32 days in Florida, Santa Monica & Oshkosh Itinerary

32 days in Florida, Santa Monica & Oshkosh Itinerary

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Route & dates

32 days in Florida, Santa Monica & Oshkosh Itinerary

Start: London
Fly + tram:  11​h 15​min
1
Miami
— 3 nights
Drive:  1​h 15​min
2
Key Largo
— 4 nights
Drive:  2​h 30​min
3
Key West
— 5 nights
Fly + Drive:  5​h 45​min
4
St. Augustine
— 1 night
Drive:  2​h
5
Orlando
— 5 nights
+3
train + taxi + Fly + Drive:  5​h
6
Pensacola Beach
— 2 nights
+2
taxi + Fly + bus:  9​h 15​min
7
Santa Monica
— 4 nights
Fly:  9​h
8
Oshkosh
— 3 nights
Fly:  17​h 15​min
End: London

3
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Go for a jaunt from Miami to Davie to see iFLY Indoor Skydiving - Fort Lauderdale about 48 minutes away. There's much more to do: enjoy the sand and surf at South Beach, get to know the fascinating history of Art Deco Historic District, admire the natural beauty at Fairchild Tropical Botanic Garden, and choose your vessel at Mark the Shark.

To see other places to visit, where to stay, reviews, and other tourist information, read Miami trip itinerary planner.

London, UK to Miami is an approximately 11.5-hour combination of flight and tram. You can also do a combination of flight and train. You'll gain 5 hours traveling from London to Miami due to the time zone difference. Traveling from London in July, you will find days in Miami are a bit warmer (38°C), and nights are warmer (30°C). Finish up your sightseeing early on the 18th (Thu) so you can go by car to Key Largo.

Things to do in Miami

Parks Outdoors Historic Sites

Side Trips

Miami Beach, Coral Gables, iFLY Indoor Skydiving - Fort Lauderdale
Highlights from your plan
Lock & Load Miami ©
Lock & Load Miami
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

4
nights
Key Largo

Key Largo ©
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.
Change things up with these side-trips from Key Largo: Islamorada (Stand-Up Paddleboarding, A1A Watersports, & more). The adventure continues: tour the water at your own pace with Key Largo Fishing Adventures, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, stop by florida keys key lime products, and meet the residents at Dolphins Plus Marine Mammal Responder.

To plan Key Largo vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by car from Miami to Key Largo takes 1.5 hours. Alternatively, you can do a combination of bus and taxi. In July in Key Largo, expect temperatures between 37°C during the day and 28°C at night. Cap off your sightseeing on the 22nd (Mon) early enough to go by car to Key West.

Things to do in Key Largo

Outdoors Tours Wildlife

Side Trip

Islamorada
Highlights from your plan
Key Largo Fishing Adventures ©
Key Largo Fishing Adventures
Island Dolphin Care ©
Island Dolphin Care
Scuba & Snorkeling

5
nights
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.
Key West is known for adventure, museums, nightlife, wildlife, and nature. Your plan includes some of its best attractions: see the interesting displays at The Ernest Hemingway Home and Museum, take a leisurely stroll along Mallory Square, view the masterpieces at Alan S. Maltz Gallery, and contemplate the long history of Truman Little White House.

To see more things to do, ratings, and other tourist information, you can read our Key West online trip itinerary maker .

You can drive from Key Largo to Key West in 2.5 hours. Other options are to take a bus; or take a bus. In July, plan for daily highs up to 37°C, and evening lows to 32°C. Wrap up your sightseeing on the 27th (Sat) to allow time to travel to St. Augustine.

Things to do in Key West

Tours Outdoors Adventure
Highlights from your plan
Stand-Up Paddleboarding
The Ernest Hemingway Home and Museum ©

1
night
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. On the 28th (Sun), identify plant and animal life at St. Augustine Alligator Farm Zoological Park, visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc., and then kick back and relax at St. Augustine Beach. Keep things going the next day: explore and take pictures at Flagler College, tour the water at your own pace with Red Boat Water Tours, LLC, then look for all kinds of wild species at St. Augustine Wild Reserve, and finally brush up on your knowledge of spirits at St. Augustine Distillery.

To see reviews, traveler tips, ratings, and more tourist information, go to the St. Augustine route planner .

Getting from Key West to St. Augustine by combination of flight and car takes about 6 hours. Other options: do a combination of flight and bus; or drive. Expect a bit cooler evenings in St. Augustine when traveling from Key West in July, with lows around 28°C. Finish your sightseeing early on the 29th (Mon) to allow enough time to drive to Orlando.

Things to do in St. Augustine

Parks Outdoors Wildlife
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
St. Augustine Distillery ©
St. Augustine Distillery

5
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Have a day of magic on the 30th (Tue) at Walt Disney World Resort. Pack the 3rd (Sat) with family-friendly diversions at Discovery Cove. There's much more to do: find something for the whole family at Universal Orlando Resort, discover the magic at Happily Ever After Fireworks, get your game on at 7D Dark Ride Adventure, and meet the residents at SeaWorld Orlando.

For maps, other places to visit, traveler tips, and other tourist information, use the Orlando holiday site .

Traveling by car from St. Augustine to Orlando takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 38°C in July, and nighttime lows around 28°C. Wrap up your sightseeing on the 3rd (Sat) to allow time to travel to Pensacola Beach.

Things to do in Orlando

Theme Parks Parks Beaches
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

2
nights
Pensacola Beach

Pensacola Beach ©
Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. Kick off your visit on the 4th (Sun): tour the water at your own pace with Hot Spots Fishing Charters, then tour the water at your own pace with Dolphin Express, and then contemplate the long history of Fort Pickens Area. On the 5th (Mon), you'll have a packed day of sightseeing: enjoy the sand and surf at Gulf Islands National Seashore and then stroll through Navarre Beach.

For more things to do and more tourist information, go to the Pensacola Beach trip builder site .

You can do a combination of train, taxi, flight, and car from Orlando to Pensacola Beach in 5 hours. Alternatively, you can drive; or do a combination of bus and taxi. Due to the time zone difference, you'll gain 1 hour traveling from Orlando to Pensacola Beach. In August, daily temperatures in Pensacola Beach can reach 38°C, while at night they dip to 28°C. Wrap up your sightseeing on the 5th (Mon) early enough to travel to Santa Monica.

Things to do in Pensacola Beach

Outdoors Beaches Parks

Side Trip

Navarre Beach
Highlights from your plan
Hot Spots Fishing Charters ©
Hot Spots Fishing Charters
Navarre Beach ©
Navarre Beach
Fort Pickens Area ©
Fort Pickens Area

4
nights
Santa Monica

Santa Monica ©
A famed resort town since the early 20th century, Santa Monica sits on the picturesque Santa Monica Bay, bordered on three sides by the city of Los Angeles.
Santa Monica is known for nature, shopping, spas, theme parks, and parks. Your plan includes some of its best attractions: take a leisurely stroll along Santa Monica Pier, look for gifts at Bergamot Station, go for a walk through 26-Mile Bike Path, and admire nature's wide array of creatures at Santa Monica Pier Aquarium.

To see where to stay, ratings, maps, and tourist information, go to the Santa Monica vacation planner.

Getting from Pensacola Beach to Santa Monica by combination of taxi, flight, and bus takes about 9.5 hours. Other options: do a combination of car, flight, and bus; or drive. The time zone difference moving from Central Standard Time to Pacific Standard Time is minus 2 hours. In August, Santa Monica is little chillier than Pensacola Beach - with highs of 28°C and lows of 21°C. Finish your sightseeing early on the 10th (Sat) to allow enough time to travel to Oshkosh.

Things to do in Santa Monica

Parks Museums Historic Sites

Side Trips

The Getty Villa, Two Rodeo Drive
Highlights from your plan
Santa Monica State Beach ©
Santa Monica State Beach
Santa Monica Pier ©
Santa Monica Pier
Annenberg Community Beach House ©
Annenberg Community Beach House

3
nights
Oshkosh

Oshkosh ©
Oshkosh is a city in Winnebago County, Wisconsin, United States, located where the Fox River enters Lake Winnebago from the west. Change things up with these side-trips from Oshkosh: Road America (in Elkhart Lake), Bookworm Gardens (in Sheboygan) and Horicon Marsh (in Mayville). And it doesn't end there: see the interesting displays at EAA Aviation Museum, identify plant and animal life at Heckrodt Wetland Reserve, stroll through Outagamie County Pet Exercise Area, Appleton, WI, and play a few rounds at Whistling Straits Golf Course - Straits and Irish.

To find reviews, photos, ratings, and other tourist information, go to the Oshkosh trip itinerary tool .

The Route module can help you plan travel from Santa Monica to Oshkosh. The time zone difference moving from Pacific Standard Time (PST) to Central Standard Time (CST) is 2 hours. Traveling from Santa Monica in August, expect little chillier with lows of 18°C in Oshkosh. Wrap up your sightseeing by early afternoon on the 14th (Wed) to allow time for travel back home.

Things to do in Oshkosh

Parks Wildlife Museums

Side Trips

Horicon Marsh, Road America, Bookworm Gardens, Outagamie County Pet Exercise Area, Appleton, WI, Whistling Straits Golf Course - Straits and Irish
Highlights from your plan
Bookworm Gardens ©
Bookworm Gardens
EAA Aviation Museum ©
EAA Aviation Museum
Road America ©
Road America

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