A coastal area with turquoise waters, a line of buildings, palm trees, and a road with vehicles under a cloudy sky ends the scene.

The Full Islamorada Experience

5+ Night Stay Itinerary in Islamorada, Fl

Ready for the ultimate island adventure? With six nights of unparalleled relaxation and exploration, our Full Islamorada Experience offers the best of both worlds. From sunrise kayak paddles and reef adventures to sunset cruises and beachfront dining, each day brings a new opportunity to immerse yourself in the beauty and culture of Islamorada. Whether you’re lounging by the pool, fishing off the marina, or exploring local wildlife and history, this extended stay is the perfect way to embrace island life.

Chesapeake Beach Resort

Check-in & Tiki Time

Day 1

  • Welcome with Champagne and a guided walk of the property
  • Unpack and unwind with a dip in the pool or a bike ride through the area
  • Test your skills with chess, cornhole, or checkers on the beach
  • Dinner at Wahoo’s Bar & Grill
  • Evening: Cruisin’ Tikis sunset cruise from our marina
Colorful kayaks lined up on a sandy beach with palm trees and lounge chairs in the background.

Sunrise Paddle & Reef Adventure

Day 2

  • Early morning clear kayak paddle as the sun rises over the Atlantic
  • Hot breakfast at the Sunrise Room
  • Morning snorkeling trip to Alligator Reef or Hen & Chickens Reef
  • Afternoon: Relax by the pool, enjoy a spa treatment, or fish from the marina
  • Dinner at Marker 88, offering sunset views and fresh local flavors
Aerial view of a coastal resort with a lagoon, palm trees, and buildings surrounded by turquoise water and lush greenery under a blue sky.

Island Culture & Wildlife

Day 3

  • Visit Theater of the Sea for marine shows and up-close animal encounters
  • Afternoon kayaking to Indian Key Historic State Park
  • Shop and explore at Rain Barrel Village
  • Happy hour at Florida Keys Brewing Co., followed by dinner at Square Grouper
  • Optional: Stargazing or beach bonfire at the resort
A beachfront scene with palm trees, lounge chairs, and a building under a clear blue sky, viewed from the water’s edge.

Sandbar & Sunset Vibes

Day 4

  • Spend the day at the Islamorada Sandbar — accessible by boat or guided charter
  • Afternoon leisure: nap in a hammock, play beach games, or enjoy the spa
  • 3 PM: Live beachside entertainment on select afternoons
  • Dinner at Morada Bay Beach Café, right on the sand
A small boat is docked near a sign for boat rentals by the water, with palm trees and a clear sky in the background.

Adventure or Rest

Day 5

  • Optional activities: reef diving, parasailing, paddleboarding, or another Cruisin’ Tikis sunset cruise
  • Join Saturday yoga at 8 AM, or simply relax by the pool
  • Dine at your favorite restaurant one last time, or ask the front desk for a hidden local gem
Two tropical drinks with straws sit in front of a crate containing a pineapple, orange, and green leaves, against a blurred background.

Departure

Day 6

  • Final breakfast at the Sunrise Room
  • Late check-out available upon request