Love traveling…
Too busy to plan?

Do you need a vacation?

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

Let us take the work out of travel planning by 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 a stress-free vacation tailored to your preferences.

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.

I’m busy. Help me.

BILLED HOURLY

Need help with dinner reservations, visa applications, booking tours, or getting tickets to a show? Let us act as your personal travel concierge.

Manage my trip for me.

PACKAGES START AT $650

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

Embark on a dream getaway

Do you have an idea for an upcoming vacation but don’t have the time to do the research and compare rates?

Are you interested in a specific hotel and want a professional to manage the booking?

Or are you open to suggestions based on your interests?

Begin by booking a free consultation and let’s get you on vacation!

Vacation on Santorini

Travel Inspo

Discover the best vegan spots in New York City with our guide! From delicious plant-based eateries to hidden vegan gems, we'll take you on a culinary journey through the city that never sleeps. Whether you're a local or visiting for the first time, o
I was drooling over all of the spices at @essexolivespice In #EssexMarket on my recent trip to New York. Owner Saad Bourkadi came to New York 25 years ago - coming from four generations of farmers in Morocco, he’s just a delight to talk to. #
Those who travel are never done growing. #travel #wander #wanderlust Credit: @buttonpoetry