Quietly appointed private aircraft cabin at dusk
Ollie's desk is open · 365 Aviation

Private flying,
personally arranged.

One direct line for aircraft, access and every detail around the journey, backed by the worldwide reach of 365 Aviation.

Experience

15+ years

Access

Worldwide

Response

24 hours

Standards

ARGUS · Wyvern

Ollie, founder of Fly with Ollie
Oliver — founderFig. 02
00The person you deal with

Hi, I'm Ollie.

Aviation entrepreneur and keynote speaker. I arrange every charter, experience and helicopter transfer personally — no account managers, no portals, just one direct line that's answered 24/7.

I work under the 365 Aviation umbrella, but every enquiry that arrives through this page comes straight to me. You deal with the broker, not the brand — from the first message to wheels down.

Based
London, UK
Umbrella
365 Aviation
Reach
Worldwide, 24/7

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02Experiences · Live365

The flight is only the beginning.

Packaged experiences built around the calendar that matters, jet, transfers, stay and access, handled as one trip through the Live365 programme.

Monaco Grand Prix

May · Monte Carlo

Monaco Grand Prix

Terrace hospitality over the harbour, a berth-side yacht, jet into Nice and helicopter onwards.

Castelfalfi, Tuscany

Trending stay · Italy

Castelfalfi, Tuscany

A restored medieval estate among the vines. Fly into Florence or Pisa, transfer by road or rotor.

Courchevel 1850

Ski season · French Alps

Courchevel 1850

Jet into Chambéry, helicopter to the altiport, chalet and tables arranged before you land.

Trending stays this season

Request a stay →
  • Cheval Blanc

    Courchevel

  • Hôtel du Cap-Eden-Roc

    Antibes

  • Castelfalfi

    Tuscany

  • Aman

    Mykonos

03Lifestyle

The black book concierge

One number for everything either side of the flight. Members get first sight of VIP events, private dinners and closed-door experiences, and a real person on the end of the line at three in the morning.

Hotels & residences
Suite upgrades, late checkouts and sold-out keys in the cities you actually travel to.
Tables & nightlife
Last-minute reservations and hosted tables, often the same evening.
Tickets & events
Grand Prix paddocks, finals, fashion week and private invitations.
Gifting & details
Flowers on arrival, bespoke gifts, proposals and celebrations handled quietly.
Hotel concierge desk with a leather book and room key

05 / LifestyleFig. 05

04Partners · 365 Aviation

In good company.

Through 365 Aviation, my clients have access to a circle of award-winning brands, from Nobu on board to private viewings and members-only spaces on the ground.

  • Inflight diningNobu Catering
  • Members' club40 Duke · Selfridges
  • Superyacht voyagesVilla Yachting
  • Private experiencesMaison Hennessy
  • Private showcasesBreguet
  • Exclusive staysHeavens Portfolio
Safety & membershipsARGUSWyvernNBAAAsBAAACA Accredited
05Empty legs · WhatsApp channel

The same jet,
up to 75% less.

When an aircraft repositions, the seats would otherwise fly empty. I post every one I can source to my WhatsApp channel the moment it's released. Whole cabin, private terminal, first to reply takes it.

24–72h

Typical notice

Whole

Cabin is yours

Free

To follow

Just posted

−65%

From

Farnborough

To

Nice

Date

Fri 02 Oct

Aircraft

Phenom 300 · 7 pax

Whole jet

£14,200£4,950

Examples of recent empty legs. Live availability is posted on the channel.

Trusted personally

The standard is personal.

One broker, clear pricing and licensed operators, from first message to wheels down.

“Ollie had three options and written pricing back to me inside forty minutes on a Sunday. We were airborne out of Farnborough the next morning.”

James H.

Farnborough → Geneva · Citation XLS

“I've used two of the big brokers before. The difference here is you speak to the same person every time, and the price you're quoted is the price you pay.”

Priya S.

Luton → Nice · Challenger 350

AOC-licensed operators only

Written all-in pricing

Client funds handled properly

One named point of contact

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07Questions

Everything you need to know.

The essentials, answered clearly.

Usually within the hour. Once I know your route, dates and passenger count, I come back with two or three aircraft options, operator details and a written all-in price. Same-day departures are possible from London terminals when availability is tight but not impossible.

Every quote includes aircraft hire, crew, fuel, landing and handling fees, VIP terminal access and catering. There are no hidden fuel surcharges or post-flight add-ons. If you need ground transport, helicopter connections or a yacht continuation, I quote those together so you see the full picture.

When a jet flies one way, it often has to return empty or reposition for its next trip. I sell those sectors at up to 75% below the normal charter price. Same aircraft, same crew, same private terminal, the whole cabin is yours.

Follow the Fly with Ollie WhatsApp channel. New empty legs are posted there the moment an operator releases them, usually 24 to 72 hours before departure. Reply to me directly to secure one, first to confirm takes it.

Still have a question?

Message Ollie on WhatsApp
06Enquire

Tell me about the trip

Send the outline and I'll come back with options, usually within the hour. If it's urgent, WhatsApp is fastest.

Your details are used only to answer this enquiry and are never shared.

Fly with Ollie

Charter · Empty legs · Helicopters · Yachts · Concierge

oliver@flywithollie.com

London · Worldwide · 24/7

Fly with Ollie is the personal aviation desk of Oliver, operating under the 365 Aviation umbrella. All flights are arranged with licensed, insurance-verified third-party AOC operators. Prices shown are indicative and confirmed in writing before booking.

© 2026 Fly with Ollie