Local-led Wynwood, Little Havana, South Beach tours and Chicago bike rentals for memorable city experiences.
Guided food tours, street art walks, bike tours, and flexible bike rental options in Miami and Chicago.
land-adventures · Miami
Discover Miami’s Wynwood district on a private walking tour combining vibrant street art and delicious local food. Savor iconic dishes and admire famous murals on this unforgettable three-hour adventure.
Bobby's Bike Hike is a Miami-based tour operator offering guided walking and bike experiences across Miami and bike rental services in Chicago. The company organizes neighborhood-focused food and culture walking tours in Wynwood, Little Havana, South Beach, and Miami Beach, plus bike-and-food adventures that highlight local cuisine and iconic city views.
In Miami, tours include the Wynwood Walls Food & Graffiti Art Walking Tour, Wynwood Walls Street Art Walking Tour, Little Havana Food & Culture Walking Tour, South Beach Food & Fun Walking Tour, and the Miami Beach Bikes, Bites & Views (Adults Only) bike and food tour. Several Miami tours run three hours, with options for VIP beverage add-ons like a Craft Drink package or a Mojito.
For Chicago, Bobby's Bike Hike provides multiple bike rental durations — half-day, full-day (same day return), and two-day rentals — plus guided routes such as the Chicago Family Food and Bike Tour and a highlights walking tour of top city attractions. Rentals come with complimentary maps, helmets, and locks.
All descriptions and trip options are based on published tour summaries. The operator emphasizes neighborhood-specific storytelling, local food stops, and practical support for riders and walkers alike, such as safety gear and route maps. This combination of guided tours and rental services makes Bobby's Bike Hike a practical choice for visitors seeking food-focused walks, street art tours, scenic bike rides, and flexible rental options.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Headquartered in Miami
Guided walks and bike experiences
Half, full, and multi-day options
Family-friendly and adults-only tours
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Bobby's Bike Hike listing.
Bobby's Bike Hike offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Book Wynwood art walks, Little Havana food tours, South Beach strolls, or Chicago bike rentals — secure online reservations available.
land-adventures · Miami
Discover Miami's Wynwood District through its world-renowned street art on this immersive 2-hour walking tour. Experience vibrant murals and a neighborhood transformed by creativity and culture.
land-adventures · Miami
Discover Miami’s Little Havana on a three-hour walking tour filled with authentic Cuban food, rich history, and cultural landmarks. Savor iconic dishes and experience true local flavor in this vibrant neighborhood.
land-adventures · Miami Beach
Discover Miami Beach’s vibrant culture and cuisine on the Miami Beach Bikes, Bites & Views Food Tour. This 4.5-hour guided bike and food adventure blends stunning coastal views with authentic local flavors.
bike-charters · Chicago
Take a ride along Chicago’s spectacular 20-Mile Lakefront Trail with Full Day Bike Rentals. This service offers convenient, same-day rentals complete with helmets and maps for a safe, scenic urban cycling experience.
land-adventures · Chicago
Pedal through Chicago on a 4-hour family bike tour, tasting famous local dishes while visiting top attractions like Millennium Park and Navy Pier. Enjoy a lively mix of food, culture, and biking at a comfortable pace for all ages.
food-tour · Miami
Discover Miami’s South Beach through a three-hour walking tour that highlights iconic local flavors and lively culture. Taste your way through vibrant neighborhoods and uncover culinary stories that make this tour unforgettable.
land-adventures · Chicago
Discover Chicago’s scenic Lakefront Trail with 2 Day Bike Rental. Convenient gear, safety tips, and easy access to miles of bike lanes await urban cyclists ready to roll.
land-adventures · Chicago
Discover prime lakefront cycling with easy bike rentals near Chicago’s iconic 20-Mile Lakefront Trail. Enjoy a half-day of city adventure on two wheels.
land-adventures · Chicago
Experience Chicago’s iconic landmarks on foot—from the Magnificent Mile to Millennium Park and the Riverwalk—in this focused two-hour walking tour.
water-activities · Chicago
Paddle away from city crowds with Bobby's Kayak Rentals on Lake Michigan. Enjoy stunning Chicago skyline views from clear waters at Ohio Street Beach in just two hours.
water-activities · Chicago
Paddle Lake Michigan’s turquoise waters with Bobby’s Kayak Rentals near Chicago’s Ohio Street Beach. Enjoy serene city views and easy water access on this unique 1-hour adventure.
land-adventures · City Name
Discover a fantastic cycling experience right outside the city with Bobby's Bike Hike. Perfect for families and cyclists of all levels, this business makes outdoor biking accessible and fun with expert-guided routes and rentals.
land-adventures · Chicago
Discover Chicago’s festive heart with a two-hour holiday walking tour featuring dazzling lights, Christkindlmarket, and the iconic holiday tree.
land-adventures · Chicago
Ride through Chicago’s scenic lakefront and iconic neighborhoods on a top-rated 3-hour bike tour. Discover historic mansions, urban beaches, and local spots off the beaten path.
land-adventures · Chicago
Ride through Chicago’s urban parks and iconic landmarks on this scenic 3-hour city bike tour. Discover Buckingham Fountain, The Bean, and the stunning lakefront views.
food-tours · Chicago
Dive into Chicago’s Chinatown with a three-hour walking tour that blends authentic regional Chinese food with vibrant cultural history.
land-adventures · Chicago
Taste Chicago’s iconic deep-dish pizza and Italian Beef on a lively three-hour walking tour that blends culinary history with local landmarks. A VIP Craft Beer option makes this food experience truly unique.
others · Chicago
Pedal through Chicago’s iconic neighborhoods while tasting deep-dish pizza, Chicago-style hot dogs, and craft brews on this 4.5-hour food and bike tour with Bobby’s Bike Hike.
land-adventures · Chicago
Ride Chicago’s iconic Lakefront Trail with Bobby’s Bike Hike’s 3 Day Bike Rental. Conveniently located near Michigan Avenue, enjoy easy access to 150 miles of safe bike lanes and complimentary gear.
motorized-land · Chicago
Cycle Chicago’s renowned Lakefront Trail with a full-day bike rental from Bobby’s Bike Hike. Access 150 miles of bike lanes with helmets, locks, and maps included for a seamless urban ride.
land-adventures · Chicago
Pedal through Chicago’s Near West Side on a four-hour bike tour that pairs authentic local dishes with neighborhood history. Join Bobby’s Bike Hike for a taste-filled ride that hits iconic eateries from burgers to pierogi and ends with chocolate.
land-adventures · Chicago
Step into Chicago’s holiday glow with Bobby’s Bike Hike’s festive walking tour. Taste the city’s deep dish pizza, soak up Christkindlmarket’s charm, and stroll beneath dazzling lights on this three-hour winter outing.
land-adventures · Chicago
Discover Chicago’s Lakefront Trail on two wheels with a 2 Hour Bike Rental. Enjoy 150 miles of safe bike lanes, city skyline views, and personalized maps for a perfect urban cycling adventure.
land-adventures · Chicago
Explore Chicago’s top culinary delights and iconic landmarks on a 5-hour walking tour that perfectly pairs food with city stories. Experience deep-dish pizza, Italian beef, and more while discovering the history behind every dish and district.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.