TravelPledge’s Top 10 Bestselling Vacations of 2019

Now that the fall gala season is behind us, we thought we’d share with you our ten bestselling vacations at benefit auctions in 2019!

Luxury Getaway in the Heart of Tuscany

Cortona, Italy

Enjoy a wonderful week in Tuscany with a vacation package full of extras! Stay in a 2-Bedroom Luxury Apartment in the heart of the historic city of Cortona and be hosted by one of the most highly rated Tuscany-based vacation providers. Located on one of the city’s most characteristic streets, you will enjoy the historic center and beauty of Cortona. This location is a perfect starting point for day trips to discover the beautiful artistic cities of Tuscany and Umbria. If you have more than four in your group, your hosts will work with you to add them to your trip.

– 7 nights in a 2-Bedroom Luxury Apartment in the city center
– Welcome with your local assistant and personal introduction to Cortona
– Wine tasting in traditional enoteca in the town center
– Midweek cleaning and final cleaning
– Pre-arrival and in-house local English speaking concierge and booking services
– All visitor taxes and consumption fees (A/C etc)

Five Nights in Telluride, Colorado

Telluride, Colorado

Five night getaway to Telluride! There is no place quite like Telluride; great snow conditions, crowd-free runs, expansive side country, and endless peaks of the San Juans providing a recipe for non-stop outdoor thrills. Beyond skiing, there is no shortage of activities from ice-skating, snowshoeing, sleigh rides and big tire bike tours in the winter to fly fishing and horseback riding in the summer.

Regardless of the season, it’s the Telluride views and immaculate mountain air that will take your breath away. It is the perfect base for exploring the region’s abundant outdoor attractions and world-class dining. Stay at a landmark hotel and residence renowned for its authentic mountain spirit and unsurpassed service. Discover luxurious accommodations, world-class amenities and memorable dining options.

All-Inclusive St. Lucia for Two

Choc Bay, Saint Lucia

5 nights all-inclusive to the St James’ Resort in St. Lucia – a vibrant, colorful and refreshingly casual all-Inclusive resort in Saint Lucia. Distinguished by its romantic beachfront setting just minutes from the world-class Rodney Bay Marina, Cap Estate Golf Course, and capital city of Castries, St. James’s Club Morgan Bay offers relaxation, romance and a hint of adventure. The perfect vacation destination for families, couples or weddings, this resort offers a host of beachfront fun and relaxation for everyone.

– Ocean View Suite King bed Accommodations for two adults
– All inclusive (food,beverage and non-motorized water sports)

Guests can enjoy countless water sports at St. James’s Club Morgan Bay such as kayaking, windsurfing, stand-up paddle boarding, Hobie Cat sailing, waterskiing, wakeboarding, banana boat rides, pool activities, and much more. Lessons are also available upon request.

Luxury Fishing & Golf Vacation Villa

Los Suenos, Costa Rica

Enjoy 7 nights in Costa Rica’s Pacific Coast which boasts the world’s best sport fishing. Want 30-plus billfish shots a day? Or, astonish your family with Costa Rica’s amazing eco-adventures. When you arrive at the airport in San Jose, our wonderful English-speaking assistant, Carolina, will greet you. She’ll help you select the right eco-tours, fishing charters – even your own secluded mountaintop gourmet dinner as you watch the sun melt gently into the Pacific Ocean.

Package includes:
-Fully-equipped 2 bedroom/ 2 bath condo with view of rainforest and golf course
-Personal English-speaking concierge
-Discount certificates for use at the country’s best eco-tours and fishing charters

Gaze up at Volcano Arenal (yes, it’s active) while immersed in one of its hot water springs. Raft Class 1-5 white water rivers, bungee jump a 256’ deep gorge, or glide through the rainforest canopy. Drive dune buggies on the beach or trek through creeks and forest by ATV on your way to a spectacular view of the Pacific Ocean. Ride horseback down the beach at sunset, or take a Crocodile River Safari. Enjoy hot spring spas, golf and tennis courses and the world’s best surfing is nearby in the “Endless Summer” surf town of Jaco (Ha-KOE).

2 BR Weekend in Park City, Utah

Park City, UT

Enjoy four nights in a fabulous three bedroom vacation rental in Park City Utah. There is truly a seemingly endless amount of activities to partake in during the summer in Park City.

Come take a week or even a month to unwind from your busy life and enjoy cool mountain breezes under the warming sun while spending time relaxing and feeding your adventurous side all at the same time. Deer Valley Resort, Park City Mountain Resort, and Canyons Resort all remain open during the summer months offering a plethora of trails for hiking and mountain biking.

Couples Boca Resort Weekend Spa Getaway

Boca Raton, FL

Two night weekend stay and couples spa treatment along with breakfast each day. A Waldorf Astoria Resort has reigned as an icon of elegance for more than 80 years. Today, the resort remains faithful to its glamorous past, while radiating a vibrant energy, offering infinite amenities to every type of guest. Situated on 356-acres in fabled South Florida, this eclectic, private village offers the best of all worlds: an award-winning spa, championship golf and tennis, expansive beach and luxury marina – all just steps from your door. Includes:

– 2 Nights luxury Accommodations
– Breakfast for two each day
– One Couples Spa Signature Treatment
– Two Ritual Baths

Romantic Getaway to Napa Luxury

Calistoga, CA

Enjoy 3 nights in a one Bedroom Lodge in Calistoga, CA. Nestled among 100-year old oaks along a seasonal creek—the Oak Creek lodge in Napa Valley also offer 1,200 square feet of indoor-outdoor living space and the rustically-appealing amenities of our other one-bedroom lodges plus expansive views and welcome seclusion. Features one king bed and one queen sofa bed. Outdoor shower and bath garden, Outdoor gas fireplace and sun deck, Private outdoor hot tub, Premium View & enhanced privacy

– 3 nights in Napa Luxury for two people
– Welcome bottle of Napa Valley chardonnay
– Exclusive access to local wineries

A Napa luxury resort nestled in a secluded Upper Napa Valley canyon on 157 lush, oak-lined acres is a rarefied luxury retreat where nature not only coexists with, but helps create, a completely new level of connection, comfort and contentment. Every detail, each dedicated staff member, conspire to bring a deep sense of enrichment and renewal. From a celebration of Napa wine and food to restorative Napa spa offerings, experience a seamless mingling of the outdoors and in for endless inspiration.

Picturesque Farmhouse Vacation in France!

Lagarrigue, France

Lagarrigue Summer Terrace

Seven nights in an amazing three bedroom house in France (Lot River Valley). Create family memories. Children and adults love the pool and easy way of life, as well as exploring the countryside, local caves, rivers and villages.

NEARBY: The must-see medieval pilgrimage site, Rocamadour, is within an hour’s drive, and one can bicycle to the charming medieval hillside villages of Calvignac and St. Cirq La Popie (voted the favorite of “les plus belles villages de France” by the French). The world-renown prehistoric sites and caves (Pech Merle, Gouffre de Padirac, etc.), are nearby. Boating and kayaking, hiking, bicycling, horseback riding, and wine-tasting are all within easy reach. Every day there are fresh markets in the surrounding area.

This is a dream location for cooks. Local specialties include strawberries, saffron, truffles, eau de prune, lamb, canard, foie gras, and abundant wines of the regional appellation, Cahors. The Roman bastide town of Cajarc nearby offers shopping, bank, post office, bakeries, and restaurants. Being here is like stepping back in time, but with modern conveniences.

Historical Greece Cruise for Two!

Greek Isles

Enjoy an amazing 7 night cruise for two! Experience a harmonious balance between conventional cruising and private yachting, along with an exciting voyage of discovery, unraveling the wonders of Classical Greece. Departing and returning to Marina Zea, Athens, you’ll explore the islands and towns of Kea, Delos, Mykonos, Santorini, Rethymnon/Crete, Kythira, Monemvassia, Nafplion, and Hydra.

-Accommodation in double or twin Category B cabins with private SH/WC & air conditioning
-Buffet breakfast and two meals daily, including a welcome cocktail
-Optional visits to 4 UNESCO sites, private BBQ (weather permitting), Captain’s Honor Night
-Corinth Canal Crossing
-Local theme evening
-Use of fishing and snorkeling equipment

Amazing Cabo San Lucas Vacation for Two!

Cabo San Lucas, Mexico

Experience 3 nights in a one bedroom guest room. Decorated in classic Baja Style, these casitas offer 925 sq ft of indoor/outdoor living space, located on the ground floor with beautiful views of the gardens and partial views of the Sea. These Cabo beach resort casitas feature one king bed adorned with a dramatic artful backdrop, warm lighting and soft netting drape.

– 3 nights in a luxury casitas
– $250 resort credit to use however you like
– Concierge services

The blue Pacific and the Sea of Cortez are home to an array of Cabo San Lucas activities including outstanding snorkeling, sailing and sport fishing. Play championship golf in Cabo and take in the stunning views of the sea and surrounding desert. If you are a thrill-seeker, ride the dunes or go on a whale watching journey. For a tranquil experience, unwind at a world-renowned Cabo spa or sample eclectic shopping with exciting nightlife just steps away.

Running a benefit auction in 2020? Find vacations, cruises, golf and more at:


Al McDonald is the Chief Product Officer for TravelPledge and author of the e-book “The Definitive Guide to Silent Auction Fundraisers.” Al has helped thousands of nonprofits exceed their auction goals through auction item procurement and advice. Al understands that successful auctions are hard work and is committed to delivering practical advice that will move the needle for you today.


  1. Avatar

    Tracy Rozler Reply

    I am interested in the Florida Trips. How can I get more information

    • Avatar

      Alex McDonald Reply

      Hi Tracy, You can create a no obligation account at to browse our entire catalog of experiences, and review more details about each trip. You can filter by experience type (e.g., vacations vs. golf rounds) and by location to narrow in on Florida. If you encounter any issues, there’s a chat window in the lower right-hand corner of the screen (after you log in) where I’ll be able to answer your questions.

Leave a Reply

Your email address will not be published.