Your Perfect Key West Vacation FAQ
Planning your Key West vacation should be exciting, not overwhelming. Below are answers to the questions we hear most often about our Vacation Planning Service.
ℹ️ What does this service provide?
Our personal Vacation Planning Service pairs you with a local Key West concierge who will create a customized itinerary based on your travel style, budget, interests, and schedule.
Instead of spending hours researching restaurants, tours, transportation, and activities, you’ll work with someone who knows the island and can help you make the most of your time in Key West.
💵 Why do I have to pay $100?
We have a team of real human experts, working directly for you to ensure you have the best vacation possible. We take our time to sort through our meticulously vetted activities providers and accommodations, to find the best fit for you and your travel companions. Your payment is an assurance that your time spent in Key West is everything it can be.
🤝 What do I get for my $100?
A personal concierge and travel planner will be assigned to you as soon as your form is submitted. You will receive a sample itinerary based on the profile created from your questionairre. You choose the best time to connect about the itinerary. Your concierge works for you, so if you want any changes made, or need questions answered– they are there to help. Once approved, your concierge will make all the necessary reservations for your itinerary. They will also be on call for the entire time leading up to your vacation, as well as during. Basically, for $100, you get a vacation secret agent, working hard to make sure you have the best time in Key West!
🔄 Is my $100 refundable?
The $100 Trip Planner Fee is non-refundable. This fee secures the dedicated time, expertise, and personalized planning provided by OurKeyWest Concierge, including destination recommendations, itinerary development, and travel research. Because these services begin immediately, the fee cannot be refunded.
📋 What is the overall cancellation policy?
Because every itinerary is custom-designed, cancellation policies vary depending on the hotels, vacation rentals, tours, attractions, transportation providers, and other vendors included in your trip. Each reservation is subject to the cancellation and refund policy of the individual vendor providing that service.
A summary of the applicable cancellation policies for each booked reservation will be included with your final itinerary and travel documents. By confirming your reservation, you acknowledge and agree to the cancellation terms of each vendor.
Please note that any non-refundable concierge or travel planning fees are separate from vendor cancellation policies and are not refundable.
📝 Can I make changes to my itinerary?
Yes, you may make changes to your itinerary as long as vendor cancellation policies are kept in mind. There may be cancellation fees associated with any last minute changes.
👤 Will I work with a real person?
Yes.
Your itinerary is personally created by a member of our local concierge team—not artificial intelligence or an automated booking platform.
If you have questions before or during your vacation, you’ll have a real local expert available to help.
🙋♂️ Why do you ask so many questions?
No two vacations are the same.
Some guests want relaxing beach days and romantic dinners, while others are looking for fishing charters, snorkeling adventures, live music, or family-friendly activities.
The questionnaire helps us understand what’s important to you so we can create recommendations that truly fit your vacation—not a generic itinerary
🌴 Why should I use OurKeyWest instead of planning everything myself?
Anyone can search online for things to do in Key West.
What you won’t find is local insight.
Our concierge team knows which tours consistently receive great feedback, the best times to visit popular attractions, where locals love to eat, and how to build an itinerary that fits your interests, pace, and budget.
Our goal isn’t simply to recommend activities—it’s to help you experience the very best of Key West with confidence.
📅 How long does it take to receive my personalized vacation plan?
Most vacation plans are completed within a few business days.
If you’re traveling soon, let us know. We’ll do our best to prioritize your request whenever possible.
🍽️ Will you recommend restaurants?
Yes!
Dining is one of the highlights of any Key West vacation.
We’ll recommend restaurants based on your preferences—from waterfront seafood and local favorites to fine dining, brunch, happy hours, and hidden neighborhood gems. We can even go the extra mile and make your reservations for you.
📞 Still Have Questions?
We’re always happy to help. 305-290-2049
If you have questions before getting started, reach out to our local concierge team by phone, text, or email. We’ll be happy to answer your questions and help you decide if our Personal Vacation Planning Service is the right fit for your trip.
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