28 days in Southwest Florida Itinerary

28 days in Southwest Florida Itinerary

Created using Inspirock United States holiday maker

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Route & dates

28 days in Southwest Florida Itinerary

Start: Washington DC
Fly + taxi:  5​h
1
Captiva Island
— 2 nights
Drive:  30​min
2
Sanibel Island
— 6 nights
Drive:  1​h 30​min
3
Marco Island
— 5 nights
Drive:  30​min
4
Naples
— 5 nights
Drive:  2​h
5
Englewood
— 5 nights
Drive:  1​h 15​min
6
Bradenton Beach, Anna Maria Island
— 4 nights
bus + Fly:  6​h 30​min
End: Washington DC

2
nights
Captiva Island

Captiva Island ©
Shop till you drop at Jungle Drums Gallery on Captiva Island, FL and 2 Islands Gallery. Step off the beaten path and head to Captiva Beach and Redfish Pass.

To see reviews, other places to visit, where to stay, and tourist information, go to the Captiva Island online journey planner .

Washington DC to Captiva Island is an approximately 5-hour combination of flight and taxi. You can also do a combination of train, flight, and taxi; or drive. Prepare for much warmer weather when traveling from Washington DC in March: high temperatures in Captiva Island hover around 81°F and lows are around 59°F. Cap off your sightseeing on the 5th (Tue) early enough to go by car to Sanibel Island.

Things to do in Captiva Island

Outdoors Tours Adventure
Highlights from your plan
Captiva Beach ©
Captiva Beach
Fishing Charters & Tours
Parasailing & Paragliding

6
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
You'll enjoy a bit of beach vacationing at Blind Pass Beach Park and Fort Myers Beach. Do your shopping at Bailey's General Store and Sanibel Island Farmer's Market. Go for a jaunt from Sanibel Island to Fort Myers Beach to see Dolphin & Whale Watching about 34 minutes away. The adventure continues: tour the water at your own pace with Tarpon Bay Explorers, browse the different shops at Periwinkle Place, take a memorable drive along Sanibel Causeway, and identify plant and animal life at Clinic for the Rehabilitation of Wildlife (CROW).

To see traveler tips, more things to do, photos, and other tourist information, read our Sanibel Island trip itinerary planning tool .

Sanibel Island is just a short distance from Captiva Island. Expect a daytime high around 81°F in March, and nighttime lows around 59°F. Wrap up your sightseeing on the 11th (Mon) to allow time to drive to Marco Island.

Things to do in Sanibel Island

Parks Outdoors Wildlife

Side Trip

Fort Myers Beach
Highlights from your plan
Blind Pass Beach Park ©
Blind Pass Beach Park
Tarpon Bay Explorers ©
Tarpon Bay Explorers
Fort Myers Beach ©
Fort Myers Beach

5
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. Explore hidden gems such as South Marco Beach and Keewaydin Island. Take a break from the city and head to Cape Romano and Waterskiing & Jetskiing. Change things up with a short trip to Fishing Charters & Tours in Everglades City (about 44 minutes away). And it doesn't end there: relax and rejuvenate at some of the top local wellness centers, tour the water at your own pace with Rose Marina Boat Rentals, stroll through Tigertail Beach, and contemplate the waterfront views at Capri Paddlecraft Park.

For more things to do, photos, maps, and other tourist information, read Marco Island trip itinerary maker site .

Getting from Sanibel Island to Marco Island by car takes about 1.5 hours. In March, plan for daily highs up to 80°F, and evening lows to 61°F. Cap off your sightseeing on the 16th (Sat) early enough to go by car to Naples.

Things to do in Marco Island

Outdoors Parks Tours

Side Trip

Fishing Charters & Tours
Highlights from your plan
South Marco Beach ©
South Marco Beach
Keewaydin Island ©
Keewaydin Island
Cape Romano ©
Cape Romano

5
nights
Naples

Naples is a city in Collier County, Florida, United States. Discover out-of-the-way places like Bonita Springs Public Beach and Clam Pass Park. Head to Third Street South and Waterside Shopsfor some retail therapy. You'll find plenty of places to visit near Naples: Fishing Charters & Tours (in Chokoloskee) and Bonita Springs (Barefoot Beach Preserve & Stand-Up Paddleboarding). There's much more to do: take a memorable tour with Tours, identify plant and animal life at Conservancy of Southwest Florida, get up close to creatures of the deep with a dolphin and whale watching tour, and learn about winemaking at The Naples Winery.

For more things to do, other places to visit, maps, and tourist information, read our Naples trip itinerary planner .

Naples is just a stone's throw from Marco Island. In March in Naples, expect temperatures between 79°F during the day and 61°F at night. Cap off your sightseeing on the 21st (Thu) early enough to go by car to Englewood.

Things to do in Naples

Outdoors Tours Parks

Side Trips

Bonita Springs, Fishing Charters & Tours
Highlights from your plan
Dolphin & Whale Watching
Bonita Springs Public Beach ©
Bonita Springs Public Beach
Stand-Up Paddleboarding

5
nights
Englewood

Englewood ©
Englewood is a census-designated place (CDP) in Charlotte and Sarasota counties in the U.S. Relax by the water at Englewood Beach and Nokomis Beach. Take a break from the city and head to Manasota Key Beach and Crescent Beach. You'll find plenty of places to visit near Englewood: Boca Grande (Boca Grande Beach & Cayo Costa State Park) and Siesta Beach (in Siesta Key). There's lots more to do: admire the majestic nature at Stump Pass Beach State Park, enjoy the sand and surf at Blind Pass Beach, see what you can catch with a fishing tour, and tour the pleasant surroundings at Venice Beach.

For reviews, photos, and other tourist information, read Englewood online travel planner .

You can drive from Naples to Englewood in 2 hours. Another option is to do a combination of bus and taxi. In March, daytime highs in Englewood are 75°F, while nighttime lows are 58°F. Cap off your sightseeing on the 26th (Tue) early enough to go by car to Bradenton Beach.

Things to do in Englewood

Outdoors Parks Beaches

Side Trips

Boca Grande, Siesta Key, Venice Beach, Nokomis Beach
Highlights from your plan
Crescent Beach ©
Crescent Beach
Manasota Key Beach ©
Manasota Key Beach
Stump Pass Beach State Park ©
Stump Pass Beach State Park

4
nights
Bradenton Beach, Anna Maria Island

Bradenton Beach ©
Bradenton Beach is a city on Anna Maria Island in Manatee County, Florida, United States. Escape the urban bustle at Bradenton Beach and Coquina Beach. You'll enjoy a bit of beach vacationing at Bean Point and Holmes Beach. There's still lots to do: tour the pleasant surroundings at Manatee Public Beach, explore and take pictures at Bradenton Beach City Pier, admire the majestic nature at Manatee Beach Park, and look for gifts at Olive Oil Outpost.

To see where to stay, reviews, photos, and more tourist information, use the Bradenton Beach trip planner .

You can drive from Englewood to Bradenton Beach in 1.5 hours. Another option is to take a bus. In March in Bradenton Beach, expect temperatures between 77°F during the day and 57°F at night. Finish your sightseeing early on the 30th (Sat) to allow enough time to travel back home.

Things to do in Bradenton Beach

Parks Outdoors Beaches

Side Trips

Holmes Beach, Anna Maria, Holmes Beach
Highlights from your plan
Bean Point ©
Bean Point
Bradenton Beach ©
Bradenton Beach
Manatee Public Beach ©
Manatee Public Beach