Hollywood Beach to Miami: A Weekend Itinerary

We planned this trip around Hollywood Beach – the Broadwalk, the Atlantic breeze, and easy hops into Miami when we wanted more energy. This is a straight diary of what worked, what we would change, and the stops we are still talking about weeks later.

If you are deciding where to sleep, start with our full Miami hotel guide – we score 69 properties on fit, not hype. For festival weekends, our Ultra Music Festival hotel guide is the right bookmark.

Where we stayed

We based ourselves on Madison Avenue in Hollywood, a short walk from the Hollywood Beach Broadwalk and the stretch of sand that runs for miles along North Ocean Drive.

The unit itself was quiet – no traffic noise, solid sleep every night. Everything around the stay was the problem. Communication with the host was slow when it existed at all, check-in details changed twice, and small maintenance issues sat unresolved for the entire trip. By the second day we stopped expecting fixes and started treating it as a place to shower and charge phones. If we do Hollywood Beach again, we are booking somewhere with a front desk and staff who pick up the phone. The Margaritaville Hollywood Beach Resort anchors this stretch of the Broadwalk – pool, beach service, and a level of accountability that short-term rentals sometimes cannot match.

Looking at Hollywood Beach? Compare the Margaritaville corridor with 69 verified stays on our Miami hotels page. Filter by neighborhood, price tier, or travel style.

Thursday: Euroland, the Broadwalk, GG’s, Quore

We started the trip at Euroland on South Federal Highway – a European grocery with a hot buffet that rewards a slow lap. Borscht, pierogis, smoked fish, stuffed cabbage, and a salad bar that goes deeper than it looks. We filled up on vkusnyashki – the Russian word that loosely translates to “treats” or “little delicious things” – and walked back toward the beach.

The Broadwalk is the main event in Hollywood: two and a half miles of beachfront path, joggers, families on bikes, and late-afternoon light that makes the water look like it was color-graded. We spread out on the sand, swam once the sun backed off, and let the Gulf Stream breeze handle the rest. There was nowhere to be.

That night we sat down at GG’s Waterfront on North Ocean Drive – a Hollywood institution since the Rat Pack era, now with Intracoastal views, a serious raw bar, and the kind of atmosphere that makes you stay for one more round. Florida stone crab is the regional draw here; we did not order claws this trip, but if you visit between roughly mid-October and May, crab season is part of the local rhythm. Ask what is running that night.

For dessert we walked across to Quore Gelato, where the scoops are infused with liquor (about 5% ABV each) and the bar seating is literal swings instead of stools. Dark chocolate and champagne flavors. More cocktail lounge than ice cream shop.

Planning your stay? Browse verified Miami hotels and lock something with flexible cancellation if your dates are still moving.

Where We’d Stay in Miami

Elite97

The March Hotel

Elite96

Mayfair House Hotel & Garden

Excellent94

StayCozy at The Grand

Browse all 69 verified stays →

Friday: Raccoon Island, Bistro Cafe, Tri-Rail, Sardelli’s

This was the day. The one we are still talking about.

We booked a Raccoon Island boat tour through GetYourGuide – a pontoon trip to a mangrove island where raccoons walk right up to you. There are similar itineraries on other platforms, but we went with GYG because the tiered packages were transparent and you could upgrade to an open drink package without it feeling like a shakedown.

Book the tour: Raccoon Island Adventure on GetYourGuide – confirm departure point and package inclusions before you commit; operators update seasonally.

We arrived early, which turned out to be the right call. Across the road from the dock is the Grand Retail Plaza – a compact mall with enough to kill time. We wandered, then grabbed a mocha and a breakfast sandwich at Caffe & Bottega inside.

The pontoon was full – about 20 people, no empty seats. The crew kept everyone loose with trivia and local stories on the ride over.

The whole ride I wished we had brought our DJI Osmo Pocket. Holding a phone over the side of a moving pontoon is a recipe for a very expensive splash. A pocket gimbal in your palm shoots stable video without the anxiety – we left ours at home and regretted it the entire crossing.

We took the guided walk once we landed, which led straight to the raccoon congregation. They were fearless. Three hours on the island was the right amount of time: enough to hang out in the shade, explore the shoreline, and still feel like you soaked it in.

A detail worth knowing: the surrounding basin is alive with seabird nesting on mangrove islets – locals call some of them Bird Key-style rookeries. Diving birds work the shallows constantly. Spiny lobster and Florida stone crab dominate the dockside conversation; we did not schedule a seafood stop this trip, but these are the flavors people fly here for when the season is right.

On the return leg, the boat skimmed past waterfront mansions that everyone photographs from the rail – the kind of homes that make you reconsider your life choices in a fun way.

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After the island, we drove to Bistro Cafe in North Miami Beach. We treat this place as a pilgrimage. The move: open their Instagram @bistrocaferest, find the plate that looks impossible, and show your server. That is how you order here. After espresso martinis and a long table of food we did not plan for, we drifted south through Park West and caught the energy building outside Club Space – sold out for Ultra Music Festival weekend. We already published where to stay for Ultra if that is your speed.

We took Tri-Rail back toward Hollywood. It has a learning curve – schedules are not intuitive and the stations feel like they were designed by someone who has never taken a train – but it was faster and cheaper than rideshare for that corridor once we figured it out. If you would rather not run around catching connections, a rental car is a reasonable call for South Florida.

We ended our Friday night at Sardelli’s Italian Steakhouse in Hollywood. It was late and they were busy, but the bartender took great care of us. The atmosphere was lively and we had a great time.

Saturday: Young Circle, the beach, Cajun Boil, Aventura, South Beach

Breakfast at Vanilla Bakery & Cafe at Young Circle – the roundabout at the center of Hollywood’s arts district. Avocado toast, good pastry case, and the kind of morning where you are not in a hurry.

A tiny shared electric car – the kind that beach-town operators run as neighborhood shuttles – dropped us back toward the water. The drive through the residential streets was all blooming trees and perfect weather.

The ocean was crystal clear, warm, and calm enough to see fish darting near the shallows – then a ray showed in close and everyone had to get out of the water. From the sand, I wished I had packed compact binoculars to see what was happening past the surf line. On calmer days, rays and dolphins still move through here; a small pair from the towel line is the move.

I picked up what looked like a white piece of stone at the waterline on Hollywood Beach. Chalky, textured, lighter than a rock should be. It turned out to be a fragment of stony coral skeleton – order Scleractinia – calcium carbonate left behind from reef-building coral. Common on South Florida Atlantic beaches, easy to mistake for limestone. We snapped a photo, ran it through Google Gemini to confirm, then put it back on the sand.

Lunch was Cajun Boil Hollywood – a Cajun-meets-Asian fusion boil shop that should not work on paper and absolutely does on the plate. If you have never seen a crawfish boil crossed with lemongrass and garlic butter, this is the place.

We drove to Aventura Mall afterward for some shopping. Walking across the parking lot, we spotted an iguana parked on the warm concrete – fully still, prehistoric looking, about the size of a house cat. Just a normal afternoon in South Florida.

Drinks at Casa D’Angelo before heading south: a precise espresso martini and a Manhattan.

South Beach at night still feels like a fever dream of palms and neon. We ended at Carmela’s Italian Ristorante on Ocean Drive. More pasta, more cocktails. Looking back at the trip spending, we ate and drank our way through most of it. No complaints.

Sunday: GG’s again, MAD Arts, Tommy Bahama, home

We went back to GG’s Waterfront for brunch because we were not done with that view. Then drove to Dania Beach for the MAD Arts exhibit – contemporary, well-curated, and worth the short detour if you like that kind of thing.

Mai tais at Tommy Bahama, then Project Hail Mary at a cinema nearby. A quiet landing for a trip that was anything but.

Gear we wished we had packed

Every trip teaches you what you forgot. These are the items we would add for a beach-and-boat weekend like this one.

• Compact binoculars – for spotting rays, dolphins, and diving birds from the sand or the Broadwalk. Small enough for a daypack. Amazon
• Beach umbrella anchor – we had one at home and forgot it. Florida sun is not optional equipment. Amazon
• Waterproof phone pouch – the boat splashes, the waves splash, and your phone will be in your hand the entire time. Amazon
• Pocket gimbal camera (DJI Osmo Pocket line) – stabilized video without a full rig. We have one and left it at home too. Amazon

Before you go

Ready to book? Check prices on Miami hotels – we only surface properties that pass our verification gate. Well over half of the 69 properties have a pool.

If your trip leans toward nightlife, read our Miami nightlife hotel picks. Traveling with a group? The girls’ weekend neighborhood breakdown covers logistics by area. For a wider look at the beach side, our Miami Beach stay guide walks through every corridor.

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