Edition III:
Alentejo, Portugal
September 2027 , 5 Nights
(Couples, Friends, Solo Travelers | Co-Ed)
Trip details below, scroll to explore:
Where We’re Staying
Throughout our journey, we’ll stay at three distinctive properties that showcase different sides of Portugal: one in Lisbon, a traditional herdade in southern Alentejo, and finally, an intimate property set within a historic tapada. More details coming soon.
What We’re Doing
Journey into the heart of Portugal’s Alentejo, an emerging wine region where centuries-old traditions meet exciting new producers. Over five nights, we will explore Lisbon and the rolling countryside of northern and southern Alentejo through curated winery visits, unforgettable dinners, vineyard picnics, traditional barbecues, and local olive oil tastings.
Depending on the timing of the harvest, guests may also have the chance to participate in the grape harvest and experience traditional winemaking practices. This thoughtfully hosted journey is designed for travelers who want to discover Portugal through its wine, food, and the people who bring both to life.
Who is this trip for?
This journey is designed for female travelers who love experiencing a destination through its food, wine, and local culture. It's for those who appreciate long lunches at vineyards, charming villages, exceptional meals, and the slower pace that allows you to truly connect with a place. Whether you're traveling solo or with a friend, partner, or family member, you'll be part of an intimate group of curious travelers who value authentic experiences, meaningful connection, and exploring beyond the highlights. Compass Collective journeys are thoughtfully designed to bring together like-minded travelers for unforgettable experiences, both with the destination and with one another.
This journey is perfect for you if:
You enjoy exceptional food and wine and are excited to learn more about the regions we'll visit.
You appreciate luxury accommodations, authentic local experiences, and a thoughtfully paced itinerary.
You're comfortable with moderate walking through vineyards, villages, and coastal towns.
You're flexible and happy to use a variety of transportation throughout the week, including walking, private transfers, and the occasional taxi.
You enjoy traveling with a small group and are respectful, open-minded, and excited to share the experience with others.
Meet Your Host
Dee
Coucou! I'm Dee, founder of Bespoke Compass Travel and your host for this Alentejo, Portugal Edition of the Compass Collective.
Alentejo is one of those places that stays with you, and sharing its magic with others is one of my greatest joys. This journey reflects what I love most about the region: exciting wines, unforgettable meals, beautiful landscapes, warm hospitality, and a slower pace that invites you to experience Portugal more deeply.
My hope is that you'll return home with wonderful memories, new friendships, and a deeper appreciation for this very special region of Portugal.
Pricing & Inclusions
TOTAL COST PER TRAVELER:
TBD
WHAT’S INCLUDED:
Five nights across three luxury five-star hotels
Daily breakfast
Private winery visits and tastings
Immersive cultural experiences
Transportation throughout the journey, including airport/train station transfers
A fully hosted experience with thoughtful Bespoke Compass touches throughout
An intimate small group experience
Due at registration: $500 non-refundable deposit
Final payment due: TBD
Rooms are priced at double occupancy (2 travelers per room).
Single Supplement available
Can choose to pay full amount upfront
WHAT’S NOT INCLUDED:
Airfare & Transfers not specified in the itinerary
Entrance fees when not mentioned
Meals/Alcohol Not Listed
Passport and Visa fees
Personal & travel insurance
Gratuities
Any item specified as “own arrangements” or "at leisure"
CANCELLATION POLICY:
All cancellations must be submitted in writing to deirdre.schwiring@fora.travel.
Deposit: $500 non-refundable.
120+ days: Deposit retained; all other payments refunded.
91–119 days: 50% of total trip cost is non-refundable.
90 days or fewer: 100% non-refundable.
See Terms & Conditions for full policy