URSUS TRAVEL
Madrid October 25 - November 2, 2026
Travel with Derrick into the soulful, artisanal heart of Spain’s capital and surrounding areas. Our curated trips are more than just travel. They are an opportunity to build kinship and be with like-minded individuals while having life changing experiences. A premium escape designed specifically for gay men, bears, and those that love them who are looking for community and authentic discovery. The founder of Ursus Travel lived in Madrid for 12 years so this will be a homecoming trip and also an inaugural trip for us!
THE VIBE
An Intimate Autumn in Iberia
This isn't just a trip; it's a home-coming to the heart of Spain. We’ve designed this experience to be intimate and communal, focusing on the hidden gems and local haunts that make Madrid truly magical in the autumn.
Built for bears and gay men who crave authenticity over tourism, our Madrid journey invites you to step into the local rhythm. We will also explore the surrounding villages and towns that make central Spain magical. Whether we're sharing tapas in a cozy taberna or exploring the golden hues of Retiro Park, you’ll find a pack that welcomes you exactly as you are.
Madrid Journey: October 25 - November 2 2026
DAY 01
October 25, 2026
The Arrival & Welcome Dinner
Arrive in Madrid and check in. We kick off the trip with a sunset cocktail overlooking the skyline, followed by an intimate welcome dinner in the center of Madrid. Your flight should depart the 24th! Flights from the USA to Europe are overnight!
Madrid, Toledo, El Escorial, Segovia, Madrid Regional Wine Bodega
DAY 02
October 26, 2026
Intro to Madrid Walking Tour/Royal Palace
A private morning tour of the historic center of Madrid. In the afternoon, we dive into the hidden taverns of Old Madrid for a curated vermouth tasting and traditional aperitivos and tapas.
DAY 03
October 27, 2026
Toledo: Ancient Iberian Roots
A short high-speed train ride brings us to the medieval capital. We wander through Toledo's narrow lanes, visiting traditional masters and quiet cloisters before heading back to Madrid.
DAY 04
October 28, 2026
Unscripted solo day for you
Time for you to do as you please. Sleep in, get a massage, rooftop tour, walk around. This day is for you to do what you feel like.
DAY 05
October 29, 2026
Deep Dive into History El Escorial/Segovia
Private transportation to the picturesque monastery of El Escorial. We detour to Valley of the Fallen on our way to historic Segovia to see the roman aqueduct and "Snow White" castle. Upon arrival we will have a generous lunch of traditional Segovian food.
DAY 06
October 30, 2026
Museum Day
For those that love art we will begin at the Museo Reina Sofia. After a short lunch we will head over to see the masterpieces of the Prado Museum. If time permits we will have a stroll through Retiro Park.
DAY 07
October 31, 2026
Wine Tasting and Charcuterie in a Madrid Bodega
We will spend the morning in a traditional Spanish bodega with wine tastings and finger foods. Capture the beauty of smalltown rural Madrid. When we finish it's back to Madrid for either a siesta or whatever you feel.
DAY 08
November 1, 2026
El Rastro (Sunday Market) & Pack Feast
Experience the energy of El Rastro Sunday flea market. After perusing antiques and oddities, the Pack gathers for one final, multi-course feast featuring the best of Castilian cuisine.
DAY 09
November 2, 2026
Farewell Breakfast & Departure
We share a final celebratory breakfast. Exchange contacts and favorite memories before heading to the airport or extending your journey in the Iberian peninsula.
Madrileño Comfort
You have several different options for your accommodation in Madrid for different budgets. You can leave it up to us (we do this professionally) or we can allow you to choose your own. We do encourage choosing accommodation that is central and close to the center of Madrid to ensure the feeling of being part of the pack. We also understand some prefer to choose themselves. We are set up to accommodate both options.
What the Coordination fee covers
- Full trip design and curated itinerary
- On-site hosting and community leadership by Derrick
- All pre-arranged reservations - Derrick will make the reservations for restaurants, tours, tastings, and transportation (We take into consideration your preferences if you want something different)
- Exclusive welcome pack and pre-trip guide
- Access to the Ursus pack community network
Paid separately by each guest
- Accommodation (Derrick can book this for you through Ursus travel - just ask
- International airfare
- Meals, tastings, tours, and ground transport (Derrick coordinates bookings and curates the travel plan, you will pay the operators directly. We are not a tour operator.
- Travel and medical insurance (mandatory)
- Personal shopping and incedentals
As your travel agent and trip host, Derrick handles all logistics and reservations. Activity, meal, and accommodation costs are paid directly by each guest. Estimated total trip budget excluding flights will be between $2500-$3500 depending on your accommodation choice.
QUESTIONS
When does the waitlist officially open?
The waitlist for our Madrid November 2026 trip is currently active. Joining the pack early gives you priority access to booking before the itinerary is released to the general public.
What is the average age of the travel pack?
We welcome anyone over the age of 18! We don't discriminate over age!
Are flights and hotels included in the trip pricing?
To provide flexibility for our guests travelling from across the globe, flights and hotels are not included. However, we are happy to provide arrival advice for Madrid-Barajas Airport. We can also help you to book your accommodation and flights... We do that professionally as a travel agent.
What is the group size for the Madrid trip?
We keep our journeys intimate to ensure a premium experience. This trip is limited to 6-8 maximum guests, allowing us to access exclusive local venues and foster genuine community.