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Captivating Canary Islands


We’ll be sailing with the President of Windstar Cruises on a gorgeous itinerary through the Canary Islands and Madiera, before ending in Lisbon, Portugal. It’s the trip of a lifetime on our favorite small-ship, yacht-style cruise line. Windstar recently won “Best Small Ship Cruise Line” at the Travel Weekly Reader’s Choice Awards, and we’d love to show you why. Join us!

Join us on Iberian archipelagos off the coast of Africa! The Canary Islands were well-known to seafarers who traveled between the Old and New Worlds, filling their Galleons with water and provisions before or after a Transatlantic crossing. Discover the Portuguese personality of Funchal, with its cable cars, mosaics and madiera. Then on to a clutch of Canary Islands, with astounding diversity. Martian landscapes on Lanzarote. Lush green La Palma. Cloud forests, cliffs and canyons on La Gomera. Tenerife with its spectacular beaches and soaring Mt. Teidi. It’s no wonder that all of these islands have been named UNESCO Biosphere Reserves. Add in colonial gems, a unique culture, and the opportunity to sail with the President of Windstar, himself (and your Huckleberry Travel advisors!), and you’ve got the makings of a beguiling Canary Islands journey!

Dates: April 20-28, 2024

Ship: Windstar’s Star Pride

Itinerary: Las Palmas to Lisbon

A day on board your Windstar ship is a day of choices, all of them good. Perhaps you’ll begin with a relaxing massage in World Spa by Windstar. Or maybe an invigorating workout in the Fitness Center. Even better, why not both? After a sumptuous lunch in Veranda, make a splash from the Watersports Platform off the ship’s stern. Everything you can think of for fun in the water is there — swimming, kayaking, and stand-up paddleboarding. And it’s all complimentary, of course. Sun yourself on deck, take a dip in the whirlpool, then catch up on email or order a cheese plate for your stateroom or suite. After dinner, dance to live music in the Lounge. This is your yacht, so of course you’re welcome on the Bridge, where the Captain and officers are delighted to share charts, routes, and vistas with you.

As you prepare for another amazing Windstar day, enjoy a nightcap anywhere you like — on deck, in the Lounge, or why not let us bring it to your suite or stateroom? Your day ends just as it began, blissfully.

Want to join us? We’d love to travel with you!

Earlier Event: March 3
Huckleberry Travel Anniversary Party!
Later Event: May 2
Rocky Mountain Happy Hour