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Discover Your Key West, LLC

786-883-1322

  • Home
  • Concierge Services
  • Activities
  • Marketing Services
  • Cruise Ship Services
  • Shop
  • Key West Packages
  • Plan Your Vacation
  • Contact Us
  • Blog
  • Privacy Policy
  • Blind Squirrel Provisions
  • Blind Squirrel VIP
Hello

Discover Your Key West Vacation Packages

Welcome to our Key West vacation packages hub! Explore tailored options for bachelor and bachelorette parties, corporate trips, family vacations, and more. Discover private charters, beach picnics, fishing adventures, and sunset sails for an unforgettable Key West experience.

Large Sportfisher Yacht with people fishing off the back and people lounging on the bow.

Key West Elite Adventure Retreat

"Key West Elite Adventure Retreat" Vacation Package

Dive into an unparalleled realm of luxury, adventure, and camaraderie with our "Key West Elite Adventure Retreat" vacation package. Ideal for those looking to bond and build memories – be it a group of old college friends, a corporate team, or an adventurous family – this tailor-made package beckons you to experience the thrill and relaxation Key West has to offer. With a design optimized for groups, especially those of people seeking the top-tier Key West vacation packages, this retreat offers the best of both excitement and leisure.


Included in the package:


Private Sandbar Charter:
Embark on a Corinthian catamaran party boat bound for a secluded sandbar. Here, pristine waters and shimmering sands become the backdrop to an unparalleled day of fun and relaxation.


Elite Fishing Adventure:
Engage with the rich fishing traditions of Key West aboard a luxurious 63' Sportfisher yacht. With seasoned experts at the helm, pursue the exhilarating catch amidst the picturesque allure of the Florida Keys.


Jet Ski Odyssey:
Unleash your inner adventurer as you navigate the cerulean Key West waters on a jet ski. Discover hidden gems, embrace the splash of the waves, and craft moments that echo through time.


Optional Upgrades:

  • All-Inclusive Gratuity: Ensure a smooth and worry-free journey by opting for pre-arranged gratuities, allowing you to immerse fully in the moment.
  • Tailored Provisioning: Add a personal touch to your voyage with pre-arranged provisions, be it on your charter boats or at your vacation rental. From refreshing beverages to select gourmet snacks, we ensure your preferences are catered to.


Pricing: Kickstart your ultimate Key West adventure at a base price of $4,500, tailored for a group of 8. We take pride in offering customization to align with diverse group dynamics, making sure each retreat is distinct and memorable.


So, whether you're a team desiring a break from the norm, a group of friends scouting the best Key West packages, or anyone in between, our "Key West Elite Adventure Retreat" promises an experience unlike any other. The vibrant hues of Key West beckon – are you ready to respond?

Ready to Unleash Your Key West Adventure?

Explore the vibrant depths of Key West and craft unforgettable memories with our exclusive "Key West Elite Adventure Retreat" package. Get in touch with us now to begin planning the ultimate escape for your group. Let us curate an experience that transcends the ordinary and leaves you with memories that will last a lifetime.


Contact us now to learn more about our tailored travel packages and take the first step towards an extraordinary Key West getaway. Our team is ready to bring your dream vacation to life, ensuring every detail is seamlessly designed to exceed your expectations. Don't miss out on this chance to embark on the adventure of a lifetime!

Let the Adventure Begin

Fabulous Luxe Escape

"Fabulous Luxe Escape" Key West Vacation Package

Whether you're planning an unforgettable bachelorette getaway, an indulgent girls' weekend, or any cherished gathering of friends, our "Fabulous Luxe Escape" in Key West offers the ultimate blend of luxury and island charm. Recognized as one of the premier Key West vacation packages, each element promises a harmonious mix of relaxation, excitement, and unforgettable moments.


Included in the Package:

  • Private Sandbar Charter: Set sail to a serene sandbar where azure waters meet sun-drenched shores. Enjoy quality time, refreshing beverages, and the company of dear friends in this tranquil setting.
  • Luxury Beach Picnic:Indulge in a specially curated beach picnic, experiencing Key West's natural beauty at its finest. Delight in gourmet treats and refreshing beverages amidst swaying palms and gentle waves.
  • Exclusive Nightlife Experience: Choose your evening's delight: Immerse yourself in the glitz and humor of a premium drag show or lose yourself in the allure of a speakeasy-themed burlesque act. Your VIP booth or table ensures you savor every moment in lavish style.
  • Wine Tasting Sunset Sail: Board a timeless schooner sailboat and glide toward a breathtaking sunset. Sip on a selection of curated wines as the sun's golden hues embrace the horizon, enhancing the magic of the moment.

Optional Upgrades:

  • Private Shopping Party: Enjoy exclusive access to some of Key West's finest boutique stores, allowing your group to shop in style with personalized stylist assistance at your fingertips.
  • Provisioning Services: Imagine stepping onto your charter boat or entering your hotel room to find an array of your favorite drinks and snacks pre-arranged. We'll take care of these finer details, ensuring a hassle-free and luxury-filled escape.


Pricing: Starting at $1650 for a group of 4. Prices will vary based on group size and specific customizations.


Embark on a journey defined by luxury and camaraderie with our "Fabulous Luxe Escape." If you're in search of top-tier Key West vacation packages, this bespoke experience awaits you and your group.

Ready to Indulge in the Ultimate Key West Getaway?

Elevate your Key West experience with our exclusive "Fabulous Luxe Escape" package, meticulously designed for an unforgettable retreat with your closest friends. Contact us now to begin planning your dream escape in the enchanting paradise of Key West. Let us craft a luxurious and personalized itinerary that promises to exceed your every expectation.

Get in Touch Today to Begin Your Luxurious Island Adventure!

Reach out to us today and discover the perfect blend of opulence, relaxation, and excitement that awaits you in Key West. Our team is dedicated to curating an extraordinary vacation tailored to your desires, ensuring every moment is imbued with the magic of the island. Don't miss this opportunity to create memories that will last a lifetime!

Create Unforgettable Memories

Key West Angler's Dream

Key West Angler's Dream Fishing Vacation Package

Introducing the "Angler's Dream" package - the pinnacle of fishing in the world-renowned Key West! Suitable for EVERY group size: from intimate trips to large corporate retreats. Perfect for team building, Winners’ Circle trips, and any fishing enthusiast – beginner or pro. Dive into our customizable, all-inclusive offerings with private charters designed especially for you. Cast your line and reel in the experience of a lifetime!


Included in the package:


Daily Fishing Expeditions:

  • Deep Sea Fishing Adventure: Set sail to the deep blue, targeting species like Marlin, Wahoo, Tuna, and Mahi-Mahi.
  • Backcountry Fishing Trip: Navigate the shallow waters of the Key West flats and channels to fish for Tarpon, Bonefish, and Permit.
  • Reef & Wreck Fishing: Explore the rich habitats around reefs and shipwrecks, targeting Grouper, Snapper, and more.


All Fishing Equipment:

State-of-the-art fishing rods, reels, and tackle.

Live bait and synthetic lures.

Captains hold licenses


Experienced Fishing Guides:

We proudly partner with the most renowned fishing captain in the Florida Keys. With their unparalleled expertise and intimate knowledge of local waters, they ensure you access to the prime fishing spots and provide invaluable guidance on techniques. Whether your preference is fly fishing, trolling, or bottom fishing, rest assured you're in the hands of the best in the business.


Post-Fishing Amenities:

Fish cleaning, filleting, and packaging service.

Ice chests and storage for your catch.


Exclusive "Catch & Dine" Experience:

On your last evening, savor a dinner at our favorite local restaurant where expert chefs will prepare and cook your catch to perfection. Enjoy this special dining experience in the company of your captain, discussing the day's highlights and immersing in the local fishing culture.


Memorable Takeaways:

Custom "Angler's Dream" fishing hat and shirt.

A digital photo album capturing your fishing highlights.

Local fish recipes for you to recreate the flavors of Key West at home.


Optional Add-ons:

  • Extending your stay? Allow us to tailor additional fishing expeditions or arrange unique adventures just for you.
  • Upgrade your fishing experience by embarking on a 63' Sportfisher Yacht, offering unparalleled luxury and state-of-the-art fishing equipment.
  • Want to do some serious team-building? Let's get your team working together in a tournament!


Notes:

  • Suitable for anglers of all skill levels.
  • Advance booking recommended to ensure availability.
  • Package can be customized for family trips, solo adventures, or group outings.


Pricing: The base rate starts at $3,150, accommodating up to 2 guests. The package can be tailored for groups of up to 41 individuals, with pricing adjustments based on customization requirements.


Catch the thrill of Key West fishing and take home memories that last a lifetime with our "Angler's Dream" package!


Book your trip today

Ready to start planning your dream vacation? Contact us today to learn more about our travel packages and deals.

Contact us
Key West Lighthouse at sunset

Historic Key West Exploration

"Historic Key West Exploration" Vacation Package

Unlock the rich tapestry of history that colors the streets of Key West with our "Historic Key West Exploration" vacation package. This experience, curated for the history enthusiast and the curious traveler alike, seamlessly weaves the tales of yesteryears into the vibrant present of Key West. As you traverse iconic landmarks and relish in exclusive moments, you'll find yourself immersed in stories and sights that define the character of this unique island paradise. It's more than just a trip; it's a journey through time that resonates with those seeking the finest Key West vacation packages.


Included in the package:


Private Guided Walking Tour:
Delve deep into the heart of Key West as a local expert recounts tales of the island's storied past, guiding you through its charming streets and alleys.


Culture Pass:
Gain access to the quartet of Key West's most iconic museums. Unearth the layered history, art, and narratives that have sculpted the island's cultural landscape.


Conch Train Tour:
Board the iconic Conch Train and journey through Key West's most celebrated spots. Relish in the nostalgic charm as you explore the town's vibrant corners.


Exclusive Sunset at the Key West Lighthouse:
Indulge in a private evening at the Key West Lighthouse and Keeper's Quarters Museum. As the sun dips below the horizon, ascend the lighthouse for a sunset view unparalleled in its beauty. Further, enjoy an intimate wine and charcuterie spread on the porch of the keeper's quarters, granting you exclusive access to the grounds during this serene escapade.


Historic Dining Experience:
Conclude your exploration with reservations at a renowned restaurant nestled in a historic Key West location. Savor culinary masterpieces that reflect the island's diverse heritage.


Optional Upgrades: Customizations are available to ensure your historical journey aligns with your unique preferences, creating a truly tailored experience.


Pricing: Embark on this historical odyssey at a base price of $920, tailored for 2. We specialize in adapting our packages to meet diverse interests and group sizes, ensuring every Key West adventure is as individual as our esteemed guests.


For travelers seeking the most enriching Key West packages, our "Historic Key West Exploration" offers an immersive dive into the island's soul. Are you ready to traverse the pages of Key West's rich history?

Book your trip today

Ready to start planning your dream vacation? Contact us today to learn more about our travel packages and deals.

Contact us

Family Fun Key West Adventure

"Family Fun Key West Adventure" Vacation Package

Overview: Embark on an enchanting family journey with our "Enchanting Family Key West Adventure" vacation package. Tailored for families with young children, this package promises an engaging blend of excitement, education, and the natural wonders of Key West. From delightful daytime activities to a captivating nighttime glow paddle experience, every moment is designed to create lasting memories for the entire family. Known for its family-friendly atmosphere, Key West offers an array of experiences that cater to all ages, ensuring a delightful vacation for everyone.

Included in the package:

Private Sandbar & Snorkel Charter:
Set sail to a secluded sandbar, offering an idyllic space for family fun and relaxation. Enjoy snorkeling amidst colorful marine life, creating a memorable experience for young ones and adults alike.


Dolphin Watch Sunset Adventure:
Delight in a mesmerizing dolphin watch during the enchanting Key West sunset, creating a magical experience for the entire family.


Interactive Educational Visits:

  • Explore the Key West Butterfly and Nature Conservatory, where children can witness the beauty of these delicate creatures up close.
  • Discover the wonders of the sea at the Key West Aquarium, providing an educational and entertaining experience for children of all ages.
  • Immerse yourselves in the rich maritime history at The Shipwreck Museum, where interactive exhibits bring the past to life.


Nighttime Glow Paddle Adventure:
Embark on an exhilarating nighttime journey around the harbor in a crystal clear kayak adorned with colorful LED lights. Enjoy the glow paint, glow sticks, and a Bluetooth speaker, creating a one-of-a-kind family adventure under the starry Key West sky.


Optional Customizations: Personalize your experience with additional activities and amenities tailored to your family's preferences.


Optional Add-On: Family Photo Session with Professional Photographer:

Capture the magic of your Key West adventure with an optional family photo session led by a seasoned professional photographer. Preserve the joy and wonder of your family moments against the stunning Key West backdrop, creating timeless keepsakes to cherish for years to come. Let the photographer expertly encapsulate the laughter, the bonding, and the natural beauty of your family's experience, ensuring that every smile and every embrace is immortalized in stunning photographs.


Pricing: Begin your Enchanting Family Key West Adventure at the all-inclusive price of $1400 for a family of 4, with the flexibility to accommodate customization requests and different family sizes.


Discover the joy of family bonding and exploration with the "Enchanting Family Key West Adventure" package. A specially curated selection of activities ensures a delightful, educational, and entertaining experience for families with young children. Let Key West become the backdrop to your family's unforgettable memories.

Book your trip today

Ready to start planning your dream vacation? Contact us today to learn more about our travel packages and deals.

Contact us

Key West Thrill Seeker's Getaway

"Key West Thrill Seeker's Getaway" Vacation Package

Prepare for an exhilarating escape with our "Key West Thrill Seeker's Getaway" vacation package. Tailored for the adventurous at heart, this experience combines the thrill of high-speed water activities, deep-sea fishing, and the freedom of exploring the island on e-bikes. With a name that perfectly captures the essence of your vacation, our package promises an adrenaline-fueled journey through the vibrant landscapes of Key West.


Included in the Package:

  • Jet Ski Island Tour: Feel the rush as you jet ski around the stunning island, exploring its hidden coves and breathtaking shores.
  • All-Day Watersports Adventure: Brace yourself for an action-packed day featuring parasailing, jet skiing, banana boat rides, and a floating water park. Dive into the excitement and create unforgettable memories on the turquoise waters of Key West.
  • E-Bike Rentals for 3 Days: Discover the island's nooks and crannies on electric bikes, allowing you to explore the beauty of Key West with ease and flexibility.
  • 3/4 Day Deep-Sea Fishing Trip: Set sail for an unforgettable deep-sea fishing expedition, chasing the thrill of reeling in the big one amidst the vast waters surrounding Key West.


Optional Add-Ons:

  • Skydiving Experience:Elevate your adventure to new heights with a heart-pounding skydiving escapade, offering panoramic views and an unmatched adrenaline rush.


Pricing: Begin your "Key West Thrill Seeker's Getaway" for a group of 4 at the competitive price of $3400. Prices can be adjusted to accommodate varying group sizes and additional customizations.


Whether you're traveling with a group of friends or an adventurous family with teenagers, our package ensures a seamless blend of excitement, adventure, and breathtaking landscapes. Explore Key West in a way that resonates with your inner thrill seeker!

Book your trip today

Ready to start planning your dream vacation? Contact us today to learn more about our travel packages and deals.

Contact us

Enchanting Key West Romantic Getaway

"Enchanting Key West Romantic Getaway" Vacation Package

Experience the epitome of romance with our "Enchanting Key West Romantic Getaway" package. Crafted for couples seeking an idyllic escape, this collection of intimate experiences promises to kindle the flames of love amidst the alluring backdrop of Key West. From private beach picnics to luxurious spa treatments and champagne-fueled sunset sails, every element is designed to create cherished moments and everlasting memories.

Included in the Package:

  • Private Luxury Beach Picnic Dinner: Indulge in an exquisite culinary affair on the pristine Key West shores, with a private dinner setup tailored to your preferences and surrounded by the gentle sound of lapping waves.
  • Private Lighthouse Sunset Experience: Bask in the warm glow of the setting sun with an exclusive and private viewing from the iconic Key West Lighthouse, creating an intimate and unforgettable moment for you and your beloved.
  • 90-Minute Couples Massage at a Top Spa: Unwind and rejuvenate with a luxurious couples massage at one of Key West's top spas, ensuring a tranquil and pampering experience to enhance your romantic journey.
  • Luxury Sunset Sail with Champagne: Set sail on a luxurious sunset cruise, sipping champagne as the golden hues of the evening sky create a breathtaking backdrop for your shared moments.

Optional Add-Ons:

  • Provisioning Services for Hotel or Vacation Rental: Elevate the romance with a customized setup in your accommodation, including champagne, a selection of fine liquors, delectable snacks, fragrant flowers, and more, enhancing the ambiance of your private haven.
  • Upgrade to Private Sunset Sail: Elevate your sailing experience to a new level of intimacy and privacy with an upgraded private sunset sail, ensuring an exclusive and unforgettable voyage for just the two of you.


Pricing: Revel in the "Enchanting Key West Romantic Getaway" for a couple, starting at $1680. Our package is flexible and can be tailored to accommodate specific preferences and additional requests to make your romantic escape truly extraordinary.


Set the stage for an enchanting romantic journey in Key West, where every moment is a celebration of love and togetherness.

Book your trip today

Ready to start planning your dream vacation? Contact us today to learn more about our travel packages and deals.

Contact us

Sunsets & Sea

Sunsets & Sea Adventure Vacation Package

Embrace the essence of Key West with our "Sunset & Sea Adventure" package, combining the tranquil beauty of sunsets with the vibrant marine life beneath the waves. This experience promises unforgettable memories as you sail, snorkel, and savor the best of the ocean.


Included in the package:

Sensational Sunset Sail:

Embark on a luxurious catamaran and set sail towards the horizon.

Toast to the setting sun with a complimentary tropical drink as the sky paints a canvas of colors.


Reef Dive & Snorkel:

Dive into the crystalline waters and explore the vibrant coral reefs teeming with marine life.

All snorkeling equipment provided, along with guidance for beginners.


The Enchanting Dry Tortugas:

Experience a day trip to the pristine Dry Tortugas National Park, known for its rich history and untouched coral reefs.

Explore Fort Jefferson, an impressive 19th-century fort, and dive into the surrounding waters for a chance to see unique marine species.


Beachside Culinary Delight:

Conclude your adventure with a beachside dinner, where the ambiance of the waves meets gourmet flavors.

Savor locally-sourced seafood and specialties, complemented by a selection of wines and tropical drinks.


Optional Upgrades:

  • Private Charters & Seaplanes: Elevate your experience with private charters, offering personalized routes, timings, and amenities tailored to your preferences, and a seaplane excursion to the Dry Tortugas


Notes:

  • All activities are suitable for beginners and enthusiasts alike.
  • Safety is our utmost priority; all tours are led by certified and experienced guides.
  • Dietary preferences for dinner can be catered to upon request.


Pricing: The base rate starts at $430 per person. Private Charters & Seaplanes Packages accommodating up to 2 guests starts at $2550. The package can be tailored for groups with pricing adjustments based on customization requirements.


Dive into the magic of Key West and create lasting memories with our "Sunset & Sea Adventure" package!

Book your trip today

Ready to start planning your dream vacation? Contact us today to learn more about our travel packages and deals.

Contact us
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Discover Your Key West LLC

Key West, FL

786-883-1322

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