A 10-day Florida Keys road trip itinerary for families with young kids, covering key stops, kid-friendly activities, and day-by-day planning.
Duration
10 days
Travelers
4
Price
$4,080
YYZ to MIA
Flight from Toronto to Miami
Sun, 5 Apr 2026, 08:00
Depart from Toronto Pearson International Airport (YYZ)
Flight duration: 3h 18m
Sun, 5 Apr 2026, 11:18
Arrive at Miami International Airport (MIA)
235
Coconut Beach Resort
Tranquil, oceanfront hotel featuring an outdoor pool, a hot tub & a private beach.
Free Wi-Fi
Free parking
Outdoor pool
Hot tub
Air conditioning
Beach access
Kitchen in some rooms
Kid-friendly
Smoke-free property
Check-in
Apr 5, 2026 2:00 PM
Check-out
Apr 9, 2026 11:00 AM
75
The Shops at Mallory Square
291 Front St, Key West, FL 33040
Restrooms available
55
Florida Keys Sandbar Adventures
5130 Overseas Hwy, Key West, FL 33040
7,738
Hogfish Bar & Grill
Bustling seafood shack by the harbor. Lively, open-air seafood eatery known for its namesake hogfish sandwich & relaxed atmosphere.
Good for children
Good for groups
Live music
Outdoor seating
Bar onsite
Serves brunch, lunch, and dinner
Serves beer, wine, and cocktails
Serves dessert and coffee
Offers takeout, delivery, and dine-in
Restrooms available
Accepts reservations
642
Sunset Tiki Bar
Cocktails & live music in a buzzy resort. Laid-back poolside haunt at the lively Galleon Resort providing tropical cocktails & live music.
Good for groups
Live music
Outdoor seating
Serves beer, wine, and cocktails
Offers takeout, delivery, and dine-in
Restrooms available
Accepts reservations
553
The Sunset Inn - Islamorada
Bright, modest rooms, some with kitchenettes, in a laid-back motor inn offering free Wi-Fi & a pool.
Free Wi-Fi
Free parking
Outdoor pool
Air conditioning
Accessible
Kid-friendly
Check-in
Apr 9, 2026 3:00 PM
Check-out
Apr 13, 2026 11:00 AM
84
Skins and Fins Charters
81924 Overseas Hwy #1, Islamorada, FL 33036
4,310
Steak 44
Modern-chic steakhouse with gourmet fare. High-end steakhouse featuring gourmet filets, seafood & classic entrees in an elegant, modern venue.
Good for groups
Free Wi‑Fi
Bar onsite
Serves dinner
Serves beer, wine, and cocktails
Serves dessert and coffee
Offers takeout, delivery, and dine-in
Restrooms available
Accepts reservations
627
A Family Fun Boat Tour Company
85920 Overseas Hwy, Islamorada, FL 33036
1,444
Hotel Breakwater South Beach
Bright, modern quarters in a beachside property with a pool, a rooftop terrace & loaner bikes.
Breakfast
Free Wi-Fi
Parking
Outdoor pool
Hot tub
Air conditioning
Fitness center
Beach access
Bar
Restaurant
Full-service laundry
Accessible
Business center
Kid-friendly
Smoke-free property
Check-in
Apr 13, 2026 4:00 PM
Check-out
Apr 15, 2026 11:00 AM
Swizzle Rum Bar & Drinkery
Stylish bar for global fare & cocktails. Fashionable late-night bar offering international eats, craft cocktails & an extensive rum menu.
2,906
Lincoln Road Shopping District
1620 Drexel Ave Suite 100, Miami, FL 33139
Restrooms available
8,310
Fogo de Chão Brazilian Steakhouse
Upmarket Brazilian churrascaria. Upscale Brazilian chain for all-you-can-eat meat carved tableside plus an extensive salad bar.
Good for children
Good for groups
Outdoor seating
Free Wi‑Fi
Bar onsite
Serves brunch, lunch, and dinner
Serves beer, wine, and cocktails
Serves dessert and coffee
Offers takeout, delivery, and dine-in
Restrooms available
Accepts reservations
MIA to YYZ
Flight from Miami to Toronto
Wed, 15 Apr 2026, 12:20
Depart from Miami International Airport (MIA)
Flight duration: 3h 19m
Wed, 15 Apr 2026, 15:39
Arrive at Toronto Pearson International Airport (YYZ)
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