31 days in Southwest Florida Itinerary

31 days in Southwest Florida Itinerary

Created using Inspirock Southwest Florida travel planner

Make it your trip
Drive
1
Bradenton
— 6 nights
Drive
2
Punta Gorda
— 6 nights
Drive
3
Marco Island
— 5 nights
Drive
4
Naples
— 7 nights
Drive
5
Sanibel Island
— 6 nights
Drive

S M T W T F S
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
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

Bradenton

— 6 nights

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.
Explore Bradenton's surroundings by going to Sarasota (St. Armands Circle, AlexArt International Art Gallery, &more), Siesta Key (The Gallery on Siesta Key, Siesta Beach, &more) and North Jetty Beach (in Casey Key). And it doesn't end there: admire the masterpieces at The Ringling, relax and rejuvenate at North River Body Therapies, get to know the resident critters at The Cat Depot, and enjoy the sand and surf at Coquina Beach.

To see more things to do and other tourist information, refer to the Bradenton trip planner.

Orlando to Bradenton is an approximately 2-hour car ride. You can also take a bus; or do a combination of train and bus. In May, daily temperatures in Bradenton can reach 87°F, while at night they dip to 68°F. Cap off your sightseeing on the 7th (Fri) early enough to go by car to Punta Gorda.

Things to do in Bradenton

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Punta Gorda

— 6 nights
Punta Gorda is a city in Charlotte County, Florida, United States. You'll find plenty of places to visit near Punta Gorda: Venice (Venice Fishing Pier, Caspersen Beach, &more), Englewood (Manasota Key Beach, Englewood Beach, &more) and Nokomis Beach (in Nokomis). The adventure continues: cast your line with a fishing tour, get outside with Sea Grape Gallery, walk around Gilchrist Park, and tee off at Riverwood Golf and Country Club.

To see other places to visit, traveler tips, reviews, and other tourist information, you can read our Punta Gorda vacation builder.

Traveling by car from Bradenton to Punta Gorda takes 1.5 hours. Alternatively, you can do a combination of bus and taxi. In May, daytime highs in Punta Gorda are 90°F, while nighttime lows are 66°F. Cap off your sightseeing on the 13th (Thu) early enough to go by car to Marco Island.

Things to do in Punta Gorda

Parks · Outdoors · Beaches · Tours

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. Venture out of the city with trips to Ochopee (Nature & Wildlife Tours, Clyde Butcher's Big Cypress Gallery, &more). There's lots more to do: see majestic marine mammals with a dolphin and whale watching tour, walk around Canine Cove, go for a stroll along the water at Marco Island Marina, and kick back and relax at Tigertail Beach.

To see traveler tips, where to stay, reviews, and more tourist information, read Marco Island visit planner.

You can drive from Punta Gorda to Marco Island in 1.5 hours. Alternatively, you can do a combination of bus and taxi. Expect a daytime high around 88°F in May, and nighttime lows around 69°F. Finish your sightseeing early on the 18th (Tue) to allow enough time to drive to Naples.

Things to do in Marco Island

Parks · Outdoors · Beaches · Wildlife

Side Trip

Naples

— 7 nights
Venture out of the city with trips to Fort Myers (List Distillery, Edison and Ford Winter Estates, &more), Fort Myers Beach (Fort Myers Beach, Dolphin & Whale Watching, &more) and Bonita Springs (Barefoot Beach Preserve & Bonita Springs Public Beach).

For ratings, maps, traveler tips, and tourist information, read our Naples trip planner.

Naples is just a stone's throw from Marco Island. May in Naples sees daily highs of 88°F and lows of 70°F at night. Finish up your sightseeing early on the 25th (Tue) so you can go by car to Sanibel Island.

Things to do in Naples

Parks · Outdoors · Museums · Beaches

Side Trips

Sanibel Island

— 6 nights
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Change things up with a short trip to Southwest Florida Military Museum & Library in Cape Coral (about 32 minutes away). There's lots more to do: identify plant and animal life at J.N. "Ding" Darling National Wildlife Refuge, take a tour by water with Boat Tours & Water Sports, look for gifts at Bailey's General Store, and enjoy the sea views from Sanibel Island Lighthouse.

For other places to visit, traveler tips, where to stay, and other tourist information, go to the Sanibel Island travel route builder app.

Getting from Naples to Sanibel Island by car takes about 1.5 hours. May in Sanibel Island sees daily highs of 90°F and lows of 69°F at night. Wrap up your sightseeing on the 31st (Mon) to allow time to drive back home.

Things to do in Sanibel Island

Parks · Outdoors · Museums · Beaches

Side Trips