Florida · 3 to 4 days · about 165 miles

Overseas Highway Island Hop

Bay-side resorts, turquoise water and Key West.

The Overseas Highway strings the Keys together over open water. Slow it down with nights in Islamorada and Marathon before the last bridges deliver you to Key West.

Where to stay, night by night

1. Stop 1 · 1 night

   Islamorada, FL

   Barefoot luxury on the sportfishing capital.

   Our pick: Cheeca Lodge & Spa

   Also worth a look: The Moorings Village

   Boutique inns in IslamoradaPrivate homes on Vrbo

2. Stop 2 · 1 night

   Marathon, FL

   Island resorts in the middle Keys.

   Our pick: Tranquility Bay Beachfront Resort

   Boutique inns in MarathonPrivate homes on Vrbo

3. Stop 3 · 2 nights

   Key West, FL

   Historic resorts and guesthouses in Old Town.

   Our pick: Ocean Key Resort & Spa

   Also worth a look: Pier House Resort & Spa

   Boutique inns in Key WestPrivate homes on Vrbo

When to go

December to April is dry and mild; summer is hurricane season.

Read the full drive guide

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