The Hindu Charters Guide to a Perfect Day in Key West
Local favorites from our crew—because sailing is only half the adventure.
Key West is more than turquoise water and golden sunsets. It’s farmers markets and funky music, mangroves and martinis, parrots and pastries. When you’re not aboard one of our beautiful sailing vessels, here’s how the Hindu Charters crew spends their time ashore.
1. Key West Artisan Market at Truman Waterfront Park
Get a large Agua Fresca. Sample exotic fruits and cheeses from around the world. Support local artists and makers.
Held weekly (rain or shine) at Truman Waterfront Park, this vibrant open-air market features:
- Fresh local produce
- Eat-in or take-away food vendors
- Handmade arts & crafts
- Island-inspired merchandise
It’s colorful, community-driven, and the perfect way to ease into island time before your sail.
2. Green Parrot Bar – Sound Check Sessions
Low-commitment afternoon fun with serious local flavor.
Now in its 10th consecutive year of being voted Key West’s “Best Live Music Venue” by the Keys Weekly People’s Choice Awards, the Green Parrot is more than a bar—it’s an icon.
Catch a sound check in the afternoon, grab a cold drink, and settle in for authentic, unpolished island rhythm. The Parrot has been many things to many people over many years—and that spirit hasn’t changed a bit.
3. Andy’s Cabana Thursday Open Mic Night
(Across from Blue Heaven)
On Thursdays, locals let their hair down. Musicians gather, guitars come out, and the island’s creative pulse is on full display. It’s intimate, it’s unfiltered, and it’s pure Key West.
4. Kirby’s Closet – Dress Happy
Our crew doesn’t get many chances to dress up—but when we do, we head straight to Kirby’s.
This women’s boutique serves up Tropical Glam in the heart of downtown. Bright, fun, and unique pieces encourage you to “Dress Happy.” Affordable, welcoming, and full of sparkle—it’s a little slice of island fashion magic.
5. Happy Hour Favorites
Our go-to spots:
- Boat House Bar & Grill
- Martin’s
- The Saint Hotel Key West
- Old Town Tavern (Late night happy hour starts at 11 PM!)
Island cocktails. Fresh seafood. Laid-back elegance. You really can’t go wrong.
6. Breakfast at Frenchie’s Cafe
Gaston will wag his tail and greet you at the door. Stephanie and Xavier will take exceptional care of you while lighting up your taste buds with pastries so delicate they practically melt in your mouth.
Start your day here before heading out on the water.
7. Fort Zachary Taylor Historic State Park
Pack a picnic. Plan to spend the day.
This beautiful sandy beach is perfect for swimming and snorkeling—kids love using goggles to study sea life. It’s also one of the best sunset spots on the island, where you can watch the nightly parade of sail drift across the horizon.
8. Kayak Through the Mangroves
Explore the quiet side of Key West with:
- Lazy Dog Adventures
- Kayak Kings Key West
These exhilarating, human-powered adventures wind through mangrove tunnels and shallow backwaters—an unforgettable way to experience the island’s natural beauty.
9. Wildlife & Wonder
- Key West Wildlife Center
- Nancy Forrester’s Secret Garden
Visit rescued birds and learn about local conservation efforts. It’s intimate, educational, and a beautiful reminder of how special this ecosystem truly is.
10. The Studios of Key West & Books & Books
Check the event calendar. See what’s on display. Take a class if you’re staying awhile.
Then wander into Books & Books and leave with a story of your own.
And Then… Go Sailing.
There’s no better way to complete your Key West adventure than by stepping aboard one of our wind-driven vessels.
Whether you choose the refined elegance of the classic schooner, the modern luxury of our 75-foot catamaran, or the thrill of a powerful racing cutter, you’ll experience Key West the way it was meant to be seen—from the water.
Craft cocktails in hand. Salt air on your skin. No engines. No crowds. Just horizon.
Sail as you are with Hindu Charters.
Book your sunset, brunch, or private charter today—and make your time in Key West unforgettable.