A sandy beach with lounge chairs, umbrellas, palm trees, and cornhole boards under a bright blue sky by the ocean.

Keys Discovery Getaway

3 Night Stay Itinerary in Islamorada, Fl

Craving a few more days in paradise? The Keys Discovery Getaway at Chesapeake Beach Resort is perfect for travelers who want to explore, unwind, and soak in the best of Islamorada. Over three nights, you’ll enjoy dolphin encounters, clear kayak paddles, and poolside relaxation. Dive into local culture with art galleries, live music, and coastal cuisine — then cap off your days with unforgettable views and toes-in-the-sand dining. It’s island living at its finest.

A boat docked by the water with a "Boat Rentals" sign on a sunny day, palm trees, and a clear blue sky in the background.

Arrival & Sunset Cruise

Day 1

  • Arrive and check in with Champagne on the house
  • Walk the beach, relax by the pool, or enjoy your ocean-view balcony
  • Borrow a bike for a sunset ride through Old Highway and the local marina district
  • Dinner at Wahoo’s Bar & Grill, steps from the resort
  • Evening: Sunset cruise with Cruisin’ Tikis from our private marina
Aerial view of a tropical resort with a swimming pool, palm trees, lounge chairs, and nearby beach access.

Sunrise, Dolphins & Poolside Play

Day 2

  • Greet the day with a peaceful clear kayak sunrise paddle
  • Enjoy breakfast in the Sunrise Room
  • Mid-morning: Head to Theater of the Sea for dolphin, sea lion, and marine life experiences
  • Lunch at Mangrove Mike’s
  • Afternoon options:
    Cool off in the pool or relax in the spa
    Play beach games like giant chess and cornhole
    Grab a fishing rod and try your luck at the marina
  • Friday guests can enjoy 8 AM yoga on the beach and live music at 3 PM
  • Dinner at Chef Michael’s — famous for fresh-caught hogfish
Sandy beach with lounge chairs, umbrellas, and palm trees under a clear blue sky, featuring bean bag toss boards on the sand.
A pristine beach scene with palm trees, white sand, lounge chairs, and a clear blue sky overlooking a calm sea enhances tranquility.

Sandbar Escape & Local Flavor

Day 3

  • Morning boat rental or charter to the Islamorada Sandbar — crystal-clear waters, music, and sunshine
  • Return in the afternoon for a nap in a hammock or beachside cocktails
  • Explore local art galleries or shop at Rain Barrel Village
  • Dinner at Pierre’s Restaurant — refined island dining
Aerial view of a tropical resort surrounded by clear turquoise water and lush greenery under a blue sky with scattered clouds.

Departure

Day 4

  • Enjoy a final breakfast at the Sunrise Room
  • Check-out and take home memories and maybe a local souvenir