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Daily Mileage: 4 – 11 miles
You won’t find many walking adventures that let you explore Portugal’s romantic Alentejo—a remote region less well-traveled than the neighboring Algarve, but just as scenic. Here, you’ll walk uncrowded country paths, explore dramatic cliffs above crashing ocean waves, amble through airy forests of gnarled cork, and stroll through meadows teeming with vibrant wildflowers and aromatic herbs. Along the way, you’ll stay in exceptional boutique accommodations, including a five-star hotel dating back to the 18th-century—the oldest hotel on the Iberian Peninsula. Relax on expansive country estates and enjoy fresh, local cuisine, rich wines, and a wealth of optional activities—including horseback riding, mountain biking, and poolside lounging. With detailed route notes, audio navigation app, and a friendly local rep, this self-guided adventure brings you the authentic Portugal.
Country Walkers is proud to support Wine to Water with a donation on behalf of each guest on this tour. Wine to Water is an international organization providing access to clean drinking water and emergency supplies in water-challenged regions. We believe in giving back to the places that have enriched the lives of our guests. We’re committed to identifying and supporting sustainable initiatives in a variety of areas including education, world health, economic equality, safe drinking water, the environment, and the preservation of cultural traditions.
Terrain Description for Portugal: Sintra & Rota Vicentina
This tour is one of our Self-Guided Walking Adventures, rated easy to moderate, with an average of 4–11 miles of walking per day; options are available on most days. Throughout this tour, cumulative elevation gains and losses are up to 1,800 feet. The first portion of the tour is in the Sintra-Cascais Natural Park. Walks here follow a variety of terrain—over uneven cobbled paths, stone stairways, packed-earth, grassy single tracks, sandy beach, country dirt roads, and paved paths—through forested, cliffside, coastal, and brushland landscapes. Footing in many places may require attention, particularly when wet. The second portion of the tour follows the coastal Rota Vicentina over gently undulating terrain. Walks here follow both packed-earth and deep-sand single tracks through small sections of pine, evergreen, oak, and eucalyptus forest and along high dramatic cliffs, which may challenge those with vertigo. These walks have little coverage from the sun, which, depending upon the temperature, can increase the rigor of this tour. This diverse and rewarding itinerary leads you through some of Portugal’s most scenic corners, from the undulating slopes, hilltop stone castles, and coastal vistas of the Portuguese Riviera to the seaside cliffs, fishing villages, and sprawling beaches of the Alentejo. Reaching these locations requires travel times of 2.5 hours on Day 3, 45 minutes on Day 5, and 2.5 hours on Day 7. Remember: preparation is key to your enjoyment; the more you walk or participate in aerobic exercise prior to your trip, the more rewarding your experience will be!
| Tour Day | Choose Your Route Options | Miles per Option | Hours per Option** | Elevation per Option*** | Activity Level |
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| 1 | Walk | 3.9 | 02:30 | +850/-850 | easy-moderate |
| 2 | ShortMedium | 4.710.7 | 03:0006:00 | +300/-1800+300/-1800 | moderatemoderate |
| 3 | Walk | 5.9 | 03:00 | easy-moderate | |
| 4 | ShortMediumLong | 46.69.4 | 03:0004:0006:00 | +850/-800+850/-800+850/-800 | easy-moderateeasy-moderateeasy-moderate |
| 5 | ShortMedium | 5.27.8 | 03:0004:30 | +500+750/-550 | easy-moderateeasy-moderate |
| 6 | Walk | 8.2 | 04:30 | -750 | easy-moderate |
Alternate options may be available.
**Route mileage, hours, and elevation gain/loss are all approximate
***Elevation gain/loss indicated if greater than 500 feet
Itinerary
Arrival Day & Tour Day 1
Lawrence’s Hotel
Located just a short walk from Sintra village center sits Lawrence’s Hotel, providing travelers with a romantic, relaxing atmosphere since the 18th century. The oldest hotel on the Iberian Peninsula, the Lawrence Hotel’s reputation for tranquility is widely known. Towering ivy-covered trees shelter the hotel’s 16 guest rooms, each offering a mix of old-world style and contemporary comfort. Modern amenities include wireless high-speed internet, individual climate control, and in-room safes. Brass room keys, polished oak floors, and inward-opening, screen-free windows with sprawling countryside views highlight the hotel’s classic European charm.
Day 2
Farol Hotel
Dramatically set on the Atlantic waterfront, the Farol Hotel in Cascais enjoys a splendid location, just a 10-minute walk from the city center. This remodeled 19th-century mansion was once owned by the Count of Cabral. Air-conditioned rooms are tastefully decorated, each large and airy and offering views of palms and lush gardens. Take a dip in the saltwater pool. Browse the collection of artistic touches throughout the property. Enjoy dinner al fresco or indoors with ocean views at The Mix or at Sushi Design. Mostly, just relax amid the upscale atmosphere of one of the finest hotels in Cascais.
Days 3, 4
Herdade do Touril
The five whitewashed farm buildings of the Herdade do Touril are set on a tranquil 900 acres within view of the Atlantic Ocean. This working cattle-breeding estate has been run by the same family since 1826. Its thoughtful design keeps you connected to the Alentejo’s rural beauty, with outdoor terraces, open spaces that afford breathtaking views, brightly colored, air-conditioned guest rooms, and a pool that is ideal for a post-walk swim. Enjoy three-course meals prepared with fresh ingredients during your stay.
Days 5, 6
Herdade da Matinha
The airy and spacious Herdad da Mathina features 35 independent guest rooms spread out across four houses on an immaculately maintained estate in Cercal. Located within the South West Alentejo and Vicentine Coast Natural Park, the property is a quiet enclave for adventurers to unwind and recuperate. Whether you stay in one of the guest rooms that open up to a patio garden or one directly overlooking the Cercal mountain range, relaxing comfort abounds. The hotel’s on-site restaurant, Mesa, serves breakfast, lunch, and dinner daily utilizing fresh herbs and produce grown on self-sustaining farms located on its grounds.
Day 7
Pestana Arco da Rua Augusta
The newly constructed Pestana Arco da Rua Augusta is a sprawling, elegant hotel that provides road-weary travelers with all the comforts and amenities they need to relax and recuperate. The hotel’s central location provides guests with easy access to Lisbon’s many great sites. Guest rooms feature a variety of architectural details that are native to this region of Portugal, including broad tile-lined walls, expansive wood paneling, vaulted ceilings, and wide stone floors. Catch up with friends back home on complimentary WiFi while you dine on seasonal vegetables, freshly caught fish, and regional favorites at the hotel restaurant.
What's Included |
Tour Only | Air Package |
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| Boutique accommodations |
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| 10 on-tour meals: 6 breakfasts, 4 dinners |
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| Ride with GPS (custom downloadable GPS route notes and turn-by-turn voice navigation; smartphone required) |
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| Orientation meeting with a Country Walkers representative |
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| Local representative available 24/7 |
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| Scheduled on-tour taxi and luggage transportation (Please note: If unable to walk, it is possible to travel with your luggage from one accommodation to the next at no additional charge.) |
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| Roundtrip international airfare | Not Included |
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| Business-class upgrades available | Not Included |
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| One extra night in Sintra and one extra night in Lisbon | Not Included |
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| Pre- and post-tour breakfasts | Not Included |
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| Detailed information for your independent travel to/from arrival and departure airports | Not Included |
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Please note: Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. Prices include all airline surcharges and Government taxes and fees. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What’s Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.
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