48 Hours in Dunedin

Located just north of Clearwater and under an hour from the beautiful Tampa International Airport, Dunedin is a small-town paradise with almost four miles of beautifully relaxing waterfront to enjoy. If a quiet Gulf-side weekend away from tourist destinations is what you need, this is the perfect place to consider.

Where to Stay: Fenway Hotel

It's hard to beat the combination of location, price, and amenities that you will find at the Fenway Hotel in Dunedin. Part of Marriott's Autograph Collection, this boutique hotel offers the charm of a unique property with the service (and status/points) you expect from a Marriott.

Guests who stay at the Fenway enjoy access to a fantastic outdoor pool, bicycle rentals right outside the lobby, a prime location on the water near downtown Dunedin, and ultra-close access to one of the best restaurants and the most popular rooftop bar in town.

The rooms at the Fenway are all large single rooms or spacious suites, with many featuring views of the pool area or across the street to the Dunedin Channel.

Since it is part of Marriott's Autograph Collection, you can always expect to find plenty of unique flair at the Fenway Hotel. Everything about this place revolves around music, so don't be surprised to find musicians performing in the lobby on most evenings!

Day One: Seafood, Relaxing Poolside, Steak

Fresh seafood always tastes better right on the water, so we are heading to Olde Bay Cafe for lunch as soon as we get into town. This popular local spot is located right in a marina, and they offer everything you would expect from a casual seafood joint. Make sure that you start with an order of the warm Peel & Eat Shrimp.

After lunch, you'll probably want to take a quick stroll down to the end of the pier. If you happen to catch someone fishing, feel free to kick back and watch for a while.

From there, it's time to check in to wherever you might be staying, where we're going to recommend spending the rest of the afternoon at the pool! If you're following our advice and staying at the Fenway Hotel, their pool area is calm and quiet, and there is usually a waiter available to keep the cold drinks coming. 

(If relaxing at the pool isn't for you, an alternative option here is to rent bicycles and hit the Pinellas Trail for as many miles as you like in either direction!)

On our first night in Dunedin, we'll stay close to the hotel. Actually, we're not leaving the hotel at all. That's because HEW Chophouse, located right in the Fenway Hotel, is a first-class steakhouse with a casual vibe that is perfect for a great meal celebrating whatever you like here in Florida.

The steaks are always cooked to perfection at HEW, and don't dare pass on the pork belly wings if they happen to be on the menu!

Following dinner, head upstairs to the hotel's rooftop bar for a couple of cocktails taking in the gorgeous panoramic views of the waterfront.

Day Two – Fishing, Beaches, Fine Dining

There is nothing quite like a Gulf Coast fishing charter, and there is no shortage of fishing charters available in Dunedin. Spend your first morning in town out on the water and enjoy the feeling of reeling in a big one!

Following a morning of fishing, lunch at Lucky Lobster Co. will be the perfect transition into our afternoon activity. You can skip the menu here. Just order the Lobster BLT Sliders.

Caladesi Island State Park and Honeymoon Island State Park are the top two attractions near Dunedin, and you can't spend 48 hours here without visiting at least one of them. You'll have to plan ahead to make the ferry schedule work, but you won't want to miss out on seeing some of the most beautiful white-sand beaches in the entire world.

If a great meal is what brings you to Dunedin, dinner at the Black Pearl will not disappoint. This former barbershop and mayor's office turned fine dining restaurant serves classic French and New American cuisine. Be sure to make reservations well in advance of your trip!

7venth Sun Brewing Company, Caledonia Brewing, Dunedin Brewery, Dunedin House of Beer, Soggy Bottom Brewery, and Woodwright Brewing Company are ALL located within walking distance of both The Black Pearl and the Fenway Hotel, so beer lovers can take their pick of locations for a nightcap following dinner!

Day Three – Fine Art, Brunch, Shopping

On the morning of our third day in Dunedin, we're grabbing a tall coffee from the hotel lobby and heading over to the Dunedin Fine Art Center for a quick stroll through their collection of exhibits.

Our final meal of the trip is a late brunch at the popular Cafe Alfresco, located right on the Pinellas Trail. They serve a fantastic brunch menu from 9 am until 2 pm every Saturday and Sunday, and we highly recommend the Eggs Alfresco or the southern classic Biscuits & Gravy.

Following brunch at Cafe Alfresco, you'll want to spend a few hours checking out the boutique stores that line the streets of downtown Dunedin. There are some fantastic art prints and handcrafted items from local artists in each of the little stores located here.

Just like that, we are already out of time to spend in lovely Dunedin.

But after spending 48 hours here, you'll surely see that there is an incredible amount of things to see and do.

Want to Stay Even Longer?

Dunedin is a terrific day trip for the Villages of Citrus Hills residents.

The Villages of Citrus Hills is a Florida Retirement Community with single-family homes and maintenance-free villas that have been built with today’s demanding baby-boomer in mind. But what makes the promise of Florida Retirement in the Villages of Citrus Hills truly come together for today’s new breed of active adult retiree is its extraordinary collection of world-class community country club amenities and extensive social activities.

The Villages of Citrus Hills offers a variety of home styles and neighborhoods to choose from.

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