Key West & Beyond: A Laid-Back Island Getaway – February 18-24, 2026
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This is a Level I Activity Tour – Click Here for a Description
Itinerary
Day One – February 18: Arrival in Miami
Our tropical getaway begins with an early morning flight from Portland to vibrant Miami. Upon arrival, we’ll check into our hotel in the heart of the city’s lively Brickell district. After time to settle in, we’ll gather for a welcome dinner at a local favorite—savoring warm breezes, flavorful cuisine, and the first taste of Florida sunshine.
Day Two – February 19: Miami to Key West
This morning we step back into Miami’s elegant past with a guided visit to Vizcaya Museum & Gardens—an exquisite European-style villa surrounded by lush subtropical gardens and bay front views. Then we’re off on one of America’s most scenic drives: the Overseas Highway. With water on both sides, we’ll travel across a string of coral islands to enchanting Key West. After checking in at our waterfront resort, we’ll head to Mallory Square to take part in the island’s world-famous sunset celebration. Tonight, we dine at a lively restaurant on historic Duval Street.
Day Three – February 20: Old Town Key West & More
Enjoy a free morning to explore charming Old Town at your own pace with your included hop-on-hop-off trolley pass. Stroll past gingerbread-trimmed houses, visit art galleries, or stop for a slice of Key lime pie. In the afternoon, we’ll visit the colorful Southernmost Point and tour Truman’s Little White House, once a presidential retreat. This evening, we’ll board a luxury catamaran for a dinner cruise—sailing into the golden light of sunset with music, laughter, and a delicious meal on the water.
Day Four – February 21: Shipwrecks, Hemingway & a Lighthouse
Step into maritime history this morning at the Key West Shipwreck Museum, where the stories of daring salvagers come alive. After lunch on your own, we’ll tour the Hemingway Home, where the famed author wrote some of his greatest works, and climb the iconic Key West Lighthouse for sweeping island views. Tonight’s dinner is a culinary delight at another local favorite, perched above the water at Sunset Pier—an unforgettable setting to toast another beautiful day.
Day Five – February 22: Key West to Key Largo
After breakfast, we’ll visit the fascinating Fort East Martello Museum, home to quirky Key West history and the mysterious Robert the Doll. Then we journey north along the scenic highway to Key Largo. Along the way, we’ll stop for a casual lunch before arriving at our bayside hotel. Tonight, we’ll dine dockside at Skippers—watching boats drift by as we enjoy fresh seafood and warm tropical breezes.
Day Six – February 23: Coral Reef State Park to the Everglades
Get ready for a day of natural beauty and adventure. We begin at Pennekamp Coral Reef State Park, where we’ll board a glass-bottom boat to view the vibrant marine life of America’s first undersea park. After a waterfront lunch, we’ll venture into the untamed beauty of the Everglades with a visit to the Everglades Alligator Farm—complete with thrilling wildlife encounters. Later, we return to Miami and enjoy our final dinner together, savoring the memories of an unforgettable week.
Day Seven – February 24: Miami then Home
Our final morning begins with a relaxed breakfast and some free time before we head to the colorful Art Deco District of Miami Beach. At the Art Deco Museum, we’ll learn about the city’s iconic pastel architecture and cultural history. Enjoy a bit more time to stroll Ocean Drive or pick up souvenirs before we transfer to the airport for our flight home—bringing back stories of sunshine, sea air, and island charm.