Itinerary for 1 week

Question

Hi! Planning a trip to the Keys/Miami for family of 4 - 2 adults and 2 older teenagers. We do like to be on the move but also want to make sure we don't miss out on anything, lol. Does the following schedule sound like it could work? Anything you would change? Also, any suggestions on the tbd's?

Day 1 - arrive in Miami, lunch in Key Largo (tbd), arrive in Key West (Havana Cabana Hotel ?) in time for late dinner (tbd)

Day 2 - Tour Key West, Hemmingway house, Southern most point, Audubon House, Mallory Square, Duval Street, lunch (tbd) and dinner(tbd)

Day 3 - Fishing charter (6 hours), drive to Islamorada and check in to hotel (The Islander?)

Day 4 - Explore Islamorada, Robbie's, 2 breweries, Theater of the Seas ?, dinner (tbd)

Day 5 - Morning in Islamorada, Afternoon Everglades tour (maybe?), drive to South beach, (Kimpton Surfcomber Hotel?) Dinner in South Beach area

Day 6 - Explore South beach area, go to beach, dinner Espanola Way

Day 7 - Beach time until flight at 5 pm

Answer

Your one-week itinerary for the Florida Keys and Miami looks quite well-paced for a family of four, balancing sightseeing, water activities, and relaxation. Here’s a detailed review and some suggestions for improvements and TBD options.

Day 1 - Miami to Key West: Driving from Miami to Key West is about 3.5–4 hours without stops, so factoring in lunch and a break is realistic. Key Largo is a good halfway point.

Lunch TBD: Consider Mrs. Mac’s Kitchen in Key Largo for classic seafood and casual fare, or Key Largo Conch House for local specialties.
Hotel: Havana Cabana Hotel is a solid choice with a pool and comfortable rooms; consider proximity to Duval Street for walking access.
Dinner TBD: For a late dinner, Blue Heaven is iconic and casual, while Latitudes (on Sunset Key, reservations required) offers a fine dining experience.

Day 2 - Key West sightseeing: You have a full day planned, which is doable but ambitious.

Consider starting early at the Hemingway Home to avoid crowds.
Lunch TBD: El Siboney or Conch Republic Seafood Company are great options.
Dinner TBD: For family-friendly but memorable dinner, Hogfish Bar & Grill or Garbo’s Grill (food truck) are popular.
Note: Southernmost Point can be busy; consider going early morning or evening for photos.

Day 3 - Fishing and drive to Islamorada: A 6-hour fishing charter in Key West is reasonable; be mindful of fatigue after the drive. Driving to Islamorada will take ~2.5 hours.

Hotel TBD: The Islander is good for families and near local attractions like Robbie’s Marina.

Day 4 - Islamorada: This day looks well-balanced between relaxation and activities.

Robbie’s is great for feeding tarpon and casual souvenir shopping.
Breweries: Islamorada Beer Company and Florida Keys Brewing Co. are local favorites.
Theater of the Sea: Good for dolphin/sea lion shows; plan your timing so it doesn’t conflict with lunch or dinner.
Dinner TBD: Morada Bay Beach Café offers sunset views and seafood, or Lazy Days for family-friendly options.

Day 5 - Islamorada to South Beach: This is a long day: morning in Islamorada, Everglades tour, then drive to Miami South Beach (~4 hours). Consider logistics carefully.

Everglades tour options: Airboat tours at Everglades National Park or Shark Valley Tram Tours for less strenuous activity.
Hotel TBD: Kimpton Surfcomber is a good beachfront property; check for family-friendly room configurations.
Dinner TBD: South Beach has multiple options; Joe’s Stone Crab or Big Pink for casual meals.

Day 6 - South Beach: Time to relax on the beach. Consider adding a short art deco walking tour or Lincoln Road shopping.

Dinner: Espanola Way offers multiple restaurants; Havana 1957 or Tapas y Tintos are good family-friendly choices.

Day 7 - Departure: Beach time in the morning is ideal. Ensure you account for travel time to Miami airport (about 30–40 minutes from South Beach) to reach your 5 pm flight comfortably.

Additional Notes:

Consider adjusting Day 5 to focus either on Islamorada or the Everglades to avoid a very long and exhausting day.
Public transportation is limited in the Keys; renting a car is almost essential for this itinerary.
Book popular activities (fishing charter, Theater of the Sea, Everglades tour) in advance to secure slots.
Key West is very walkable, but in South Beach, walking to restaurants is possible; otherwise, rideshare is convenient.
Sun protection and hydration are important for all outdoor activities, especially for teens and adults alike.

Overall, the itinerary is feasible with minor adjustments for travel fatigue and timing. It balances sightseeing, water activities, and relaxation well for a family with teenagers.

Itinerary for 1 week

More Florida Keys Travel Questions

The attractions mentioned in this question

Popular Destinations

Popular Travel Questions