Like the history of explorers who hailed from this region, cycling through Portugal is a sensory adventure that ignites your spirit to explore. The endless mountain roads carved through lush vegetation and rocky terrain, the towering peaks, deep valleys, terraced vineyards and panoramic views at every bend invite you to explore further and further.
Through charming villages with their whitewashed houses and cobbled streets of timeless charm that immerse us in centuries of history and culture. The grand palaces, castles, churches and medieval monasteries, show us the splendor of Portugal’s past. Throughout the journey, we will encounter the warm smiles and friendly faces of the locals as we dine in traditional family restaurants, sip wonderful wines in picturesque vineyards and local taverns and spend our nights in stunning, authentic boutique accommodations, creating real connections with the people and culture of Portugal.
This is a meaningful motorcycle ride of the best kind, and it’s one you won’t want to miss!
2-9/6/2026 SOLD OUT
September (Sukkot) - 3 last spots
8 days/7 nights
7
Lisbon, Portugal
Lisbon, Portugal
1450
medium
99% asphalt
1990
Yes - recommended
easy+
A shared room with another rider is included as standard. See supplements for single room pricing.
All of our accommodations have been carefully selected to create an authentic experience without compromising on luxury.
Includes comprehensive insurance with a deductible of $1500-$2000 (depending on model)
We arrange the rental through our preferred supplier. Your contract will be directly with the supplier and you will be required to comply with their terms and conditions.
Breakfast and Dinner
Indulgent Gourmet Meals – A Culinary Experience
Customized to Personal Requests
Leading and managed by an experienced member of the Caribou team.
Qualified as an international tour guide with extensive knowledge of the destination,
Trained in advanced riding
Qualified in first aid.
On every trip without exception, there is full support by an escort vehicle! It will carry all our luggage as well as essentials, tools, a medical kit (in addition to the one carried by the main guide), cold drinks and snacks. There is always a free seat for any participant who might want to take a break.
From the airport to the hotel upon arrival and from the hotel to the airport on the day of departure.
All entrance fees to all attractions during the trip are included – and there are many attractions on each trip.
T-shirt
Hat
Stickers
Neck warmer
Keychain
A portion of the proceeds from each trip participant goes directly to the Make-A-Wish Foundation whose sole mission is to grant life-changing wishes to children ages 3-18 with serious illnesses.
While fulfilling our own dreams, we also fulfill the dreams and wishes of these young children.
Which makes the experience even more meaningful!
We will hold a face-to-face meeting at least two weeks before departure.
During the meeting, we will present the trip in detail and answer any questions you may have. This is also an opportunity to get to know your travel partners and raise a toast together.
If you are unable to attend the meeting, we will arrange a personal video call.
You will need to book a flight and arrive at your destination before the trip begins. We will suggest a flight itinerary based on time/cost considerations. Although we provide you with a travel agent to take care of this, you are under no obligation to purchase through them.
If you purchase through another agent or directly, please ensure the following:
Do not book your flight until we have notified you that this departure is guaranteed.
Make sure to arrive before the trip begins (send us a copy of your flight for confirmation before purchasing)
You must take out travel insurance in case of cancellation (Passport Card).
At the beginning of the trip, we create a small cash pool that everyone contributes to (about 25 euros per day). This is used for coffee breaks, lunches and fuel.
This approach really helps to speed up all the stops along the way.
We try to eat light lunches along the way to stay alert for our rides (and also because we have very pampered dinners). We either have picnic meals prepared by the crew of the accompanying vehicle or we order a full table of appetizers to share.
Payment is taken from the small cash register.
All beverages, whether alcoholic or not, are not included.
It is mandatory to take out travel insurance that covers emergency evacuation, medical bills, etc.
Souvenirs
Laundry
Damage to the motorcycle (motorcycle insurance is included in the rental but there is a deductible of $1500-$2000 depending on the model). Please note that this amount will be held on your credit card or paid as a deposit.
Towing, oil, spare parts, labor or other indirect costs resulting from damage to your motorcycle.
Emergency transportation
Anything not specifically stated as included.
Mandatory riding protective equipment:
Full-face helmet
Protective riding jacket
Knee protection: Knee pads or protective riding gaiters
Riding gloves
High-top shoes (above the ankle) or riding boots.
