Azores & Madeira: Portugal's Atlantic Islands
9 Days, 8 Nights
16
$14,995 USD
Single Supplement: $5,000 USD
limited edition
Few places pack so much variety into such a compact corner of the Atlantic. In the Azores, São Miguel's volcanic heart reveals itself in misty crater lakes, bubbling thermal springs and green pastures that roll down to the sea. In Madeira, mountains rise straight from the Atlantic, laurel forests shelter centuries-old water channels and Funchal's markets hum with island flavour. Ride and hike by day, then trade the trail for thermal pools, spa treatments and long dinners overlooking the sea. It's Atlantic Portugal, from wild to refined.
Experience Portugal’s wild side, where volcanic peaks rise from the sea, crater lakes shimmer in ancient calderas and thermal waters bubble beneath lush green landscapes. From whale-rich waters to dramatic coastal cliffs, the Azores and Madeira reveal a world shaped by the Atlantic.
Discover two distinct expressions of island life. In the Azores, rugged volcanic landscapes and a slower pace foster a deep connection to nature. In Madeira, lush gardens, winding levada trails and elegant hospitality lend the journey a more refined rhythm.
Linking two remote Atlantic archipelagos requires local knowledge and thoughtful planning. We’ve brought together the region’s most rewarding rides, walks, experiences and stays, creating a journey that feels effortless while revealing the distinct character of each island.
Day by Day
No two trips are ever the same, but this will give you a taste of what your journey will be like.
Rendezvous
Trip Start: Octant Furnas Hotel, Furnas
Time: 9:30 am
Nearest International Airport: João Paulo II Airport, Ponta Delgada (PDL)
Farewell
Trip End: Madeira Airport, Madeira
Time: TBC
Nearest International Airport: Cristiano Ronaldo Madeira International Airport (FNC)
* Itineraries are subject to change. Please confirm exact Rendezvous and Farewell locations upon booking.
Day 1
Arrive on São Miguel and ease into island life with a first ride along quiet country roads to the coastal town of Vila Franca do Campo. Continue to Furnas, where steam rises from the earth, and settle into Octant Furnas with time for a first soak before welcome cocktails and dinner.
Daily ride: 49 km (30 mi) | Elevation 1,055 m (3,461 ft)
Day 2
Ride through one of São Miguel’s least-visited corners, where cedar forests and hydrangea-lined lanes lead to dramatic Atlantic viewpoints. Back in Furnas, a private walk takes you into the island’s geothermal heart, followed by dinner featuring the day’s catch in a small fishing village.
Daily ride: 48 km (30 mi) | Elevation 900 m (2,953 ft)
Long option: 74 km (46 mi) | Elevation 1,500 m (4,920 ft)
Day 3
Head offshore by private Zodiac with a marine biologist in search of sperm whales and dolphins. After a guided walk through historic Ponta Delgada, check in to your west coast retreat for dinner at MôMô.
Whale watching in a private zodiac
Private guided tour of Ponta Delgada
Day 4
Swap bikes for boots on a hike across the Serra Devassa plateau to the Grota do Inferno viewpoint, one of São Miguel’s most celebrated views. A picnic lunch and a free afternoon lead into a last evening on São Miguel in historic Ponta Delgada.
Daily hike: 6 km (4 mi)
Day 5
Fly to Madeira and enjoy free time in Funchal for lunch and exploring at your own pace. In the afternoon, a private guide introduces you to the city's historic streets and traditional crafts before you check in to The Reserve at Savoy Palace, your base for the final four nights.
Private gastronomic tour of Funchal
Day 6
Follow a historic levada through Madeira’s UNESCO-listed laurel forest, past waterfalls and across deep valleys. Lunch in a local family’s home on the north coast is followed by a free afternoon and dinner at one of your guides’ favourite restaurants.
Daily hike: 9 km (5 mi)
Day 7
Hike the high ridgelines of Madeira’s central mountains, where on a clear day the clouds sit below you. Stop at Monte Palace Tropical Garden on the way back to Funchal, then enjoy a free evening at The Reserve.
Daily hike: 9 km (5 mi)
Monte Palace Gardens visit
Day 8
Walk sheer sea cliffs on one of Madeira’s finest coastal trails, then cruise the coastline by private boat, with lunch on board and time to swim and snorkel. Tonight, raise a glass at a farewell dinner in the chef’s own home.
Daily hike: 10 km (6 mi)
Day 9
After a last breakfast at The Reserve, a private transfer takes you to Madeira Airport. Safe travels, and until next time!
Dates & availability
Can't find your dates?
Get in touch to craft a Bespoke itinerary or request an additional date to privatize.
Featured stays
Octant Hotels Furnas
Location: Furnas, Portugal
Sensi Azores Nature & Spa
Location: Sao Miguel Island, Portugal
The Reserve at Savoy Palace
Location: Funchal, Portugal
What's included
All breakfasts, lunches and dinners as indicated on the itinerary.
All accommodation as indicated on the itinerary.
Thoughtfully selected local wines, beers, cocktails or non-alcoholic beverages with all meals.
Appropriate bike for terrain, equipped with handlebar bag and helmet.
Use of two lightweight, telescoping walking sticks, a waist pack and a biodegradable B&R water bottle.
Use of a smartphone with downloaded GPS routes provided via RideWithGPS.
Services of B&R guide(s).
All special events, private tours, guest experts and entrance fees.
All gratuities for baggage, porters and hotel services.
Internal flight Azores to Madeira.
Transportation from pick up to drop off.
Baggage transportation.
What's Not Included: International flights, travel protection, gratuity for your B&R guides.
This trip is carbon neutral. Learn more about our Sustainability commitment.
Good to know
Weather
Island weather in the Azores and Madeira can shift quickly, especially in coastal and mountain areas. Pack layers and be ready for sun, wind, mist and light rain, sometimes all in the same day.
Staying Connected
Some routes and activities take you off the beaten path, where cell service can be limited. All hotels offer reliable Wi-Fi.
Seasickness
This trip includes a whale-watching excursion by Zodiac and a day on a private boat, and sea conditions can vary. If you're prone to seasickness, bring preventative medication.
Island Pace
The Azores offer beautiful hotels and warm hospitality, but service can feel more relaxed and less polished than what travellers may expect from luxury hotels in mainland Europe or North America. Consider it part of settling into island time.
Equipment
Carbon Performance Road Bike
Touring Bike
E-Bike
Why choose a Small Group trip?
An Effortless Journey
Our expert Experience Designers are perfectionists, using first-hand knowledge of routes, restaurants and hotels to create an unforgettable experience. This means all the planning is taken care of for you. All you need to do is enjoy.
Active Exploration
From emerging destinations to iconic sights, B&R trips show you the world in a new way on our expertly developed cycling, walking and hiking routes. Travelling through historic villages and romantic vineyards and up to striking viewpoints, our routes offer a variety of challenges for every activity level.
Friends for Life
Your fellow travellers are as passionate and curious about the world as you are, which means the conversations and laughs will be as free flowing as your drink of choice. Don't be surprised if your group starts planning a reunion before the trip is done.
Room for Surprises
We love a plan, but we adore a spontaneous moment even more. Whether it's an impromptu al fresco meal or a moon-lit musical performance, our advice is to expect the unexpected.
