29 days in Southwest Florida Itinerary

29 days in Southwest Florida Itinerary

Created using Inspirock Southwest Florida visit planner

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

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1
night
Captiva Island

Kick off your visit on the 4th (Fri): take in the exciting artwork at Jungle Drums Gallery on Captiva Island, FL, then take in the spiritual surroundings of Captiva Chapel By-The-Sea, and then enjoy the sand and surf at Captiva Beach. Get ready for a full day of sightseeing on the next day: get a taste of the local shopping with 2 Islands Gallery, soothe aching muscles at Ambu Yoga, then see what you can catch with a fishing tour, and finally visit Captiva Pass.

To see reviews, other places to visit, where to stay, and tourist information, you can read our Captiva Island planning tool.

New York City to Captiva Island is an approximately 6.5-hour flight. You can also drive; or do a combination of bus and taxi. Traveling from New York City in December, expect Captiva Island to be much hotter, temps between 80°F and 62°F. Cap off your sightseeing on the 5th (Sat) early enough to go by car to Sanibel Island.

Things to do in Captiva Island

Outdoors · Tours · Beaches · Parks

5
nights
Sanibel Island

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
You'll get in some beach time at Blind Pass Beach Park and Gulfside Beach. Do some cultural sightseeing at Sanibel Historical Museum and Village and Southwest Florida Military Museum & Library. Step out of Sanibel Island to go to Cape Coral and see Snook Hut Bait & Tackle, which is approximately 34 minutes away. Next up on the itinerary: cast your line with a fishing tour, identify plant and animal life at Clinic for the Rehabilitation of Wildlife (CROW), take a memorable drive along Sanibel Causeway, and kick back and relax at Bowman's Beach.

To find other places to visit, maps, where to stay, and other tourist information, go to the Sanibel Island trip site.

Sanibel Island is just a short distance from Captiva Island. Expect a daytime high around 80°F in December, and nighttime lows around 62°F. Finish your sightseeing early on the 10th (Thu) to allow enough time to drive to Naples.

Things to do in Sanibel Island

Parks · Outdoors · Wildlife · Beaches

Side Trip

7
nights
Naples

Satisfy your inner culture vulture at Artis-Naples and Edison and Ford Winter Estates. Take a break from the city and head to Fishing Charters & Tours and Everglades Day Safari. You'll find plenty of places to visit near Naples: Six Mile Cypress Slough Preserve (in Fort Myers), Fort Myers Beach (in Fort Myers Beach) and Octagon Wildlife Sanctuary And Rehabilitation Center (in Punta Gorda).

To find more things to do, ratings, where to stay, and other tourist information, you can read our Naples trip builder app.

Traveling by car from Sanibel Island to Naples takes 1.5 hours. Expect a daytime high around 80°F in December, and nighttime lows around 63°F. Wrap up your sightseeing on the 17th (Thu) early enough to drive to Marco Island.

Things to do in Naples

Wildlife · Parks · Outdoors · Museums

Side Trips

6
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. You'll enjoy a bit of beach vacationing at South Marco Beach and Tigertail Beach. Marco Island Historical Museum and Skunk Ape Research Center are good opportunities to explore the local culture. Get out of town with these interesting Marco Island side-trips: Museum of the Everglades (in Everglades City), Ochopee (Nature & Wildlife Tours & Loop Road) and Smallwood Store (in Chokoloskee). There's much more to do: get a new perspective on things with Boat Tours & Water Sports, look for all kinds of wild species at Otter Mound Preserve, kick back and relax at Keewaydin Island, and contemplate the waterfront views at Capri Paddlecraft Park.

To see ratings, reviews, where to stay, and other tourist information, read Marco Island trip planner.

Marco Island is just a stone's throw from Naples. Expect a daytime high around 80°F in December, and nighttime lows around 61°F. Finish your sightseeing early on the 23rd (Wed) so you can drive to Bradenton Beach.

Things to do in Marco Island

Parks · Outdoors · Wildlife · Beaches

Side Trips

2
nights

Bradenton Beach is a city on Anna Maria Island in Manatee County, Florida, United States. Kick off your visit on the 24th (Thu): stroll through Bradenton Beach, get to know the fascinating history of Coquina Baywalk, then kick back and relax at Bean Point, and finally look for gifts at Anna Maria Rocks. On the 25th (Fri), you'll have a packed day of sightseeing: take a leisurely stroll along Bradenton Beach City Pier, then cast your line with a fishing tour, then kick back and relax at Coquina Beach, and finally enjoy the sand and surf at Manatee Public Beach.

To find photos, other places to visit, more things to do, and other tourist information, you can read our Bradenton Beach trip planner.

You can drive from Marco Island to Bradenton Beach in 3 hours. Other options are to do a combination of taxi and bus; or do a combination of taxi and bus. In December in Bradenton Beach, expect temperatures between 78°F during the day and 59°F at night. Finish up your sightseeing early on the 25th (Fri) so you can go by car to Sarasota.

Things to do in Bradenton Beach

Parks · Outdoors · Beaches · Wildlife

Side Trips

7
nights
Sarasota

Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Satisfy your inner culture vulture at The Ringling and Cortez Cultural Center. You'll discover tucked-away gems like Robinson Nature Preserve and Stump Pass Beach State Park. Change things up with these side-trips from Sarasota: Venice (Venice Beach & Venice Fishing Pier), Emerson Point Preserve (in Palmetto) and Spa NorthWest (in Bradenton). There's lots more to do: enjoy the sand and surf at Turtle Beach, tour the pleasant surroundings at Englewood Beach, walk around Siesta Beach, and identify plant and animal life at South Lido Park.

To see more things to do, traveler tips, where to stay, and tourist information, you can read our Sarasota trip maker website.

You can drive from Bradenton Beach to Sarasota in an hour. December in Sarasota sees daily highs of 78°F and lows of 59°F at night. Finish your sightseeing early on the 1st (Fri) to allow enough time to travel back home.

Things to do in Sarasota

Parks · Outdoors · Beaches · Wildlife

Side Trips