Summer Itineraries in Florida

Long daylight hours and peak-season energy — plans built for the busiest, brightest stretch of the year.

55 itineraries

Springs, Stillness & Small Splashes: 3 Days of Old Florida for Families

3 Days · Young Families

Ocala area, Florida

Springs, Stillness & Small Splashes: 3 Days of Old Florida for Families

4 stops

Sand, Circus Gold & Black Water: 3 Days in Sarasota

3 Days · Teen Families

Sarasota area, Florida

Sand, Circus Gold & Black Water: 3 Days in Sarasota

4 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

Sand, Silence & Gilded Halls: 3 Days Solo in Sarasota

3 Days · Solo

Sarasota area, Florida

Sand, Silence & Gilded Halls: 3 Days Solo in Sarasota

6 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 & Squadron Skies: 3 Days in Pensacola

3 Days · Teen Families

Pensacola, Florida, Florida

Salt Air & Squadron Skies: 3 Days in Pensacola

6 stops

Turtles, Tides & Teen Time: 3 Days Along the Palm Beach Coast

3 Days · Teen Families

Palm Beach area, Florida

Turtles, Tides & Teen Time: 3 Days Along the Palm Beach Coast

5 stops

Salt Air & Sand Dollars: 3 Days on Amelia Island

3 Days · Teen Families

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Sand Dollars: 3 Days on Amelia Island

7 stops

Salt Air & Sentinel Skies: 3 Days Solo in Pensacola

3 Days · Solo

Pensacola, Florida, Florida

Salt Air & Sentinel Skies: 3 Days Solo in Pensacola

6 stops

Salt Air & Solitude: Three Days Alone on the First Coast

3 Days · Solo

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Solitude: Three Days Alone on the First Coast

5 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

Orchids, Tides, and Gulf Light: 2 Days in Sarasota

2 Days · Couples

Sarasota area, Florida

Orchids, Tides, and Gulf Light: 2 Days in Sarasota

4 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

Turtles, Tides, and Twilight: Two Days Along Palm Beach's Northern Shore

2 Days · Couples

Palm Beach area, Florida

Turtles, Tides, and Twilight: Two Days Along Palm Beach's Northern Shore

3 stops

Turtles, Tides & Tiny Footprints: 2 Days on the Palm Beach Coast

2 Days · Young Families

Palm Beach area, Florida

Turtles, Tides & Tiny Footprints: 2 Days on the Palm Beach Coast

4 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

Sandcastles & Salt Air: A Family Escape to Amelia Island

2 Days · Young Families

First Coast (Amelia Island, Jacksonville), Florida

Sandcastles & Salt Air: A Family Escape to Amelia Island

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

Sand, Sun, and Slow Mornings: 2 Days in Sarasota with the Kids

2 Days · Young Families

Sarasota area, Florida

Sand, Sun, and Slow Mornings: 2 Days in Sarasota with the Kids

4 stops

Salt Air & Sea Wall Light: Two Days on Amelia Island

2 Days · Couples

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Sea Wall Light: Two Days on Amelia Island

6 stops

Salt Air & Sunset Bastions: Two Days in Pensacola

2 Days · Couples

Pensacola, Florida, Florida

Salt Air & Sunset Bastions: Two Days in Pensacola

4 stops

Salt Air & Small Steps: Two Gulf Coast Days for Little Explorers

2 Days · Young Families

Pensacola, Florida, Florida

Salt Air & Small Steps: Two Gulf Coast Days for Little Explorers

3 stops

Sea Turtles & Salt Air: A Palm Beach Escape for Two

3 Days · Couples

Palm Beach area, Florida

Sea Turtles & Salt Air: A Palm Beach Escape for Two

4 stops

Salt Air & Small Steps: 3 Days in Pensacola with Little Ones

3 Days · Young Families

Pensacola, Florida, Florida

Salt Air & Small Steps: 3 Days in Pensacola with Little Ones

4 stops

Sand, Salt Marsh, and Small-Town Time: 3 Days on Amelia Island with Kids

3 Days · Young Families

First Coast (Amelia Island, Jacksonville), Florida

Sand, Salt Marsh, and Small-Town Time: 3 Days on Amelia Island with Kids

6 stops

Sea Turtles, Sandcastles & Slow Island Days: 3 Days in Palm Beach with Little Ones

3 Days · Young Families

Palm Beach area, Florida

Sea Turtles, Sandcastles & Slow Island Days: 3 Days in Palm Beach with Little Ones

5 stops

Orchids, Sand, and Black Water: Three Days of Gulf Coast Romance

3 Days · Couples

Sarasota area, Florida

Orchids, Sand, and Black Water: Three Days of Gulf Coast Romance

4 stops

Salt Air & Slow Sunsets: 3 Days on Amelia Island

3 Days · Couples

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Slow Sunsets: 3 Days on Amelia Island

5 stops

Salt Air & Sunset Gold: 3 Days in Pensacola for Two

3 Days · Couples

Pensacola, Florida, Florida

Salt Air & Sunset Gold: 3 Days in Pensacola for Two

6 stops

Sand, Shade & Sea Glass: 3 Days in Sarasota with Little Ones

3 Days · Young Families

Sarasota area, Florida

Sand, Shade & Sea Glass: 3 Days in Sarasota with Little Ones

4 stops

Slow Sun and Soft Sand: 4 Days in Miami with Little Ones

4 Days · Young Families

Miami, Florida

Slow Sun and Soft Sand: 4 Days in Miami with Little Ones

5 stops

Castles, Coasters & Springs: 3 Days of Orlando Magic for Teens and Parents

3 Days · Teen Families

Orlando, Florida

Castles, Coasters & Springs: 3 Days of Orlando Magic for Teens and Parents

6 stops

Sun, Sand & Cuban Nights: 3 Days in Miami with the Family

3 Days · Teen Families

Miami, Florida

Sun, Sand & Cuban Nights: 3 Days in Miami with the Family

8 stops

Slow Magic: 4 Gentle Days in Orlando with Little Ones

4 Days · Young Families

Orlando, Florida

Slow Magic: 4 Gentle Days in Orlando with Little Ones

6 stops

Turtles, Tides & Golden Hour: A Palm Beach Day for Two

1 Day · Couples

Palm Beach area, Florida

Turtles, Tides & Golden Hour: A Palm Beach Day for Two

2 stops

Turquoise Hours: A Springs Retreat for Two

3 Days · Couples

Florida Springs (North Central), Florida

Turquoise Hours: A Springs Retreat for Two

4 stops

Springs, Sinkholes & Sleepy Prairies: 3 Days in Gainesville with Little Ones

3 Days · Young Families

Gainesville area, Florida

Springs, Sinkholes & Sleepy Prairies: 3 Days in Gainesville with Little Ones

3 stops

Sun, Sand, and Sea Life: 3 Days in Tampa Bay

3 Days · Teen Families

Tampa Bay area, Florida

Sun, Sand, and Sea Life: 3 Days in Tampa Bay

6 stops

Springs, Sand & Slow Mornings: 4 Days of Old Florida with the Kids

4 Days · Young Families

Ocala area, Florida

Springs, Sand & Slow Mornings: 4 Days of Old Florida with the Kids

6 stops

Salt Air & Slow Sunsets: 4 Days in Pensacola for Two

4 Days · Couples

Pensacola, Florida, Florida

Salt Air & Slow Sunsets: 4 Days in Pensacola for Two

8 stops

Salt Air & Slow Gold: 4 Days of Sarasota for Two

4 Days · Couples

Sarasota area, Florida

Salt Air & Slow Gold: 4 Days of Sarasota for Two

6 stops

Salt Air & Sand Dollars: 4 Days on Amelia Island

4 Days · Teen Families

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Sand Dollars: 4 Days on Amelia Island

6 stops

Springs, Sunbeams & Small-Town Sweetness: 3 Days in Greater Orlando

3 Days · Young Families

Greater Orlando (non-theme park), Florida

Springs, Sunbeams & Small-Town Sweetness: 3 Days in Greater Orlando

6 stops

Sand, Circus Kings & Cypress Shadows: 4 Days in Sarasota

4 Days · Teen Families

Sarasota area, Florida

Sand, Circus Kings & Cypress Shadows: 4 Days in Sarasota

6 stops

Turtles, Tides, and Golden Hour: 4 Days in Palm Beach

4 Days · Couples

Palm Beach area, Florida

Turtles, Tides, and Golden Hour: 4 Days in Palm Beach

6 stops

Salt Air & Squadron Skies: 4 Days in Pensacola

4 Days · Teen Families

Pensacola, Florida, Florida

Salt Air & Squadron Skies: 4 Days in Pensacola

6 stops

Butterflies, Banyans & Beach Naps: 4 Days in Fort Lauderdale with the Kids

4 Days · Young Families

Fort Lauderdale area, Florida

Butterflies, Banyans & Beach Naps: 4 Days in Fort Lauderdale with the Kids

8 stops

Cobblestones & Cannon Smoke: A Family Weekend in St. Augustine

3 Days · Young Families

St. Augustine, Florida, Florida

Cobblestones & Cannon Smoke: A Family Weekend in St. Augustine

5 stops

Springs, Silence & Starlight: A Couples' Escape to Old Florida

3 Days · Couples

Ocala area, Florida

Springs, Silence & Starlight: A Couples' Escape to Old Florida

6 stops

Turtles, Tides & Island Time: 4 Days in Palm Beach

4 Days · Teen Families

Palm Beach area, Florida

Turtles, Tides & Island Time: 4 Days in Palm Beach

5 stops

Sandy Toes & Dolphin Tails: 4 Days in Tampa Bay with the Kids

4 Days · Young Families

Tampa Bay area, Florida

Sandy Toes & Dolphin Tails: 4 Days in Tampa Bay with the Kids

7 stops

Salt Air & Slow Mornings: 4 Days on Amelia Island

4 Days · Couples

First Coast (Amelia Island, Jacksonville), Florida

Salt Air & Slow Mornings: 4 Days on Amelia Island

6 stops

Spanish Moss & Marsh Light: 3 Days in Tallahassee with Little Ones

3 Days · Young Families

Tallahassee area, Florida

Spanish Moss & Marsh Light: 3 Days in Tallahassee with Little Ones

4 stops

Turquoise Mornings & Quiet Afternoons: 4 Days in Florida's Spring Country

4 Days · Young Families

Florida Springs (North Central), Florida

Turquoise Mornings & Quiet Afternoons: 4 Days in Florida's Spring Country

4 stops

Butterflies, Banyans & Boulevard Nights: 3 Days in Fort Lauderdale

3 Days · Teen Families

Fort Lauderdale area, Florida

Butterflies, Banyans & Boulevard Nights: 3 Days in Fort Lauderdale

7 stops

More Collections

We use cookies to improve your experience and analyze site usage. Essential cookies are always active. You can customize your preferences or accept all cookies. Cookie Policy