Hidden Gems of the Canary Islands & Madeira

 
Santa Cruz de Tenerife to Santa Cruz de Tenerife
Tue Nov 17, 2026 - Fri Nov 27, 2026,
 10 days
 on Wind Spirit
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Starting from $3,499 USD
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Santa Cruz de Tenerife to Santa Cruz de Tenerife
Explore the Canary Islands and Madeira where landscapes are infinitely diverse and temperatures are uniformly pleasant year-round, including islands well off the beaten path like Porto Santos and El Hierro. So many attractions vie for your attention. Spanish and Portuguese cuisines with a unique African twist. Unconventional volcanic vineyards rubbing elbows with bananas, pineapples and palm trees. Authentic “Columbus slept here" stories on Porto Santos and La Gomera. If you’re feeling energetic you can ride a camel across a volcanic moonscape, trek through prehistoric laurel forests, or explore natural wonders like Porto Santo’s 5.5-mile golden beach or El Hierro’s blissfully beautiful natural rock pools. An overnight in Funchal gives you time to visit Madeira’s many wineries, hike historic levadas, and ride a wicker toboggan down steep city streets.
voyage map
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Day 1: Santa Cruz de Tenerife
Here in this privileged setting you’ll discover two UNESCO World Heritage Site beaches of tantalizing beauty; San Cristóbal de La Laguna; and the island’s symbol, Teide National Park. Wide avenues, exotic landscapes, and striking examples of modernist architecture complete one of the world’s most popular destinations.
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Day 2: Lanzarote
Nature is the star on this small volcanic island. Enjoy the afternoon on the beach or follow the island’s famous wine trail, tasting as you go. This, the most northerly of the Canary Islands, welcomes you with laid-back hospitality and genuine warmth. This region of petrified lava makes up the National Park of Timanfaya and its Mountains of Fire, where visions of a lifeless, prehistoric earth, with enormous craters of an incandescent red color, can be seen on a bus or even a camel tour.  This unique atmosphere has made it a UNESCO Biosphere Reserve and one of the most impressive natural parks in all of Spain. 
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Day 4: Funchal
Considered one of Portugal’s main tourist attractions and home of world-famous footballer Cristiano Ronaldo, Funchal is known for its style and beauty.  Visit Cabo Girao, the highest sea cliff in Europe or take a trip to the Pica da Torre for an incredible view of Camara de Lobos, a delightful fishing village. With a long history of Madeira winemaking, there’ll be time here for a little wine tasting, a meal at one of the many 5-star restaurants, sightseeing to 15th century Cathedral of Our Lady of the Assumption, shopping the bargains to be found here, or experiencing the vibrant night life.
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Day 5: Funchal
Considered one of Portugal’s main tourist attractions and home of world-famous footballer Cristiano Ronaldo, Funchal is known for its style and beauty.  Visit Cabo Girao, the highest sea cliff in Europe or take a trip to the Pica da Torre for an incredible view of Camara de Lobos, a delightful fishing village. With a long history of Madeira winemaking, there’ll be time here for a little wine tasting, a meal at one of the many 5-star restaurants, sightseeing to 15th century Cathedral of Our Lady of the Assumption, shopping the bargains to be found here, or experiencing the vibrant night life.
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Day 6: PORTO SANTO, MADEIRA
PORTO SANTO, MADEIRA
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Day 8: San Sebastian
Though you won’t find canaries here you will find people who can whistle like them. Whistled speech helped shepherds communicate across the steep ravines and in the lush cloud forest of Garajonay National Park, a UNESCO World Heritage Site. Columbus paused here on all three voyages so you’re in good company as you explore historic San Sebastián, but with all the natural beauty around, you’ll find your gaze drawn inexorably up the terraced hillsides and across to views of Mount Teide.
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Day 9: El Hierro
El Hierro is a small ship exclusive port and the smallest and westernmost Canary Island, is a hidden gem known for its rugged landscapes, volcanic terrain, and rich biodiversity. With stunning natural rock pools, prehistoric laurel forests, and dramatic coastlines, it offers a tranquil escape for nature lovers, hikers, and those seeking a unique adventure. The island’s unique ecosystems, including a marine reserve, attract divers from around the world. El Hierro also boasts charming villages, picturesque hiking trails, and peaceful surroundings, making it a perfect destination for those looking to disconnect and enjoy untouched natural beauty. It is a UNESCO Biosphere Reserve, preserving its diverse habitats.
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Day 10: Santa Cruz de Palma
Santa Cruz de Palma has a distinct Caribbean feel with its colorful houses and relaxed, casual feel. Walk along the cobblestone streets of this charming port that once was a connecting port on the route to the Americas. Learn about the town’s history at the Island Museum of La Palma located in a 16th century monastery and the Naval Museum housed in a full-sized reproduction of the Santa Maria. And see some of the 15 large telescopes along the ridge of Caldera del Taburieint National Park.
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Day 11: Santa Cruz de Tenerife
Here in this privileged setting you’ll discover two UNESCO World Heritage Site beaches of tantalizing beauty; San Cristóbal de La Laguna; and the island’s symbol, Teide National Park. Wide avenues, exotic landscapes, and striking examples of modernist architecture complete one of the world’s most popular destinations.
Popular Highlights
El Hierro
Known for its rugged landscapes, volcanic terrain, and rich biodiversity, El Hierro is a small ship exclusive and a haven for nature lovers and hikers.
Funchal
Enjoy an overnight in Funchal, as your ship docks just a 10-minute walk from town.  Ride a tobaggon down the steep streets, taste Madeira’s famous fortified wine, and take in the lush green island landscape.
Lanzarote
On Lanzarote, sip award-winning wines and learn how grapes are grown in volcanic soil / lunar landscapes
Porto Santo
Explore Porto Santo, a small island that typically receives less than 10 cruise ship calls per year.  Enjoy beautiful viewpoints and golden sandy beaches – Porto Santo is a favorite among Madeira locals for vacation.
Santa Cruz de La Palma
In Santa Cruz de La Palma, take a star gazing excursion and join your expert guide as you learn how to use a telescope and enjoy clear views of the sky without light pollution.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Tue Nov 17
Santa Cruz de Tenerife
Arrive:  
Depart:  4:00 PM
Watersports Platform: 
Wed Nov 18
Lanzarote
Arrive:  11:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Nov 19
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Nov 20
Funchal
Arrive:  1:00 PM
Depart:  
Watersports Platform: 
Sat Nov 21
Funchal
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Sun Nov 22
PORTO SANTO, MADEIRA
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Nov 23
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Nov 24
San Sebastian
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Nov 25
El Hierro
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Nov 26
Santa Cruz de Palma
Arrive:  7:00 AM
Depart:  2:30 PM
Watersports Platform: 
Fri Nov 27
Santa Cruz de Tenerife
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
? Call for Availability
Category B
Category B
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $3,499 per guest
? All-inclusive price from $3,499 per guest
Category BX Deluxe
Category BX Deluxe
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $3,799 per guest
? All-inclusive price from $3,799 per guest
Category A
Category A
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $4,099 per guest
? All-inclusive price from $4,099 per guest
Category AX Deluxe
Category AX Deluxe
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $4,299 per guest
? All-inclusive price from $4,299 per guest
Owner's Suite
Owner's Suite
With an expansive 220 square feet, the Owner’s Suite gives you everything offered in a stateroom, plus lots more, including a beautiful sitting area and separate in-room dining space.
? Call for Availability
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Marina
*Select voyages
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Thankful For Travel Sales Event
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Tue, Nov 17 - Fri, Nov 27, 2026
WIND SPIRIT
$3,499
$3,499
THIS
SAILING
Fri, Nov 27 - Mon, Dec 7, 2026
WIND SPIRIT
$3,499
$3,499
Mon, Dec 7 - Thu, Dec 17, 2026
WIND SPIRIT
$3,499
$3,499
Thu, Dec 17 - Sun, Dec 27, 2026
WIND SPIRIT
$3,599
$3,599
Sun, Dec 27 - Wed, Jan 6, 2027
WIND SPIRIT
$3,699
$3,699
Wed, Jan 6 - Sat, Jan 16, 2027
WIND SPIRIT
$4,199
$4,199
Sat, Jan 16 - Tue, Jan 26, 2027
WIND SPIRIT
$3,799
$3,799