48 Hours in Dunedin – Florida for Boomers

Located just north of Clearwater and less than an hour from beautiful Tampa International AirportDunedin is a small town paradise with nearly four miles of beautiful and relaxing shoreline to enjoy. If a quiet weekend on the Gulf side away from tourist destinations is what you need, this is the perfect place to consider.

Where to stay: Hotel Fenway

It’s hard to beat the combination of location, price, and amenities you’ll find at the Hotel Fenway in Dunedin. As part of Marriott’s Autograph Collection, this boutique hotel offers the charm of a one-of-a-kind property with the service (and status / points) you expect from a Marriott.

Guests staying at the Fenway enjoy access to a fantastic outdoor pool, bike rentals just 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 Fenway’s rooms are all large single rooms or spacious suites, many with views of the pool area or across the street from the Dunedin canal.

Since it is part of the Marriott autograph collection, you can always expect to find a lot of unique flair at the Fenway Hotel. Everything in this venue revolves around music, so don’t be surprised to find musicians performing in the lobby most nights!


Day one: seafood, relaxing by the pool, steak

Fresh seafood always tastes best directly in the water, so we headed to Olde Bay Cafe for lunch as soon as we get to town. This popular local spot is located right on a marina, and they offer everything you’d expect from casual seafood. Be sure to start with an order for Peel & Eat Hot Shrimp.

After lunch you will probably want to take a quick walk to the end of the pier. If you find someone fishing, feel free to relax and watch for a while.

From there, it is time to register at the place where you are staying, where we will recommend spending the rest of the afternoon in the pool. If you follow our advice and stay at the Fenway Hotel, the pool area is calm and quiet, and there is usually a waiter available to keep drinks cold.

(If relaxing by the pool isn’t for you, an alternative option here is to rent bikes and Pinellas Trail As many miles as you want in any direction!)

On our first night in Dunedin, we will stay close to the hotel. In fact, we won’t be leaving the hotel at all. That is because HEW Chophouse, located right at the Fenway Hotel, is a first-class steakhouse with a casual atmosphere that is perfect for a great meal celebrating whatever you want here in Florida.

Steaks are always cooked to perfection at HEW, and don’t you dare pass up the pork belly wings if they’re on the menu!

After dinner, take the stairs to the hotel’s rooftop bar for a couple of cocktails and beautiful panoramic views of the boardwalk.

Day two: fishing, beaches, good food

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

After a morning of fishing, lunch at Lucky Lobster Co. it will be the perfect transition to our evening activity. You can skip the menu here. Just order the Lobster BLT sliders.

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

If good food is what brings you to Dunedin, dine at the Black pearl Will not disappoint you. This former barber shop and mayor’s office turned into a fine restaurant serving classic French and New American cuisine. Be sure to make reservations well in advance of your trip!

Seventh Sun Brewing Company, Caledonia Brewing, Dunedin Brewery, Dunedin Beer House, Soggy Bottom Brewery, and Woodwright Brewing Company ALL are located within walking distance of The Black Pearl and Fenway Hotel, so beer lovers can choose spots for an after-dinner drink.


On the morning of our third day in Dunedin, we had a tall coffee in the hotel lobby and headed to the Dunedin Fine Arts Center for a quick tour of your collection of exhibits.

Our last meal of the trip is a late brunch at the popular Outdoor cafe, located right on the Pinellas Trail. They serve a fantastic brunch menu from 9am to 2pm every Saturday and Sunday, and we highly recommend the Open Air Eggs or the Southern classic Biscuits & Gravy.

After brunch at Cafe Alfresco, you’ll want to spend a few hours browsing the boutique shops that line the streets of downtown Dunedin. There are some fantastic art prints and handmade items from local artists in each of the little shops located here.

Just like that, we no longer have time to spend in lovely Dunedin.

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

Do you want to stay even longer?

Valencia Del Sol’s Tampa’s convenient location makes it easy to enjoy fun in the sun along Florida’s Gulf Coast.

Offering a robust and extraordinary lifestyle for those 55 and older, Valencia del Sol caters to residents looking to socialize and stay physically active. Active adults will enjoy the 25,000-square-foot clubhouse that offers a variety of resort-style amenities including a fitness center, large clubroom, relaxing pool and spa, tennis and pickleball courts, as well as a restaurant with seating in indoors and outdoors.

A full-time on-site Lifestyle Director will be dedicated to organizing a wide variety of fun events, clubs, and opportunities to make new friends throughout the year. This amazing new community features an impressive selection of twin villas and single family homes that provide the ultimate in 55+ living at an incredible value.

You can request more information, including floor plans and current prices, here: