Sailing, Stargazing & the High Desert
Sept 11th-14th, 2026
Embark on a four-day stargazing journey that begins on the riverbanks of Portland and
carries you into the heart of Central Oregon’s high desert. From sailing at sunset with
live music, to Equinox sky-watching guided by an astronomer, to a starlight paddle on
Cascade Lakes, this weekend combines nature, culture, and connection for an
unforgettable dark-sky escape.
Day 1 — Portland (September 19)
Day 2 — Brasada Ranch & Stargazing
Day 3 — Brasada Ranch & Cascade Lakes
ITINERARY:
DAY 1 – Sailing on the Willamette River
Check in at the Kimpton RiverPlace Hotel, nestled along Portland’s lively South Waterfront. Take time to settle in, relax, and enjoy dinner at your leisure at one of the many acclaimed riverfront restaurants.
As evening falls, a short stroll along the docks brings you to the Schooner Rose — an elegant, 85-foot vintage sailboat awaiting your group. At 7 p.m., step aboard for a private evening reserved for Club Members. We’ll sail at dusk, gliding north as Portland’s bridges lift in welcome. Hand-selected Italian and Argentinian wines flow as you mingle with fellow travelers, while the city lights shimmer against the river — the perfect prologue to your stargazing journey.
DAY 2 - Brasada Ranch & Stargazing
Wake to the river’s calm before embarking on a scenic private transfer to Central Oregon (approx. 3 hours). Along the way, pause at the historic Timberline Lodge — a National Historic Landmark perched on the slopes of Mount Hood — for a short scenic walk and time for lunch on your own. From there, your journey continues across the dramatic high desert along the Metolius River, a drive as stunning as the destination itself.
Arrive at Brasada Ranch, an upscale retreat surrounded by sweeping Cascade views. The afternoon is yours to enjoy at leisure — whether that means teeing off on the private championship golf course, indulging in a rejuvenating spa treatment, or exploring the landscape by bike or on foot.
As night falls, gather for a special stargazing experience under the moonless Equinox sky. Guided by a local astronomer, you’ll trace constellations across a celestial canvas. A cozy fire pit and roasted s’mores add a sweet, playful finish to the evening.
Day 3 — Brasada Ranch & Cascade Lakes
Savor another day at leisure at Brasada Ranch, perhaps with a round of golf or a guided horseback ride across the high-desert landscape.
In the evening, your driver-guide will take you into the heart of the Cascade Range for a remarkable starlit paddling experience. Beginning at 7 PM, you’ll slip quietly onto one of the pristine, high-elevation Cascade Lakes, where still waters mirror the night sky.
Guided by a naturalist, this two-hour journey reveals not only the constellations of the Equinox sky, but also the hidden wonders of the lakes and surrounding forest. Hear age-old star myths woven with astronomy, listen for the nocturnal stirrings of wildlife, and take in the profound silence of the evening hours.
By the time you return to the ranch close to midnight, the day’s revelations — natural, cultural, and celestial — will linger as brightly as the heavens above.
Day 4 — Return to Portland
After breakfast, a private transfer will return you to Portland, carrying with you the memories of nights spent beneath Oregon’s Equinox skies.
On the way, pause just outside Hood River at a family-run apple orchard for a stroll among the trees and a farewell toast.
Additional Information
Members Rate:
● $4,723 per couple / $3,461 per single traveller (when minimum number is reached)
Non-members Rate:
● $5,323 per couple / $3,761 per single traveller (when minimum number is reached)
What’s Included
● Lodging for the duration of the program, including all taxes and fees
● All scheduled activities and private excursions, led by expert local guides
● Entry fees and necessary equipment for all listed activities
● Meals as outlined in your itinerary
What’s Not Included
● Transportation to/from your starting and ending destinations
● Golfing at Brasada
● Horseback riding at Brasada
● Travel insurance (highly recommended)
● Gratuities for guides, drivers, and service staff
RESERVE WITH US
Let’s start planning with a quick call. Together, we’ll confirm the destinations, pace, and experiences are just right for you.
Our Office
- USA
- 1661 SE 3rd Ave Portland, Oregon 97214
Questions?
That’s OK, we have answers. Read our FAQs below.
Do I need Travel Insurance?
Yes, Curiosity Roads and its partners on the ground require all travelers purchase trip protection coverage. If you already have an insurance, that’s great! Otherwise, we recommend Wanderwell. It is the first Certified B Corp travel insurance provider and they have world-class service, support, and coverage. At least 1% of your purchase premium price will be donated to the Planet Impact Fund through 1% for the Planet network.
How much physical activity should I expect?
The tour includes a moderate amount of walking, mostly at a relaxed pace. On Day 3, the paddling portion takes place in a stable canoe, and most guests find it very comfortable. That said, if you’d prefer not to paddle, the stargazing experience is just as magical from the shore as it is from the water — so you won’t miss out either way.
Can you help buying airfare?
While we don’t book airfare directly, we’re happy to refer you to a trusted partner who can assist with both the international and local legs of your flight.