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Trip Itinerary
Immerse yourself in California’s wine country, a premier bike tour destination where exquisite wines and sublime cycling roads await.
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Where to Arrive
Airport:
Sonoma County Airport (STS), San Francisco International Airport (SFO) or Oakland International Airport (OAK)
Pick-up location:
Harmon Guest House
Pick-up time:
9:00 AM
Where to Depart
Airport:
Sonoma County Airport (STS), San Francisco International Airport (SFO) or Oakland International Airport (OAK)
Drop-off location:
Harmon Guest House
Drop-off time:
12:00 PM
Additional Arrival Information
We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Charles M. Schulz-Sonoma County Airport (STS).
The easiest way to arrive in Healdsburg is to book your flight to the Santa Rosa Airport (STS) and take a taxi for about $30. There is also car and limo service available at SFO for approximately $275 to get you to Healdsburg if you prefer.
Your Trek Travel guides will meet you in the lobby of the Harmon Guest House (227 Healdsburg Ave, Healdsburg, CA 95448) at 9:00 AM on the first day of the trip. After a round of introductions, your Trek Travel guides will discuss bike safety and specific cycling tips for riding through the wine country. They’ll spend some time familiarizing you with the Trek bicycle you’ll be riding and will make sure that you and your bike are the perfect fit before cycling to a picnic lunch and a tasting.
If you will be late for the pick-up or are going to miss it altogether, please inform your guides. If you cannot reach them, please call our hotel, Harmon Guest House (707-431-8220) and leave a message with your expected arrival time and contact details. The Sonoma County Airport Express shuttle (800-327-2024) from SFO to Sonoma County Airport for around $30/person. Taxi from Sonoma County Airport to our first hotel is approximately a 13-mile taxi ride.
Additional Departure Information
You will say farewell to your guides at 12:00 PM at the Harmon Guest House. Taxi and shuttle services are available from the hotel if you are flying out from the Sonoma County Airport (STS) or a different airport. If you plan to fly out of the Bay area, please avoid scheduling your flight any earlier than 5:30 PM.
Ride tranquil byways through the Alexander and Dry Creek Valleys
Overview
Your Trek Travel guides will meet you in the lobby of the Harmon Guest House at 9:00 AM on the first day of the trip. After introductions and the bike fit, cycle along tranquil byways through the Alexander and Dry Creek Valleys. You’ll pass many distinctive wineries in the Dry Creek Valley, home to more than 50 wineries, and one of the top Zinfandel producing regions. If you're up for a challenge, tackle Rockpile Road, a beautiful detour through the Lake Sonoma Recreation Area with views of Lake Sonoma. We continue to CAST Winery for a picnic lunch and wine tasting. Dry Creek Valley is renowned for its Fumé Blanc (Sauvignon Blanc) and Zinfandel grapes. Tonight, we dine at Spoonbar for refined Californian fare.
Hotel
Harmon Guest House
Meals included
Lunch | Social Hour | Dinner
Highlight of the Day
CAST Winery
Take in CAST vineyard's breathtaking views of Northern Dry Creek Valley and the confluence of Dry Creek and Dutcher Creek.
Ride Options
Ride Option 1
TODAY'S RIDE:
Healdsburg to Dry Creek Loop - Approximately 38 mi | 61 km and 1,785 ft | 544 m
Ride Option 2
AVID OPTION:
Healdsburg to Dry Creek Loop with Rockpile Road - Approximately 46 mi | 74 km and 2,700 ft | 822 m
Activities
Activity 1
TODAY'S ACTIVITY:
Wine Tasting at CAST Vineyards
Visit the majestic redwoods at Armstrong Redwoods State Natural Reserve
Overview
Today you'll ride through the scenic Russian River Valley, famed for its Pinot Noir, en route to Armstrong Woods Park. Avid riders can test their legs on the week’s toughest climb—Sweetwater Springs—with sections reaching a 20% grade. At the park, pause to admire the towering redwoods, including the oldest (1,400 years) and tallest (310 feet) trees. We'll stop for lunch in Guerneville or at Korbel’s on-site gourmet deli—perhaps with a glass of bubbly to match. Spend the afternoon relaxing at the hotel or head to Healdsburg for boutique shopping and wine tastings on the square. Starting at 3:00 PM, you’ll also have the chance to visit favorite wineries in Dry Creek Valley (advance tasting reservations and transport are recommended). This evening, we’ll gather for a farm-to-table feast at Valette, where Sonoma’s rich agricultural roots shine through every dish.
Hotel
Harmon Guest House
Meals included
Breakfast | Lunch | Dinner
Highlight of the Day
Armstrong Redwood State Natural Reserve
Armstrong Redwoods preserves stately and magnificent coast redwoods (Sequoia sempervirens), the tallest living trees on our planet!
Ride Options
Ride Option 1
TODAY'S RIDE:
Healdsburg to Armstrong Return - Approximately 35 mi | 56 km and 1790 ft | 546 m
Ride Option 2
AVID OPTION:
Healdsburg to Sweetwater Springs – Armstrong With Westside Rd. Return Approximately 52 mi | 83 km and 3,451 ft | 1,051 m
Take a leisurely stroll through Healdsburg
Overview
Take a final morning spin through the charming Alexander Valley to loosen up your legs or enjoy a peaceful morning in Healdsburg relaxing at the hotel. Or feel free to take a stroll for a coffee at our guide's favorite cafe, Black Oak. If you choose to ride, upon your return, hurry out to Healdsburg’s town square for a little last minute shopping or wine tasting. After a wine and food pairing at Williamson Wines, you’ll say farewell to your guides at 12:00 PM at the Harmon Guest House, before heading off on your next adventure.
Meals included
Breakfast
Highlight of the Day
Ride Options
Ride Option 1
TODAY'S RIDE:
Dutcher Creek Loop - Approximately 39 mi | 63 km and 1,600 ft | 487 m
Ride Option 2
SHORT OPTION:
Dutcher Creek Geyserville Loop - Approximately 32 mi | 51 km and 800 ft | 426
Activities
Activity 1
TODAY'S ACTIVITY:
Wine and Food Pairing at Williamson Wines
If a date is marked as Private, it is reserved for a private group.
Don’t see exactly what you are looking for or looking for a custom date?
Call our trip consultants at 866-464-8735
Trek Travel offers three hotel levels to match your style. Luxury hotels provide elegant, thoughtful touches with exceptional hospitality. Explorer hotels blend modern amenities with local charm in unique settings. Comfort hotels are casual and conveniently located near Trek Travel activities.
Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).
Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).
Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).
Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).
Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).
Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).
Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).
Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).
Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).
Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).
Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).
Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).
Explore beautiful destinations with a curated blend of guided activities, local cuisine, handpicked accommodations, and itineraries to suit every traveler, from laid-back adventures to luxurious escapes.
Venture off the beaten path to unforgettable places, with fully-supported routes that combine gravel and paved roads in classic Trek Travel style.
Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.
See the pros in action at the biggest cycling events of the year.
Step into adventure with carefully designed routes, unparalleled hospitality, and deep-routed local connections.
Train like the pros in some of their favorite riding destinations.
Enjoy a bike tour on your schedule with just your chosen travel companions.
Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself