You need a vacation.

You need a vacation.

Trust us.
You do.

At Oscar & Olive, we understand that you have discerning taste—because we do, too. 

Let us take the work out of travel planning by finding airfare, booking hotels, advising on experiences, and curating the perfect itinerary for your next trip. 

Leave the details to us so you can relax and enjoy the vacation you deserve.

Travel services

Just book my hotel.

GRATIS

Know where you want to stay? Let us book your hotel and pass the perks on to you!

I need some guidance.

$450

After a virtual getting-to-know-you session, we’ll create up to three full itineraries for your consideration and book your selected hotels (booking airfare incurs a small additional fee).

I’m busy.
Help me.

BILLED HOURLY

Need help with dinner reservations, visa applications, booking tours, or getting tickets to a show? We’ll be your personal travel concierge.

Manage my trip for me.

PACKAGES START AT $650

Hand the legwork off to us—we can book hotels and airfare, plan excursions, orchestrate dinner reservations, and more. 

“Travel is fatal to prejudice, bigotry, and narrow-mindedness.” – Mark Twain

Let’s work together.

Please fill out the form below and we’ll reach out to set up a meeting.

Travel Inspo