People-Powered Vacation Planning

  • Flightfox is a platform where experts find travelers the best flights
  • Airbnb is a platform where anyone can rent homes to other travelers
  • Vayable is where anyone can run tours for other travelers

To entice our experts to get their creative hats on we decided to award not only the winning entry $500 but 2nd prize $250 and 3rd prize $100. This got our experts working hard.

The Rules

  • Return trip for 2 adults over 2 weeks starting from San Francisco
  • Must use for accommodation
  • Must use for experiences
  • Cost of $3000 per person (all inclusive)

We were so thrilled with the outcome but judging the winners was no easy feat. We received 28 very different options, ranging from staying in a refurbished luxury aeroplane, sleeping in a 1-square metre house, to hot air ballooning and wine & cheese tasting classes in Paris.

View the Flightfox Crowdsourced Travel Contest

1st: San Francisco, New York & Paris

Awarded to Flightfox expert “Dizem”

Days 1 - 2

Drive from the Bay Area through the Monterey Bay and onto Big Sur, home of the nation's most pristine coastline and iconic Californian scenery. Spend two nights camping at spots along the coastline with an experienced Big Sur camper who knows all the best trails and beaches.

Days 3 - 4

On Day 3, enjoy a tour of S.F.'s most artsy and entrepreneurial neighborhoods - Hayes Valley, Dolores Park, and the Inner Mission - as you snack at the city's three premier independent ice creameries while learning about each of the quirky neighborhoods they are home to. (3 hours)

Stay for 2 nights on a 27 ft Ericson Sailboat and take an affordable get-away above the water. It's a perfect place for: one person, a romantic getaway for couples, and a personable gathering with a group of friends.

The next day join Milton, a homeless person himself, on a truly unique tour where he'll tell you about what it's like to be homeless, the issues many homeless people face, and social services available to those in need. The Tenderloin is a unique part of San Francisco where you'll visit some shelters, day centers for children, and soup kitchens. (2 hours)

Enjoy an interactive cooking and cultural experience with exotic modern persian cuisine on beautiful coast of Half Moon Bay. You will join Mitra in her gourmet kitchen with a breath-taking ocean view, listen to an eccentric mix of music, and create your own masterpiece. (4 hours)

Days 5 - 7

Fly to New York City and stay for 3 nights in a beautiful garden apartment in Brooklyn, NY.

On Day 6, discover New York beyond Manhattan and explore the different boroughs in the back of a comfortable BMW motorcycle. The tour can be fully customized. (2 hours)

The following day, visit four incredible New York pizzerias while learning all about the ingredients, ovens, methodology and histories that make them so unique! This tour has been featured on the Travel Channel, Cooking Channel and Discovery Channel. (4 hours)

Days 8 - 12

Fly to Paris and spend 5 nights in an amazing apartment located in the Marais, central Paris. Literally hundreds of places around to have a drink and eat, truly the best neighborhood for all your shopping needs! The very quiet, studio apartment consists of a living room, one separate bedroom with a full size bed, bathroom with bathtub / hair drier and a fully equiped kitchen so you can cook at home if you want.

Balloon ride over the Fontainebleau area on Day 9 to rediscover the true meaning of nature, as once enjoyed by Alfred Sisley and his other impressionist friends. Fly above the emerald green forests, home to wild boar and deer and hunting ground to the Kings of France - above rivers and romantic little villages….less than an hour away from Paris. (3 hours)

Day 10: With a unique and refreshing approach, your sommelier will take you through a variety of themes to build up your wine knowledge. He will teach you how champagne is made and how to taste wine properly. We’ll go together through the main wine regions of France – the grapes they grow, the style of wine they make. This tasting class is both informative and fun. In just two hours, you will learn a lot, and will taste good French wines. (2 hours)

On Day 11, you'll start by eating the biggest salad in town for 12 Euros at Abesses (perfect if you visited Montmartre in the morning). You'll visit the best and cheapest leather bag place in Paris, then to Paris' Chinatown & the tens of thousands of cheap clothing stores that this area offers. After this, we'll go to the Jewish/Gay area to check out second hand stores. Last but not least, Opera & Saint-Lazare, heart of Paris with two last nice stores and a coffee in front of one of the best and hidden view spots in Paris. (4 hours)

A visit to Paris wouldn't be complete without a tour of the Louvre. On your last day, you'll be taken for a 1 hour tour that allows you to skip the line. Uriel will show you the Mona Lisa, Italian and French paintings of 17th and 18th Century, and the most famous Greek Sculptures (Victory of Samothrace, Venus of Milo). The tickets are for a full day in the Louvre, so when the tour is over, you can obviously stick around and discover other parts of the museum. (1 hour)

Day 13 - Return flight back to San Francisco

2nd: San Francisco, New York, Kiev, Bucharest, Budapest & Warsaw

Awarded to Flightfox expert “RushmoreAir”.

Days 1 - 3

Fly to New York in the evening and land in the morning on Day 2. Spend one night in a hostel on Brighton Beach.

Once you dump your bags, you will join a provocative tour for know-it-all New Yorkers and first time visitors alike. Visit New York's new and old immigrant neighborhoods: The Lower East Side, and Little Italy, where we explore the tenement lined streets and the stories that spill out of them across generations and languages. Chinatown, a massive neighborhood of windy streets and hidden excitements--all the while, tour-takers snack on globe-spanning treats that have become decidedly local. (3 hours)

Then escape from the sirens, car noises, and bustle of the city as you glide across the Hudson with us. As the sun sets, you'll see the skyline transform and the nightlife of the city come alive all from a distance. We'll hit up some landmarks like Ellis Island, Battery Park, and the Statue of Liberty as well so there will be lots of photo-ops for those of you who are visiting. (2 hours)

The next day see Greenwich Village as never before with an authentic gastronomical experience. Along the way, find out how the Village has maintained its unique character throughout the years, from the Dutch and English colonial periods to its Beat Poet and avant-garde arts center roots to today, including how it has evolved to become the current pulse of downtown Manhattan. (2 hours)

At night, you will fly out of New York to Kiev, Ukraine.

Days 4 - 6

Arrive in Kiev on Day 4 and stay for 3 nights in a light, cozy apartment close to the metro.

For days 5 and 6, you can participate in Swing and Salsa lessons with Andrei. Beginning dancers and pros will be introduced to Kiev's dance scene, which is known to host a fun and social community. As a semi-professional dancer and instructor, Andrei knows a thing or two about where to find the best parties and he's always happy to introduce newcomers to the scene. (2 days)

Days 7 - 9

Fly to Bucharest on Day 7 and stay for 3 nights in a mansion at the very center of the city. It still has original features like 4 metres high ceiling, oak stairs, oak parquet and original sandstone. The house, built in 1915, offers travelers modern accommodation with a romantic touch. Your Florentine style bedroom is 15 sqm, it has a queen size bed, a big wardrobe and a desk.

Tour the city landmarks with Beatris, including Revolution Square, Parliament Palace -the second largest building in the world after the Pentagon, Village Museum, Opera House, and the Athenaeum. (4 hours)

On Day 8, you will take a full day tour from Bucharest on a picturesque route through Carpathian Mountains. (10 hours)

On your final day in Bucharest, take a fascinating tour on Dictator Nicolae Ceausescu's life and achievements. The tour will include the place of birth and the prison where he was held during teen years, Doftana. We will be tracing the communist dictator's steps, seeing places where the Ceausescu couple has stayed to the place where they were executed, on Christmas Eve in 1989. (12 hours)

Days 10 - 12

Fly to Budapest and spend 3 nights in an apartment next to Saint Stephen Basilica and the magnificent Liberty Square.

More than 100,000 acres of forest is waiting for you to discover in Hungary. You will find pinewood, beech, oak trees, and all kind of animals, stories, experiences with a beautiful panoramic view on Budapest. You can horseback ride, try traditional Hungarian archery, enjoy homemade traditional hungarian food and drinks, and walk with a dog pack. (6 hours)

Budapest's most important and beautiful cemetery is also the biggest open-air statue park of Europe, yet tourists rarely find it. The greatest Hungarian artists and politicians lie here. By walking through the cemetery with a knowledgeable guide you will learn a lot about Hungarian history. (2 hours)

Days 13 - 14

Fly to Warsaw, Poland and spend one night in a chocolate-themed apartment! Original, artistic, modern, two-level apartment with balcony in the heart of Warsaw. There are two comfortable double beds and two exclusive hammocks. Large windows with a nice view and and walls in colour of chocolate and eggplant shall ensure perfect respite.

For your final day before returning to San Francisco, you will take a memorable tour around Warsaw and see the most mystical, bizzare and beautiful blocks of flats. Nat will be your guide through the world of urban prehistory and it's almost psychadelic ugliness.

Day 15 - Return flight back to San Francisco

3rd: San Francisco, Dublin, Amsterdam, Berlin & London

Awarded to Flightfox expert “Hagen2001”

Days 1 - 3

Fly to Dublin, Ireland and spend 3 nights in a private double bedroom hosted by Cassandra and Jordan and their 2 cats.

Take one day to relax and the other to get away from the hustle and bustle of Dublin as you journey through the Dublin and Wicklow mountains on a walking trek. (5 hours)

Days 4 - 5

Fly into Amsterdam and stay for 2 nights on a luxury plane! The entire airplane has been converted into a single luxury suite for two guests. This means you have the complete craft at your disposal – including its top-flight facilities, which include a Jacuzzi, infrared sauna, mini bar, 3 flat screen televisions, and free wireless internet.

Daniel will take you on a great night out in Amsterdam. Whether it's re-purposed squat bars or live music joints, Amsterdam has so much to offer to those who want to venture off the beaten path and live it up like locals do. (4 hours)

Days 6 - 8

Fly to Berlin and spend two nights relaxing and unwinding while fishing, swimming, diving, kayaking and sunbathing on a raft in the Brandenburg Mecklenburg Lake District.

Also get to really know one of Berlin’s liveliest outdoor spaces, comprehend its history, its landscape architecture and how the two are twined together. Take the Mauerpark Landscape Tour with Elfie. (2 hours)

Spend your last night in Berlin at a nice renovated flat, furnished to pop into DDR style! The sunny apartment is located on the fourth floor of an historical building of the former famous "Stalin Allee", Socialist Classicism of street, building a flagship project of East Germany's reconstruction program. You can breathe the air of a DDR Typically apartment. You can walk under the trees boarder That Karl Marx Allee and walk up to Alexander Platz in Few Minutes.

Days 9 - 12

Fly to London and stay for two nights at the converted water tower in North Kensington (as in the winning itinerary).

No matter what you're into (whether it's music, culture, art, food, history, or more), tell Gregory and he will create a tour individually designed for you. He's been a tour guide for 10 years and knows all the ins and outs of London. It can be anything from seeing where Bob Marley lived to the seat that Charles Dickens sat on whilst writing. (2 hours)

On Day 10, explore the big smoke in unconventional style, led by a London native who loves taking people off the beaten track with excursions that take in both landmarks and little-known hideaways. Striving to help you get the most out of London, the tour covers themes from Harry Potter, The Blitz, Sex Drugs Rock n Roll, Royalists and the Romans. This will be the best way to spend a day using all modes of transport including buses, tube, boat, and your very own two feet. (10 hours)

For your remaining two nights, you stay in a tree house enjoying sweeping sea and countryside views. From your lofty position enjoy water views of Falmouth Bay and spectacular sunsets over the fields and orchards of Tregaminion. The beautiful beach of Porthallow is an easy, ten minute walk away. At night, enjoy the peace and quiet of this secluded location and fall asleep to the rustling of leaves in the trees. The area offers a fantastic selection of restaurants and pubs, inspiring craft shops and galleries and a great range of outdoor activities, including coastal walking, sailing, surfing, cycling, golf, diving and horse riding.

Day 13 - Return flight back to San Francisco