53 days in Southwest Gulf Coast & Richmond Itinerary

Captiva Island is known for adventure, wildlife, and beaches. Your trip includes some of its best attractions: tour the pleasant surroundings at Captiva Beach, explore the activities along Captiva Pass, glide through the air with a parasailing or paragliding tour, and take in the exciting artwork at 2 Islands Gallery.

For where to stay, maps, more things to do, and more tourist information, read our Captiva Island trip builder.

Portland to Captiva Island is an approximately 8.5-hour flight. You can also drive; or do a combination of train, bus, and taxi. The time zone difference when traveling from Portland to Captiva Island is 3 hours. Plan for much warmer temperatures traveling from Portland in April, with highs in Captiva Island at 87°F and lows at 66°F. Wrap up your sightseeing on the 4th (Mon) to allow time to drive to Sanibel Island.

Sanibel Island is known for wildlife, beaches, and historic sites. Your trip includes some of its best attractions: look for all kinds of wild species at J.N. "Ding" Darling National Wildlife Refuge, get a new perspective on things with Boat Tours & Water Sports, examine the collection at The Bailey-Matthews National Shell Museum, and contemplate the long history of Sanibel Historical Museum and Village.

To find other places to visit, ratings, and other tourist information, go to the Sanibel Island vacation tool.

Sanibel Island is very close to Captiva Island. April in Sanibel Island sees daily highs of 87°F and lows of 66°F at night. Wrap up your sightseeing on the 11th (Mon) to allow time to drive to Naples.

Change things up with these side-trips from Naples: Fort Myers (Spas, Edison and Ford Winter Estates, &more) and Fort Myers Beach (Dolphin & Whale Watching, Fort Myers Beach, &more).

To see traveler tips, more things to do, reviews, and other tourist information, refer to the Naples trip planner.

You can drive from Sanibel Island to Naples in 1.5 hours. April in Naples sees daily highs of 85°F and lows of 67°F at night. Cap off your sightseeing on the 18th (Mon) early enough to go by car to Marco Island.

Take a break from Marco Island with a short trip to Museum of the Everglades in Everglades City, about 42 minutes away.

For where to stay, other places to visit, photos, and other tourist information, read Marco Island trip planner.

Marco Island is just a stone's throw from Naples. Expect a daytime high around 85°F in April, and nighttime lows around 66°F. Cap off your sightseeing on the 24th (Sun) early enough to go by car to Punta Gorda.

Change things up with these side-trips from Punta Gorda: Venice (Venice Beach, Caspersen Beach, &more), Englewood (Manasota Key Beach, Stump Pass Beach State Park, &more) and Boca Grande (Cayo Costa State Park & Boca Grande Beach).

To see more things to do, where to stay, reviews, and tourist information, go to the Punta Gorda tour itinerary planning website.

Drive from Marco Island to Punta Gorda in 1.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. April in Punta Gorda sees daily highs of 87°F and lows of 63°F at night. Wrap up your sightseeing on the 30th (Sat) early enough to drive to Bradenton.

Get out of town with these interesting Bradenton side-trips: Sarasota (Save Our Seabirds, St. Armands Circle, &more). The adventure continues: take a pleasant ride with a tour on horseback, steep yourself in history at Ca d'Zan, indulge your taste buds at Siesta Key Rum, and identify plant and animal life at Robinson Nature Preserve.

To see other places to visit, photos, reviews, and other tourist information, read our Bradenton trip itinerary builder.

You can drive from Punta Gorda to Bradenton in 1.5 hours. Other options are to do a combination of shuttle and bus; or do a combination of taxi and bus. Expect a daytime high around 83°F in April, and nighttime lows around 65°F. Cap off your sightseeing on the 6th (Fri) early enough to catch the flight to Richmond.

Change things up with these side-trips from Richmond: Boat Tours & Water Sports (in Yorktown), Washington DC (Old Stone House, Washington Monument, &more) and Williamsburg (Busch Gardens Williamsburg, Abby Aldrich Rockefeller Folk Art Museum, &more). Next up on the itinerary: take in nature's colorful creations at Monticello, steep yourself in history at Pamplin Historical Park, indulge your senses at Central Virginia Wine Tours & Transportation, and take in the waterfront at Virginia Beach Boardwalk.

To see traveler tips, photos, maps, and tourist information, go to the Richmond trip builder app.

Getting from Bradenton to Richmond by flight takes about 4 hours. Other options: drive; or take a bus. Prepare for a bit cooler weather when traveling from Bradenton in May: high temperatures in Richmond hover around 78°F and lows are around 57°F. Wrap up your sightseeing on the 23rd (Mon) to allow time to fly back home.