The best way for your donors to travel to Cuba

The most important key to success in auction fundraising events is offering desirable items worth the high bids you seek. One that certainly fits the bill: a bucket-list trip to Havana, Cuba.

From an easing of travel restrictions to the passing of longtime president Fidel Castro, Cuba has dominated the headlines throughout 2016.

Celebrities like Ava Gardner, Frank Sinatra and most famously Ernest Hemingway flocked to the Caribbean nation in the 1950s – but economic embargoes and tourism bans soon made it difficult for the vast majority of Americans to visit the island’s beaches, culture and cuisine.

Cuban travel for nonprofitsIn 2016, a series of regulation changes made travel to Cuba much simpler. Today, 10 major airlines (including United, Delta, American and Southwest) are sending a total of 20 flights from the U.S. to Havana daily, eliminating the need to coordinate charter flights or enter through a different country.

In addition to greater accessibility, it’s easier than ever to stay connected on the island. Business Insider reports, “Several U.S. mobile carriers have signed voice, text and data-roaming agreements with Etecsa, the Cuban telecommunications provider,” plus the number of Wi-fi hotspots continues to grow.

As a result of the changes, the New York Times noted last week that Cuba was in the U.S. top five most searched and booked destinations on Cyber Monday this year. It was also the fastest-growing destination throughout the year, up 153 percent from 2015.

Imagine giving your donors the chance to support your cause while buying an incredible excursion to Cuba.

Although tourism is still prohibited, your winning bidders can still enjoy all Cuba has to offer. Read on to see how Winspire takes care of the details for travelers to ensure their vacation is unforgettable.

Trips for education and culture

Fully guided group tours to Cuba have been permitted for some time. However, as of March 2016, the U.S. government allows citizens to also make “individual people-to-people educational trips”.

To that end, Winspire put together our signature Havana Highlights Experience. The itinerary meets the criteria of education, as winning bidders are introduced to the culture of Cuba through guided visits to Havana’s most popular destinations. They’ll also have plenty of free time to explore on their own and customize their trip—the best of both worlds.

Check out just a few of the guided excursions your donors will enjoy.

Winspire's 'Havana Highlights Experience" Auction Travel Package to Cuba
Panoramic tour of Havana

Each traveler’s adventure begins with a 3-hour tour of Havana while riding in a vintage car. They’ll soak in the embassies, mansions and flowering trees of the city as the driver introduces its many landmarks, such as the Malecon, a beautiful seaside boulevard in Havana; Revolution Square (Plaza de la Revolucion); and Miramar, Havana’s most upscale residential area.

The Havana Hemingway knew

Travelers journey to Finca Vigia, the former residence of the prominent American writer Ernest Hemingway, and Cojimar, where Hemingway was inspired to write The Old Man and the Sea.

Auction Travel Packages to Havana, Cuba

Vinales Valley

In a 9-hour journey with a private chauffeur and multilingual guide, travelers head out on a Jeep to Vinales Valley, a UNESCO World Heritage site where some of the world’s best tobacco is grown. Rich red earth, majestic palm trees and robust capped mountains make for one of Cuba’s most breathtaking sights. Plus travelers can now bring back those famous Cuban cigars for personal consumption without hangups in customs.

Top-rated lodging

Guests enjoy a 4-night stay for two in a standard room at a top rated hotel in the heart of Havana, such as Hotel Saratoga or comparable. While lodging may not be considered “luxury” by North American standards, these hotels are where discriminating travelers stay while visiting Cuba’s capital.

White glove service from start to finish

Upon arrival at Havana International Airport, donors are met at the gate and directed to Preferential Immigration, the customs booth for diplomats and airline crew. They can relax at the VIP Lounge while their luggage is taken care of, then depart for the hotel by private transfer. (Note: Winspire doesn’t currently offer packages with airfare, but information about commercial and charter flight options will be provided.)

Cuban Auction Travel ExperiencesTo ensure a seamless experience, we’ve partnered with top Cuba travel provider Cuba Travel Network. With offices in the U.S. and Cuba, Cuba Travel Network’s team of over 50 travel professionals is available to provide personal assistance and address last-minute needs, which can make all the difference in your donors’ overall experience.

For more information and to reserve this Experience at no upfront cost to your organization, click below. You can easily reserve the trip in your Suitcase, include it in your event, and even sell the trip to multiple bidders.


With travel to the once-isolated Caribbean island easier and more desirable than it has been in decades, it’s the perfect time to offer this bucket-list trip to your donors.