33 days in Southwest Florida & Key West Itinerary

33 days in Southwest Florida & Key West Itinerary

Created using Inspirock Florida route planner
Make it your trip
Drive
1
Bradenton Beach, Anna Maria Island
— 2 nights
Drive
2
Sarasota
— 6 nights
Drive
3
Matlacha
— 4 nights
Drive
4
Sanibel Island
— 5 nights
Taxi to Fort Myers Beach, FL, Ferry to Key West
5
Key West
— 3 nights
Ferry to Marco Island, FL, Taxi to Naples
6
Naples
— 7 nights
Drive
7
Marco Island
— 5 nights
Drive

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Bradenton Beach, Anna Maria Island — 2 nights

Bradenton Beach is a city on Anna Maria Island in Manatee County, Florida, United States. Bradenton Beach is known for beaches, wildlife, and sightseeing. Your trip includes some of its best attractions: get a new perspective on things with Boat Tours & Water Sports, tour the pleasant surroundings at Coquina Beach, relax and rejuvenate at Longboat Massage, and walk around Joan M. Durante Community Park.

To find more things to do, other places to visit, reviews, and tourist information, read our Bradenton Beach trip itinerary builder tool.

Ocala to Bradenton Beach is an approximately 3-hour car ride. You can also do a combination of bus and taxi. Traveling from Ocala in November, Bradenton Beach is a bit warmer at night with lows of 62°F. Cap off your sightseeing on the 3rd (Wed) early enough to go by car to Sarasota.
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Parks · Outdoors · Beaches · Shopping
Side Trips

Sarasota — 6 nights

Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. Get out of town with these interesting Sarasota side-trips: Sunshine Skyway Bridge (in Tampa), St. Petersburg (Duncan McClellan Gallery & St. Jude the Apostle Cathedral Church) and Englewood Beach (in Englewood). There's still lots to do: find your balance on the water with some of the best stand-up paddleboarding in the area, observe the fascinating underwater world at Mote Marine Laboratory & Aquarium, browse the different shops at St. Armands Circle, and brush up on your knowledge of spirits at Siesta Key Rum.

For other places to visit, ratings, more things to do, and other tourist information, read our Sarasota trip planner.

Sarasota is very close to Bradenton Beach. In November, daytime highs in Sarasota are 80°F, while nighttime lows are 62°F. Wrap up your sightseeing on the 9th (Tue) to allow time to drive to Matlacha.
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Parks · Outdoors · Historic Sites · Beaches
Side Trips

Matlacha — 4 nights

Matlacha is a census-designated place (CDP) in Lee County, Florida, United States. Explore the numerous day-trip ideas around Matlacha: Punta Gorda (Sea Grape Gallery, Fishing Charters & Tours, &more) and Boca Grande Guide Service (in Boca Grande). There's lots more to do: get outside with Venture Out, sample the fine beverages at Wicked Dolphin Distillery, relax and rejuvenate at Spa 33, and take in the waterfront at Cape Coral.

To find traveler tips, ratings, reviews, and more tourist information, read our Matlacha road trip planner.

You can drive from Sarasota to Matlacha in 1.5 hours. Expect a daytime high around 82°F in November, and nighttime lows around 63°F. Finish up your sightseeing early on the 13th (Sat) so you can go by car to Sanibel Island.
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Outdoors · Parks · Shopping · Tours
Side Trips

Sanibel Island — 5 nights

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Sanibel Island is known for parks, beaches, and historic sites. Your trip includes some of its best attractions: hunt for treasures at Sanibel Island Farmer's Market, soothe aching muscles at Ambu Yoga, see what you can catch with a fishing tour, and cruise along Sanibel Causeway.

For ratings, maps, photos, and other tourist information, read Sanibel Island travel planning app.

Traveling by car from Matlacha to Sanibel Island takes an hour. In November, daytime highs in Sanibel Island are 82°F, while nighttime lows are 63°F. Finish up your sightseeing early on the 18th (Thu) so you can travel to Key West.
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Parks · Outdoors · Wildlife · Tours
Side Trip

Key West — 3 nights

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.
Go for a jaunt from Key West to Big Pine Key to see Bahia Honda State Park about 50 minutes away. The adventure continues: see the interesting displays at The Ernest Hemingway Home and Museum, take in nature's colorful creations at Audubon House & Tropical Gardens, make a trip to Southernmost Point, and tour the pleasant surroundings at Key West Butterfly & Nature Conservatory.

To see traveler tips, more things to do, where to stay, and more tourist information, use the Key West itinerary builder app.

Do a combination of taxi and ferry from Sanibel Island to Key West in 5 hours. Alternatively, you can drive; or do a combination of taxi and bus. Traveling from Sanibel Island in November, plan for a bit warmer nights in Key West, with lows around 73°F. Cap off your sightseeing on the 21st (Sun) early enough to travel to Naples.
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Parks · Museums · Outdoors · Beaches
Side Trip

Naples — 7 nights

Get out of town with these interesting Naples side-trips: Wiener Museum of Decorative Arts (WMODA) (in Dania Beach), Sawgrass Mills (in Sunrise) and Fort Lauderdale (International Swimming Hall of Fame, Fort Lauderdale Beach, &more).

To find more things to do, ratings, reviews, and more tourist information, read our Naples online trip maker.

Do a combination of ferry and taxi from Key West to Naples in 4 hours. Alternatively, you can drive; or take a bus. Plan for a bit cooler nights when traveling from Key West in November since evenings lows in Naples dip to 65°F. Finish your sightseeing early on the 28th (Sun) to allow enough time to drive to Marco Island.
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Parks · Outdoors · Wildlife · Shopping
Side Trips

Marco Island — 5 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. Change things up with these side-trips from Marco Island: Everglades City (Museum of the Everglades & Speed Boats Tours) and Ochopee (Clyde Butcher's Big Cypress Gallery & H.P. Williams Roadside Park). There's lots more to do: kick back and relax at South Marco Beach, tour the pleasant surroundings at Keewaydin Island, stroll around Canine Cove, and don't miss a visit to Marco Island Center for the Arts.

For traveler tips, reviews, and other tourist information, go to the Marco Island day trip site.

Marco Island is very close to Naples. In November in Marco Island, expect temperatures between 81°F during the day and 64°F at night. On the 3rd (Fri), wrap the sightseeing up by early afternoon so you can drive back home.
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Parks · Outdoors · Beaches · Shopping
Side Trips