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Chicago to San Francisco Road Trip
16 days, Chicago to San Francisco
Itinerary
Day 1Chicago
Arrive at any time.
This group tour departs the city early on Day 2. We recommend booking pre-tour accommodation in Chicago if you'd like to spend any time exploring the sights and sounds the city has to offer. It is, afterall, a massive sports hub (pro hockey, baseball, basketball and soccer teams!), home to an award-winning skyline, and has a history–and nightlife–steeped in blues and jazz.
Your Welcome Moment: Welcome Moment - Meet Your CEO and Group
Your opportunity to meet your CEO and fellow travellers, and learn more about your tour. Opt to join the group for a local meal afterwards. Don't forget to see the notice in the lobby (or ask reception) for the official time and place to meet up with the group.
Day 2Chicago/Frontenac
Tour the Miller Brewing Company in Milwaukee and enjoy a beer tasting, then camp on the banks of the Mississippi River.
Your Foodie Moment: Miller Brewery Tour and Tasting
Enjoy an introduction video and personal tour through Miller Brewery, which has more than 155 years of brewing history. Sit back in the outdoor beer garden after the tour and enjoy a few different Miller Family samples brewed onsite at this historic Milwaukee landmark.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Meals included:
DinnerDay 3Frontenac/Sioux Falls
Enjoy a free morning at the largest shopping mall in America – the Mall of America. Afterwards, venture into South Dakota and head into the Great Plains and lands of the Sioux.
Mall of America visit
Stop off at one of the largest shopping malls in the United States. Not a shopaholic? No problem! There is an indoor theme park in the centre of the mall, a perfect shopping distraction.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Drive time includes a stop at the Mall of America in the Twin Cities.
Optional Activities - Day 3 HideShow
Sioux Falls Visit
FreeWalk the paths around these shallow cascading waterfalls or relax in the grass under the shade of the trees in these serene surroundings.
Meals included:
Breakfast | DinnerDay 4Sioux Falls/Badlands National Park
Travel through the Badlands before reaching the Black Hills.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Optional Activities - Day 4 HideShow
Original South Dakota 1880's Town Visit
12-19USD per personEnvision life on the prairie 100 years ago on this visit to a town made up of more than 30 original buildings from the 1880s to 1920s. Authentically equipped with furniture, antiques, and photographs, this town even has a museum dedicated to the many props used in Kevin Costner's famous movie "Dances with Wolves." Enjoy live entertainment or opt to dress up for some "old-time" photos.
Meals included:
Breakfast | Lunch | DinnerDay 5Badlands National Park/Custer State Park
Discover moon-like landscapes on the trails of the Badlands, then drive to Custer SP. Dodge free-roaming bison herds while exploring Custer's diverse lands.
Explore the spectacular, bizarre, and moon-like landscape at Badlands National Park. Discover Wall Drug, an American roadside wonder before reaching the famous Black Hills in the heart of South Dakota. Then take the scenic route to Custer State Park.
Badlands National Park Visit
The Lakota gave the area its name, "mako sica" meaning "land bad." Discover the park on short hiking trails and enjoy the feeling of true isolation – visitors can look for miles and see no sign of civilization. Keep eyes peeled for the thousands of delightful prairie dogs that pop up and down in the grasslands and the more elusive bison, bighorn sheep, and black-footed ferrets that live in the park.
Private Vehicle
Approximate Distance to Custer: 250km (155 mi)
Wall Drug Visit
Discover an American roadside wonder that made "Wall" such a famous place to visit. It all started in the 1930s with free ice water for thirsty tourists coming from the east; today, almost 100 stores and exhibits operate under a single entity making up "America's Favourite Roadside Attraction."
Optional Activities - Day 5 HideShow
Custer State Park Hike
FreeExplore this fascinating terrain 1,621m (5,318 ft) above sea level. Find your adventure on short hikes through hills, mountainous lakes, rolling prairies, and breathtaking vistas.
Horseback Riding
37-90USD per personMeals included:
Breakfast | Lunch | DinnerDay 6Custer State Park/Devils Tower
Check out the larger than life ex-presidents of Mount Rushmore, tour around Crazy Horse Memorial, and stop off at Deadwood en route to Devils Tower in Wyoming.
Mount Rushmore National Memorial Visit
Visit one of America’s most inspiring symbols of democracy and freedom. Be amazed at the impressive granite faces of four of the most influential presidents of the United States: George Washington, Thomas Jefferson, Teddy Roosevelt, and Abraham Lincoln. Each stone head is as tall as a six-story building.
Crazy Horse Memorial Visit
Visit the spectacular Crazy Horse Memorial, which was made to honour the culture, tradition, and living heritage of North American Indians. The words of Chief Standing Bear, "My fellow chiefs and I would like the white man to know the red man has great heroes, too" convinced sculptor Korczak Ziolkowski to create a Memorial for the Lakota people in 1939. Currently 60-90 years away from completion, the memorial, once finished, will be the largest sculpture in the world.
Deadwood Visit
Explore the once lawless town of Deadwood created by the Black Hills Gold Rush, which brought gunfighters, gamblers, and prostitutes. The town achieved notoriety for the murder of "Wild Bill" Hickok. Watch the famous shootout at the Old Style Saloon #10 and witness the shooting of Wild Bill. Check out the fabulous Midnight Star, Kevin Costner's casino, and try your luck at one of the slot machines.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Meals included:
Breakfast | DinnerDay 7Devils Tower/Bozeman
Check out the the Little Bighorn Battlefield National Monument en route to the university town of Bozeman, Montana.
Little Bighorn Battlefield National Monument Visit
The Little Bighorn Battlefield National Monument is the site where the Battle of Little Bighorn took place – where the Lakota and Cheyenne Indians fought off the U.S. Army's 7th Cavalry to defend their land and way of life. The battle was a major upset and overwhelming victory for the Lakota and Cheyenne tribes, as they defeated the U.S. army and killed Lt. Col. George A. Custer, which later inspired the movie Custer's Last Stand. An iconic site of American history, today it is home to a number of memorials commemorating the battle. Stop for a stretch and to take in this piece of U.S. history.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Meals included:
Breakfast | LunchDay 8Bozeman/Yellowstone National Park
Travel to Yellowstone, the world's first national park, and be in awe of the colourful geysers, powerful waterfalls, exciting wildlife, and contrasting scenic beauty around every corner.
Yellowstone is beyond special. Geysers, waterfalls, wildlife, and scenic beauty are around every corner just waiting to be explored. In fact, Yellowstone National Park is a super volcano with the world’s largest active geyser field, boasting more than 10,000 geysers. The Park is also home to more wild animals than almost anywhere else in the U.S., including roaming bison, gray wolves, elk, black bears, and, of course, the famous grizzly bear.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Yellowstone Northern Loop Excursion
Explore the Northern Loop in Yellowstone National Park, which features beautiful scenery, exciting wildlife, and spectacular hydrothermal features. Tour the ever-maturing Mammoth Hot Springs, walk the Porcelain Basin trail through Norris Geyser Basin, check out the vibrant Grand Prismatic Spring, and discover the impressive waterfalls and natural colours of the Grand Canyon of Yellowstone!
Meals included:
Breakfast | Lunch | DinnerDay 9Yellowstone National Park
Spend the day exploring the highlights of the Southern Loop.
Travel through some of the most famous landmarks of Yellowstone, including Old Faithful, Grand Prismatic Spring, West Thumb, and Yellowstone Lake.
Walking
Lace up your shoes and get to the next stop under your own power.
Yellowstone South Loop Excursion
Travel through the Southern Loop of Yellowstone National Park, which features some of the most breathtaking and diverse natural scenery. Watch Old Faithful erupt and take in the geysers in West Thumb with Yellowstone Lake as the backdrop.
Meals included:
Breakfast | Lunch | DinnerDay 10Yellowstone National Park/Jackson
Cross the Continental Divide en route to Grand Teton National Park. Enjoy the view of more than 12 peaks that make up this beautiful drive. Opt to visit a cowboy bar for Western line dancing and live music.
Stop at Jenny Lake in Grand Teton National Park and take in the tranquil surroundings.
In the late afternoon, reach Jackson and marvel at the town square’s elk antler arches. In the evening, enjoy a night out with a true wild western atmosphere at the One Million Dollar Bar.
Grand Teton National Park Visit
Visit Grand Teton National Park, a natural playground that offers serene landscapes, alluring wildlife, hidden waterfalls, and hundreds of hiking trails throughout the park. Towering above pristine lakes and alpine terrain, the Teton Range includes more than 8 peaks at an elevation greater than 12,000 ft (39370m).
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Optional Activities - Day 10 HideShow
Million Dollar Bar Visit
Free-20USD per personEnjoy a night out in a true Western town. Opt to go to the One Million Dollar Bar, Wyoming's landmark watering hole, known for its western dancing, live entertainment, and fascinating decor, including knobbed pine architecture and genuine saddle barstools. (Bar entry and drinking age in the United States is 21.)
Jenny Lake Shuttle
19USD per personStop at beautiful Jenny Lake and take a boat ride across the lake. Hike 3km (1.9 mi) to discover Hidden Falls and Inspiration Point on the other side of the lake.
Meals included:
Breakfast | LunchDay 11Jackson/Twin Falls
Choose to go whitewater rafting or horseback riding during a free morning, then cross the border into Idaho. Stop off at Shoshone Falls en route.
Free Time
Enjoy a free morning for whitewater rafting or horseback riding.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Optional Activities - Day 11 HideShow
Jackson Horseback Riding
35-85USD per personSaddle up and take a scenic ride through mountain trails into an area of unspoilt natural beauty. Enjoy peaceful surroundings along the famous Snake River and see if you can spot various wildlife in their natural habitat.
Whitewater Rafting on Snake River
Enjoy a guided tour along the Snake River and learn about the history and geology of the area. Pass by limestone cliffs and over class II and III rapids like The Lunchcounter and the Big Kahuna. Float down the river, keep an eye out for wildlife, and take in the stunning scenery!
Meals included:
Breakfast | Lunch | DinnerDay 12Twin Falls/Reno
Sit back and relax during a road trip day, crossing into Nevada. Enjoy the bright lights both in and outside the casinos in "The Biggest Little City in the World."
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Meals included:
Breakfast | LunchDay 13Reno/Lake Tahoe
Arrive to Lake Tahoe after a short drive. Enjoy a free afternoon for hiking, lake activities or relaxing.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Meals included:
Lunch | DinnerDay 14Lake Tahoe/Yosemite National Park
Marvel at the spectacular views of Yosemite National Park's magnificent peaks and granite domes while enjoying one of most scenic drives in California: Tioga Pass!
With a keen eye and a little luck, spot black bears, deer or coyotes.
Tioga Pass Drive
Take this scenic route through the Sierra Nevada mountain range connecting Bishop with the Yosemite Valley floor. Pass by lakes, meadows, and groves, and keep your eyes peeled for wildlife along the way. (Seasonal July through mid October.)
Yosemite National Park Visit
Picturesque valleys, vast wilderness, powerful waterfalls, elusive wildlife, ancient sequoias and more than 16 types of granite make up this internationally recognized national park. Hike the trails, get up close to ancient rock formations and take panoramic photos of this gorgeous landscape. Keep an eye out for black bears, deer, and coyotes.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Meals included:
Breakfast | Lunch | DinnerDay 15Yosemite National Park
Enjoy free time in Yosemite National Park.
Full day to explore Yosemite National Park. Hike the many trails Yosemite has to offer and be inspired by this beautiful and amazing landscape. Option to rent bikes in Yosemite Valley.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Yosemite National Park Visit
Picturesque valleys, vast wilderness, powerful waterfalls, elusive wildlife, ancient sequoias and more than 16 types of granite make up this internationally recognized national park. Hike the trails, get up close to ancient rock formations and take panoramic photos of this gorgeous landscape. Keep an eye out for black bears, deer, and coyotes.
Your Discover Moment
Located in California's Sierra Nevadas, Yosemite is home to a variety of habitats and wildlife, including spotted owls, mule deer, bobcats and American black bears. Valley visitors come to hike, rock climb, raft, around the spectacular granite cliffs, waterfalls, and giant sequoias.
Optional Activities - Day 15 HideShow
Yosemite National Park Hike
FreePanoramic vistas, gushing waterfalls, and elusive wildlife await. Bring water, wear a hat and sunscreen, and hike Yosemite NP. Keep an eye out for black bears, deer, and coyotes.
Yosemite Bike Rental
30-40USD per personSet your wheels in motion with tandem, hand crank or mountain bikes, and opt to cycle some of the 20km (12mi) of paved trails throughout the valley floor. Bring a water bottle, stop to shoot photos, and enjoy some of the most picturesque spots in Yosemite NP.
Choose between a half-day rental or a full-day, and be aware that this activity is available on a first-come, first-served basis. Please note the price for a half-day bike rental is $30 USD and the price for a full-day bike rental is $40USD.
Meals included:
Breakfast | Lunch | DinnerDay 16Yosemite National Park/San Francisco
Catch a glimpse of the Golden Gate Bridge on the way into one of America's most popular cities. Trip ends upon arrival to San Francisco. Take an optional cable car ride over the steep hills or explore the city by bicycle.
Arrive at one of the most iconic cities in the world: San Francisco. The CEO will point out some popular sites on the drive into town.
There's a lot to see and do in San Francisco. We recommend spending extra time here if you'd like to explore the city; speak to your sales agent to book extra accommodation, or pre book a sunset sail off the coast of the city.
If you are departing on arrival to San Francisco, you will not have enough time to participate in the Sunset Sailing extra. Post-tour accommodation is required to purchase this extra.
Private Vehicle
Settle in and scan the scenery from the convenience of a private vehicle.
Departure Day
Depart on arrival to San Francisco. Your CEO can help with any onward travel arrangements you require.
Optional Activities - Day 16 HideShow
Golden Gate Bridge Visit
FreeWhat trip to San Fran would be complete without seeing the Golden Gate Bridge? Depending on time, step foot on this famous red suspension bridge or find a great viewing point to take some photos.
Haight-Ashbury Visit
FreeCheck out this neighbourhood known as the centre of counterculture ideals, drugs, and music during the hippie movement in the 60s. Today, find locally-owned restaurants and bars, boutiques, booksellers, head shops and record stores.
Alcatraz Visit
33USD per personTravel out to Alcatraz Island for a cell-house audio tour of the infamous federal penitentiary. While there, check out the natural side of the rock—with its gardens, tide pools, bird colonies, and stunning views of San Francisco Bay. Tours often sell out, so book a ticket online (far in advance!) to secure a spot.
Bike Rental San Francisco
8-32USD per personRent a bike to peddle across the Golden Gate Bridge, through the scenic Marina district or perhaps to Golden Gate park.
Fisherman's Wharf Visit
FreeVisit San Francisco's famous Fishermen's Wharf, walk the piers, check out the marine life, shop and sample the fresh seafood.
Cable Car Ride San Francisco
7USD per personIconic to San Francisco, travel back in time and hop on the world's last manually operated cable car system.
Sunset Sailing San Francisco (Mon-Wed)
Depart from Fisherman's Wharf and catch a glimpse of marine life as we sail around San Francisco Bay. Admire the city's remarkable skyline, get up close and personal with the infamous Alcatraz Island, and sail underneath the Golden Gate Bridge. Enjoy the sunset and make a mental note to return.