South Florida Sunshine Getaway: Miami, Key West & The Keys

Introduction
South Florida Sunshine Getaway: Miami, Key West & The Keys image

Miami, Key West & The Keys / 7 Days

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South Florida Sunshine Getaway: Miami, Key West & The Keys

Escape to the sun-drenched beauty of South Florida on this seven-day journey through Miami, Key West, and the Florida Keys. From Miami’s Art Deco flair to the laid-back rhythm of island life, this is a perfectly paced getaway filled with sunshine, scenery, history, and fun. Join us and experience the best of South Florida—one sunset at a time!

Tropical Adventure Overview

Tropical Adventure Overview image

At a glance

Day 1 - Arrival in Miami and Welcome Dinner

18-Feb-2025
Day 1 - Arrival in Miami and Welcome Dinner image

Arrive in Miami and Enjoy a Welcome Dinner

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Early Morning Flight from Portland to Miami

Feb 18, 2025
Portland

Feb 18, 2025
Miami
Our tropical getaway begins with an early morning flight from Portland to vibrant Miami.
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Hotel in Brickell District, Miami

Check inTuesday, Feb 18, 2025
Upon arrival, we’ll check into our hotel in the heart of the city’s lively Brickell district.
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Welcome Dinner at Local Favorite

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 2 - Miami to Key West

19-Feb-2025
Day 2 - Miami to Key West image

Scenic Drive to Key West and Sunset Celebration

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Guided Visit to Vizcaya Museum & Gardens

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.
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Drive on Overseas Highway to Key West

DepartureMiami
DestinationKey West
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.
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Waterfront Resort in 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.
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Mallory Square Sunset Celebration

Head to Mallory Square to take part in the island’s world-famous sunset celebration.
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Dinner on Duval Street

Tonight, we dine at a lively restaurant on historic Duval Street.

Day 3 - Old Town Key West & More

20-Feb-2025
Day 3 - Old Town Key West & More image

Explore Old Town, Southernmost Point, and Sunset Cruise

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Free Morning in Old Town Key West

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.
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Visit to Southernmost Point

In the afternoon, we’ll visit the colorful Southernmost Point.
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Tour of Truman’s Little White House

Tour Truman’s Little White House, once a presidential retreat.
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Luxury Catamaran Dinner Cruise

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 4 - Shipwrecks, Hemingway & a Lighthouse

21-Feb-2025
Day 4 - Shipwrecks, Hemingway & a Lighthouse image

Maritime History, Hemingway Home, and Lighthouse Views

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Key West Shipwreck Museum

Step into maritime history this morning at the Key West Shipwreck Museum, where the stories of daring salvagers come alive.
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Tour of Hemingway Home

Tour the Hemingway Home, where the famed author wrote some of his greatest works.
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Climb Key West Lighthouse

Climb the iconic Key West Lighthouse for sweeping island views.
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Dinner at Sunset Pier

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 5 - Key West to Key Largo

22-Feb-2025
Day 5 - Key West to Key Largo image

Journey from Key West to Key Largo and Dockside Dining

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Visit to Fort East Martello Museum

Visit the fascinating Fort East Martello Museum, home to quirky Key West history and the mysterious Robert the Doll.
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Drive from Key West to Key Largo

DepartureKey West
DestinationKey Largo
Journey north along the scenic highway to Key Largo, with a stop for a casual lunch along the way.
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Bayside Hotel in Key Largo

Arrive at our bayside hotel in Key Largo.
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Dinner at Skippers Dockside

Dine dockside at Skippers—watching boats drift by as we enjoy fresh seafood and warm tropical breezes.

Day 6 - Coral Reef State Park to the Everglades

23-Feb-2025
Day 6 - Coral Reef State Park to the Everglades image

Glass-Bottom Boat, Everglades Wildlife, Miami Return

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Glass-Bottom Boat at Pennekamp Coral Reef State Park

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.
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Waterfront Lunch

After a waterfront lunch, we’ll venture into the untamed beauty of the Everglades with a visit to the Everglades Alligator Farm.
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Visit to Everglades Alligator Farm

Venture into the untamed beauty of the Everglades with a visit to the Everglades Alligator Farm—complete with thrilling wildlife encounters.
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Return to Miami

DepartureEverglades
DestinationMiami
Later, we return to Miami and enjoy our final dinner together, savoring the memories of an unforgettable week.
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Final Dinner in Miami

Enjoy our final dinner together, savoring the memories of an unforgettable week.

Day 7 - Miami Beach, Art Deco & Departure

24-Feb-2025
Day 7 - Miami Beach, Art Deco & Departure image

Art Deco District, Ocean Drive, and Departure

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Relaxed Breakfast

Our final morning begins with a relaxed breakfast and some free time before we head to the colorful Art Deco District of Miami Beach.
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Visit to Art Deco Museum

At the Art Deco Museum, we’ll learn about the city’s iconic pastel architecture and cultural history.
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Stroll Ocean Drive and Souvenir Shopping

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.
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Transfer to Airport

DepartureMiami Beach
DestinationMiami Airport
Transfer to the airport for our flight home.
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Map

1. Brickell District, Miami

Brickell, Miami, FL

2. Vizcaya Museum & Gardens

3251 S Miami Ave, Miami, FL 33129

3. Mallory Square

400 Wall St, Key West, FL 33040

4. Duval Street

Duval St, Key West, FL 33040

5. Southernmost Point

Whitehead St & South St, Key West, FL 33040

6. Truman's Little White House

111 Front St, Key West, FL 33040

7. Key West Shipwreck Museum

1 Whitehead St, Key West, FL 33040

8. Hemingway Home

907 Whitehead St, Key West, FL 33040

9. Key West Lighthouse

938 Whitehead St, Key West, FL 33040

10. Sunset Pier

0 Duval St, Key West, FL 33040

11. Fort East Martello Museum

3501 S Roosevelt Blvd, Key West, FL 33040

12. Key Largo

Key Largo, FL 33037

13. Skippers Dockside

528 Caribbean Dr, Key Largo, FL 33037

14. Pennekamp Coral Reef State Park

102601 Overseas Hwy, Key Largo, FL 33037

15. Everglades Alligator Farm

40351 SW 192nd Ave, Homestead, FL 33034

16. Art Deco Museum

1001 Ocean Dr, Miami Beach, FL 33139

17. Ocean Drive

Ocean Dr, Miami Beach, FL 33139

18. Miami International Airport

2100 NW 42nd Ave, Miami, FL 33126