14 days in Southeast Florida Itinerary

14 days in Southeast Florida Itinerary

Created using Inspirock Southeast Florida holiday builder

Make it your trip
Fly
1
Miami
— 2 nights
Drive
2
Key Largo
— 3 nights
Drive
3
Islamorada
— 3 nights
Drive
4
Big Pine Key
— 1 night
Drive
5
Key West
— 4 nights
Fly

S M T W T F S
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29

Miami

— 2 nights

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Change things up with a short trip to Shark Valley Visitor Center in Everglades National Park (about 1 hour away). The adventure continues: tour the pleasant surroundings at South Beach, admire the striking features of Freedom Tower at Miami Dade College, appreciate the extensive heritage of Lincoln Road, and wander the streets of Art Deco Historic District.

For where to stay, other places to visit, photos, and tourist information, you can read our Miami trip planner.

San Diego to Miami is an approximately 7-hour flight. You can also drive; or take a bus. The time zone difference moving from Pacific Standard Time to Eastern Standard Time is 3 hours. Plan for a bit warmer temperatures traveling from San Diego in May, with highs in Miami at 87°F and lows at 74°F. Wrap up your sightseeing on the 14th (Fri) early enough to drive to Key Largo.

Things to do in Miami

Parks · Outdoors · Historic Sites · Neighborhoods

Side Trips

Key Largo

— 3 nights

Diving Capital of the World

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Explore Key Largo's surroundings by going to Everglades National Park (Mrazek Pond & Anhinga Trail). Next up on the itinerary: see some colorful creatures with a scuba or snorkeling tour, look for gifts at Scooby's Popcorn, take a tour of African Queen Canal Cruise, and explore the gorgeous colors at Spiegel Grove.

For other places to visit, where to stay, traveler tips, and other tourist information, go to the Key Largo online day trip planner.

Traveling by car from Miami to Key Largo takes 1.5 hours. Alternatively, you can take a bus. May in Key Largo sees daily highs of 85°F and lows of 72°F at night. Finish your sightseeing early on the 17th (Mon) so you can drive to Islamorada.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

Side Trip

Islamorada

— 3 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.
Change things up with these side-trips from Islamorada: Marathon (Shady Palm Art Gallery & Photography, The Turtle Hospital, &more). There's lots more to do: cast your line with a fishing tour, view the masterpieces at Michelle Nicole Lowe Art Gallery, identify plant and animal life at Dolphin Research Center, and indulge your thirst for a good beer at Islamorada Brewery & Distillery.

For ratings, traveler tips, other places to visit, and tourist information, read our Islamorada trip itinerary maker.

Islamorada is just a short distance from Key Largo. In May, daily temperatures in Islamorada can reach 88°F, while at night they dip to 77°F. Finish your sightseeing early on the 20th (Thu) so you can drive to Big Pine Key.

Things to do in Islamorada

Outdoors · Wildlife · Parks · Breweries & Distilleries

Side Trip

Big Pine Key

— 1 night
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. On the 21st (Fri), enjoy the sand and surf at Bahia Honda State Park and then get a new perspective on things with Boat Tours & Water Sports.

To see ratings, where to stay, more things to do, and tourist information, read our Big Pine Key trip itinerary website.

You can drive from Islamorada to Big Pine Key in 1.5 hours. Another option is to take a bus. In May, plan for daily highs up to 88°F, and evening lows to 77°F. Finish your sightseeing early on the 21st (Fri) so you can drive to Key West.

Things to do in Big Pine Key

Outdoors · Tours · Wildlife · Beaches

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, steep yourself in history at Truman Little White House, see some colorful creatures with a scuba or snorkeling tour, and identify plant and animal life at Key West Butterfly & Nature Conservatory.

Inspirock's itinerary builder makes planning a Key West trip simple and quick.

Drive from Big Pine Key to Key West in an hour. Alternatively, you can take a shuttle; or take a bus. In May in Key West, expect temperatures between 85°F during the day and 77°F at night. Wrap up your sightseeing on the 25th (Tue) early enough to travel back home.

Things to do in Key West

Parks · Outdoors · Historic Sites · Museums