California's mountains, coast and beaches offer the perfect setting for a three-week bike trip. Begin on the western slope of the spectacular High Sierra, ride across the Golden Gate Bridge and then head south past Santa Cruz, Monterey, Big Sur and Santa Barbara. At trip end, celebrate with a final ride to the Santa Monica Pier.

Overview Details Itinerary What to Pack FAQs Before You Go


Bike California: from the Sierras to San Francisco, from Santa Barbara to Santa Monica!

California is big, and it is beautiful. From chilly mornings on the northern cliffs to sun-soaked days on sandy SoCal beaches, the variety of landscapes along its 800-mile-long coast offer endless opportunities to explore.

And it’s not just a matter of beautiful coastline-California is also ideal for biking. Our bike ride starts with climbing up through the redwoods, crosses the Golden Gate and winds down the coast through Monterey and Santa Barbara all the way to Santa Monica.

At each step of the way, we’ll bike as a group. Taking on a three-week bike trip is
no small feat. You’ve got to be fit. You’ve got to be committed. But if you are, you’re in for a treat because you’re going to do all this, see all this and experience all this in a wonderful, warm, supportive, encouraging, enthusiastic Overland group with two rock-star leaders.

What’s your dream? See the redwoods? Cross the Golden Gate? Roll down the coast through Carmel? Surf at Pismo Beach? It’s all here for you. In a giant, beautiful state that’s just waiting to be explored.


Questions? Contact us!

Kenna had a great time away from her family and technology; on the trip, she was in a new situation and environment where she was able to have fun, build confidence and make new friends.

- Noah Franzblau, Mountain Lakes, New Jersey

Day 1: Trip Start

We’ll meet in San Francisco and take a shuttle to Leggett, in the heart of the redwoods. In the afternoon, we’ll build our bikes and learn how to load them, practice riding as a group and prepare for our journey.

Days 2-7: Redwoods and Rugged Coastlines

Building our fitness and increasing our mileages, we’ll grow comfortable riding with weight and as a group. We’ll climb out of Leggett on our first day, then hug the coast as we explore small northern California towns and ride past dramatic Pacific bluffs.

Days 8 & 9: Marin County and San Francisco

Increasing our mileage to 50 miles per day, we’ll bike past historic Pt. Reyes Station and Tomales Bay, across the Marin headlands, and over the Golden Gate Bridge into San Francisco. Views of Alcatraz and San Francisco Bay will greet us as we cross the bridge.

Days 10 & 11: San Francisco to Monterey

We’ll take a scenic route through San Francisco’s hilly neighborhoods, and we’ll rejoin Route 1 south of the city for a coastal section renowned for its stunning
beaches and bountiful wildlife. We’ll skirt around Santa Cruz, watching surfers tackle big waves and pedaling past the famed Natural Bridge, and then continue south through farmland and Monterey, home of Steinbeck’s Cannery Row.

Days 12-15: Big Sur and Surfing

the beautiful Big Sur region of California, we’ll see the Santa Lucia Mountains rising up to the east and a stunning shoreline to the west. Around San Luis Obispo, the terrain levels out, the hills become gentler and eucalyptus and palm trees provide welcome shade. Entering Southern California, we’ll take a break from biking for a morning of surf lessons.

Days 16-20: Southern California

After surfing, we’ll continue riding south through the Spanish-influenced city of Santa Barbara. We’ll marvel at the grand mountains of Los Padres National Forest and skirt around Oxnard before a final night on the coast. We’ll finish our ride at the Santa Monica Pier and enjoy a celebratory dinner before saying our goodbyes.



18 nights of frontcountry camping. All campgrounds will have flush toilets. Many facilities will include showers and laundry.

1 night in a hostel in Santa Monica. The hostel is a dormitory style accommodation. The rooms are divided by gender.

Itinerary may vary by group and is subject to change.
Download PDF


  • Medium-Sized Duffel Bag or Pair of Panniers
    Panniers are saddlebags sold in pairs that attach to either side of your rear rack. If you are renting panniers from Overland, pack your belongings in a collapsible bag (3,000-5,000 cubic inch/ 50-80 liters). We will have your bag available at the end of the trip for travel home. The cost of renting panniers from Overland is included in a bike rental (or they can be rented separately for $50). If you are bringing your own panniers you will want large panniers, 2,400-3,000 cubic inches (40-50 liters) total, designed for bike touring. One large pannier has internal dimensions of approximately 17" x 13" x 7". You should be able to fit all of your belongings, besides your sleeping bag and pad, into your two panniers and have some space for group gear. If flying to trip start, you can tape your panniers together so that they count as a single piece of checked luggage.


  • Navy Overland T-Shirt (1)
    We will send every student an Overland T-shirt prior to the trip. Please wear this T-shirt to trip start.
  • Synthetic High-Visibility T-Shirts (3) & Vest (1)
    A high-visibility outer layer is required at all times while biking (high-visibility is a neon or fluorescent color, typically yellow, orange or pink). On warm days a high-visibility T-shirt will be sufficient. The vest should be large enough to wear over warm layers while riding on cooler days. Please visit the Overland Store if you need to purchase these items. High-visibility bike jerseys are acceptable but not necessary.
  • Bike Shorts (2)
    Biking-specific shorts with a padded seat.
  • Shorts (1)
    Comfortable shorts to wear around camp.
  • Athletic Socks (4)
  • Wool and/or Synthetic Socks (1)
  • Synthetic Long Underwear Top & Bottom (1)
  • T-Shirt (1)
  • Lightweight Long-Sleeve T-Shirt (1)
  • Underwear (4)
  • Winter Hat
  • Swimsuit (optional)
    If we swim, many students will wear shorts (and a sports bra for girls).

Outer Layers

  • Fleece Jacket or Pullover
  • Waterproof Raincoat
    Choose high-visibility if available.
  • Waterproof Rain Pants (optional)
    Waterproof material required (not just water resistant). Rain pants provide protection from wind and rain and serve as an extra warm layer.

General Gear

  • Sleeping Bag
    A lightweight, compact sleeping bag rated to 30 degrees Fahrenheit or less. We recommend either synthetic or treated down material. Your sleeping bag should compress into a stuff sack no larger than 20" in length.
  • Sleeping Pad
    ¾-length or full-length closed cell foam (thin and firm) or self-inflating.
  • Bowl, Mug & Utensils
    6" to 8" plastic dish or bowl with top, insulated plastic mug, spoon, fork and knife. These don't need to be special camping utensils (a Tupperware dish and regular utensils are fine).
  • Headlamp
  • Water Bottle
    A 24-ounce bike bottle is ideal (on arrival you will receive a second bottle from us).
  • Hydration System
    A CamelBak or Platypus (or similar) with a 2- or 3-liter capacity. Must be a high-visibility color (if it is not hi-vis, you must cover it with hi-vis fabric or tape). The hydration system should be designed to primarily carry water (if it is too big it will be uncomfortable to wear all day).

Bike Gear

  • Touring Bicycle & Rear Rack
    You may choose to rent a bicycle and rear rack from Overland to use during your trip or you can bring your own. Please note: the American Challenge, European Challenge and Canadian Rockies & Montana 2-week require specific bikes—keep this in mind if you are buying a new bike now and plan on doing one of these trips in a future summer. Please see the Right Bicycle for Your Overland Trip for more information about acceptable bikes and traveling with your bike.
  • Clipless Pedals or Toe Cages
    The bikes we rent come with flat pedals appropriate for biking in running shoes. If you are renting a bike from Overland, you should bring your own "clipless" pedals (and bike shoes) or toe cages to attach to the flat pedals.
  • Bungee Cords
    These should be 18-24" in length. Bungee cords are included with an Overland bike rental.
  • Bike Helmet
    If you are flying to trip start, carry your helmet on the plane with you.
  • Spare Bike Parts
    The following are included with an Overland Bike Rental. If you are bringing your own bicycle you will need to bring: four spare spokes (two rear & two front); one spare tube (matched to the size and diameter of your bike's tires); one spare set of brake pads; one tire patch kit; and one set of tire levers.
  • Water Bottle Cages
    Two cages, attached to the bike frame. Some smaller-sized bike frames cannot accommodate two cages. If this is the case, you will be able to carry water bottles in your panniers or on your rack. All Overland rental bikes come with two water bottle cages.
  • Chamois Cream (optional)
    Special cream to reduce chafing and saddle sores. You can purchase chamois cream at any bike shop.
  • Bike Gloves (optional)
    Well-padded for comfort.


  • Shoes for Biking
    Bike touring or mountain biking shoes with bottom treads and "clipless" recessed cleats. A popular style of clipless shoes and pedals are SPDs. You may also ride in running shoes and bring toe cages to attach to your pedals. Please do not bring racing shoes as they have hard soles that are uncomfortable to walk in.
  • Sandals
    Flip flops or Crocs work well


  • Pre-trip Training Calendar
    Please bring your completed and signed calendar to trip start.
  • Synthetic Camping Towel (1)
    A medium-size synthetic camping towel (synthetic camping towels dry much faster than regular towels).
  • Gallon Sized Ziploc Bags (10)
    To organize and waterproof your gear and small items.
  • Large Trash Bags (5)
    To waterproof your gear.
  • Travel Size Toiletries
  • Sunglasses
  • Sunscreen (SPF 15+) & Chapstick (with SPF protection)
  • Personal Journal or Book (optional)
  • Camera, Charger & Extra Batteries (optional)
    A digital or disposable camera.

Important Documents

  • Health Insurance Card
    Please bring an original or copy of your health insurance card.
  • Photo Identification
    If you are not flying: Overland does not require photo identification. If you are flying within the U.S.: The TSA website has two relevant pieces of information. (1) “TSA does not require children under 18 to provide identification when traveling with a companion within the United States.” This language indicates that TSA staff can insist that an under-18 year old who does not have a companion (we interpret this as a companion who is 18 or over traveling with them—not just checking them in) must have TSA-compliant identification. Our experience is that this requirement is inconsistently enforced but, since it might be enforced, we recommend that all Overland students who are flying to/from their trip have TSA-compliant identification. (2) “Contact the airline for questions regarding specific ID requirements for travelers under 18.” This is always smart to do as airline policies vary widely and change frequently.

Spending Money

  • Spending Money & Miscellaneous Expenses
    Each student should bring a debit card, an ATM card or a prepaid Visa card to cover spending money and miscellaneous expenses. Spending Money: While all meals and activities are included in the trip fee, we recommend $25/week for spending money (for example: for souvenirs or an occasional drink or snack beyond what is provided to the group as a whole). Miscellaneous Expenses: Most Overland students will incur some expenses while traveling (for example: an equipment repair or baggage fees at trip end). Please add $100 to the debit/ATM/Visa card (in addition to spending money), to cover these expenses.

Things to know

  • We travel light at Overland; please only bring the items on your packing list.
  • Your group will have access to laundry periodically.
  • Please do not bring your smart phone (or any other electronics).
    Please visit the FAQ tab for more information on our cell phone and electronics policy.
  • Do not bring any type of knife or multi-tool (such as a Swiss Army knife or Leatherman tool).
  • There are no reimbursements for lost, damaged or stolen items.
    Please schedule expensive items—phones, cameras, bicycles, etc.—on your homeowners insurance policy.
  • A high-visibility outer layer is required at all times while biking. See packing descriptions for more details.
  • If you are flying to your trip start, pack your sleeping pad and bike shoes in your bike box or checked bag. Take your helmet and sleeping bag with you on the plane as carry-on items, in case your checked luggage fails to arrive on time. Pack all remaining items in your checked duffel bag or in your checked panniers. You can tape or strap your panniers together to check them as one piece of luggage; see luggage description for more details.
  • Please wear the navy Overland T-shirt that you receive from Overland to your trip start location.
  • What is the weather like on California?

    You can expect typical summery weather with lots of sunshine, some rain, warm days and cool nights.

  • What are the arrival and departure airports for my child’s trip?

    You will need to arrange transportation for your child to San Francisco International Airport (SFO) at trip start and from Los Angeles International Airport (LAX) at trip end. We will provide more specific travel information once we have placed your child on a trip.

  • How often will my child have access to showers and laundry?

    Our groups in California have regular access to showers. Most groups will do laundry once a week.

  • Please tell me about safety at Overland.

    Safety and risk management are at the forefront of our decision-making–from trip planning to leader training to supporting our groups in the field. We cannot guarantee absolute safety–no program can. All recreational activities include inherent risks. Therefore, we strive to manage the risks that we can, knowing we cannot eliminate them. We work hard to recruit, train and support our trip leaders so they can create the kind of trips that have made us successful for over 30 years. Please click here to read more about our approach to risk management and our accreditation by the American Camp Association.

  • Does my child need to have previous experience?

    While no previous experience is required, we have high expectations of our students. We expect your child–with your help–to select a trip that is appropriate for his or her interests and abilities. You should spend some time familiarizing yourself with the details of the specific trip and help your child understand what to expect. We also expect our students to prepare ahead of time: to review the packing list, gather clothing and gear and complete whatever training the trip requires (for recommended training please see the Before You Go tab). Once the trip begins, your child should be ready–and excited–to contribute to a wholesome and enthusiastic group where each group member feels welcomed and valued.

  • Please tell me about Overland's admissions process.

    When we receive your application, if your first choice is available, we will: (1) call you to acknowledge our receipt of your application, (2) send you an email with a link to our Admissions Review Forms, and (3) charge a deposit of $795 to your credit card to hold your place in the trip pending a favorable admissions review. If your first choice is not available, we will call you to discuss your second choice, third choice or other options. For more information, and to access our application, please visit our Apply page.

  • What are Overland’s policies on phones, electronics and communication?

    To maximize independence and self-reliance, we do not permit phone calls, emails or text messages to or from our campers. Your child will call home on arrival and departure with our phones and assistance, and in the case of an emergency. If your child brings a phone for use while en route to Overland, please do not send an expensive smartphone, instead, an inexpensive prepaid cell phone will do. All phones will be collected on arrival and returned at departure. While we will take reasonable steps to prevent damage, theft or loss, we take no responsibility for phones and we will not make any reimbursements for lost, damaged or stolen phones.


    Cameras are welcome but please do not bring any other electronics (e.g., iPods, iPads, Kindles or other readers, GPS or similar devices). All electronics (except cameras) will be mailed home on arrival (at your risk and expense).


    We are committed to providing extraordinary support to you and your child; to that end, the Overland office is staffed from 8:30 a.m. to 8:30 p.m. seven days a week during the summer. Outside of office hours our answering service provides emergency coverage. Our leaders in the field are in touch with our office regularly; they carry cell phones (and in some cases satellite phones). Anytime a camper is treated for an injury or illness by a doctor or other medical personnel, parents are notified by our office. A director will call the parents to explain the nature of the injury or illness, the sequence of events leading up to the injury and/or the steps leading to the treatment. Parents are typically able to speak with the medical personnel, with the leaders and with their child.

  • Can I send mail to my child during a trip?

    Getting a letter, card or postcard while on an Overland trip is always exciting. Please keep in mind that sending mail to your child on an Overland trip is different than sending mail to camp because your child will be on the move. Our experience has been that mail often does not arrive on time, and, sometimes, even when it does, post offices, campgrounds and other mail stops do not reliably deliver mail to our groups. For these reasons:


    1. Please do not send anything valuable – please send letters, cards or postcards only.  If mail is late, lost or misdirected, Overland’s leaders and staff are not able to return to the post office (or other mail stop) to collect it.

    2. Please use the US Postal Service first-class mail only; do not use UPS, FedEx or DHL (many of our mail stops accept US Postal Service mail only).

    3. Please do not send overnight letters: many overnighted letters arrive before or after we arrive and are then sent back. For this same reason, please do not send mail that requires a signature upon delivery.

    4. Please allow one week for postal delivery to U.S. mail stops.

    5. Please allow two weeks for postal delivery to international mail stops.

Bike from California’s Sierra Nevada to Santa Monica!

Students going on California should prepare for:

  • Full days of outdoor activities led by two caring Overland leaders
  • Camping out and cooking meals as a group
  • 16 days of biking with an average of 50 miles per day
  • A fun, supportive and wholesome Overland experience

We expect you to arrive to your trip fully prepared for all activities.

Preparing for the Biking

Daily rides on California average 50 miles over varying terrain. There are six days over 60 miles and the longest day is approximately 70 miles. The itinerary includes one buffer day to allow for delays en route (most groups will find that they spend this day partially or completely off of the bikes) and a second day off the bikes to go surfing.

Overland bicycle tours are self-contained—there is no van support. You will carry all of your belongings, plus some group gear and food, on a sturdy rack mounted over the back wheel of your bike. You will hang panniers (these are saddlebags, pronounced “pan-yers”) off the rack and attach gear like your sleeping bag and sleeping pad to the top of the rack using bungee cords. On average, you will carry 40 pounds of equipment on your bike (not including the weight of the bike).

You should come prepared and recognize that some days will be more challenging and longer than others. Delays occur due to a wide range of variables—weather patterns change and road conditions vary. You, or someone in your group, might get a flat tire or encounter another mechanical issue that could delay your group. On some days your group will arrive at camp in the early afternoon, with plenty of time to explore, play games or go swimming, while on other days your group will spend more time on the bike.

Every California participant should complete all of the spring training rides, and, once on the trip, must be able to maintain 10 mph over challenging terrain on a fully loaded bicycle. Please keep the following responsible riding practices in mind as you complete your spring training rides.

Responsible riding practices

Always, no exceptions.

To the extent possible, ride on bike paths, bike lanes, and bike routes.

You have the same rights and responsibilities as drivers. Obey traffic signals and stop signs. Ride with traffic; use the rightmost lane headed in the direction you are going.

Make your intentions clear to everyone on the road. Ride in a straight line and don’t swerve between parked cars. Signal turns, and check behind you before turning or changing lanes.

Ride where people can see you and wear a hi-vis top. Ride with your rear light on and flashing. Make eye contact with others and don’t ride on sidewalks. When possible, ride with others.

Watch for turning vehicles and ride outside the door zone of parked cars. Look out for debris, potholes, and other road hazards. Cross railroad tracks at right angles.

Check that your tires are sufficiently inflated, brakes are working, chain runs smoothly, and quick release levers are closed. Carry tools and supplies that are appropriate for your ride.

Pre-trip Training:

  • 4 weeks before your trip: one ride of 6 to 8 miles and a second ride of 8 to 10 miles.
  • 3 weeks before your trip: one ride of 8 to 10 miles and a second ride of 10 to 12 miles.
  • 2 weeks before your trip: one ride of 10 to 12 miles and a second ride of 12 to 14 miles.
  • 1 week before your trip: one ride of 12 to 14 miles and a second ride of 14 to 16 miles.

All training rides should be at an average speed of 12 miles per hour. Fully-loaded, our groups average 10 miles per hour while riding. You will take multiple short breaks (five minutes or less) throughout the day—for water and snacks, to rest and stretch, to enjoy the view and relax!

Please refer to the Pre-Trip Training Calendar where you will record your training in the weeks leading up to trip start.

Preparing for an Overland Experience

Overland trips are wholesome, structured experiences with high expectations of each student’s behavior. You are expected to be enthusiastic, positive, helpful and supportive of your trip mates and your leaders. We ask that you leave your cell phone and electronics at home (cameras are always welcome), so you can fully engage with your group and your trip. Arriving ready for a challenge—and prepared to contribute to an enthusiastic group—will go a long way toward creating a successful trip. Please contact us if you’d like to discuss preparing for your Overland trip!