Canary Islands & Madeira
January 6-16, 2027
Join Rhonda and Paul for an unforgettable adventure aboard Windstar’s elegant sailing yacht, Wind Spirit, as we explore the stunning Canary Islands & Madeira over 10 days in January 2027. Experience breathtaking landscapes, beautiful beaches, charming coastal towns, and warm winter sunshine, all while enjoying the intimate, relaxed luxury that Windstar is known for. Looking for more inspiration - check out the videos below!
Canary Islands & Madeira
Picture yourself cruising into a world where sunshine seems to have signed a lifetime contract, and every stop feels like it’s been handpicked for maximum “wow.” The Canary Islands dazzle with golden beaches, moon-like volcanic landscapes, and charming seaside towns where the sangria flows as easily as the sea breeze. Then there’s Madeira—Portugal’s lush “Island of Eternal Spring”—where you can wander through gardens bursting with color, sip world-famous Madeira wine, and feel like you’ve stumbled onto the set of a postcard. Together, they’re the perfect blend of relaxation, adventure, and just enough brag-worthy beauty to make your friends jealous for years.
37 Unique Facts about the Canary Islands (excellent overview):
Windstar Cruises - Wind Spirit
Windstar operates a fleet of small luxury cruise ships that blend the romance of sailing with upscale amenities. Known for their intimate atmosphere and personalized service, the Wind Spirit carries just 148 guests, creating a yacht-like experience rather than a traditional large cruise ship feel. The line emphasizes destination-focused itineraries with longer port stays and access to smaller, less-visited ports that larger ships cannot reach.
Wind Spirit is one of Windstar's three classic sailing yachts, accommodating 148 guests in 74 staterooms. This elegant vessel features four masts with computer-controlled sails that can be deployed when wind conditions are favorable, offering guests the authentic experience of sail-assisted cruising. The ship is undergoing a comprehensive renovation, featuring updated staterooms, enhanced dining venues, and refreshed public spaces while maintaining its intimate, sophisticated ambiance.
Wind Spirit Renovation
The Wind Spirit is in the midst of a major renovation including a redesign of the lobby, pool bar, pool/hot tub, and the main dining room. Although I could not find a current video, I was able to find pictures of the renovation of her twin sister ship, Wind Star. I hope to have additional details in the near future.
Hidden Gems of the Canary Islands & Madeira
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Jan 6 - Santa Cruz de Tenerife (4pm departure) Embarkation Day 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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Jan 7 - Lanzarote (11am-4pm) 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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Jan 8 - AT SEA |
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Jan 9 - Funchal (1pm arrival) 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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Jan 10 - Funchal (11:59pm departure) |
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Jan 11 - Porto Santo, Madeira (8am-5pm) Often called the "Golden Island," it's renowned for its stunning 6-mile stretch of pristine sandy beach - a rarity in this volcanic region where most beaches are pebbly or rocky. Home to unique local wines and traditional cuisine, the port is small so larger ships often skip this gem. |
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Jan 12 - AT SEA |
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Jan 13 - Santa Cruz de Palma (8am-10pm) 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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Jan 14 - El Hierro (8am-10pm) El Hierro, a UNESCO Biosphere Reserve, 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. |
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Jan 15 - San Sebastian (7am-2:30pm) 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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Jan 16 - Santa Cruz de Tenerife (12am) Departure Day |
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So What Does It Cost?
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| Category |
Double Pricing (Total for 2 People) |
Solo Cabin Pricing (Total for 1 Person) |
| B (Army Green) | $6,686 | $5,346 |
| BX (Purple) | $7,256 | $5,845 |
| A (Dark Green) | $7,826 | $6,343 |
| AX (Orange) | $8,206 | $6,676 |
| All-Inclusive: Drinks, Tips, Wifi |
All-Inclusive: Drinks, Tips, Wifi |
Next Steps
- Please read the Deposit and Cancellation Terms below.
- Register and select your cabin on this registration page. If you know your MyTrips account info, login. If not, fill out the form. Alternatively, you can email or text me and tell me which cabin you would like: rhonda.reinhardt @ cruiseplanners.com
- For the credit card authorization, please authorize 15% of the total cost as the deposi.
- I will make a temporary booking for you, email it to you for approval, and then put down the deposit.
Deposit Terms
- Deposit of 15% of reservation total is required within 3 days of booking to secure a reservation.
- Final Payment is due 90 days prior to departure.
Cancellation Terms
Bookings cancelled at 121 days or greater from travel will be subject to a $50 per person cancellation fee. A full refund, excluding the cancellation fee, will be made for cancellations received by Windstar Cruises at 121 days or greater from travel by any mode of transportation booked through Windstar Cruises (sea or land, air travel is non-refundable once purchased). Guests who cancel after that date for any reason, including medical or family reasons, are subject to Windstar Cruises cancellation schedule.
Cancellation Schedule:
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120-90 days before commencing travel |
15% of gross fare (deposit) |
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89-60 days before commencing travel |
35% of gross fare |
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59-30 days before commencing travel |
50% of gross fare |
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29-0 days before commencing travel |
100% of gross fare |
