Our Services
A memorable trip is in the details.
Where you stay. The neighborhood vibe. The restaurant worth planning a night around. The experience that makes the trip.
Oscar & Olive does the research and brings the pieces together.
Design my trip.
You know you want to go to Portugal. Or Japan. Or maybe somewhere warm in February. You have a general idea of the trip you want, but you’d rather have someone else do the research and turn it into an actual plan.
We’ll start with an intake so I understand how you like to travel, what matters to you, and what you want to spend. From there, I’ll design a custom itinerary with hotel and restaurant recommendations, experiences, and excursions. One round of revisions is included, and once the itinerary is approved, I’ll handle the hotel and excursion bookings and restaurant reservations.
Planning fees start at $750
Find me a hotel.
You know where you’re going, but not where you want to stay. Tell me your dates, budget, and what matters to you in a hotel, and I’ll research the options and send you three recommendations. Once you choose, I’ll handle the booking.
$250
Book my hotel.
Already know where you want to stay? Send me the hotel and your dates, and I’ll take care of the booking.
Complimentary
Room upgrades, complimentary breakfast, early check-in and late checkout, restaurant, bar, or spa credits, welcome amenities, and other extras that make a good hotel stay even better.
The extras.
Let’s work together.
Tell us a little about the trip you have in mind and we’ll be in touch.

