Portugal Magic: Lisbon, Cascais, Porto & The Isle of Madeira
12 Days
12 days/11 nights—$10,376 /person (single add $2114)
Couples, Friends, and Solos
May 14—25, 2025
All Breakfasts, 9 Lunches, 8 Dinners
Premier Hotels & Meals
Gracious Lisbon, Cascais Beach, Porto’s Duoro Wine Valley, Camino de Santiago, Evora, and the Isle of Madeira
When Europeans think of white beaches, castles, Fado music, dessert wine, designer tiles & pottery, Roman ruins, El Camino, abundant seafood, & even the unique use of cork —plus endless sunshine & a yearly mild climate – they choose Portugal! Join us for more bucket list items than you ever dreamed of combined in one tour: The Portuguese Way of Santiago, Lisbon’s storied history and bustle, and the creamy Cascais coast with Peña Castle in Sintra will enchant you. The Roman ruins and pedestrian shopping streets in Evora of the Alentejo region, the medieval stonewalls and festivals of Obidos, and canals of Aveiro will delight your senses. The pilgrim spirit of Fatima and intoxicatingly beautiful port-wine Douro valley will make you want to stay forever. And then we finish off the tour with 3 sun-drenched days on Portugal’s dreamy island of Madeira, 500 miles off the coast of Africa in warm Atlantic waters, which will leave an indelible mark on your thirsting travel soul.
Highlights
Arrive in Lisbon and a 5-star Italian royal villa in Portugal’s most famous beach town—Cascais— your homebase on the coast for 5 gorgeous nights.
Tour historic Lisbon’s vibrant architecture, plazas, tilework, shopping and restaurant-filled streets. Enjoy a spectacular meal overlooking the city of 7 hills.
Visit Sintra’s storybook Peña Castle inside its iconic multi colored towers. Enjoy a great walk through the hilly town and sample cozy shops and bars.
Travel back in time to the medieval walled city of Obidos and marvel at its architecture and charming hospitality and cafes.
Venture east to the Alentejo region’s ancient Roman town of Evora. 1st century’s Temple of Diana stands proudly among great shops in Plaza Giraldo and the famous Chapel of Bones.
Visit Portugal’s holy city Fatima, renowned for the sighting of the Blessed Virgin Mary. Join worldwide pilgrims at the impressive Sanctuary for a peaceful moment.
The Porto region in the north awaits with soulful Fado music, ceramic tiles, port wine and seafood.
Tour the Douro Valley by boat and mountain pass to the vineyards that produce the world’s best port wine.
Venture north across the border of Spain to the historic El Camino de Santiago. Walk the final portion of the famous trail into Campostelo.
Check out the canals navigated by colorful boats in the seafaring west coast town of Aveiro.
A short flight to the paradise of Madeira will open your eyes to prehistoric laurel flora, beautiful coast on the west, and the vibe of Funchal.
Get your tastebuds ready for a poncha cocktail, espetada barbeque or peixa espada for dinner, and Madeira wine with your island dessert.
Don’t miss the Skywalk, Cable Car, or Toboggan ride that will imprint memories of a lifetime.
Who’s Your Host?
Captain Joe Sacchetti is a U.S. Army Ranger-qualified paratrooper in the 82nd Airborne and author of Guts, Smarts & Love, who served 2 tours in Iraq and was awarded the Bronze Star for actions in combat.
A Track & Field All-American and Welterweight Boxing Champ in the 82nd Airborne, Joe escorted the Olympic torch through his Pennsylvania hometown in 1980 on the way to Lake Placid as a kid, and from that moment knew he wanted to see the world!
After MIT’s Business Exec Ed program, Joe started Highroads Traveler to make sophisticated global travel easily accessible to small groups of 20 by “hosting” them, now via Legacy Collectibles.
It’s rare to mesh the world of combat vet and sophisticated traveler, yet Joe is on a journey to be the world’s first Army Ranger to visit every country on the globe. 160 out of 227 so far, and it’s much more than stamping a passport.
Connecting with people around the globe in their language makes every trip more fun. From European roots, Joe is comfortable in half a dozen or so, and always learning more.
Playing music is another fantastic people connector so he & his wife Domenica always keep an eye out for a piano to gather round at happy hour. It doesn’t take much nudging from her to get Joe to play either!
Why “Hosted?”
Go with a Pro.
You’ve saved up and are ready to take the trip of a lifetime. Do you really have time to plan all the details and get it all perfect? If yes, great! Yet for most, pretty much no way. And how about when you get there making your way to the best hotels, sites and restaurants? Most say… daunting. Our solution – let’s go together and make your greatest trip ever.
“Taste, touch and see what the world has to offer” is Joe & Domenica’s mantra, and now you’re invited to come share the journey to the best places in the world with their small-group hosted tours.
What's Included
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All Breakfasts, Selected Lunches, Selected Dinners
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Bon Voyage gift(s) for your International Tour
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Expertise and service from your Highroads Traveler Host, Joe
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Additional regional guides and experts on several trips
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Comprehensive Trip Detailer with all-you-need-to-know info
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Guided tours at historic sites and select attractions as noted in the Trip Detailer
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All gratuities at hotels and restaurants
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Special events, including wine tastings and select attractions as mentioned in the Trip Detailer
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Park and other entry fees
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Fares for trains, ferries and other modes of travel as listed in the Trip Detailer
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Select coach transfers
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Baggage transfers
Not Included:
Leader gratuities, transportation to and from your Highroads Traveler trip start & end locations, and on-your-own meals & activities.
Ready to Embark on Your Next Adventure?
You've read about the incredible experiences waiting for you on this tour—now it's time to turn that dream into reality! Imagine exploring stunning landscapes, immersing yourself in vibrant cultures, and creating memories that will last a lifetime. Don't wait any longer to make this trip happen.
Start Planning Your Journey Today!
Click the button below to book your tour and secure your spot. Adventure awaits!
Gallery & Testimonials
As an Army Ranger for 25 years, I served as Joe Sacchetti‘s 2nd-in- command during Desert Storm, and there is nowhere in the world that I wouldn’t follow him, He cares about people. If I had the money, I would go on every trip he takes.
Master Sergeant Al A. , 45th anniversary D-Day (1994) Jump Team, Army Ranger, Green Beret, Bronze Star, Master Parachutist
We first met Joe on the island of Martinique while he was leading his group on a New Year’s trip. Ooh la la, he lives life like a true Frenchman! C’est Bon, such joeux de vie!
Christian C. , Sergeant, French Maritime Marines
