photo ops at Vietnam Veterans Memorial, and go all around town with Bi-Partisan Tour Company.

For traveler tips, ratings, other places to visit, and tourist information, read our Washington DC trip itinerary maker app.

Fly from Orlando to Washington DC in 3.5 hours. Alternatively, you can drive; or take a train. Traveling from Orlando in January, expect Washington DC to be cooler, temps between 7°C and -1°C. Finish up your sightseeing early on the 7th (Sun) so you can catch the train to Philadelphia.
more
Museums · Tours · Zoos & Aquariums · Parks

Philadelphia, United States — 1 night

Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S. democracy, as it was once the meeting place for the country's Founding Fathers.
Start off your visit on the 8th (Mon): take in the architecture and design of University of Pennsylvania, admire the masterpieces at Philadelphia Museum of Art, admire the masterpieces at Barnes Foundation, then steep yourself in history at Independence Hall, and finally stroll around Wissahickon Valley Park.

To see where to stay, ratings, more things to do, and more tourist information, use the Philadelphia online itinerary builder.

Getting from Washington DC to Philadelphia by train takes about 2.5 hours. Other options: drive; or take a bus. In January, daily temperatures in Philadelphia can reach 5°C, while at night they dip to -3°C. Wrap up your sightseeing on the 8th (Mon) early enough to fly to Montreal.
more
Museums · Parks · Historic Sites

Montreal, Canada — 3 nights

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.
You'll explore the less-touristy side of things at Beer Tastings & Tours and Musee des beaux-arts de Montreal. The adventure continues: walk around Mount Royal Park, explore the landscape on two wheels at Place des Arts, examine the collection at Pointe-a-Calliere, Montreal Archaeology and History Complex, and take in the architecture and atmosphere at Saint Joseph's Oratory of Mount Royal.

To find traveler tips, reviews, where to stay, and more tourist information, go to the Montreal sightseeing planner.

You can fly from Philadelphia to Montreal in 5 hours. Other options are to drive; or take a bus. Traveling from Philadelphia in January, expect Montreal to be slightly colder, temps between -5°C and -13°C. Wrap up your sightseeing on the 11th (Thu) to allow time to fly to Boston.
more
Museums · Parks · Tours · Breweries & Distilleries

Boston, United States — 1 night

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.
Start off your visit on the 12th (Fri): wander the streets of North End, stroll around Boston Public Garden, then explore the different monuments and memorials at Mount Auburn Cemetery, and finally admire the masterpieces at Museum of Fine Arts.

To find more things to do, traveler tips, where to stay, and other tourist information, read Boston journey planner.

You can fly from Montreal to Boston in 4.5 hours. Alternatively, you can drive; or take a bus. Traveling from Montreal in January, expect Boston to be a bit warmer, temps between 3°C and -5°C. Finish your sightseeing early on the 12th (Fri) to allow enough time to fly to New York City.
more
Museums · Parks · Neighborhoods · Historic Sites
Side Trip

New York City, United States — 4 nights

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Step off the beaten path and head to The Museum of Modern Art (MoMA) and New York Public Library. There's still lots to do: take in panoramic vistas at Empire State Building, take in the architecture and atmosphere at St. Patrick's Cathedral, pause for some photo ops at Statue of Liberty National Monument, and take in the pleasant sights at Times Square.

For where to stay, traveler tips, more things to do, and tourist information, read New York City holiday builder website.

You can fly from Boston to New York City in 2.5 hours. Alternatively, you can drive; or take a train. In January, daily temperatures in New York City can reach 5°C, while at night they dip to -5°C. Wrap up your sightseeing on the 16th (Tue) to allow time to fly back home.
more
Parks · Museums · Historic Sites · Neighborhoods

United States travel guide

4.5
Specialty Museums · Nightlife · Beaches
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.
more

Canada travel guide

4.6
Parks · Specialty Museums · Waterfalls
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.
more