Itinerary and accommodation help. PLEASE xxx

Question

Hi all, my two adult daughters and I are planning a 10-night trip to South Beach Miami and the Florida Keys arriving late in the evening on the 7th August and departing late in the evening on the 17th August. I am seeking real advice (rather than AI generated) on how we should divide our time in the keys and destinations that are considered a must visit.

The AI inventories would have you jumping in the car every five minutes to tick of all sights but that is not what we want. I would rather visit fewer places but get a real feel for them without thinking seen that done that.

We have visited South Beach before, so we are planning three nights (two full days as we arrive so late) prior to picking up a hire car and heading to the keys.

So, we have seven nights and a final day to head back to Miami for a flight around 5pm.

We are looking at the usual stops including Key Largo, Islamorada, Marathon, Bahia Honda Key and Key West. We would be grateful for any advice on how to tailor our trip. For example, should we skip any of the above and just have fewer overnights at say Islamorada and Key West? Is Key Largo a must etc? Is there a particular side of the Keys we should be looking at to avoid seaweed at that time of year (I read that somewhere)?

We are looking for chill vibes and to get a feel for the place rather than a whistle stop box ticking exercise. I guess more is less as we only have ten nights.

In terms of accommodation, we are happy to share a big room, and our budget would be between $250 - $350 per night but could go higher for something highly recommended.

We all love a few cocktails and good food preferably beach side/outdoors so any suggestions for that would also be much appreciated.

Many thanks in advance.

Answer

For a relaxed 10-night trip to South Beach and the Florida Keys, your idea of slowing down and enjoying fewer places is exactly the way to go. Here’s a suggested approach based on real travel experiences and local recommendations.

Since you already know South Beach, your plan to spend 3 nights there works well, giving you two full days to enjoy the area without rush. Focus on beach time, casual strolls along Lincoln Road, and a few iconic cocktails on Ocean Drive or rooftop bars.

For the Keys portion, with seven nights available, a slower itinerary with fewer overnight stops is ideal. Key Largo is convenient but can be skipped if you’re more interested in authentic Keys experiences rather than hotel resort vibes—it’s mostly a gateway with diving/snorkeling opportunities. If snorkeling or visiting John Pennekamp Coral Reef is a priority, then one night here is sufficient.

Islamorada (2 nights): Stay here to enjoy a relaxed fishing village vibe. Great for seafood and sunset cocktails. Recommended spots include Morada Bay Beach Café for casual beachside dining and The Islander Resort for laid-back poolside drinks. You can visit local art galleries or take a short snorkel or kayak trip.
Marathon (2 nights): Ideal for a more central Keys feel. Visit the Turtle Hospital or take a kayak/paddleboard tour through mangroves. Sombrero Beach is excellent for a calm afternoon. Accommodations like Tranquility Bay or Faro Blanco Resort offer comfortable rooms within your budget and pool access.
Key West (3 nights): Spend the longest here to soak up the lively atmosphere, historic streets, and vibrant dining scene. Explore Duval Street, Mallory Square, and the quieter parts like Higgs Beach or Fort Zachary Taylor. Sunset drinks at the iconic Sunset Pier or a sailboat charter will make the visit memorable.

Regarding Bahia Honda Key, it is gorgeous but can be done as a day stop from Marathon rather than overnight, especially since your goal is a chill pace. Spend a few hours at the beach or on the scenic trails and then continue on.

On the issue of seaweed in August, the Atlantic side of the Keys can sometimes have Sargassum, but generally the Gulf side (Marathon through Key West) tends to be less affected. So choosing accommodations on the Gulf-facing side can help minimize this issue.

Accommodation Tips: Look for resorts or boutique hotels that offer larger rooms or suites to comfortably share. Options like Isla Bella Beach Resort (Marathon), Cheeca Lodge & Spa (Islamorada), or small boutique inns in Key West like Heron House or The Marker can fit your budget and offer a pool or beach access.
Dining & Cocktails: Prioritize casual outdoor dining and local seafood. Examples include Morada Bay (Islamorada), Island Fish Company (Marathon), Louie’s Backyard or Latitudes at Sunset Key (Key West) for special meals. Local rum or cocktail bars near the water enhance the experience.
Transportation: Renting a car is essential for the Keys to move at your own pace. Plan relaxed driving days with 1-2 hour drives and stops along the way for viewpoints, beaches, or snorkeling. Avoid overpacking each day.

Sample Keys itinerary:

Day 1: Drive from Miami to Islamorada (1 night if skipping Key Largo, 2 nights otherwise)
Day 2: Full day in Islamorada – relax, enjoy beach, sunset cocktails
Day 3: Drive to Marathon, stop at Bahia Honda Key on the way
Day 4: Marathon – Turtle Hospital, Sombrero Beach, poolside relaxation
Day 5: Marathon to Key West – casual stops along Overseas Highway
Day 6-7: Key West – explore at a relaxed pace, Mallory Square, beaches, local dining
Day 8: Key West – last day, perhaps a sailing trip or snorkeling, then drive back to Miami on Day 9 for flight prep

This approach minimizes hotel hopping, keeps driving times reasonable, and ensures you enjoy the unique vibes of each Key without feeling rushed.

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