29 days in Florida & Oregon Itinerary

29 days in Florida & Oregon Itinerary

Created using Inspirock United States trip planner

Plan created by another user. Make it yours
1
Key Largo
— 2 nights
2
Islamorada
— 1 night
3
Marathon
— 3 nights
4
Key West
— 5 nights
5
Cannon Beach
— 4 nights
6
Amelia Island
— 1 night
7
St. Augustine
— 5 nights
8
Fort Myers Beach
— 2 nights
9
Marco Island
— 4 nights
10
Everglades City
— 1 night

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Learn more about your trip

2
nights
Key Largo

Key Largo ©

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.
You'll explore the less-touristy side of things at Anhinga Trail and Capt. Sterling's Everglades Eco-Tours. Get in touch with nature at Molasses Reef and Everglades Alligator Farm. Take a break from Key Largo with a short trip to Homestead Miami Speedway in Homestead, about 44 minutes away. And it doesn't end there: explore the gorgeous colors at Spiegel Grove, identify plant and animal life at Grecian Rocks, push the limits with Jetpack Water Flights, and fulfill a lifelong dream with a swim-with-the-dolphins experience.

To see ratings, photos, reviews, and other tourist information, read our Key Largo trip itinerary planner.

Fort Lauderdale to Key Largo is an approximately 2-hour car ride. You can also take a shuttle; or do a combination of train and bus. November in Key Largo sees daily highs of 81°F and lows of 68°F at night. Wrap up your sightseeing on the 4th (Wed) early enough to drive to Islamorada.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

Side Trips

Find places to stay Nov 2 — 4:
Highlights from your plan
Spiegel Grove ©
Spiegel Grove
Anhinga Trail ©
Anhinga Trail
Capt. Sterling's Everglades Eco-Tours ©
Capt. Sterling's Everglades Eco-Tours

1
night
Islamorada

Islamorada ©

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.
Kick off your visit on the 5th (Thu): fulfill a lifelong dream with Theater of the Sea, head outdoors with Takedown Charters, and then indulge your thirst for a good beer at Florida Keys Brewing Company.

To see maps and other tourist information, you can read our Islamorada journey planning tool.

Islamorada is just a short distance from Key Largo. In November, daily temperatures in Islamorada can reach 82°F, while at night they dip to 72°F. Finish your sightseeing early on the 5th (Thu) to allow enough time to drive to Marathon.

Things to do in Islamorada

Outdoors · Tours · Wildlife · Breweries & Distilleries
Find places to stay Nov 4 — 5:
Highlights from your plan
Theater of the Sea ©
Theater of the Sea
Florida Keys Brewing Company ©
Florida Keys Brewing Company
Takedown Charters ©
Takedown Charters

3
nights
Marathon

Marathon ©

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Take a break from the city and head to Dolphin Research Center and Everglades National Park. Discover out-of-the-way places like Crane Point Museum & Nature Center and Ultimate HeliTours. There's still lots to do: tour the pleasant surroundings at Bahia Honda State Park, identify plant and animal life at The Turtle Hospital, discover the deep blue sea with a scuba or snorkeling tour, and enjoy the sand and surf at Sunset Park Beach.

To find where to stay, more things to do, traveler tips, and tourist information, you can read our Marathon trip itinerary planner.

You can drive from Islamorada to Marathon in an hour. Another option is to take a bus. In November in Marathon, expect temperatures between 82°F during the day and 72°F at night. Cap off your sightseeing on the 8th (Sun) early enough to go by car to Key West.

Things to do in Marathon

Parks · Outdoors · Wildlife · Nature

Side Trips

Find places to stay Nov 5 — 8:
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
Bahia Honda State Park ©
Bahia Honda State Park

5
nights
Key West

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.
Get outdoors at Dolphin & Whale Watching and Fort Zachary Taylor. Get a sense of the local culture at Key West Historic Seaport and U.S. Coast Guard Cutter Ingham Maritime Museum. Spend the 9th (Mon) exploring nature at Dry Tortugas National Park. There's still lots to do: identify plant and animal life at Key West Butterfly & Nature Conservatory, steep yourself in history at Key West Shipwreck Treasure Museum, examine the collection at The Ernest Hemingway Home and Museum, and take an in-depth tour of Key West Lighthouse and Keeper's Quarters Museum.

For ratings, reviews, and more tourist information, go to the Key West holiday builder tool.

You can drive from Marathon to Key West in 1.5 hours. Another option is to take a bus. Expect a daytime high around 81°F in November, and nighttime lows around 73°F. Wrap up your sightseeing by early afternoon on the 13th (Fri) to allow time for travel to Cannon Beach.

Things to do in Key West

Historic Sites · Parks · Nature · Museums
Find places to stay Nov 8 — 13:
Highlights from your plan
Dolphin & Whale Watching
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea
Key West Butterfly & Nature Conservatory ©
Key West Butterfly & Nature Conservatory

4
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. You'll explore the less-touristy side of things at Haystack Rock and Cannon Beach. Get in touch with nature at Hug Point State Park and Oswald West State Park. There's still lots to do: admire the majestic nature at Ecola State Park, kick back and relax at Short Sands Beach, tour the pleasant surroundings at Manzanita Beach, and look for all kinds of wild species at Hug Point State Recreation Site.

Ask Inspirock to suggest an itinerary and make planning a trip to Cannon Beach fast, fun, and easy.

You can fly from Key West to Cannon Beach in 13.5 hours. Other options are to drive; or do a combination of ferry, taxi, bus, and train. You'll gain 3 hours traveling from Key West to Cannon Beach due to the time zone difference. In November, Cannon Beach is colder than Key West - with highs of 55°F and lows of 42°F. Cap off your sightseeing on the 17th (Tue) early enough to travel to Amelia Island.

Things to do in Cannon Beach

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Nov 13 — 17:
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Hug Point State Park ©
Hug Point State Park

1
night
Amelia Island

Amelia Island ©
The southernmost Sea Island off the coast of Florida, Amelia Island takes its name from Princess Amelia of England.
Kick off your visit on the 18th (Wed): take a memorable tour with SemperFi Charters, immerse yourself in nature at Fort Clinch State Park, and then take a pleasant ride with Amelia Island Horseback Riding.

For more things to do, maps, and tourist information, you can read our Amelia Island trip itinerary builder tool.

You can fly from Cannon Beach to Amelia Island in 14 hours. Other options are to drive; or do a combination of bus, train, and taxi. The time zone difference moving from Pacific Standard Time (PST) to Eastern Standard Time (EST) is 3 hours. Traveling from Cannon Beach in November, things will get a bit warmer in Amelia Island: highs are around 74°F and lows about 58°F. Finish up your sightseeing early on the 18th (Wed) so you can go by car to St. Augustine.

Things to do in Amelia Island

Tours · Outdoors · Wildlife · Historic Sites
Find places to stay Nov 17 — 18:
Highlights from your plan
Fort Clinch State Park ©
Fort Clinch State Park
Amelia Island Horseback Riding ©
Amelia Island Horseback Riding
SemperFi Charters ©
SemperFi Charters

5
nights
St. Augustine

St. Augustine ©
St. Popular historic sites such as Ponce de Leon Inlet Lighthouse & Museum and Old City are in your itinerary. Fort Matanzas National Monument and Cathedral Basilica of St. Augustine are good opportunities to explore the local culture. You'll find plenty of places to visit near St. Augustine: Stetson Mansion (in DeLand) and Dunlawton Sugar Mill Gardens (in Port Orange). Next up on the itinerary: identify plant and animal life at St. Augustine Wild Reserve, tour the pleasant surroundings at St. Augustine Beach, take a tour by water with Boat Tours & Water Sports, and see the interesting displays at Lightner Museum.

To see reviews, more things to do, and tourist information, read our St. Augustine road trip planner.

You can drive from Amelia Island to St. Augustine in 1.5 hours. Alternatively, you can do a combination of taxi and bus. Expect a daytime high around 73°F in November, and nighttime lows around 59°F. Wrap up your sightseeing on the 23rd (Mon) early enough to drive to Fort Myers Beach.

Things to do in St. Augustine

Historic Sites · Parks · Nature · Wildlife

Side Trips

Find places to stay Nov 18 — 23:
Highlights from your plan
Ponce de Leon Inlet Lighthouse & Museum ©
Ponce de Leon Inlet Lighthouse & Museum
Fort Matanzas National Monument ©
Fort Matanzas National Monument
St. Augustine Wild Reserve ©
St. Augustine Wild Reserve

2
nights
Fort Myers Beach

Fort Myers Beach is a town located on Estero Island in Lee County, Florida, United States. On the 24th (Tue), enjoy the sand and surf at Barefoot Beach Preserve, immerse yourself in nature at Lovers Key State Park, and then see majestic marine mammals with a dolphin and whale watching tour. Get ready for a full day of sightseeing on the next day: take in nature's colorful creations at Edison and Ford Winter Estates, then take a memorable drive along Sanibel Causeway, and then tour the pleasant surroundings at Bowman's Beach.

To see traveler tips, maps, other places to visit, and tourist information, you can read our Fort Myers Beach planner.

Getting from St. Augustine to Fort Myers Beach by car takes about 5.5 hours. Other options: fly; or take a bus. When traveling from St. Augustine in November, plan for somewhat warmer days and about the same nights in Fort Myers Beach: temperatures range from 82°F by day to 63°F at night. Finish your sightseeing early on the 25th (Wed) so you can drive to Marco Island.

Things to do in Fort Myers Beach

Parks · Outdoors · Wildlife · Beaches

Side Trips

Find places to stay Nov 23 — 25:
Highlights from your plan
Dolphin & Whale Watching
Lovers Key State Park ©
Lovers Key State Park
Barefoot Beach Preserve ©
Barefoot Beach Preserve

4
nights
Marco Island

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Step off the beaten path and head to South Marco Beach and Loop Road. Get outdoors at Keewaydin Island and Island Bike Shop- Marco Island. There's much more to do: identify plant and animal life at Wildlife Areas, kick back and relax at Tigertail Beach, relax and rejuvenate at some of the best spas, and contemplate the waterfront views at Capri Paddlecraft Park.

To see more things to do, maps, other places to visit, and other tourist information, go to the Marco Island road trip planning app.

You can drive from Fort Myers Beach to Marco Island in 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of taxi and bus. In November, plan for daily highs up to 81°F, and evening lows to 64°F. Wrap up your sightseeing by early afternoon on the 29th (Sun) to allow time for the car ride to Everglades City.

Things to do in Marco Island

Outdoors · Parks · Beaches · Wildlife

Side Trip

Find places to stay Nov 25 — 29:
Highlights from your plan
Dolphin & Whale Watching
Keewaydin Island ©
Keewaydin Island
South Marco Beach ©
South Marco Beach

1
night
Everglades City

Everglades City ©
Everglades City is a city in Collier County, Florida, United States, of which it is the former county seat. On the 30th (Mon), hike along Kirby Storter Roadside Park, then stroll through Ten Thousand Islands National Wildlife Refuge, then contemplate the waterfront views at Chokoloskee Bay, and finally get a dose of the wild on a nature and wildlife tour.

Plan my Everglades City trip by asking Inpirock to come up with tips and suggestions.

Getting from Marco Island to Everglades City by car takes about an hour. In November in Everglades City, expect temperatures between 81°F during the day and 64°F at night. Wrap up your sightseeing on the 30th (Mon) to allow time to drive back home.

Things to do in Everglades City

Parks · Outdoors · Wildlife · Nature

Side Trips

Find places to stay Nov 29 — 30:
Highlights from your plan
Ten Thousand Islands  National Wildlife Refuge ©
Kirby Storter Roadside Park ©
Kirby Storter Roadside Park
Speed Boats Tours

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