29 days in Southwest Florida Itinerary

29 days in Southwest Florida Itinerary

Created using Inspirock Southwest Florida vacation planner

Plan created by another user. Make it yours
1
Captiva Island
— 1 night
2
Sanibel Island
— 5 nights
3
Naples
— 6 nights
4
Marco Island
— 7 nights
5
Bradenton Beach, Anna Maria Island
— 3 nights
6
Bradenton
— 6 nights

S M T W T F S
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1
night
Captiva Island

Captiva Island ©
Kick off your visit on the 15th (Fri): visit Redfish Pass, then take in the exciting artwork at 2 Islands Gallery, and then stroll through Captiva Beach. Get ready for a full day of sightseeing on the 16th (Sat): soothe aching muscles at Ambu Yoga, see what you can catch with a fishing tour, then make a trip to Captiva Island Historical Society's History Gallery, and finally take in the spiritual surroundings of Captiva Chapel By-The-Sea.

To find other places to visit, maps, photos, and tourist information, go to the Captiva Island trip planner.

Rochester to Captiva Island is an approximately 6-hour flight. You can also drive; or do a combination of bus and taxi. Prepare for warmer weather when traveling from Rochester in January: high temperatures in Captiva Island hover around 75°F and lows are around 56°F. Finish your sightseeing early on the 16th (Sat) so you can drive to Sanibel Island.

Things to do in Captiva Island

Outdoors · Beaches · Wildlife · Parks
Highlights from your plan
Captiva Beach ©
Captiva Beach
Fishing Charters & Tours
Captiva Chapel By-The-Sea ©
Captiva Chapel By-The-Sea

5
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
You'll explore the less-touristy side of things at Sanibel Causeway and Blind Pass Beach Park. Sanibel Historical Museum and Village and Sanibel Island Lighthouse will appeal to history buffs. Venture out of the city with trips to Wicked Dolphin Rum Distillery (in Cape Coral) and Captain Ted's Tackle (in Port Charlotte). Next up on the itinerary: get a new perspective on things with Boat Tours & Water Sports, identify plant and animal life at Sanibel Captiva Conservation Foundation, browse the eclectic array of goods at Sanibel Island Farmer's Market, and walk around Pond Apple Park.

To see other places to visit, ratings, where to stay, and other tourist information, go to the Sanibel Island day trip tool.

Sanibel Island is just a stone's throw from Captiva Island. In January in Sanibel Island, expect temperatures between 75°F during the day and 56°F at night. Finish up your sightseeing early on the 21st (Thu) so you can go by car to Naples.

Things to do in Sanibel Island

Parks · Wildlife · Outdoors · Beaches

Side Trips

Highlights from your plan
Sanibel Causeway ©
Sanibel Causeway
Blind Pass Beach Park ©
Blind Pass Beach Park
Gulfside Beach ©
Gulfside Beach

6
nights
Naples

Naples ©
Take a break from the city and head to Clam Pass Park and Rookery Bay National Estuarine Research Reserve. Explore hidden gems such as Bonita Springs Public Beach and Big Cypress National Preserve. Explore the numerous day-trip ideas around Naples: Everglades Area Tours (in Everglades City), Little Hickory Beach Park (in Bonita Springs) and Fort Myers Beach (in Fort Myers Beach). Spend the 24th (Sun) spotting exotic species with Everglades Day Safari.

To find more things to do, ratings, maps, and other tourist information, read our Naples travel planner.

Traveling by car from Sanibel Island to Naples takes 1.5 hours. In January, daytime highs in Naples are 75°F, while nighttime lows are 58°F. Wrap up your sightseeing on the 27th (Wed) to allow time to drive to Marco Island.

Things to do in Naples

Parks · Wildlife · Outdoors · Beaches

Side Trips

Highlights from your plan
Bonita Springs Public Beach ©
Bonita Springs Public Beach
Everglades Day Safari ©
Everglades Day Safari
Everglades Area Tours ©
Everglades Area Tours

7
nights
Marco Island

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. Popular historic sites such as Smallwood Store and San Marco Catholic Church are in your itinerary. You'll explore the less-touristy side of things at South Marco Beach and Florida Saltwater Adventures. Venture out of the city with trips to Museum of the Everglades (in Everglades City) and Ochopee (Loop Road, Clyde Butcher's Big Cypress Gallery, &more). There's still lots to do: tour the pleasant surroundings at Keewaydin Island, enjoy the sand and surf at Cape Romano, take an in-depth tour of Marco Island Historical Museum, and walk around Frank E. Mackle Park.

For traveler tips, maps, ratings, and tourist information, refer to the Marco Island trip maker website.

You can drive from Naples to Marco Island in an hour. Alternatively, you can take a bus. Plan for slightly colder nights when traveling from Naples in January since evenings lows in Marco Island dip to 53°F. Wrap up your sightseeing on the 3rd (Wed) early enough to drive to Bradenton Beach.

Things to do in Marco Island

Parks · Outdoors · Museums · Beaches

Side Trips

Highlights from your plan
Florida Saltwater Adventures ©
Florida Saltwater Adventures
Keewaydin Island ©
Keewaydin Island
South Marco Beach ©
South Marco Beach

3
nights

Bradenton Beach ©
Bradenton Beach is a city on Anna Maria Island in Manatee County, Florida, United States. You'll explore the less-touristy side of things at Bean Point and Boat Tours & Water Sports. Escape the urban bustle at Manatee Public Beach and Bradenton Beach. Next up on the itinerary: stroll through Coquina Beach, take an in-depth tour of Anna Maria Island Historical Museum, relax and rejuvenate at some of the best spas, and walk around Coquina Baywalk.

To find other places to visit, where to stay, ratings, and other tourist information, read our Bradenton Beach road trip planning site.

Getting from Marco Island to Bradenton Beach by car takes about 3 hours. Other options: do a combination of taxi and bus; or do a combination of taxi and bus. In February in Bradenton Beach, expect temperatures between 75°F during the day and 56°F at night. Wrap up your sightseeing on the 6th (Sat) to allow time to drive to Bradenton.

Things to do in Bradenton Beach

Parks · Outdoors · Beaches · Wildlife

Side Trips

Highlights from your plan
Bean Point ©
Bean Point
Bradenton Beach ©
Bradenton Beach
Manatee Public Beach ©
Manatee Public Beach

6
nights
Bradenton

Bradenton ©

Friendly City

Bradenton boasts a handful of historical buildings, but its real claim to fame is as the home of Tropicana Products and its quirky culture.
Get some historical perspective at De Soto National Memorial and Historic Spanish Point. Escape the urban bustle at Robinson Nature Preserve and Manasota Key Beach. Venture out of the city with trips to Englewood (Englewood Beach, Stump Pass Beach State Park, &more), Venice Beach (in Venice) and Legacy Trail (in Sarasota). There's much more to do: stroll through North Jetty Beach, identify plant and animal life at Emerson Point Preserve, kick back and relax at Turtle Beach, and see some colorful creatures with a scuba or snorkeling tour.

To see traveler tips, maps, other places to visit, and other tourist information, you can read our Bradenton trip planner.

Bradenton is just a stone's throw from Bradenton Beach. In February, daytime highs in Bradenton are 75°F, while nighttime lows are 56°F. Wrap up your sightseeing on the 12th (Fri) early enough to travel back home.

Things to do in Bradenton

Parks · Outdoors · Beaches · Wildlife

Side Trips

Highlights from your plan
Stump Pass Beach State Park ©
Stump Pass Beach State Park
Crescent Beach ©
Crescent Beach
North Jetty Beach ©
North Jetty Beach