Fine-tuning itinerary

Question

We are about to embark on a South Florida trip planned around seeing the 3 national parks with extra time for Miami area and the Keys. Have gotten a lot of good advice reading through this forum and have some final questions about our itinerary. All of these destinations are new to us. We tend to fill our days with activities but like to take our time and not rush through every destination. For this trip we also want to have time to just relax around the pool or beach. We love to hike, cycle, kayak, and snorkel but due to my husband’s recent injury we have cancelled those plans for now and hope that if he recovers enough we can plan some excursions closer to the day of. Walking/hiking is ok but probably only a couple miles a day at this point.

After 3 nights in Miami and then 3 in Homestead visiting the Everglades and Biscayne NP, we plan to take our time getting down to Marathon but don’t have specific stops in mind yet. The travel day is a Saturday the last weekend in April so expect there will be heavy traffic. Had to drop the planned snorkel excursion so will probably just stop at some of the state parks and maybe check out Islamorada. I have collected restaurant recommendations for Marathon since we are staying there but would love some suggestions for a nice lunch in Islamorada or elsewhere on the way down. I have the Florida Rambler mile marker guide bookmarked on my phone so that should keep us from missing any highlights. We booked 2 nights at the Isla Bella resort in Marathon mainly because of its location at the old 7 Mile Bridge, which would have been perfect for my husband’s usual 4 mile morning run. Thought about changing to someplace in Islamorada since running is ruled out for now but Isla Bella looks lovely with water views from all the rooms so we are sticking with it. I am not a runner so we can both walk the bridge together!

We will take our time driving to Key West, unless we spend so much time relaxing in Marathon that we want to get to where the action is! We have the afternoon sea plane to Dry Tortugas booked on the day after we arrive so we will return our car to the airport when we go to catch the plane. We definitely want to do a sunset sail one evening. Prefer one with a smaller crowd, more adult-oriented but not a party scene. The ones that have caught my eye are Danger Charters, Argo Navis, Fishmonster, and Spirit of Independence. They all have availability for the nights we are there. I am just going by websites and online reviews. Would appreciate advice from anyone with personal knowledge of these boats. Would like to hold off as long as possible to book so we will have a more reliable weather forecast. Any suggestions about how far in advance we should book before they would sell out? This would be a weeknight May 1 or 2.

We have 4 nights in Key West so the rest of our time will be mostly unscheduled wandering around, seeing some sights (Hemingway House, Truman White House, etc.) and listening to music. I have the KeyWestconcierge.com live music schedule bookmarked but since we won’t really be familiar with any of the performers we will probably go by ear or crowds. The Songwriter’s Fest is happening while we are there so that should be fun. I would really love to get out to the reef for some snorkeling and hopeful that by the time we get to Key West my husband will have recovered enough to go or won’t mind if I go on my own. Would appreciate some recommendations for outfitters for a half-day excursion or suggestions for the best areas to get to for good snorkeling.

Many thanks for any suggestions or advice on our plans. We are really looking forward to it.

Answer

Your South Florida and Keys itinerary sounds thoughtfully planned, balancing national parks, relaxation, and the Keys’ charm. Given your preferences and your husband’s current injury, there are a few refinements and suggestions to help make the most of your trip.

For your drive from Homestead down to Marathon, taking your time is wise, especially on a weekend with expected heavy traffic. Since snorkeling is off the table for now, consider stopping at a few scenic state parks and casual viewpoints along the Overseas Highway rather than cramming too many stops:

Long Key State Park – short, easy walks along the boardwalks and beach access; a great spot for a picnic or brief rest.
Islamorada – you can explore the small shops and galleries, or have a leisurely lunch at local favorites such as Lorelei Restaurant & Cabana Bar (good water views) or Islamorada Fish Company.
Anne’s Beach – quick stop for a stroll along the boardwalk, very accessible and relaxing.

Marathon’s Isla Bella Resort is an excellent choice for views and comfort. Even if running is off the agenda, walking the Old Seven Mile Bridge together offers a beautiful experience without the intensity of a run. Since your focus is on relaxation and scenic enjoyment, this location is ideal. For lunch or casual outings in Marathon, consider:

Keys Fisheries – great for fresh seafood and a laid-back atmosphere.
La Moderna – good Cuban fare in a relaxed setting.
Sunset Grille & Raw Bar – perfect for an early evening meal with water views.

Regarding the sunset sail, your preference for a smaller, adult-oriented cruise aligns well with the operators you’ve researched:

Danger Charters: Known for attentive service, smaller groups, and sunset-focused experiences.
Argo Navis: Offers private charters and flexible scheduling; good for quieter trips.
Fishmonster: Slightly larger group but very experienced crew; good reviews for sunset cruises.
Spirit of Independence: Historic schooner, more scenic and relaxed than party-oriented; ideal for a mellow evening.

Booking about 2–3 weeks in advance for a weeknight in May is usually sufficient, especially if you are flexible on the exact evening, but waiting too long can limit preferred times or specific boats.

Once in Key West, your plan to explore at leisure is perfect. For your snorkeling outing, consider half-day trips offered by these outfitters:

Fury Water Adventures – offers reef and shallow-water snorkeling, very well-reviewed and family-friendly.
Sebago Watersports – small groups, flexible departures, guides focus on local reefs.
Danger Charters – some of their trips include snorkeling options as well.

Top snorkeling areas include the Key West National Wildlife Refuge, Sand Key, and the coral reefs near the Dry Tortugas if you’re already doing that seaplane trip. Many outfitters provide full equipment and short guided introductions, so even if your husband doesn’t go, you can still have a great experience.

For wandering and enjoying Key West evenings, walking around Duval Street and the quieter side streets works well, particularly with the Songwriter’s Fest providing live music. Sunset at Mallory Square remains a quintessential Key West experience, even if you prefer a smaller crowd on other evenings.

Overall, your itinerary balances activity and relaxation. By keeping your excursions flexible, planning light stops between major destinations, and securing your sunset cruise 2–3 weeks ahead, you should have a smooth, enjoyable trip that combines sightseeing, beach/pool relaxation, and a taste of local culture and dining.

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