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PEF TAKES PORTUGAL!

Sep 11–18, 2027 · A curated week for PEF membersHosted by Ben Wright (PEF Colorado Co-Lead) · Produced by Race2Adventure
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Sep 11 - 18, 2027

About this trip

This isn't a tour. It's a week with a curated group of post-exit founders — the peers who've been through the same particular thing you have, and who show up ready to have the conversations that don't happen anywhere else. The country is the backdrop. The room is the point.Over 8 nights, we'll run through Porto, hike the castles of Sintra, bike across Evora, paddle the Algarves, and eat and drink our way through one of the most beautiful countries the planet has to offer — with time built in for founder-to-founder conversation that carries the week beyond the itinerary.

Trip Highlights

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At a glance

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About this trip

Saturday, September 11, 2027

Sunday, September 12, 2027

Monday, September 13, 2027

Tuesday, September 14, 2027

Wednesday, September 15, 2027

Thursday, September 16, 2027

Friday, September 17, 2027

Saturday, September 18, 2027

Sunday, September 19, 2027

Why This Trip Is for PEF+ Members

Why This Trip Is for PEF+ Members image

WHY THIS TRIP IS FOR PEF+ MEMBERS

Every guest is a PEF+ member. That's the design choice this trip is built on — and it's what makes the room work. You've built something. You've sold something. And you know the specific weight of the questions that follow. Those questions get answered in a very specific room: with peers who have lived the same chapter and don't need it explained. This is that room. Set in Portugal. For a week.

What's different about this trip:

  • Every guest is a PEF+ member — same life stage, same context, no explaining needed• Facilitated peer moments woven into the week — opening circle, founder walks, a mid-trip long lunch conversation, and a closing circle

  • A curated group of xx, small enough to actually know each other by the end

  • At least one PEF-exclusive access moment you couldn't book on your own

  • Hosted by Ben Wright — PEF Colorado Co-Lead, PEF Forums Facilitator, two-time founder (two exits), and founder of Peak Adventures.

  • Produced on the ground by Race2Adventure.

Map of the trip locations

Map

A. Porto

Porto, Portugal

B. Sintra

Sintra, Portugal

C. Lisbon

Lisbon, Portugal

D. Cascais

Cascais, Portugal

E. Evora

Évora, Portugal

F. Monsaraz Castle

Monsaraz, 7200-175 Reguengos de Monsaraz, Portugal

G. Lagos

Lagos, Portugal

H. Faro Airport

Aeroporto de Faro, 8006-901 Faro, Portugal
Saturday, September 11, 2027

Day 1 - Welcome to Porto

September 11, 2027
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Arrive in Porto and Begin Adventure

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Vila Foz Hotel & Spa

Check in5 p.m.

Check in to one of Porto's best hotels, Vila Foz, strategically located in the heart of the city. Registration ensues at 5pm, with team and guest introductions. Passed apps and cocktails will kickoff the week long adventure.

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Passed apps and cocktails will kickoff the week long adventure

After dinner, we'll gather for 45-minute opening circle. What each person is carrying into the week, what they hope to leave with. This sets the tone for the group - and every conversation for the next seven days is warmer because of it.

Sunday, September 12, 2027

Day 2 - Trail Hike/Run and Port Tasting

September 12, 2027
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Trail Hike, City Walk, and Port Tasting in Porto

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Trail Hike/Run #1

DateSunday, Sep 12, 2027

Our first full day together is packed with off-the-beaten-path exercise, a core culinary staple of Porto for lunch, followed by a robust port wine tasting at Taylor's.

DateSunday, Sep 12, 2027
At Taylor's Port, guests can enjoy breathtaking views of the Douro River and Porto skyline while indulging in guided tours that explore the rich history of port wine. The historic cellars, dating back to 1692, provide a unique backdrop for innovative wine and food pairings, alongside art exhibitions that enhance the tasting experience.
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Private after-hours session - small group

After the port tasting at Taylor's, we've arranged a private after-hours session - small group, senior host, and the kind of conversation that only happens when the tourists have gone home.

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Guided walking tour through the city of Porto

We'll then embark on a guided walking tour through the city of Porto, PEF+ members are free to roam the city for the remainder of the evening.

Monday, September 13, 2027

Day 3 - Sintra Castles Hike

September 13, 2027
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Hiking Sintra's Castles and Arrival in Cascais

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Sintra Castles Hike

DateMonday, Sep 13, 2027

This morning we'll make our way down Portugal from Porto to Lisbon and its surrounding areas.

The outskirts of Lisbon are lined with astonishing castles, each with its own personality. A 2.5K hike will help tell the story behind centuries old architecture.

The Sintra hike is walked in pairs. We rotate partners twice. It's a simple move that turns a 2.5K into two of the most substantial conversations of the week.

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Andaz Lisbon, by Hyatt (HOTEL SUBJECT TO CHANGE)

Check inMonday, Sep 13, 2027
Check outWednesday, Sep 15, 2027
Experience the vibrant spirit of Lisbon at Andaz Lisbon, located in the city's heart near the Tagus River. Enjoy breathtaking skyline views from the rooftop bar and indulge in innovative dining that celebrates local cuisine. With a focus on personalized service and a unique artistic atmosphere, your stay promises to be truly memorable.
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Dinner at Cascais Hotel

DateMonday, Sep 13, 2027
Dinner will be served at our hotel for the next two nights in Cascais.
Tuesday, September 14, 2027

Day 4 - Lisbon Run / Hike and City Tour

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Run / Hike, and Tuk-Tuk City Tour in Lisbon

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Run or Hike Around Cascais

DateTuesday, Sep 14, 2027
We'll begin our day with a gorgeous run or hike around the jewel that is Cascais.
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Lunch in Lisbon

After a rinse and refresh at the hotel, we'll head into Lisbon for lunch and afternoon city tour by tuk-tuk.
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Lisbon City Tour by Tuk-Tuk

Afternoon city tour by tuk-tuk. There's no better way to cover ground here so sit back, relax, and enjoy the ride, equipped with a personal driver/guide.
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Pastel de Nata Bakery Visit

No tour around Lisbon is complete without a stop at the famed bakery serving Pastel de Nata. Save room for this dessert!
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Wednesday, September 15, 2027

Day 5 - Sipping, Biking, and Touring Evora

September 15, 2027
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Wine Tasting, Biking, and Farm Dinner in Evora

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Early Departure from Lisbon to Evora

After an early departure from Lisbon, we'll move away from the coast and into Portugal's mountainous interior.

Lunch is served at the Fitapreta Winery. This is our long-lunch moment: two hours, a rotating seating chart, and a light conversation prompt about identity, purpose, and what each of us is building next.

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Post lunch everyone will have three options: bike, bone chapel walking tour, or free time at our next hotel, Evora's Octant.

Check inWednesday, Sep 15, 2027
Check outThursday, Sep 16, 2027
Octant Hotels Évora offers a serene retreat surrounded by picturesque vineyards and lush landscapes, just a short distance from Évora's historic city center. Enjoy stylish rooms with modern amenities, unwind at the wellness center, and savor local cuisine with farm-to-table dining options. Outdoor activities like wine tours and guided nature walks add to the experience.
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Farm to Table Dinner at the Octant

DateWednesday, Sep 15, 2027
This evening we'll experience a gorgeous farm to table experience on the terrace of the Octant.
Thursday, September 16, 2027

Day 6 - Lagos and the Southern Coast

September 16, 2027
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Run, Hike, and Relax on Portugal’s Southern Coast

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Heading for the Southern Coast

It's time to head for the southern coast of Portugal. You'll feel the downslope and a bit of a slower pace from here on in.
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Run/Hike through Monsaraz Castle

DateThursday, Sep 16, 2027
Our next run/hike takes you through the Monsaraz Castle, with a well deserved lunch at Sahida to follow.
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SAHIDA offers a delightful journey through Mediterranean cuisine with signature dishes that highlight local flavors. Enjoy a warm atmosphere complemented by friendly service. With a diverse wine selection and artistic decor, every meal becomes a memorable experience.
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Cascade Wellness Resort

Check inThursday, Sep 16, 2027
Check outSunday, Sep 19, 2027

We'll arrive at the Cascade Wellness Center, just outside of Lagos. This is our home for the next 3 nights. Unpack, relax, and dinner will be served on the resort's patio later that evening.

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Dinner on the Resort's Patio

DateThursday, Sep 16, 2027
Dinner will be served on the resort's patio later that evening.
Friday, September 17, 2027

Day 7 - Beaches and Algarves

September 17, 2027
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Kayaking the Algarves and Lagos Seaside

Kayak Exploration of the Algarves

DateFriday, Sep 17, 2027
This morning we'll be exploring the algarves via kayak! Paddling through the algarves isn't as simple as it used to be. We'll ensure access through the best outfitters and private guides in the region.
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Lunch Overlooking the Sea

DateFriday, Sep 17, 2027
Lunch overlooking the sea to follow.
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Dinner on Your Own in Lagos

Tonight, you're on your own in one of the most mesmerizing seaside towns the continent of Europe has to offer - Lagos. There are way too many restaurants to choose from in these narrow tiled streets.
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Saturday, September 18, 2027

Day 8 - Final Beach Walk and Celebration

September 18, 2027
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Final beach walk/run on the southern coast + Final party

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Final Beach Walk/Run on the Southern Coast

DateSaturday, Sep 18, 2027
We'll walk or run off last night's indulgence with some morning exercise on the beach.
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Seaside Local Coastal Lunch

DateSaturday, Sep 18, 2027

Resort Relaxation and Activities

DateSaturday, Sep 18, 2027

After a seaside local coastal lunch, we'll head back to the resort for some much needed R&R. Spa treatments, swimming pools, tennis courts, and a driving range are all for the taking.

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Closing circle

Before dinner, we'll gather for a closing circle. What each person is taking home from the week, what commitments they're making to themselves and to the group.

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Final Dinner Party

Tonight we'll celebrate an epic week of exercise, exploration, and community.
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Sunday, September 19, 2027

Day 9 - Depart Portugal via Faro Airport

September 19, 2027
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Farewell to Portugal and Departure

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Depart Portugal via Faro Airport

We've done it. We have run, walked, biked, paddles, tuk-tuk'd, eaten, and drank our way through Portugal. All in comfort, style, with a little bit of sweat and determination mixed in. PEF just took Portugal!

What's included

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What's included

✓ 8 nights hotel lodging
Based on double occupancy

✓ Almost every single meal
Dinners on rooftop terraces, lunches at city center staples, farm to table in the mountains, nibbles in wineries, and meals on the beach

✓ All ground transport
All transport throughout the country, from luxury bus, to tuk tuks through Lisbon, to bikes through Evora, to kayaks through the Algarves

✓ All sporting events
Whether you're hiking, running, biking, or paddling, we've curated the best courses off the beaten path

✓ Professional Guides

✓ Facilitated peer moments
Opening and closing circles, founder walks, and a curated founder dinner - designed to make the deeper conversation easy, without over-programming the week

What's not included

✗ Air into Portugal
Your flight into Porto and out of Faro

✗ Airport transfers

Host + producer

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YOUR HOST Ben Wright

— PEF Colorado Co-Lead, PEF Forums Facilitator, two-time founder with two exits (Atlas Integrated, acquired by Williams Media; Upsuite, acquired by IWG). Founder of Peak Adventures and Next Cap Ventures. Ben hosts the week — the peer container, the opening, the pairings, the mid-trip conversation, the closing — and designs an experience built for post-exit founders specifically.

PRODUCED BY RACE2ADVENTURE

Merritt Hopper and the Race2Adventure team produce and guide the trip on the ground — logistics, routes, local guides, activities, and the operational expertise that makes a week like this possible. 4.8 ★ across 18 reviews.

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Who this is for

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WHO THIS IS FOR

This trip is designed for PEF+ members who:

  • Have built and exited a company, and are sitting with the specific chapter that follows

  • Want a week with peers who understand that chapter without needing it explained

  • Enjoy real physical activity — hiking, running, biking, paddling — at any fitness level

  • Are open to real conversation, not just networking

Companions and families: The core trip is designed for PEF+ members only. Whether that opens up will be decided by the group itself once it's formed — some cohorts want a members-only experience, others want a companion day or two woven in. We'll ask the confirmed group before opening any companion access.

 

Kids: The pacing of this trip (long dinners, early starts, wine tastings, city touring) is designed for adults. If you're planning a family trip to Portugal, we're happy to help you plan one — separately from this experience.