Choose Your Experience

Welcome to your Galena getaway, made easy. At Olive Tree Rentals, your stay is about more than just where you sleep — it’s about creating a seamless, memorable experience from the moment you arrive. Our concierge packages are designed to take the planning off your plate, offering personalized recommendations, curated experiences, and thoughtful extras that help you make the most of your time in Galena. Whether you’re here to relax, explore, celebrate, or simply slow down, we’re here to help shape a stay that feels effortless and uniquely yours.

To make this experience even more personal, we’ve partnered with Christine, the owner of Basket Case and a longtime Galena local who has called this community home for over 25 years. Christine knows Galena and The Galena Territory inside and out — from the can’t-miss spots on Main Street to the quieter experiences that most visitors never find on their own. She’ll be your behind-the-scenes guide, helping curate recommendations, plan experiences, and add thoughtful touches that turn a great stay into a truly memorable one.

Why Use Our Concierge?

Planning a getaway should feel exciting — not overwhelming. Our concierge service exists to take the mental load off your trip so you can simply enjoy your time in Galena. Whether you’re visiting for the first time or returning to a place you already love, having a local in your corner means you’ll spend less time researching and more time experiencing.

Our concierge partner is a Galena local who knows the rhythm of the seasons, what’s worth your time, and how to match experiences to your travel style. From dining recommendations and activity planning to thoughtful touches waiting for you when you arrive, this service is designed to make your stay feel intentional, personal, and easy.

How It Works

Choose the concierge package that best fits your stay.
Complete a short questionnaire so we can understand your group, interests, and goals for your trip.
You will be contacted within 24 Hours by Basket Case Galena to confirm receipt of your request along with a payment link for your chosen package.
Your personalized recommendations and experience planning will be prepared ahead of your arrival.
Arrive in Galena with a plan in place — and space to relax and enjoy every moment.

Concierge Packages

Our concierge services are designed to make your Galena getaway feel thoughtful, effortless, and tailored to you. Whether you enjoy planning your own reservations or prefer a hands-off, fully coordinated experience, these packages give you local insight and support so you can focus on enjoying your stay.

Curated Itinerary Package (Plan-It-Yourself)

$125 per stay (*does not include any reservations)
Best for guests who want local guidance but prefer to book their own reservations.

Includes:
• Guest completes a short itinerary questionnaire
• A custom, personalized itinerary based on:
– Group size and ages
– Budget comfort level
– Interests (wine, food, shopping, spa, outdoor activities, downtime)
• A suggested daily schedule that is flexible and not over-packed
• Restaurant and activity recommendations with booking notes
• Local tips, including best times to visit, reservations needed, and walking vs. driving guidance

This package gives you a thoughtful plan and trusted local recommendations, while still allowing you the freedom to book and adjust as you go.

Full Concierge Planning Package (Done-For-You)

$275 per stay (*Does not include payment for any experiences, reservations, etc.)

Price varies based on group size and number of reservations. Best for girls’ weekends, birthdays, bachelorettes, and milestone trips.

Includes:
• Guest questionnaire and optional planning call
• A fully customized, day-by-day itinerary
• Reservation coordination for:
– Dining
– Wine tastings
– Experiences
– Transportation, as needed

• Reservations held using the guest’s credit card
• Vendor confirmations and final itinerary sent prior to arrival
• One round of itinerary revisions

This package is designed for guests who want to arrive with everything already planned, reserved, and organized — allowing you to simply enjoy your time in Galena.

Plan My Stay