Itinerary

Day 1: Meet in San Jose. Cruise 17-mile drive and Pebble Beach on your way to Carmel-by-the-Sea

Meet us in San Jose, CA. Head out to bicycle one of the most famous roads in the region: iconic 17-Mile Drive. Stunning coastal vistas unspool as we ride past Pebble Beach’s fabled mansions and golf course, through pine forest and along the oceanfront, passing the reefs and tide pools of Bird Rock, the white sands of breathtaking Fanshell Beach and the famed Lone Cypress tree.
Watch for deer, black cormorants, brown pelicans and California sea lions. Spend tonight at the Pine Inn or Tradewinds in Carmel-by-the-Sea, where Clint Eastwood once held office as mayor.
Meals: Lunch, Dinner Lodging: Pine Inn or Tradewinds
distance: 30 miles (or more) Elevation +1453 ft / -1196 ft

Day 2: Ride the coast south from Carmel across the Bixby bridge to Pfeiffer Big Sur State Park– home to the southern-most redwood forest.

Pedal the weathered coastline from Carmel-by-the-Sea to the community of Big Sur. Follow the dramatic knolls and tumbled rock headlands of the Cabrillo Highway (aka Highway One): enormous live oaks, green-and-gold hillsides, pale sand dunes and the blue Pacific Ocean.
Ride across Bixby Bridge, a historic open-spandrel arch bridge that brought automobile travel to the central coast.
Finish cycling early in the afternoon. Relax at the hotel or take advantage of the beach or one the amazing hikes at Pfeiffer Big Sur State Park. Stay at the Fernwood Resort
Meals: Breakfast, Lunch, Dinner Lodging: Fernwood Resort, Big Sur
Distance: 31 miles, Elevation +2234 ft / -2320 ft.

Day 3: Pedal the most dramatic and remote section of central California coastline

Ride south today from Big Sur to Ragged Point on the most spectacular, rugged, and remote section of the central California coastline. The road is carved into the seaside cliffs and a new stunning seascape opens up around every corner.
It’s a long day so you may want a boost over the first (or last) climb. This is not a problem at all – whatever transportation you choose the vistas are unforgettable!
Contemplate the end of a great day with cliff-top cuisine and a great view at Ragged Point Inn
Meals: Breakfast, Lunch, Dinner. Lodging: Ragged Point Inn
Distance: 50 miles (or less), Elevation +5315 ft / -5117 ft.

Day 4: Rest up at Ragged Point, or head out for more exploring.

Yesterday was a long day on the bikes, so we take the day off here to enjoy the views from “on high” today before descending from Ragged Point.
You can spend time relaxing, watching the water for whales or enjoying the area on a short, easy walk from the inn, or take on one of the more challenging trails like the Cliffside Trail to a waterfall or the solitude of the Baldwin Ranch Trail which heads up into the hills.
In addition, we will offer a shuttle (or you can cycle, of course) back up the coast to Lime Kiln State Park to explore the trails, the beach and the historic lime kiln. Dinner is on your own tonight.
Meals: Breakfast, Dinner. Lunch is on your own today, or on day 7. Lodging: Ragged Point Inn

Day 5: Rolling coastal hills. Hearst Castle, an elephant seal beach, delightful Cambria

Take one last look from on-high before we descend from Ragged Point. South of here, a swath of rolling hills guards the coastline from the steep mountains and the road runs closer to the water.
The rock outcroppings dotting the waters just offshore may be a hazard to ships, but they also provide prime marine life habitat.
Pause to visit one of only two beaches in California where elephant seals come ashore in late fall to mate and teach their young to swim.
After lunch by the beach, enjoy a guided tour of journalism baron William Randolph Hearst’s opulent home in San Simeon – Hearst Castle.
Lodging is at Cambria’s Rigdon House a historic boutique hotel. Dinner is on your own in town, with plenty to choose from within easy walking distance.
Meals: Breakfast, Lunch, Dinner. Lodging: Rigdon House
Distance: 24 miles (or more), Elevation +972 ft / -1257 ft. (or more)

Day 6: Cycle through Morro Bay on your way to Pismo Beach and dig your toes into the sand!

Today’s ride is a veritable variety show. Sweeping curves of coastline are punctuated by surfers and beachgoers. Rolling fields and pastures are dotted with live oaks, racehorses, and honest-to-goodness cowboys.
While the mileage is longer today, the hills are not as challenging as they were along Big Sur. Refuel your legs with a seaside picnic lunch in Morro Bay beneath landmark Morro Rock.
Continue bicycling south to the white sands of Pismo Beach, halfway point between San Francisco and Los Angeles.
Go for a swim in the ocean to cool off, or just soak up some rays by the surf. Relax and enjoy beachfront lodging and dining at SeaVenture Beach Hotel the only hotel and restaurant (literally) on Pismo Beach!
Meals: Breakfast, Lunch, Dinner. Lodging: SeaVenture Beach Hotel
Distance: 48 miles Elevation +1737 ft / -1773 ft

Day 7: “Wine”down with a tour through Edna Valley’s vineyards. Return to San Jose.

Wind (“wine?”) down with a peaceful inland ride on country roads past the vineyards of Edna Valley outside San Luis Obispo, known predominantly for its Chardonnays and Pinot Noirs. Have lunch on your own (if we haven’t already) while we load bikes for the drive back to San Jose (about 3.5 hours, traffic depending).
Meals: Breakfast, lunch is on your own today or on day 4.
Distance: 19 miles (or more) Elevation +1333 ft / -1145 ft (or more)

While it is indeed a spectacular route, much of the cycling on this tour is along Highway One. Riders should be comfortable cycling on a highway with some traffic.

* This is a general itinerary. Tour itineraries are subject to change based on the group, available accommodations and other unforeseen circumstances such as the weather, local conditions, government intervention, that may affect the quality of the trip and/or safety of the participants. Please view this itinerary as an outline as to what to expect on this tour.

Lodging

Big Sur Coast

Pinn Inn or Tradewinds
Fernwood Resort, Big Sur
Ragged Point Inn
Rigdon House
SeaVenture Beach Hotel
The hotels, Inns, and B&B’s we use are always among the finest the area has to offer. We work closely with the innkeepers to make sure they understand your needs and ours, whether that is having a place to store your bike, an early morning breakfast or a convenient place to park the van, they are as committed to your vacation experience as we are.

Lodging is based upon two people to a room with a private bath. If you’re traveling solo on any of our trips, we’ll assign you a roommate of the same gender and often of the same age bracket. There is no extra charge if we can’t find you a roommate, even if you sign up the day before the trip starts. You can guarantee yourself a private room and bath if you pay the Single Room Fee. Occasionally a room with two beds consists of one bed plus a roll away bed or sofa bed.

Included:

• Deluxe lodging
• Meals: all included except 1 lunch and 1 dinner. Snacks and beverages between meals
• Road / Hybrid Bike, ( E-bike rent possible for an extra fee of $200.00)
• Helmet and Wahoo GPS device
• Park and other entry fees
• Luggage transfer.
• Hearst Castle, hiking

Not included:

• Night before and after the tour.
• Flights to and from the tour
• Alcoholic beverages at meals
• Gratuities guides

Pricing / Tour dates

Tour price 2025: $4747.- pp, Single fee: $ 1282.- This is not required. It is an optional fee to allow a solo traveler to guarantee a private room for the duration of the tour.
Upgrade E-bike: $200.-pp
Tour Dates 2025:
02 Jun – 08 Jun

Conditions

Deposit 25% For all private tours $500.–pp is non-refundable.
The deposit payment for a tour must be paid within two weeks after the booking is confirmed.
The remaining payment is due 90 days before the start of the tour.
For tours that are booked within 90 days before the start of the tour you will pay 100% of the tour price
Deposit amount of $500.-pp are non-refundable for Private tours.

Information

Meals and dining:
We know how important breakfast is to make sure your day starts off right. Most breakfasts are served at the inn where we spend the night and are either a set menu or a continental breakfast buffet. But if there is a local restaurant with a reputation for a great breakfast, we can guarantee we will find it and you will be treated to a nutritious meal to start the day.
Lunch is provided at a state park or similar scenic setting midway during the day’s ride. Guests are always surprised at the variety and quality of lunches we prepare. Besides sandwich fixings and cold drinks, we offer fresh fruits and vegetables and hot lunches such as tortellini with pesto or veggie burritos. If you prefer a certain item of food or drink, just let your tour guide know and we will be sure to prepare just the right lunch to keep your energy up for the rest of the day.
During the day water, fruit juices, soft drinks, energy bars, fruit, and snacks are available from the van. A cold beer from our cooler waits at the end of the day, and you can relive the day’s highlights at our wine and cheese party before dinner.
Dinner is eaten together at the best restaurant in the area. At most restaurants, you order what you want from the menu. Except for alcohol, everything is included, even appetizers, salad, soup, and dessert. If we have to shuttle everyone a short distance to get to that special place, we do it. We like to eat well.