Labor Day weekend is a treasured time to embrace the final stretch of summer, and Key West stands out as one of the most lively, scenic, and experience-rich places to spend it. At The Reach, Curio Collection by Hilton, guests are invited to step into a world of beachfront fun, relaxed sophistication, and unforgettable moments. Our team has thoughtfully curated a list of the top 10 Labor Day activities, blending the best of Key West with exclusive experiences right here at the resort.
Whether you’re looking to unwind under the stars, discover vibrant island culture, or dive into a weekend full of seaside games and culinary delights, The Reach offers the ideal destination to create lasting holiday memories.
Visit our Special Offers page to reserve your stay and take advantage of exclusive Labor Day deals.
1. Beachside Welcome and Island Games
Start your weekend the island way. Guests arriving on Friday are welcomed with refreshing snow cones served right on the beach, setting the tone for a carefree and festive stay. The fun continues on Saturday with oceanfront basket pong, where guests of all ages can engage in some lighthearted competition while enjoying ocean views and sunshine. These opening-day activities help you settle into the Key West vibe with ease.
2. Sunday Beach Olympics
Sunday brings a highlight of the weekend with our action-packed Beach Olympics. This spirited event features family-friendly challenges like foam “axe” throwing, tug of war, sack races, and relay competitions. It is an open invitation for guests to connect, compete, and share laughter in a relaxed beachside setting.
3. Sunset Sails with Barefoot Billy’s
One of the most iconic experiences in Key West is the Sunset Cruise, and Barefoot Billy’s delivers it in style. Step aboard a sleek catamaran and enjoy gourmet bites such as sushi, Thai-inspired small plates, and a hand-curated charcuterie platter paired with fine wine. Watch the sky shift into hues of gold and coral as the sun dips beneath the horizon.
4. Exploring Duval Street and Local Music
No trip to Key West is complete without exploring Duval Street, the heart of the island’s culture and nightlife. Stroll past colorful storefronts, discover vibrant street art, and catch live performances by local musicians. From energetic band sets to soulful acoustic sessions, Duval’s music scene adds rhythm to your weekend adventure.
6. Jet Ski Tours with Barefoot Billy’s
For thrill-seekers, Barefoot Billy’s offers guided jet ski tours that take you along Key West’s scenic coastline. Feel the ocean spray and enjoy panoramic views as you cruise past famous landmarks and hidden gems. It is a great way to add adventure to your weekend.
7. Brunch or Dinner at Four Marlins
Our signature oceanfront restaurant, Four Marlins, invites you to indulge in seasonal flavors and island-inspired dishes. Join us for brunch with a mimosa in hand or savor a sunset dinner paired with fresh seafood and live music. The combination of exquisite cuisine and a stunning seaside backdrop makes for a truly memorable dining experience.
8. Best of Both Worlds: Events at Casa Marina
Guests of The Reach are also welcome to enjoy Casa Marina events, located just a short walk away. This includes sunglasses crafting. twisted tie-dye arts, and more. It is a great way to enjoy even more variety and fun between both properties.
9. Cornhole and Lawn Games
Throughout the weekend, The Reach offers laid-back recreational fun with lawn games like cornhole, perfect for impromptu matches with friends or new acquaintances. Grab a cocktail, find a spot in the shade, and embrace the casual camaraderie that defines Key West.
10. Relax Poolside with Tropical Refreshments
Sometimes, the best part of a holiday weekend is doing absolutely nothing at all. Lounge by our sparkling pool with a frozen cocktail or a tropical mocktail in hand, and soak up the island sun. Elevate your relaxation by renting a private cabana, perfect for groups or couples who want a bit more space and shade. Whether you’re catching up on a beach read, enjoying light bites from Four Marlins, or simply unwinding with ocean breezes and water views, our poolside scene is the perfect complement to your active weekend itinerary.
Plan Your Perfect Labor Day Weekend at The Reach
With a thoughtfully designed mix of relaxation, adventure, and island culture, The Reach is your go-to destination for Labor Day Weekend 2025. Whether you’re splashing in the surf, savoring local flavors, or enjoying the friendly energy of a beachside game, this is the place to slow down and soak it all in.
Book your stay now through our Special Offers page, and for more details on resort happenings, visit our Events Page. We cannot wait to welcome you for a truly unforgettable holiday weekend.
