Windstar Canary Islands Cruises
The Ultimate Luxury Small-Ship Escape to Europe's Islands of Eternal Spring
Imagine sailing between dramatic volcanic islands where black lava fields meet golden beaches, centuries-old villages overlook the Atlantic Ocean, and every sunrise reveals an entirely different landscape. Windstar's intimate yachts carry fewer than 350 guests to secluded ports, UNESCO treasures, and volcanic vineyards across Spain's Canary Islands and Madeira.
Are Windstar Canary Islands Cruises Worth It?
Yes. Windstar Canary Islands cruises offer extraordinary value for discerning travelers seeking small-ship intimacy, UNESCO world heritage discovery, volcanic landscapes, and authentic Spanish & Portuguese Atlantic heritage. Carrying under 350 guests, Windstar drops anchor in boutique harbors like La Gomera, El Hierro, and Porto Santo where 5,000-guest liners cannot follow, providing James Beard Foundation regional dining, open bridge policies, and uncrowded teak deck relaxation.
Why the Canary Islands Are Different
Europe's most geographically diverse archipelago, located off the coast of Africa.
Black Sand Beaches & Volcanic Peaks
Surreal volcanic terrain, soaring peaks including Mount Teide, and dramatic lava coastlines.
UNESCO World Heritage Treasures
Ancient laurel forests of Garajonay, historic San Cristóbal de La Laguna, and Teide National Park.
Lava Vineyards & Gastronomy
Award-winning volcanic wines, fresh Atlantic seafood, artisan cheeses, and traditional tapas.
The Islands of Eternal Spring
Pleasant year-round climate with comfortable temperatures throughout autumn, winter, and spring.
Why Windstar Is Perfect Here
Fewer Than 350 Guests
No endless lines, no crowded promenades, and an unhurried, intimate yachting atmosphere.
Access to Smaller Ports
Reach boutique harbors in La Gomera, El Hierro, and Porto Santo that megaships bypass.
Personalized Yacht Service
A 1:1.5 crew-to-guest ratio ensures highly attentive, warm, and customized service.
Uncrowded Destination Immersion
Longer port stays and overnight options let you experience local island life, volcanic sunsets, and authentic culture without ever feeling rushed.
Island Personality Compass
Which Canary Islands experience feels most like your travel style?
Volcanic Landscapes Experience
Dramatic lava fields, volcanic craters, and otherworldly landscapes.
Lanzarote
Timanfaya Fire Mountains & volcanic crater wine pits
Tenerife
Soaring Mount Teide peak & surreal lunar rock formations
El Hierro
Raw volcanic sea cliffs & natural swimming tide pools
What Makes These Cruises Special
Unmatched island diversity, volcanic landscapes, and authentic heritage on every sailing.
Lanzarote's Fire Mountains
Walk through Timanfaya National Park and marvel at volcanic crater vineyards grown in black ash pits.
La Gomera Garajonay Rainforest
Discover mist-covered ancient laurel woods and deep ravines preserving prehistoric flora unique to Europe.
Madeira & Canary Volcanic Wines
Savor crisp Malvasia wines and fresh Atlantic seafood served in picturesque island harbors.
Windstar Canary Islands & Yacht Cruising Showcase
Experience the romance of intimate yacht sailing, uncrowded volcanic island harbors, and luxury small-ship exploration with Windstar Cruises.
Why Book Through Trips & Ships Luxury Travel?
Expert advisory services that transform a simple booking into an extraordinary journey.
Personalized Itinerary Design
Matching your travel style to the ideal sailing date, ship, and island ports.
Suite & Stateroom Selection
Expert advice on deck placement, motion comfort, and balcony preferences.
Pre/Post Hotel & Flight Support
Arranging seamless flights, airport transfers, and boutique hotel extensions.
Which Windstar Canary Islands Itinerary Is Right for You?
Choose your voyage based on desired experiences and regional highlights.
The Colorful Canary Islands
Combines historic European departure cities with the dramatic volcanic beauty of Madeira and the Canaries.
Best For
First-time visitors, couples, food & wine lovers, and scenic cruising
Highlights
- Lisbon → Madeira → Tenerife → La Gomera → Lanzarote → Cádiz
- Duration: 8 to 10 Nights
- Curated small-group shore excursions
Hidden Gems of the Canary Islands & Madeira
Explores lesser-visited islands bypassed by large cruise ships, emphasizing quiet harbors and local traditions.
Best For
Authentic culture, off-the-beaten-path travelers, and dramatic landscapes
Highlights
- Tenerife → El Hierro → Porto Santo → Madeira → La Gomera → Lanzarote
- Duration: 9 to 10 Nights
- Curated small-group shore excursions
Canary Island Idyll
Focuses intensely on the Canary archipelago with minimal transit sea days and extended port stays.
Best For
Repeat Windstar guests, minimal sea days, hiking, and culinary focus
Highlights
- Roundtrip from Santa Cruz de Tenerife
- Duration: 7 to 9 Nights
- Curated small-group shore excursions
Sample 9-Night Atlantic Voyage Route
Lisbon to Cádiz via Madeira, Tenerife, La Gomera & Lanzarote
Lisbon, Portugal
DAY 01
Embark in Portugal's elegant historic capital with views over the Tagus River.
Funchal, Madeira
DAY 03
Botanical gardens, Monte cable cars, levada walks & famous Madeira wine cellars.
Santa Cruz de Tenerife
DAY 05
Mount Teide National Park and UNESCO La Laguna colonial old town.
San Sebastián de La Gomera
DAY 06
Garajonay ancient cloud forest & Silbo Gomero UNESCO whistled language.
Arrecife, Lanzarote
DAY 07
Timanfaya volcanic craters, César Manrique art & La Geria lava vineyards.
Cádiz, Spain
DAY 09
Disembark in one of Europe's most ancient port cities in sunny Andalucia.
Windstar Ships Sailing the Canary Islands
Star Pride - All-Suite Motor Yacht
An all-suite luxury yacht offering expansive suites, flexible dining, and contemporary elegance.
Wind Spirit - 4-Masted Sailing Yacht
An iconic sailing yacht offering the romance of towering sails combined with luxury boutique service.
Santa Cruz de Tenerife - Tenerife, Spain
Santa Cruz de Tenerife - Tenerife, Spain
Santa Cruz de Tenerife - Tenerife, Spain
The largest island in the archipelago, dominated by Spain's highest peak and rich colonial architecture.
Arrecife & Puerto del Carmen - Lanzarote, Spain
Arrecife & Puerto del Carmen - Lanzarote, Spain
Arrecife & Puerto del Carmen - Lanzarote, Spain
A surreal volcanic wonderland of lava tunnels, black earth vineyards, and white villages.
San Sebastián de La Gomera - La Gomera, Spain
San Sebastián de La Gomera - La Gomera, Spain
San Sebastián de La Gomera - La Gomera, Spain
A lush, serene island featuring mist-covered cloud forests and rich indigenous heritage.
Las Palmas de Gran Canaria - Gran Canaria, Spain
Las Palmas de Gran Canaria - Gran Canaria, Spain
Las Palmas de Gran Canaria - Gran Canaria, Spain
A miniature continent offering a bustling historic capital, dramatic dunes, and green mountain valleys.
Funchal - Madeira, Portugal
Funchal - Madeira, Portugal
Funchal - Madeira, Portugal
A Portuguese island paradise of cliffside gardens, fortified wine cellars, and dramatic coastal drives.
Puerto de la Estaca - El Hierro, Spain (Select Sailings)
Puerto de la Estaca - El Hierro, Spain (Select Sailings)
Puerto de la Estaca - El Hierro, Spain (Select Sailings)
The tranquil, eco-focused westernmost island offering untouched natural beauty and quiet villages.
Vila Baleira - Porto Santo, Portugal (Select Sailings)
Vila Baleira - Porto Santo, Portugal (Select Sailings)
Vila Baleira - Porto Santo, Portugal (Select Sailings)
Madeira's serene neighbor featuring miles of golden sand and a peaceful island lifestyle.
Seven Islands. Seven Personalities. One Atlantic Journey.
From Lanzarote's black lava craters to Madeira's lush mountain gardens - discover these islands the way they deserve: by intimate yacht.
Windstar vs. Large Cruise Ships
Comparing boutique yacht-style cruising to high-density commercial resort vessels.
Windstar Small Yacht
INTIMATE & SECLUDED EXPERIENCE
- →Fewer than 350 guests
- →Boutique yacht size
- →Small & secluded harbors
- →Personalized 1:1.5 service
- →Open seating & intimate dining
- →Minimal lines & crowds
- →High destination immersion
Large Cruise Ships
HIGH-DENSITY COMMERCIAL RESORT
- →3,000–7,000+ guests
- →Floating mega-resort size
- →Major commercial container terminals
- →High-volume service
- →Assigned dining & queues
- →Significant lines & crowds
- →Moderate destination immersion
Spacious Suites Designed for Relaxed Luxury
Ocean View Suite
Spacious suite with large ocean-view windows, queen bed, marble bathroom, and generous sitting area.
Balcony & French Balcony Suites
Features floor-to-ceiling sliding glass doors opening to sea breezes and island panoramas.
Star Suites
Expansive top-tier suite configurations with separate living areas, upgraded amenities, and VIP service.
Dining: One of Windstar's Greatest Strengths
From open-seating Amphora to outdoor Candles dinners under Atlantic stars, Windstar's dining focuses on regional flavors and authentic ingredients.
Amphora Restaurant
Main Fine DiningOpen-seating dining room serving daily international menus and regional Atlantic seafood specialties.
Veranda
Casual Breakfast & LunchAlfresco buffet and made-to-order dining with panoramic ocean views of approaching coastlines.
Candles
Specialty Outdoor GrillSignature sunset steakhouse and seafood grill under the open stars.
Basil + Bamboo
Specialty Venue (Star Pride)Creative Mediterranean and Asian fusion cuisine served in an intimate setting.
Shore Excursions That Go Beyond Sightseeing
Intimate small-group experiences led by expert local naturalists and guides.
Volcano & Fire Mountains
Explore Timanfaya National Park and Mount Teide's lunar volcanic landscapes.
Laurel Forest & Levada Hikes
Walk through Garajonay's cloud forests and Madeira's scenic water levadas.
Volcanic Wine & Market Tours
Sample Malvasia wines grown in lava craters and shop local food markets with the Chef.
Marine & Wildlife Encounters
Look for resident whales, dolphins, and pelagic seabirds along Atlantic coastal waters.
Windstar Knows the Way to Romance
Experience the magic of sailing aboard a Windstar yacht — intimate, unhurried, and immersed in Europe's most breathtaking island destinations.
Windstar Cruises: Best Small Ship Cruise
Discover why discerning travelers consistently name Windstar the world's best small ship cruise experience.
- Stern watersports platform vs pool deck crowds
- Boutique local entertainment vs broadway musicals
"Many travelers underestimate how different each island feels. Tenerife offers dramatic volcanic landscapes, Lanzarote feels almost otherworldly, La Gomera is lush and peaceful, while Madeira adds a distinctly Portuguese character. Windstar's thoughtfully designed itineraries allow guests to appreciate those contrasts without ever feeling rushed."
Planning Your Perfect Canary Islands Cruise
Expert advice on seasons, booking windows, weather microclimates, and flights across Spain's Canary Islands and Madeira.
Peak Winter Escape (December - April)
Ideal sub-tropical weather with daily temperatures averaging 70°F to 78°F, steady Atlantic trade winds, and crystal-clear mountain visibility. The premier escape from northern winter cold.
Best For
Winter sunshine, volcano trekking, whale watching, & outdoor dining
Highlights
- 70°F to 78°F average daily temperatures with minimal rainfall
- Steady trade winds providing smooth sailing conditions for Windstar yachts
- Prime sea turtle & pilot whale watching off Tenerife & La Gomera
- We recommend reserving 8 to 12 months early for prime suite selection
Spring & Early Summer (May - June)
Tranquil ocean waters, wild mountain slopes in full flower bloom across Madeira & La Gomera, and uncrowded island harbors.
Best For
Botanical garden tours, quiet island calls, & unhurried pacing
Highlights
- Warm turquoise waters ideal for shore excursions & coastal swimming
- Funchal's legendary botanical gardens in full spring bloom
- Fewer island tourists for an intimate, authentic local atmosphere
- Exceptional value with special promotional stateroom offers
Autumn & Wine Harvest (September - November)
Savor the grape harvest in Lanzarote's La Geria volcanic pits and Madeira's terraced mountain vineyards, accompanied by warm Atlantic sea breezes.
Best For
Food & wine connoisseurs, volcanic vineyard tours, & warm ocean swimming
Highlights
- La Geria volcanic crater grape harvest & Malvasia wine tastings
- Warmest Atlantic ocean sea temperatures of the entire year
- Traditional island tapas and artisan cheese harvest festivals
- Comfortable hiking weather across Teide and Garajonay cloud forests
Festive Holiday Sailings (Late December)
Celebrate Christmas and New Year's under the stars aboard an intimate luxury yacht, highlighted by Funchal's world-famous New Year's fireworks display.
Best For
Milestone holiday celebrations, New Year yacht galas, & winter sun
Highlights
- Front-row yacht anchorage for Funchal's world-famous New Year fireworks
- Festive gala dinners curated by James Beard Foundation guest chefs
- Special holiday teak-deck BBQs with acoustic live music
- Highest demand sailings of the year - reserve 10 to 14 months in advance
Will the Atlantic Be Rough?
Sea conditions vary by season and prevailing weather. Most sailings enjoy comfortable conditions, but Atlantic swells can occur. Mid-ship cabins on lower decks and packing preferred motion remedies ensure a comfortable journey.
ANGELA HUGHES MOTION COMFORT TIPS
- Choose mid-ship cabin locations
- Select lower deck suites when possible
- Pack preferred motion remedies
- Look toward the open horizon when needed
5 Common Mistakes to Avoid
Ensure a seamless Canary Islands cruise by avoiding these planning pitfalls.
Booking solely on price
Choose based on itinerary experience rather than just the lowest rate.
Skipping pre-cruise hotel nights
Arrive at least two nights early to recover from jet lag and prevent flight delays.
Underestimating walking
Cobblestones, volcanic slopes, and town hills require sturdy walking shoes.
Waiting to book excursions
Intimate small-group tours often fill up before departure.
Ignoring microclimates
Sea level sun can quickly turn cool in mountain elevations like Mount Teide; pack layers.
A Journey Designed for Curious Travelers
Couples & Honeymooners
Romantic sailaways, sunset outdoor dining, quiet lounges, and boutique harbors.
You Enjoy:
- •Intimate small-ship pacing
- •Authentic destination access
- •Personalized yacht service
Recommended For You:
Experienced Cruisers
Travelers who have outgrown mega-ships and desire less waiting, fewer crowds, and personal service.
You Enjoy:
- •Intimate small-ship pacing
- •Authentic destination access
- •Personalized yacht service
Recommended For You:
Food & Wine Lovers
Appreciate regional volcanic wines, Atlantic seafood, market visits with the Chef, and open-seating dining.
You Enjoy:
- •Intimate small-ship pacing
- •Authentic destination access
- •Personalized yacht service
Recommended For You:
Active Outdoor Explorers
Enthusiastic about hiking Garajonay forest, climbing Mount Teide, levada walks, and marine wildlife.
You Enjoy:
- •Intimate small-ship pacing
- •Authentic destination access
- •Personalized yacht service
Recommended For You:
Common Myths About Windstar
MYTH: "Small ships feel cramped."
MYTH: "Small ships feel cramped."
Reality: With far fewer guests, public decks, lounges, and dining rooms feel remarkably open and spacious.
MYTH: "There won't be enough to do."
MYTH: "There won't be enough to do."
Reality: The destination is the primary entertainment. Evenings offer live acoustic music, stargazing, and lectures.
MYTH: "Luxury means formal."
MYTH: "Luxury means formal."
Reality: Windstar emphasizes casual luxury. No tuxedos or formal gowns are ever required.
MYTH: "The Canary Islands are only beach destinations."
MYTH: "The Canary Islands are only beach destinations."
Reality: They offer soaring volcanoes, UNESCO rainforests, ancient whistled languages, lava vineyards, and rich gastronomy.
Angela Hughes Authority & Credentials
CEO — Trips & Ships Luxury Travel
Angela Hughes
Angela Hughes has spent more than four decades in luxury travel, visiting over 121 countries. Recognized as 2024 Luxury Travel Influencer of the Year and named one of TravelPulse's Most Influential Women in Travel (2026), she helps clients curate extraordinary small-ship vacations tailored to their travel style.
"The Canary Islands surprise even seasoned travelers. Each island has its own personality, from Lanzarote's dramatic volcanic landscapes to Madeira's lush gardens and Tenerife's vibrant culture. Windstar's intimate ships allow you to experience these destinations at a pace that feels personal and authentic. It's one of Europe's most rewarding small-ship cruise experiences."
— Angela Hughes, On Active River CruisingKEY QUALIFICATIONS & ACHIEVEMENTS
- CEO of Trips & Ships Luxury Travel
- Founder of Luxury Travel University
- More than 40 years in the travel industry
- Visited more than 121 countries
- Global luxury travel speaker and trainer
- Weekly travel industry columnist
- Travel Leaders Network Advisory Board member
- 2024 Luxury Travel Influencer of the Year
- Named one of the Most Influential Women in Travel (2026) by TravelPulse
- Featured in leading travel publications worldwide
- International expert in luxury cruises, river cruising, expedition travel & safaris
- Expert in premium custom vacations
Frequently Asked Questions
Everything you need to know about Windstar Canary Islands Cruises.
Yes. Windstar Canary Islands Cruises are an excellent choice for travelers who value destination-focused itineraries, personalized service, and intimate small-ship experiences over large-scale entertainment. The combination of fewer guests, immersive ports, exceptional dining, and yacht-style cruising makes Windstar one of the strongest luxury options in the Canary Islands.
Depending on the itinerary, Windstar visits Tenerife, Lanzarote, La Gomera, Gran Canaria, El Hierro, and La Palma. Many itineraries also include Madeira, Portugal, creating a broader Atlantic island experience.
Seasonally, Windstar operates voyages in the Canary Islands using ships such as Star Pride (all-suite yacht) and Wind Spirit (4-masted sailing yacht). Deployment varies by season and itinerary.
There is no single best month because the Canary Islands enjoy a mild climate year-round. Many travelers prefer November–February for winter sunshine, March–April for nature and hiking, May for pleasant weather and lighter crowds, or September–October for warm seas.
Most Windstar Canary Islands itineraries range from 8 to 10 nights, while longer Star Collector voyages combine the Canary Islands with Portugal, Spain, or the Mediterranean for extended luxury vacations.
Windstar offers both Cruise Only and All-Inclusive fare options. The All-Inclusive package includes Wi-Fi, unlimited select beverages, and gratuities.
For many luxury travelers, yes. Windstar's smaller ships offer more personalized service, easier embarkation, fewer crowds, access to smaller ports, and a quieter onboard atmosphere focused on the destination.
Yes. Windstar's relaxed atmosphere, friendly crew, and manageable ship size make it an excellent introduction to luxury cruising without formal dress codes or mega-ship crowds.
Yes. Windstar is especially popular with couples celebrating honeymoons, anniversaries, retirement trips, and romantic getaways due to its intimate ships, open-air dining, and scenic sailaways.
Trips & Ships Luxury Travel recommends booking 9 to 18 months in advance for the best suite selection, especially for holiday departures and popular spring/autumn dates.
Pack lightweight clothing, comfortable walking shoes, layers for cooler evenings, swimwear, sun protection, a light rain jacket, and smart-casual evening attire. Mountain excursions like Mount Teide require warmer layers.
Many Windstar Canary Islands itineraries include Madeira, Portugal. Highlights include Funchal, botanical gardens, Madeira wine tasting, cable cars, and scenic levada walks.
Booking through Trips & Ships Luxury Travel provides access to experienced luxury advisors who help compare itineraries, select suites, coordinate flights and hotels, and arrange custom land experiences with dedicated care.
Angela Hughes brings over 40 years of travel experience, visits to 121+ countries, Advisory Board leadership, and recognition as 2024 Luxury Travel Influencer of the Year to every client recommendation.
Choose based on your travel style and priorities: select 'The Colorful Canary Islands' for first-timers, 'Hidden Gems' for off-the-beaten-path ports like El Hierro, or 'Canary Island Idyll' for roundtrip Tenerife convenience.
Ready to Explore the Canary Islands by Yacht?
Speak with our luxury travel advisors to design your perfect itinerary.
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