Active Retirees Itineraries in Florida — 57 Verified

Sunlight, Salt Air & Slow Afternoons: 5 Days in Miami

5 Days · Active Retirees

Miami, Florida

Sunlight, Salt Air & Slow Afternoons: 5 Days in Miami

5 stops

Gardens, Gulf, and Gentle Currents: 4 Days in Sarasota

4 Days · Active Retirees

Sarasota area, Florida

Gardens, Gulf, and Gentle Currents: 4 Days in Sarasota

6 stops

Salt Air & Storied Streets: 4 Days in Pensacola

4 Days · Active Retirees

Pensacola, Florida, Florida

Salt Air & Storied Streets: 4 Days in Pensacola

8 stops

Turtles, Tides & Tiki Breezes: 4 Days in Palm Beach

4 Days · Active Retirees

Palm Beach area, Florida

Turtles, Tides & Tiki Breezes: 4 Days in Palm Beach

6 stops

Salt Air & Slow Mornings: 4 Days on Amelia Island

4 Days · Active Retirees

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Slow Mornings: 4 Days on Amelia Island

6 stops

Salt Air & Sunlit Stories: 4 Days in Pensacola

4 Days · Active Retirees

Pensacola, Florida, Florida

Salt Air & Sunlit Stories: 4 Days in Pensacola

6 stops

Salt Air & Slow Mornings: Four Days on Amelia Island

4 Days · Active Retirees

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Slow Mornings: Four Days on Amelia Island

5 stops

Gulf Light & Garden Shade: 4 Days in Sarasota

4 Days · Active Retirees

Sarasota area, Florida

Gulf Light & Garden Shade: 4 Days in Sarasota

4 stops

Lakeside Hours & Spring-Fed Mornings: Two Unhurried Days in Central Florida

2 Days · Active Retirees

Greater Orlando (non-theme park), Florida

Lakeside Hours & Spring-Fed Mornings: Two Unhurried Days in Central Florida

4 stops

Gentle Wonder: Two Slow Days in Orlando's Garden of Imagination

2 Days · Active Retirees

Orlando, Florida

Gentle Wonder: Two Slow Days in Orlando's Garden of Imagination

4 stops

Coquina Stone & Slow Afternoons: 2 Days in St. Augustine

2 Days · Active Retirees

St. Augustine, Florida, Florida

Coquina Stone & Slow Afternoons: 2 Days in St. Augustine

4 stops

Springs, Sky, and Saw-Grass: Two Gentle Days Around Gainesville

2 Days · Active Retirees

Gainesville area, Florida

Springs, Sky, and Saw-Grass: Two Gentle Days Around Gainesville

3 stops

Marble Halls & Marsh Light: A Gentle Two Days in Tallahassee

2 Days · Active Retirees

Tallahassee area, Florida

Marble Halls & Marsh Light: A Gentle Two Days in Tallahassee

3 stops

Marble Halls & Marsh Light: Two Easy Days in Tallahassee

2 Days · Active Retirees

Tallahassee area, Florida

Marble Halls & Marsh Light: Two Easy Days in Tallahassee

4 stops

Coquina Streets & Cannon Smoke: Two Slow Days in St. Augustine

2 Days · Active Retirees

St. Augustine, Florida, Florida

Coquina Streets & Cannon Smoke: Two Slow Days in St. Augustine

4 stops

Sinkholes, Springs & Sawgrass Skies: Two Slow Days in Gainesville

2 Days · Active Retirees

Gainesville area, Florida

Sinkholes, Springs & Sawgrass Skies: Two Slow Days in Gainesville

3 stops

Gulf Light & Garden Peacocks: Two Unhurried Days in Tampa Bay

2 Days · Active Retirees

Tampa Bay area, Florida

Gulf Light & Garden Peacocks: Two Unhurried Days in Tampa Bay

4 stops

Banyan Shade & Butterfly Wings: Two Unhurried Days in Fort Lauderdale

2 Days · Active Retirees

Fort Lauderdale area, Florida

Banyan Shade & Butterfly Wings: Two Unhurried Days in Fort Lauderdale

4 stops

Lakeside Light & Spring-Fed Quiet: Two Days Beyond the Parks

2 Days · Active Retirees

Greater Orlando (non-theme park), Florida

Lakeside Light & Spring-Fed Quiet: Two Days Beyond the Parks

4 stops

Art Deco Light & Cuban Rhythms: 3 Days in Miami

3 Days · Active Retirees

Miami, Florida

Art Deco Light & Cuban Rhythms: 3 Days in Miami

4 stops

Banyan Shade & Butterfly Wings: Three Easy Days in Fort Lauderdale

3 Days · Active Retirees

Fort Lauderdale area, Florida

Banyan Shade & Butterfly Wings: Three Easy Days in Fort Lauderdale

7 stops

Gulf Light & Garden Shade: 3 Days in Tampa Bay

3 Days · Active Retirees

Tampa Bay area, Florida

Gulf Light & Garden Shade: 3 Days in Tampa Bay

8 stops

Coquina Light: Three Slow Days in America's Oldest City

3 Days · Active Retirees

St. Augustine, Florida, Florida

Coquina Light: Three Slow Days in America's Oldest City

6 stops

Banyan Shade & Butterfly Wings: 3 Unhurried Days in Fort Lauderdale

3 Days · Active Retirees

Fort Lauderdale area, Florida

Banyan Shade & Butterfly Wings: 3 Unhurried Days in Fort Lauderdale

8 stops

Springs, Citrus, and Lakeside Streets: 3 Days in Old Florida

3 Days · Active Retirees

Greater Orlando (non-theme park), Florida

Springs, Citrus, and Lakeside Streets: 3 Days in Old Florida

4 stops

Sinkholes, Springs & Saw-Grass Sky: 3 Days in Gainesville

3 Days · Active Retirees

Gainesville area, Florida

Sinkholes, Springs & Saw-Grass Sky: 3 Days in Gainesville

5 stops

Oak Canopies & Marsh Light: 3 Days in Tallahassee

3 Days · Active Retirees

Tallahassee area, Florida

Oak Canopies & Marsh Light: 3 Days in Tallahassee

6 stops

Turquoise Stillness: A Slow Autumn Weekend in Florida's Spring Country

2 Days · Active Retirees

Florida Springs (North Central), Florida

Turquoise Stillness: A Slow Autumn Weekend in Florida's Spring Country

2 stops

Silver Water, Quiet Pines: Two Easy Days Around Ocala

2 Days · Active Retirees

Ocala area, Florida

Silver Water, Quiet Pines: Two Easy Days Around Ocala

2 stops

Silver Water, Slow Days: A Lake Cabin Escape Near Ocala

2 Days · Active Retirees

Ocala area, Florida

Silver Water, Slow Days: A Lake Cabin Escape Near Ocala

2 stops

Springs, Slow Mornings, and Cool Turquoise Water: 3 Days in North Central Florida

3 Days · Active Retirees

Florida Springs (North Central), Florida

Springs, Slow Mornings, and Cool Turquoise Water: 3 Days in North Central Florida

4 stops

Silver Water & Longleaf Shade: 3 Days in Ocala Country

3 Days · Active Retirees

Ocala area, Florida

Silver Water & Longleaf Shade: 3 Days in Ocala Country

6 stops

Orchids, Tides & Gilded Halls: Two Easy Days on the Gulf Coast

2 Days · Active Retirees

Sarasota area, Florida

Orchids, Tides & Gilded Halls: Two Easy Days on the Gulf Coast

4 stops

Salt Air & Brick Streets: Two Days on Amelia Island

2 Days · Active Retirees

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Brick Streets: Two Days on Amelia Island

5 stops

Palafox Light & Fortress Wind: Two Gentle Days in Pensacola

2 Days · Active Retirees

Pensacola, Florida, Florida

Palafox Light & Fortress Wind: Two Gentle Days in Pensacola

3 stops

Turtles, Tides, and Old Florida Light: Two Days on Palm Beach's Shore

2 Days · Active Retirees

Palm Beach area, Florida

Turtles, Tides, and Old Florida Light: Two Days on Palm Beach's Shore

3 stops

Gardens, Gulf, and Golden Light: Two Easy Days in Sarasota

2 Days · Active Retirees

Sarasota area, Florida

Gardens, Gulf, and Golden Light: Two Easy Days in Sarasota

3 stops

Salt Air & Storied Streets: Two Easy Days in Pensacola

2 Days · Active Retirees

Pensacola, Florida, Florida

Salt Air & Storied Streets: Two Easy Days in Pensacola

3 stops

Salt Air & Brick Streets: Two Easy Days on Amelia Island

2 Days · Active Retirees

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Brick Streets: Two Easy Days on Amelia Island

3 stops

Salt Air & Slow Mornings: 3 Days on Amelia Island

3 Days · Active Retirees

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Slow Mornings: 3 Days on Amelia Island

5 stops

Salt Air & Storied Streets: 3 Days in Pensacola

3 Days · Active Retirees

Pensacola, Florida, Florida

Salt Air & Storied Streets: 3 Days in Pensacola

4 stops

Turtles, Tides, and Island Time: 3 Days in Palm Beach

3 Days · Active Retirees

Palm Beach area, Florida

Turtles, Tides, and Island Time: 3 Days in Palm Beach

3 stops

Gardens, Gulf, and Gilded Halls: 3 Days in Sarasota

3 Days · Active Retirees

Sarasota area, Florida

Gardens, Gulf, and Gilded Halls: 3 Days in Sarasota

4 stops

Slow Light on the Shoreline: 4 Days in Miami

4 Days · Active Retirees

Miami, Florida

Slow Light on the Shoreline: 4 Days in Miami

6 stops

Gentle Days in the City Beautiful: 4 Days in Orlando

4 Days · Active Retirees

Orlando, Florida

Gentle Days in the City Beautiful: 4 Days in Orlando

6 stops

Cobblestones & Coquina: Three Slow Days in America's Oldest City

3 Days · Active Retirees

St. Augustine, Florida, Florida

Cobblestones & Coquina: Three Slow Days in America's Oldest City

6 stops

Silver Water & Longleaf Pines: 3 Days in Ocala

3 Days · Active Retirees

Ocala area, Florida

Silver Water & Longleaf Pines: 3 Days in Ocala

4 stops

Turquoise Stillness: Three Slow Days Among Florida's Springs

3 Days · Active Retirees

Florida Springs (North Central), Florida

Turquoise Stillness: Three Slow Days Among Florida's Springs

3 stops

Salt Air & Southern Grace: Three Days in Pensacola

3 Days · Active Retirees

Pensacola, Florida, Florida

Salt Air & Southern Grace: Three Days in Pensacola

5 stops

Springs, Sinkholes, and Sky: Three Slow Days in Gainesville

3 Days · Active Retirees

Gainesville area, Florida

Springs, Sinkholes, and Sky: Three Slow Days in Gainesville

4 stops

Banyan Shade & Butterfly Wings: 4 Easy Days in Fort Lauderdale

4 Days · Active Retirees

Fort Lauderdale area, Florida

Banyan Shade & Butterfly Wings: 4 Easy Days in Fort Lauderdale

8 stops

Gulf Light & Garden Shade: 4 Days in Tampa Bay

4 Days · Active Retirees

Tampa Bay area, Florida

Gulf Light & Garden Shade: 4 Days in Tampa Bay

8 stops

Springs, Citrus & Lakeside Porches: Three Slow Days in Old Florida

3 Days · Active Retirees

Greater Orlando (non-theme park), Florida

Springs, Citrus & Lakeside Porches: Three Slow Days in Old Florida

3 stops

Bay Breezes & Gilded Halls: 3 Days in Sarasota

3 Days · Active Retirees

Sarasota area, Florida

Bay Breezes & Gilded Halls: 3 Days in Sarasota

6 stops

Turtles, Tides & Golden Hours: 3 Days Along Palm Beach's Coast

3 Days · Active Retirees

Palm Beach area, Florida

Turtles, Tides & Golden Hours: 3 Days Along Palm Beach's Coast

3 stops

Salt Air & Slow Mornings: 3 Days on the First Coast

3 Days · Active Retirees

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Slow Mornings: 3 Days on the First Coast

6 stops

Spanish Moss & Marble Halls: Three Gentle Days in Tallahassee

3 Days · Active Retirees

Tallahassee area, Florida

Spanish Moss & Marble Halls: Three Gentle Days in Tallahassee

4 stops

Springs of Still Water: Two Slow Days in North Central Florida

2 Days · Active Retirees

Florida Springs (North Central), Florida

Springs of Still Water: Two Slow Days in North Central Florida

4 stops

Florida welcomes active retirees seeking meaningful travel experiences beyond the typical tourist circuit. This collection features 14 carefully curated itineraries spanning Florida's most rewarding destinations, from historic coastal towns to natural springs and vibrant cultural centers. Whether exploring Miami's shoreline, wandering St. Augustine's cobblestone streets, or discovering the springs of North Central Florida, these journeys balance cultural discovery, natural beauty, and accessible pacing. Each itinerary is designed to reveal authentic Florida—its history, wildlife, and slower rhythms—allowing travelers to experience the state's diverse character while enjoying the leisure that active retirement affords.

Frequently Asked Questions

What types of destinations are covered in these itineraries?

⌄

The itineraries span 14 Florida destinations including Miami, Orlando, St. Augustine, the Ocala area, Florida Springs, Pensacola, Gainesville, Fort Lauderdale, Tampa Bay, Sarasota, Palm Beach, the First Coast, and Tallahassee, offering a mix of coastal towns, historic cities, natural springs, and cultural centers.

How long are these trips?

⌄

The itineraries range from 3 to 4 days. Most are 3-day trips, with several 4-day options available in Miami, Orlando, Fort Lauderdale, and Tampa Bay.

What activities can active retirees expect on these itineraries?

⌄

The itineraries feature diverse activities suited to active travelers, including waterside exploration, historic walking tours, visits to natural springs, wildlife observation, botanical experiences, and cultural attractions. Examples include shoreline strolls in Miami, historic exploration in St. Augustine, and spring swimming in North Central Florida.

Are there itineraries focused on natural attractions?

⌄

Yes, several itineraries highlight Florida's natural features, including trips centered on Florida Springs, the Ocala area, Gainesville, and coastal destinations like Pensacola and the First Coast, offering experiences with water, landscape, and wildlife.

More Collections

Or see Active Retirees nationwide or browse every Florida destination.