29 days in Florida & Oregon Itinerary

29 days in Florida & Oregon Itinerary

Created using Inspirock United States trip planner

Make it your trip
Drive
1
Key Largo
— 2 nights
Drive
2
Islamorada
— 1 night
Drive
3
Marathon
— 3 nights
Drive
4
Key West
— 5 nights
Fly
5
Cannon Beach
— 4 nights
Fly
6
Amelia Island
— 1 night
Drive
7
St. Augustine
— 5 nights
Drive
8
Fort Myers Beach
— 2 nights
Drive
9
Marco Island
— 4 nights
Drive
10
Everglades City
— 1 night
Drive

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Key Largo

— 2 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.
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 Swim with Dolphins. Explore the numerous day-trip ideas around Key Largo: Homestead (Homestead Miami Speedway & Everglades Alligator Farm). There's lots more to do: explore the gorgeous colors at Spiegel Grove, push the limits with Jetpack Water Flights, and identify plant and animal life at Grecian Rocks.

To find photos, other places to visit, more things to do, and more tourist information, you can read our Key Largo trip maker app.

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. In November, plan for daily highs up to 81°F, and evening lows to 68°F. Finish up your sightseeing early on the 4th (Wed) so you can go by car to Islamorada.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

Side Trips

Islamorada

— 1 night

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 · Breweries & Distilleries · Wildlife

Marathon

— 3 nights

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 Sunset Park Beach. Discover out-of-the-way places like Everglades National Park and Ultimate HeliTours. There's still lots to do: identify plant and animal life at Crane Point Museum & Nature Center, discover the deep blue sea with a scuba or snorkeling tour, and enjoy the sand and surf at Bahia Honda State Park.

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

Key West

— 5 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.
Get outdoors at Dolphin & Whale Watching and Key West Butterfly & Nature Conservatory. Get a sense of the local culture at Key West Historic Seaport and Key West Lighthouse and Keeper's Quarters Museum. Spend the 9th (Mon) exploring nature at Dry Tortugas National Park. The adventure continues: take an in-depth tour of U.S. Coast Guard Cutter Ingham Maritime Museum, stroll the grounds of Key West Cemetery, take in the architecture and atmosphere at Saint Mary Star of the Sea, and indulge in some personalized pampering at some of the best spas.

For where to stay, traveler tips, and other tourist information, read our Key West trip itinerary maker.

Getting from Marathon to Key West by car takes about 1.5 hours. Other options: take a bus. In November, daytime highs in Key West are 81°F, while nighttime lows are 73°F. Wrap up your sightseeing by early afternoon on the 13th (Fri) to allow enough time to travel to Cannon Beach.

Things to do in Key West

Historic Sites · Parks · Nature · Museums

Cannon Beach

— 4 nights
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 · Beaches · Nature · Outdoors

Side Trips

Amelia Island

— 1 night
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 · Nature

St. Augustine

— 5 nights
St. Popular historic sites such as Ponce de Leon Inlet Lighthouse & Museum and Fort Matanzas National Monument are in your itinerary. Cathedral Basilica of St. Augustine and Old City are good opportunities to explore the local culture. You'll find plenty of places to visit near St. Augustine: Dunlawton Sugar Mill Gardens (in Port Orange) and Stetson Mansion (in DeLand). 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

Fort Myers Beach

— 2 nights
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

Marco Island

— 4 nights
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 Keewaydin Island. Get outdoors at Loop Road and Dolphin & Whale Watching. And it doesn't end there: stroll through Tigertail Beach, relax and rejuvenate at some of the best spas, explore the landscape on two wheels at Island Bike Shop- Marco Island, and contemplate the waterfront views at Capri Paddlecraft Park.

For more things to do, traveler tips, maps, and tourist information, refer to the Marco Island trip maker site.

You can drive from Fort Myers Beach to Marco Island in 1.5 hours. 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 enough time to drive to Everglades City.

Things to do in Marco Island

Outdoors · Parks · Beaches · Trails

Side Trip

Everglades City

— 1 night
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 Inspirock 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

Florida travel guide

4.4
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.

Oregon travel guide

4.5
Gardens · State Parks · Specialty Museums
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.