Key West Itineraries: Local Knowledge for Planning Your Journey
Welcome to Key West!
At Vacation Homes of Key West (VHKW), we’ve been welcoming guests to our island for over two decades. Our team spans three generations of Key West locals, some of whom have been here since the early 1970s. We’re proud of our island’s history, from the days when Duval Street had empty storefronts to when Jimmy Buffett was just another musician playing in town. Your vacation time is precious, and we want to help you make the most of it. Whether you’re staying in one of our vacation rentals or just looking for insider tips, we’re here to help you plan your trip with ease.
Insider Itineraries for Every Traveler
We take a different approach to planning Key West experiences, going beyond traditional concierge services. Our custom itineraries are designed to fit a variety of interests, age groups, and energy levels. Whether you’re here for adventure, relaxation, or something in between, we’ve got something for you. Itinerary themes include: Outdoor adventures for those who love the water and nature. Romantic escapes perfect for couples looking to unwind. Family-friendly itineraries that keep everyone entertained. Culture and history tours for those who want to explore the island’s past. Beach days and relaxation for the ultimate laid-back experience. Our itineraries are designed to be flexible—you can follow them exactly or mix and match to suit your preferences. Full access is available to all guests after booking a stay with us.
Sample Itinerary: Couple’s Dream Stay
For a taste of what we offer, here’s a sneak peek of our Couple’s Dream Stay Weekend, created by Key West local Sam Klitenick. If romance and adventure are what you’re after, this itinerary is for you.
Day 1: A Relaxed Start to Your Romantic Getaway
10:30 AM – Noon: Brunch at Sarabeth’s Enjoy a leisurely brunch at this award-winning restaurant in Old Town. The menu features fresh-squeezed juices, fluffy omelets, and scratch-made pancakes. A great way to ease into the day.
Noon – 2:00 PM: Stroll Through Old Town Walk hand-in-hand through Key West’s historic district, admiring the unique architecture and charming streets. Stop for souvenirs or simply soak in the island’s character.
2:00 PM – 3:00 PM: Lunch at Garbo’s Grill Grab a casual bite at this well-loved food truck, known for its Caribbean-Korean fusion flavors. Try the Yum Yum Shrimp Tacos and pair them with a craft beer from Grunts Bar next door.
3:00 PM – 7:00 PM: Mid-Afternoon Break Head back to your vacation rental for a little downtime. Relax, refresh, and recharge for the evening ahead. For the full itinerary, including the next two days, as well as additional curated itineraries, book your stay with VHKW.
Concierge Services with a Local Touch
We don’t just suggest activities—we make planning easy. Our in-house concierge can help with: Booking adventure tours like snorkeling, sunset sails, and eco-excursions. Arranging transportation around the island. Sharing insider tips on hidden gems and exclusive experiences. After booking, you’ll receive access to your Guest Portal, where you’ll find trip details, a Welcome Packet, and all of our local itineraries.
Plan Your Key West Escape
We’re more than just a vacation rental provider—we’re your connection to the true Key West experience. Thank you for choosing VHKW, and we look forward to helping you create unforgettable memories on the island.
Book your stay with VHKW today and gain exclusive access to curated itineraries, insider tips, and personalized travel planning for an unforgettable Key West experience.
