29 days in Florida Keys Itinerary

29 days in Florida Keys Itinerary

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Route & dates

29 days in Florida Keys Itinerary

Start: Moncton
Fly + Drive:  11​h
1
Islamorada
— 7 nights
Drive:  1​h 15​min
2
Big Pine Key
— 3 nights
bus:  45​min
3
Key West
— 10 nights
bus:  1​h 15​min
4
Marathon
— 7 nights
Drive + Fly:  11​h 15​min
End: Moncton

7
nights
Islamorada

Islamorada ©
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 a short trip to John Pennekamp Coral Reef State Park in Key Largo (about 32 minutes away). There's lots more to do: take a tour by water with Boat Tours & Water Sports, get interesting insight from Tours, admire nature's wide array of creatures at Island Dolphin Care, and sample the tasty concoctions at Florida Keys Brewing Company.

To see reviews, ratings, maps, and tourist information, read Islamorada day trip planning website .

Moncton, Canada to Islamorada is an approximately 11-hour flight. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. Expect much hotter temperatures when traveling from Moncton in May; daily highs in Islamorada reach 36°C and lows reach 29°C. Finish your sightseeing early on the 4th (Tue) to allow enough time to drive to Big Pine Key.

Things to do in Islamorada

Outdoors Parks Tours

Side Trip

Key Largo
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Scuba & Snorkeling
Fishing Charters & Tours

3
nights
Big Pine Key

Big Pine Key ©
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. Big Pine Key is known for nature, wildlife, adventure, nightlife, and shopping. Your plan includes some of its best attractions: admire the majestic nature at Bahia Honda State Park, don't miss a visit to Adolphus Busch, view the masterpieces at Artists in Paradise Gallery, and look for all kinds of wild species at Blue Hole.

To see traveler tips, where to stay, other places to visit, and other tourist information, you can read our Big Pine Key trip site .

Traveling by car from Islamorada to Big Pine Key takes 1.5 hours. Alternatively, you can take a bus. June in Big Pine Key sees daily highs of 38°C and lows of 30°C at night. Wrap up your sightseeing on the 7th (Fri) to allow time to take a bus to Key West.

Things to do in Big Pine Key

Wildlife Parks Outdoors
Highlights from your plan
National Key Deer Refuge ©
National Key Deer Refuge
Bahia Honda State Park ©
Bahia Honda State Park
Fishing Charters & Tours

10
nights
Key West

Key West ©
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.
Spend the 11th (Tue) exploring nature at Dry Tortugas National Park. There's still lots to do: see the interesting displays at The Ernest Hemingway Home and Museum, get a new perspective on things with Boat Tours & Water Sports, make a trip to Southernmost Point, and contemplate the long history of Truman Little White House.

To find more things to do, traveler tips, reviews, and tourist information, you can read our Key West visit planning website .

Take a bus from Big Pine Key to Key West in an hour. Alternatively, you can drive. June in Key West sees daily highs of 36°C and lows of 30°C at night. Wrap up your sightseeing on the 17th (Mon) to allow time to take a bus to Marathon.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Scuba & Snorkeling

7
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Marathon is known for wildlife, beaches, adventure, nature, and shopping. Your plan includes some of its best attractions: look for all kinds of wild species at The Turtle Hospital, get all the information you need at Pigeon Key Foundation, cast your line with a fishing tour, and see some colorful creatures with a scuba or snorkeling tour.

To find maps, ratings, and other tourist information, go to the Marathon trip planner .

You can take a bus from Key West to Marathon in 1.5 hours. Another option is to drive. June in Marathon sees daily highs of 38°C and lows of 30°C at night. You'll have a few hours on the 24th (Mon) to wrap things up before traveling home.

Things to do in Marathon

Parks Wildlife Outdoors

Side Trip

Sunset Park Beach
Highlights from your plan
The Turtle Hospital ©
The Turtle Hospital
Sombrero Beach ©
Sombrero Beach
Scuba & Snorkeling

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