KW 5 days or split stay

Question

Currently we are booked for 5 nights in Key West. Traveling with my parents, husband, and 2 boys (10 & 13). We've been to KW before and loved it. For the first time we are doing the drive from Miami. Should we stay in one of the other keys a night or 2 and then head to KW? If so, which one? I know KW isn't know for the beaches. Is there another Key that is?

Answer

Splitting your stay between Key West and another Key can be a great way to break up the drive from Miami and enjoy a more relaxed pace, especially with kids and parents along.

Since Key West isn’t known for expansive beaches, staying in one of the middle Keys or Upper Keys can give you access to better swimming and beach options, as well as a chance to see a different side of the Keys.

Islamorada: Roughly halfway between Miami and Key West, Islamorada is known for its calm waters, fishing opportunities, and family-friendly resorts with pools and small beaches. This is a good spot for a 1–2 night stay, especially if your family enjoys water sports or fishing.
Marathon / Coco Plum Beach: Located further south, Marathon has some nicer beaches, including Coco Plum Beach and Sombrero Beach, which are more relaxed and less crowded. Great for a short overnight stay if you want to mix in a beach day before heading to Key West.
Big Pine Key / Bahia Honda: Bahia Honda State Park has one of the best beaches in the Keys with clear water and soft sand. Staying nearby (Big Pine Key) allows you to explore this area and still be a reasonable drive from Key West the next day.

By doing a split stay, you can enjoy the journey, give the kids some time at a proper beach, and still have the full Key West experience. Many visitors recommend spending the first 1–2 nights in a mid-Keys location, then finishing in Key West for a 3–4 night stay to soak in the island vibe, restaurants, and attractions.

Consider booking accommodations in advance, as popular Keys can fill quickly, especially during spring months.
Plan your stops along the Overseas Highway—there are scenic viewpoints, bridges, and small towns worth a quick visit.
For beach time, aim for calm, family-friendly spots like Bahia Honda or Coco Plum rather than expecting sandy stretches in Key West itself.

This approach balances the drive, provides a beach experience for the kids, and allows your group to enjoy both the relaxation of the mid-Keys and the lively atmosphere of Key West.