Local Florida Keys Vacation Tips for a Memorable Island Escape


Planning your trip with Pinnacle Choice Properties means more than just finding the perfect place to stay—it’s about making the most of every moment in the Florida Keys. Whether you’re seeking outdoor adventures, local flavors, or laid-back island vibes, our local team has gathered the best Florida Keys vacation tips to help guide your journey. Explore by interest or location and start shaping your ideal itinerary.

Outdoor Activities

  • Snorkeling at John Pennekamp Coral Reef State Park – Dive into the only living coral barrier reef in the continental U.S.
  • Kayaking through mangroves – Paddle quiet, scenic waterways teeming with wildlife.
  • Deep sea and backcountry fishing – Charter a boat for a day of angling in the sportfishing capital of the world.
  • Paddleboarding on the bay – Calm, clear waters are ideal for a relaxing ride with views.
  • Sunset sailing cruises – End your day with a breezy boat ride and epic sunset.

Dining & Local Food

Lazy Days (Islamorada) – A Keys favorite for fresh seafood and oceanfront dining.

Hobo’s Café (Key Largo) – Local catch and casual fare with a Keys-style vibe.

Marker 88 (Tavernier) – Elegant dining with sunset views on the beach.

Island grill tiki bars – Relax with cocktails, live music, and waterfront views.

Food trucks and fresh seafood markets – Local favorites for grab-and-go meals.

Family-Friendly Fun

Florida Keys Aquarium Encounters – Interactive marine exhibits and hands-on feeding tanks.

Dolphin Research Center – Learn about marine mammals and enjoy family-friendly shows.

Founders Park (Islamorada) – A great spot for picnics, playgrounds, and beachfront fun.

Robbie’s of Islamorada – Feed tarpon, browse local shops, or rent paddleboards.

Glass-bottom boat tours – A fun way for all ages to see coral reefs without diving in.

Events & Seasonal Highlights

Lobster Mini-Season (July) – A must for seafood lovers and divers alike.

Island Fest (April, Islamorada) – Local art, music, food, and family fun.

Holidays in the Keys – Lighted boat parades and festive waterfront events.

Fishing tournaments – Spectator-friendly and exciting throughout the year.

Full moon parties – Monthly gatherings at local beaches and bars.

Shopping & Art

Rain Barrel Artisan Village (Islamorada)  – Eclectic shops and galleries in a fun outdoor setting.

Island Art Gallery (Tavernier) – Local art, handmade gifts, and coastal treasures.

Shell World (Key Largo) – A mix of souvenirs, décor, and nautical finds.

Weekly farmers markets – Fresh produce, crafts, and local treats.

Boutique shops – Unique fashion, home goods, and handmade jewelry.

Top Recommendations by Location

Key Largo

John Pennekamp Coral Reef State Park

Hobo’s Café

Sundowners waterfront dining

Glass-bottom boat tours

Shell World

Tavernier

Marker 88 for oceanfront dining

Old Settler’s Park for quiet, local charm

Island Art Gallery

Paddleboarding in the mangroves

Boutique shops and cafés

Islamorada

Robbie’s Marina

Lazy Days restaurant

Florida Keys Brewing Company

Rain Barrel Artisan Village

Founders Park

Enjoy local guidance and unforgettable adventures with the best Florida Keys vacation tips. Book your stay now!