Our Services
At Oscar & Olive, we offer personalized travel planning services to create memorable and seamless travel experiences.
We specialize in bespoke itineraries and cater to travelers who seek unique and immersive journeys. Our team ensures every detail is meticulously planned, from luxury accommodations and exclusive tours to hidden gems and local experiences.
Learn more about our services below.
Book my hotel.
Price: Gratis
Know where you want to stay? We can handle your hotel booking for you, making the process seamless and stress-free. We pass the perks on to you, ensuring you get the best value for your stay without lifting a finger.
With access to the best available rates (BAR) and member rates from Marriott Bonvoy, IHG Rewards, Hilton Honors, and many other loyalty programs, we can secure your stay at no added cost to you. Oscar & Olive gets paid by the hotel you have chosen, allowing us to offer this service for free.
Additionally, we have access to hundreds of hotels around the world that provide exclusive perks for travelers who book through a travel advisor like Oscar & Olive. These perks are privileges that can include early check-in and late checkout, daily credits for bars and restaurants, free Wi-Fi, complimentary parking, reduced or free resort fees, welcome messages from hotel management with snacks, chocolates, or wine, turn-down service, and more.
Let us take care of your hotel booking and elevate your stay!
Give me options.
Price: $450
After getting to know you a bit via Zoom or phone, we'll create up to three complete itineraries tailored to your preferences and travel goals.
You'll have the opportunity to review these options and choose the one that best suits your needs. Once you've selected, we'll book the hotels you prefer.
Our comprehensive service ensures a seamless travel experience from start to finish, with carefully planned itineraries and accommodations that excite (or relax!) you.
Let us take the stress out of planning so you can focus on enjoying your journey with confidence and reassurance.
Be my travel admin.
Price: Hourly rate
Need help with dinner reservations, booking tours, or getting tickets to a show? Let us act as your travel concierge.
This service, billed hourly, ensures you have a smooth and enjoyable experience at your destination. Whether you're looking for the perfect restaurant, arranging unforgettable tours, or securing seats for a must-see performance, we've got you covered.
We are happy to assist with arrangements ranging from car rentals, airport transfers, and private chauffeurs to visa applications, travel insurance, and other necessary documentation.
Do you have other needs? Send them our way, and with our expert support, you'll spend less time planning and more time enjoying your trip.
Let us handle the legwork—book hotels, plan excursions, orchestrate dinner reservations and more.
With a range of packages, our right-sized, comprehensive trip management service ensures every detail of your travel is meticulously planned and executed. This service includes an initial conversation in which we learn about your preferences and travel goals and discuss any special requests.
From there, we create complete itineraries tailored to your interests, ensuring a personalized and unforgettable experience. We manage all the hotel bookings, leveraging our access to exclusive rates and perks. Our concierge service takes care of dinner reservations, booking tours, securing tickets to shows, and any other needs you may have.
You can relax knowing we offer beginning-to-end assistance with cancellations or rescheduling before or during your vacation. Our goal is to provide a seamless, stress-free travel experience where your only focus is enjoying your trip.
Let us transform your travel dreams into reality with expertly curated itineraries and exceptional service every step of the way.
Manage my vacation.
Price: Starting at $650
