# Skylark

> Skylark is a New York-based luxury travel company that fuses a slick online booking platform with a bench of human travel advisors. Clients search five-star hotels and privately negotiated airfare online, then hand the messy parts - upgrades, transfers, spa bookings, itinerary changes - to a real person over phone, text, email or chat. Positioned as the only true hybrid online-offline agency, Skylark packages VIP hotel perks (room upgrades, complimentary breakfast, resort credits) through its Virtuoso membership and industry partnerships.

- **Founded:** 2015
- **Headquarters:** New York, United States
- **Founders:** Paul Tumpowsky (Founder & CEO)
- **Team size:** ~68 employees
- **Products:** Skylark Booking Platform, Travel Advisors, VIP Hotel Perks, Negotiated Airfare
- **Notable:** Raised $4.0M in seed funding in 2019 with backing from Bessemer Venture Partners, BCD Travel, 25Madison and others., Built one of the first true hybrid online-offline luxury travel agencies., Earned Virtuoso membership, unlocking VIP amenities at top luxury hotels.

## Products & services

- **Skylark Booking Platform** — An online site where members search and book five-star hotels and privately negotiated airfare, comparing rates and perks in one place.
- **Travel Advisors** — A team of full-service expert advisors who support clients by phone, email, text or chat - handling flights, hotels, spa appointments, guides, drivers, tours and complex itineraries.
- **VIP Hotel Perks** — Exclusive amenities via Virtuoso membership and hotel partnerships, including room upgrades, complimentary breakfast, resort credits and early check-in.
- **Negotiated Airfare** — Access to privately negotiated business- and first-class fares that are often lower than public rates.

## Achievements

- Raised $4.0M in seed funding in 2019 with backing from Bessemer Venture Partners, BCD Travel, 25Madison and others.
- Built one of the first true hybrid online-offline luxury travel agencies.
- Earned Virtuoso membership, unlocking VIP amenities at top luxury hotels.
- Grew a loyal client base known for praising deep hotel discounts plus perks like upgrades and free breakfast.

## Latest updates

- **2019-05** — Closed $4.0M seed round led by 25Madison to build out its high-touch luxury travel platform.
- **2019-01** — CEO Paul Tumpowsky shared 2019 outlook with Travel Weekly, arguing luxury travel is insulated from downturns.

## Links

- Website: https://skylark.com
- LinkedIn: https://www.linkedin.com/company/skylark-travel
- Twitter/X: https://twitter.com/skylark
- Instagram: https://www.instagram.com/skylark/
- Facebook: https://www.facebook.com/travelwithskylark

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Profile page: https://yespress.io/skylark
Published by YesPress — https://yespress.io
Last updated: 2026-07-02