3 Days, 2 Nights in the Upper Florida Keys: The Ultimate Beach Bar Road Trip from Miami

Got a few days for a quick weekend away? Florida can be the perfect destination for a re-charge!

The Upper Keys stretch from Key Largo through Islamorada. A short 90 minute drive from the Miami International Airport, you can be in the laid-back Keys by noon! No need to drive all the way to Key West...you can feel the quiet, Caribbean vibe from the moment you leave the mainland on US-1.

Miami → Key Largo → Islamorada

You'll need to rent a car at the Miami airport. Why not go all out and rent a convertible! Head south from Miami and within the hour you'll be surrounded by water on both sides.

Gilbert's Resort Tiki Bar — Key Largo, MM 107.9

107900 Overseas Hwy, Key Largo, FL 33037

Pull into Gilbert's and you might be thinking "What. Is. This?" Trust me, this is the perfect place to begin...the Tiki Bar is awesome! Sitting right at the northern gateway to the Keys, this place has been here in some form since 1903. Started as a fishing camp, it now touts itself the largest Tiki Bar in the Florida Keys. The vibe is vibing...a sandy public beach, docks packed with boats of every size imaginable, and plenty of room to let out your first "ahh, we're here" sigh. Don't miss out on one of their 12 Boobie Pina Colada varieties, where a portion of the proceeds from every drink goes to support Breast Cancer Awareness.

Dive Bar on the Bay — Tavernier, MM 105

200 Florida Ave, Tavernier, FL 33070 (Mangrove Marina)

You're going to want to post up here for the rest of the afternoon. It's perfectly, unapologetically cool. The place where locals, snow birds, the rich and not-so-rich find their community together. Think waterfront seating, fire pit, corn hole, and sand to dig your toes into. Dive Bar on the Bay was hands-down my favorite spot in the Upper Keys.

Lorelei Restaurant & Cabana Bar — Islamorada, MM 82

81924 Overseas Hwy, Islamorada, FL 33036

You'll know you're in the right place when you see the 30 ft mermaid!

This is your stop for ridiculously beautiful sunset views and great live music. A waterfront staple since 1952, they've got tons of seating and daily happy hour from 4–6 PM, with $3 domestic drafts and $4 well cocktails. Another stop in the Upper Keys where you'll want to sit all evening. I could get in trouble here! And if you love Lorelei as much as I do, you're in luck...it can be all yours for a cool $18M (Aug 2026).

Lazy Days — Islamorada, MM 79.9

79867 Overseas Hwy, Islamorada, FL 33036

Need one more stop? Or something to eat? After the sunset, head a few miles south to Lazy Days, the most award-winning restaurant in the Upper Keys. They've taken home Best Restaurant Overall, Best Waterfront Dining, Best Seafood, Best Lunch, and Best Wait Staff in the Annual Upper Keys People's Choice Awards! The oceanfront setting is gorgeous, the menu is extensive, and live music plays seven nights a week. This isn't a dive bar, it's a restaurant with amazing views. And a great way to end the day.

Where to Stay:

Cheeca Lodge & Spa, Islamorada

81801 Overseas Hwy, Islamorada, FL 33036 |

If you want to spoil yourself, this is the place. Cheeca Lodge is a 27-acre oceanfront resort that's been welcoming guests since 1946. On-site you've got a nine-hole golf course, a full-service spa, a fishing pier, six tennis courts, two pools (one adults-only), free kayaks and paddleboards, a snorkeling excursion right from the dock, and a beachfront tiki bar (in case you needed one more bar!).

Drop Anchor, Islamorada

84959 Overseas Hwy, Islamorada, FL 33036

For a more budget-friendly alternative, check out the Drop Anchor Resort, a quirky, well-loved Art Deco property with a pool, free kayaks, and a charming retro vibe at a fraction of the price. Clean rooms, a pool, a private beach. What more do you need?

Day 2: Islamorada Bar Crawl Day

Morning: Coffee + Kayak

One of the great luxuries of having a home base is that you can take your time in the morning. Grab coffee, take out a kayak, and spend an hour on the water before the day starts. This is called "strategic pacing" and it's very important. A jump in the water may be just what you need to rejuvenate for another great day of beach bars!

Today will start with the divey Keys vibe, segue into a chill Caribbean feeling for two stops, and end on a high note! Let's go!

Stop 1: Wahoo's Bar & Grill — Islamorada, MM 83.4

83413 Overseas Hwy, Islamorada, FL 33036

Wahoo's sits perched above the Whale Harbor Marina, and the view from their two waterfront decks was voted one of the 3 Best Views in South Florida by the Miami Herald. I've never seen anything like it...the deck is like a long covered bridge with barstools affording you to coolest view of the marina! What makes Wahoo's special beyond the scenery is that the seafood is as fresh as it gets — mahi-mahi, grouper, snapper, tuna, stone crab, and Florida lobster that comes directly off the fishing fleet docked below. If you spent the morning on one of the charters, bring it in — they'll cook your catch for lunch.

Stop 2: Tiki Bar at Amara Cay Resort — Islamorada, MM 80

80001 Overseas Hwy, Islamorada, FL 33036

Don't let "resort bar" make you drive past this one. Amara Cay's poolside Tiki Bar welcomes non-guests , and it's one of the most pleasant places to spend an afternoon in Islamorada. This is your chill out spot, not your party spot. It's a great midday stop — the setting is beautiful, the cocktails are tropical and strong, and the pace is delightfully unhurried.

Stop 3: Marker 88 — Islamorada (Plantation Key), MM 88

88000 Overseas Hwy, Islamorada, FL 33036

Marker 88 is a beautiful spot. The setting reminds me a an all-inclusive resort in the Caribbean. A Keys institution since 1967, Marker 88 recently underwent a top-to-bottom overhaul and you can tell. There are numerous places to sit, including tables in the sand right along the waters edge. So nice! As the sun goes down, the string lights come on over the tables and the whole place takes on a glow that makes you want to stay for one more round. So stay for one more round.

Day 2 was all about the views, both at the bars and in the resorts, but now that you've hit a few places, and hopefully had some amazing seafood, it's time to close the night on a high note!

Late Night: Hog Heaven Sports Bar & Grill — Islamorada, MM 85.3

85361 Overseas Hwy, Islamorada, FL 33036

Hog Heaven is a shape-shifter. By day, it's a relaxed oceanfront sports bar with fresh seafood, smoked BBQ, 20+ flat screens. Walk in, and you're intoxicated from the smell of BBQ, step out the back door, and you're intoxicated by how freakin' cool it is! Grab your friends and grab a beer, and you've got the recipe for a great night (and a hangover if you don't pace yourself).

Day 3: Islamorada → Miami (with one last stop)

Time to check out of your hotel and load up the car, but don't rush. Hopefully you booked a late day flight so you can take your time getting back to reality.

One More Stop Before You Go: The Lorelei (Breakfast)

81924 Overseas Hwy, Islamorada, FL 33036

Give the giant mermaid one more visit on your way back to Miami. You'll need some breakfast - and coffee.

A Few Practical Notes

Getting Around: A car is essential for this trip. Uber and Lyft operate in the Keys, but coverage can be spotty — especially late at night when you actually need them. Designate a driver, or if you choose to stay at Cheeca Lodge, both the Lorelei and Lazy Days are within reasonable walking distance (or use the resort's bike fleet).

When to Go: The Keys are gorgeous year-round, but November through April is peak season — perfect weather, less humidity, and every bar running at full capacity. Summer is hot and muggy but comes with off-season hotel rates.

Reservations: Lazy Days and Marker 88 fill up quickly for dinner, especially on weekends. Book ahead. The bar seats are generally first-come, first-served everywhere.

Sunscreen: You're going to be outside all day for three days. Pack it, apply it, reapply it, and head home with that tan skin that makes your co-workers jealous.

Did I sell you on the Upper Keys? When it gets cold and snowy up north, this is the perfect way to top up your vitamin D.

Cheers, Katherine