9 days in Key West, Islamorada & Miami Beach Itinerary

9 days in Key West, Islamorada & Miami Beach Itinerary

Created using Inspirock Florida holiday planner

Make it your trip
Fly
1
Key West
— 4 nights
Drive
2
Islamorada
— 2 nights
Drive
3
Miami Beach
— 2 nights
Fly

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Key West

— 4 nights

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Key West is known for wildlife, adventure, and museums. Your plan includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, take a leisurely stroll along Mallory Square, look for gifts at Isle Cook Key West, and brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum.

To find photos, more things to do, maps, and more tourist information, go to the Key West visit planning website.

Philadelphia to Key West is an approximately 5-hour flight. You can also drive; or take a bus. When traveling from Philadelphia in May, plan for a bit warmer days in Key West, with highs around 85°F, while nights are warmer with lows around 77°F. You'll set off for Islamorada on the 26th (Wed).

Things to do in Key West

Museums · Historic Sites · Wildlife · Tours

Islamorada

— 2 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Your day by day itinerary now includes Robbie's of Islamorada as well as Bahia Honda State Park. On the 26th (Wed), enjoy the sand and surf at Bahia Honda State Park, enjoy the sand and surf at Sombrero Beach, then see the interesting displays at Crane Point Museum & Nature Center, and finally indulge your thirst for a good beer at Islamorada Brewery & Distillery. On the next day, stop by Bass Pro Shops, see what you can catch with a fishing tour, and then discover the deep blue sea with Robbie's of Islamorada.

To see maps, other places to visit, where to stay, and more tourist information, you can read our Islamorada online travel planner.

Traveling by car from Key West to Islamorada takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 88°F in May, and nighttime lows around 77°F. Finish your sightseeing early on the 28th (Fri) to allow enough time to drive to Miami Beach.

Things to do in Islamorada

Outdoors · Parks · Wildlife · Beaches

Side Trips

Miami Beach

— 2 nights

The World's Playground

Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Kick off your visit on the 28th (Fri): see the interesting displays at Vizcaya Museum and Gardens and then look for all kinds of wild species at Shark Valley Visitor Center. Keep things going the next day: browse the different shops at Bayside Marketplace, get to know the fascinating history of Art Deco Historic District, and then stroll through South Beach.

To see traveler tips, maps, photos, and more tourist information, refer to the Miami Beach day trip planner.

Drive from Islamorada to Miami Beach in 2 hours. Alternatively, you can do a combination of shuttle and bus; or take a bus. In May, daily temperatures in Miami Beach can reach 87°F, while at night they dip to 74°F. Wrap up your sightseeing by early afternoon on the 30th (Sun) to allow enough time to fly back home.

Things to do in Miami Beach

Parks · Outdoors · Shopping · Historic Sites

Side Trips