A boat is docked at a marina under a bright blue sky, with a sign advertising boat rentals in the foreground.

Weekend Escape in the Keys

2-Night Stay Itineraries in Islamorada, Fl

Planning a short escape? Chesapeake Beach Resort offers the ideal two-night getaway in the heart of Islamorada. Enjoy Champagne on arrival, sunset tiki cruises, clear kayak paddles, and beachfront yoga all designed for maximum relaxation. Spend your days lounging poolside, biking through the island, or savoring fresh seafood by the water. With ocean views, beach games, and live music to round out the experience, this quick island retreat is the perfect way to relax, recharge, and soak in the Keys.

Two tropical drinks with straws, garnished with fruit, are next to a box containing a pineapple, oranges, and leafy greens.
Chesapeake Beach Resort

Arrival & Island Welcome

Day 1

  • Check-in and enjoy a complimentary glass of Champagne - Rosé or dry Brut
  • Settle into your room, then relax poolside or in a hammock with ocean views
  • Explore our beachfront game area with oversized chess, checkers, and cornhole
  • Borrow a bike from the resort for a relaxing ride through Islamorada
  • Dinner at Wahoo’s Bar & Grill for fresh seafood and a laid-back marina setting
  • Sunset: Cruise from our marina with Cruisin’ Tikis - a floating tiki bar offering breathtaking ocean views
People are practicing yoga outdoors on blue mats in front of a modern building with palm trees around, under a clear blue sky.
A sunny waterfront scene with a moored boat and a sign advertising boat rentals, set in a tropical locale with blue skies and palm trees.
A boat docked at a wooden pier with a person nearby, surrounded by lush greenery and palm trees, under a bright blue sky with clouds.

Sunrise, Yoga & Island Fun

Day 2

  • Begin the day with a clear kayak paddle at sunrise — launching directly from the beach
  • Refuel with a hot breakfast in the Sunrise Room, offering fresh tropical fruit, pastries, and warm entrées
  • Saturday at 8 AM: Complimentary beachfront yoga to stretch and energize your morning
  • Mid-morning visit to Robbie’s Marina to feed the tarpon or book a short snorkeling trip
  • Afternoon options:
    Lounge at Founders Park Beach or enjoy our spa and pools.
    Fish off the marina — complimentary fishing rods available at the front desk.
    Challenge a friend to a game of cornhole or giant checkers.
  • 3 PM: Live entertainment on the beach — enjoy the music, ocean breeze, and relaxed vibe
  • Dinner at Morada Bay Beach Café — a toes-in-the-sand sunset dining experience
A breakfast spread with an omelet, waffle, fruits, juice, and coffee on a table near water, along with wooden cutlery arranged neatly.
Chesapeake Beach Resort

Easy Morning & Farewell

Day 3

  • Grab a light breakfast or coffee in the Sunrise Room
  • Take one last stroll or photo op at Rain Barrel Village before check-out