Trip planning help please

Question

My husband and I will be going to Key West for our 30th anniversary in June. Neither of us have ever been, but I've always wanted to go. We will be flying into FLL on Saturday at 1:30, picking up a car, and driving to Islamorada to spend Saturday night. We will be driving to Key West on Sunday morning. We are flying out of FLL the following Sunday at 7:30 AM. Should we stay in Key west Sunday-Saturday, and spend the night before we leave in Miami? Or should we stay in Key West Sunday-Friday and spend Friday and Saturday night in Miami (south beach). We both love night life (Nashville/broadway is our fav), local eateries, historic places, and beaches. Any suggestions would be appreciated. I only have the night in Islamorada and the car booked so far. Thanks in advance!

Answer

Congratulations on your 30th anniversary! Planning a Florida Keys and Miami trip for June can be exciting, especially for first-timers to Key West. Here’s a detailed approach for your itinerary and suggestions based on your interests.

Since you’re flying into FLL and have your first night in Islamorada booked, you have a straightforward drive from Fort Lauderdale to the Upper Keys (~2.5–3 hours). From Islamorada to Key West is another ~2.5 hours, so Sunday morning departure is a good choice to maximize your first day in Key West.

Regarding the end of your trip, there are two main options:

Option 1: Stay in Key West Sunday–Saturday, then drive back to Miami late Saturday night or very early Sunday morning: This maximizes your time in Key West, which is ideal if you want to immerse yourselves in the nightlife, historic sites, and local eateries. However, the drive back to Miami for your 7:30 AM flight will be tight if you leave Saturday night—it’s around a 4-hour drive from Key West to Miami Airport, so you may need to leave very early Saturday to avoid stress.
Option 2: Stay in Key West Sunday–Friday, then spend Friday and Saturday night in Miami: This option gives you two nights in Miami (South Beach) for nightlife, beaches, and local culture without worrying about an early morning airport drive. You can enjoy a relaxed final day in Key West, then a scenic drive up the Keys to Miami (~3.5–4 hours), stopping along the way at historic or scenic spots.

Given your interests in nightlife, local eateries, historic places, and beaches, Option 2 is likely the more comfortable choice. It allows you to fully enjoy both Key West and Miami without the stress of a very early departure for your flight.

Key suggestions for Key West (Sunday–Friday):

Stroll along Duval Street for bars, live music, and vibrant nightlife. Stop at Sloppy Joe’s or The Green Parrot for local flavor and live performances.
Visit historic sites like Ernest Hemingway Home & Museum, Truman Little White House, and Key West Lighthouse.
Enjoy beaches such as Fort Zachary Taylor Historic State Park for sun and snorkeling.
Take a sunset sail or eco-tour to experience the beautiful waters and local wildlife.
Try local eateries like Blue Heaven, Garbo’s Grill, or Santiago’s Bodega for casual yet iconic meals.

Miami recommendations for Friday–Saturday:

Stay in South Beach to be close to nightlife, restaurants, and the beach.
Walk along Ocean Drive and Collins Avenue for a lively atmosphere, or explore the Wynwood Walls for art and culture.
Check out Little Havana for local Cuban cuisine and live music.
Relax on the beach during the day and enjoy rooftop bars or live music venues at night.

Additional tips:

Book accommodations as soon as possible—June is summer in Florida, and popular areas like Key West and South Beach fill up quickly.
Consider reserving any must-do tours or dinner spots in advance, especially for Key West sunset cruises or popular restaurants.
Be prepared for warm, humid weather in June and occasional afternoon showers.

In summary, spend Sunday–Friday in Key West for a rich mix of history, nightlife, and beaches, then enjoy two relaxed nights in Miami before your early flight home. This approach balances travel time, experiences, and stress, making your anniversary trip memorable.

Trip planning help please

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