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Join the Adventure in 

August 5-8, 2021

September 23-26, 2021

November 4-7, 2021

Napa and Sonoma Valley, California


What to expect on the trip?

Expect really good trails, really good wine, and really good food. 

The Napa and Sonoma valleys are the premier destination for wine lovers. There's so much to see and do, and we're going to fit in as much as we can!

Trip Dates

We will have three upcoming trips in 2021!

Note: The August inaugural trip will be limited to 15 adventurers

What's included?

Your hotel room for 3 nights, all breakfasts and lunches, two dinners, 9 wine tastings and pairings, gorgeous swag, and transportation to all the wine adventures and trails each day.

  • 3 Nights in a hotel room
  • Breakfast and lunch each day
  • Two dinners
  • 7 Wine tastings or pairings
  • Gorgeous swag
  • Transportation to and from your daily activities


Day 1: Thursday

We will get you checked into River Terrace Inn in the heart of Napa, and after taking some time to unpack and get comfortable, we’ll enjoy a delicious dinner together at an upscale restaurant near our hotel. You will get to know your new friends and we’ll go over the trails, wine and food you’ll experience over the next three days.

Day 2: Friday - Skyline Park

Terrain: Trail

Distance: 10.5k

Elevation Gain: 1362 ft

Trail type: Loop

This morning we’ll drive just a few minutes to a favorite trail of Napa locals. The trail starts with switchbacks. We spend the first two miles gradually climbing, before enjoying expansive views of Napa and Sonoma valleys, the wineries, and the Vaca and Mayacamus ranges. The trail continues onto Lake Marie, where there’s a good chance you’ll see native California birds like the great blue heron.

The lake is the top of the loop, so we’ll turn and drop into a small canyon on a single track trail for a bit, passing the fig tree, and possibly deer, before finishing the loop back where we began. The trail is wide and graded in sections, and single track and sometimes rocky in other sections.

We’ll go back to the hotel where you’ll have a chance to clean up and change before heading to the famous Gott’s Roadside in St Helena to feast on burgers, fries and ice cream. 

Our first winery visit is really special. We’ll be visiting a winery with spacious property and delicious wine. We’ll get a tour of the vineyards while tasting.

Next we’ll head to the perfectly replicated Italian castle; Castello di Amarosa in Calistoga. We’ll get to explore the chapel, great hall and other medieval style rooms and have a tasting with chocolate pairing. 

From the castle, it’s a short drive to some of the best farm to table cuisine in all of Napa Valley. We’ll enjoy each other’s company over dinner at Farmstead at Long Meadow Ranch in St. Helena. Think fresh produce, organic meats and delicious wine selected to perfectly pair with the meal.


Day 3: Saturday - Pomo Canyon

Terrain: Trail

Distance: 8.3k

Elevation gain: 549 ft

Trail type: Point to Point

We’re starting the day early so we can drive through lovely northern California towns to an incredible trail. We’ll start in Pomo Canyon, and climb through redwood forest before reaching the top of the grassy hillsides which we’ll follow to the ocean. Once you see the beach, you’ll begin the descent down. After crossing Highway 1 you’ll take the Kortum Trail. You’ll continue for 2 miles on this fairly flat trail on the cliffs above the ocean until you reach the beach. We’ll congregate and have a picnic lunch on the beach.

You’ll have a chance to change and clean-up in the public bathrooms before we drive to Healdsburg. This charming town is known for its variety of tasting rooms, delicious cuisine, art galleries, and fun shopping. While in Healdsburg, you’ll participate in two different tasting sessions, and then have some free time to browse the town. (You may want to set aside some time to peruse the Healdsburg Running Company store).

After enjoying Healdsburg, we’ll drive back to our hotel and you’ll have the rest of the evening to yourself. We recommend walking to Oxbow Market or the CIA at Copia for dinner, or booking a ride and gourmet dinner on the Napa Valley Wine Train.

Day 4: Sunday - Jack London State Park

Terrain: Trail

Distance: 8k

Elevation gain: 846 ft

Trail type: Lollipop loop

This morning we’ll run around Jack London’s historic vineyards and ranch as the sun rises. The trail starts near the vineyard and his eucalyptus grove, then climbs into the redwood forest, and to the “lake” and cabin. 

After our run, we’ll have a snack and get to explore the property together and learn a bit more about Jack London. 

We’ll end our weekend at the beautiful Hess Collection Winery with a delicious three-course lunch, wine pairings, and a tour of the art gallery and chapel. After celebrating together, we’ll shuttle you back to the airport.

**This itinerary is subject to change based on dates and availability. If a certain trail, winery, or restaurant isn’t available, a comparable one will be substituted. 

Looking forward to my adventure

Looking forward to my adventure with you guys next year 😁🎉

Helayne Heidenreich Lehman


Registration is open! 

per registrant

Don't dilly-dally! We expect these trips to sell out quickly

Private Room (no roommate)

add'l $500

Napa-Sonoma 2021

Ready to join us? Choose your trip dates below, then create an account via Regpack, our secure platform, to register for your next adventure. Complete your registration today!

Pricing and Deposit

$2000 per person ($4,000 per couple) includes everything mentioned in the itinerary. When you register, you can pick from several different payment options including pay in full, or make monthly payments.

Based on Double Occupancy

This pricing is based on double occupancy of the hotel room. If you register with a partner, you will be able to stay with them. If you register as a solo adventurer, we will pair you with someone else of the same gender.

Single Occupancy Pricing

If you prefer to have your hotel room to yourself, the cost will be $500 extra ($2500 total) to cover the additional hotel expense.

Cancellation and Transfer Policy

Our cancellation policy is as follows: 

If you need to cancel for any reason, you can receive a full refund 60 days prior to the event. 30-60 days before the event, you can receive a refund minus $500 unless we are able to transfer your registration to another participant. 0-30 days prior to the event no refunds are given.

If this event is cancelled due to Covid-19, you will receive a full refund or have the option to roll your funds over to another Wine Country trip.