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
Fly
1
Captiva Island
— 1 night
Drive
2
Sanibel Island
— 5 nights
Drive
3
Naples
— 6 nights
Drive
4
Marco Island
— 7 nights
Drive
5
Bradenton Beach, Anna Maria Island
— 3 nights
Drive
6
Bradenton
— 6 nights
Fly

S M T W T F S
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13

1
night
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 · Wildlife · Parks · Beaches
Highlights from your trip
Captiva Beach ©
Must see
Captiva Beach
4.3
Captiva Chapel By-The-Sea ©
Religious Site
Captiva Chapel By-The-Sea
4.5

5
nights
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 Blind Pass Beach Park and Sanibel Causeway. 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 trip

6
nights
Naples

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

To find photos, more things to do, ratings, and more tourist information, read our Naples trip planner.

Traveling by car from Sanibel Island to Naples takes 1.5 hours. Expect a daytime high around 75°F in January, and nighttime lows around 58°F. Wrap up your sightseeing on the 27th (Wed) early enough to drive to Marco Island.

Things to do in Naples

Parks · Wildlife · Outdoors · Beaches

Side Trips

Highlights from your trip
Everglades Area Tours ©
Walking tour
Everglades Area Tours
4.6

7
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. 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 Cape Romano. 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, see majestic marine mammals with Florida Saltwater Adventures, 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.

Marco Island is just a stone's throw from Naples. 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 trip
Cape Romano ©
Must see
Cape Romano
4.5
Florida Saltwater Adventures ©
Photography Tour
Florida Saltwater Adventures
5.0
Keewaydin Island ©
Must see
Keewaydin Island
4.7

3
nights

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 Coquina Beach. Escape the urban bustle at Manatee Public Beach and Coquina Beach. Next up on the itinerary: get interesting insight from Tours, take an in-depth tour of Anna Maria Island Historical Museum, relax and rejuvenate at some of the best spas, and stroll through 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 trip
Bean Point ©
Must see
Bean Point
4.8

6
nights
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 Campus. Escape the urban bustle at Robinson Nature Preserve and Crescent Beach. Venture out of the city with trips to Englewood (Englewood Beach, Stump Pass Beach State Park, &more), Legacy Trail (in Sarasota) and Venice Beach (in Venice). And it doesn't end there: tour the pleasant surroundings at North Jetty Beach, kick back and relax at Siesta Beach, see some colorful creatures with a scuba or snorkeling tour, and identify plant and animal life at Emerson Point Preserve.

For where to stay, other places to visit, and tourist information, refer to the Bradenton online travel planner.

Bradenton is very close to Bradenton Beach. In February in Bradenton, expect temperatures between 75°F during the day and 56°F at night. 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 trip
Crescent Beach ©
Must see
Crescent Beach
4.7
North Jetty Beach ©
Must see
North Jetty Beach
4.8