Naples History Tour: From Swamps to Billionaires
Explore the fascinating history of Naples, including the Train Depot, Palm Cottage, and the rugged pioneers of the Everglades.
Editor
Current Weather in Naples

Quick Summary
Best For
All travelers
Pace
Relaxed
Best Season
January – April (peak season)
Duration
1 day
Before the Ritz: The Historic Naples
Naples wasn't always mansions and Maseratis. It started as a mosquito-infested swamp that only the toughest pioneers could tame. This 1-day itinerary takes you back in time.
Quick Summary
Best For
Pace
Relaxed
Best Season
Morning: Old Naples Historic District
Palm Cottage
Start at the Naples Historical Society’s Historic Palm Cottage (12th Ave S). Built in 1895, it is the oldest house in Naples.
- Do: Take the guided tour. It’s fascinating to see how they lived without A/C (hint: taboddy concrete walls).
Walking Tour
The Historical Society offers a walking tour of the surrounding district. You’ll see the original cottages that have survived hurricanes and development.
Lunch: Campiello
Why here? Because it’s located in the historic Naples Mercantile Building. You are eating in a piece of history.
Afternoon: Trains & Planes
Naples Depot Museum
Located on 5th Ave S. This restored Seaboard Air Line Railway station shows how the railroad finally connected Naples to the world in the 1920s.
- See: The vintage train cars outside and the dugout canoes inside.
Holocaust Museum & Cohen Education Center
A somber but incredibly important stop. It houses over 1,000 artifacts and often has survivors or their descendants volunteering.
Read Before You Go: Read "Shadow Country" by Peter Matthiessen. It’s a (fictionalized) award-winning history of the chaotic Everglades frontier days.
Support Local History
The Naples Historical Society is a non-profit. Your ticket supports preservation.
Outbound link.
Reviews
Reader reviews are not collected on this site yet.
Enjoyed This Itinerary?
Get more expert Naples travel guides, insider tips, and a free vacation planning PDF delivered to your inbox.
You Might Also Like
ItineraryNaples Public Art & Sculptures Walking Tour
Discover Naples' outdoor art scene—sculptures on 5th Avenue, public installations, gallery walks, and the best photo-worthy art spots downtown.
3 min read
ItineraryNaples for Seniors: A Relaxed Guide to Florida's Paradise Coast
The perfect Naples, Florida guide for travelers 55+—accessible attractions, senior-friendly dining, mobility tips, and a relaxed pace for an unforgettable vacation.
6 min read
ItineraryThe Revs Institute: A Classic Car Lover's Paradise in Naples
Discover one of the world's finest automotive collections at The Revs Institute—Porsches, Alfas, racing legends, and mechanical art in Naples, Florida.
4 min read