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Islamorada

Key West

6-Day Luxury Florida Keys Escape

6 days

2 cities

30 experiences

2 hotels

2 transports

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Atlanta

Islamorada

Dec 23 – 25

Key West

Dec 25 – 28

Atlanta

Days 1-3

Dec 23 – 25

Islamorada

Hi! For your stay in Islamorada from December 23 to 25, 2026, get ready to enjoy the stunning ocean views and serene beaches that make this spot a true Florida Keys gem. Islamorada offers a perfect blend of luxury boutique resorts and peaceful natural beauty, ideal for a relaxing holiday escape. Whether you're into water activities like snorkeling and fishing or simply unwinding in a warm, tropical setting, Islamorada will delight you both!

Stay

Days 1-3

Dec 23 – 25

2 nights

Cheeca Lodge & Spa

Room, 2 Queen Beds, Resort View (Guestroom)

9.2

Wonderful1,459 reviews

Itinerary

Days 1-3

Dec 23 – 25

Day 1•Dec 23•

25°C•4 Experiences

Arrival and Settling into Island Life

Day 2•Dec 24•

25°C•4 Experiences

Exploring History and Sunset Cruises

Day 3•Dec 25•

23°C•3 Experiences

Morning Leisure and Departure to Key West

Days 3-6

Dec 25 – 28

Key West

Experience the vibrant charm of Key West's historic Old Town, with its colorful architecture and lively Duval Street. Enjoy luxurious boutique hotels and savor fresh seafood while watching stunning sunsets at Mallory Square. This leg offers a perfect blend of relaxation, culture, and festive holiday spirit in a warm, tropical setting.