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A Long Weekend in Dunedin, Florida

If you’re a Florida local, or you’re looking to pop down to Florida for a long weekend, I’ve got the perfect place for you…Dunedin! I’ll be honest, Dunedin (duh-KNEE-din) had not been on my radar until recently, but I just spent a few nights there doing some different things in the area and it was great!

It’s about a 30 minute drive from the Tampa International Airport and just north of Clearwater Beach. But it feels a WORLD away from the big touristy beach town vibe.

In this post I’m going to let you in on everything you need to know to have the perfect long weekend in Dunedin, Florida:

How I Ended Up in Dunedin

I’ve been going to Florida for a long time and at this point, there aren’t a ton of places I either 1) haven’t been to or 2) haven’t heard of. But until a few weeks ago, Dunedin wasn’t on either of those lists. So how did I end up in Dunedin? Earlier in the year, I had gone to St Pete Beach for the first time and of course because I was asking everybody I met about places they liked and didn’t like, I heard Dunedin mentioned a couple of times.

I mentally added it to the VERY long list of places in Florida that I needed to check out but didn’t think about it much beyond that. A couple of months later when I was planning out my summer travels, I found Dunedin on the map and realized it was the place to stay if you want to visit Honeymoon Island and Caladesi Island State Park. That put it on my list. THEN I realized it was only about an hour from Dunedin to Weeki Wachee Springs, which has been on my bucket list since I was a kid (you’ve heard about the mermaids right??). So now we’re talking about a win-win situation between doing my job as a travel blogger and fulfilling a childhood dream. I hopped on the Marriott Bonvoy app to see what was around the area (not expecting to find much-maybe a Courtyard Marriott??) and LOW AND BEHOLD there was a 1920s historic hotel that’s part of Marriott’s Autograph Collection right on the water downtown. Bingo. And that’s how I ended up in Dunedin.

What Dunedin is known for…

This mid-sized town sits on Florida’s main peninsula (it’s not on a barrier island) just north of Clearwater. It’s right on the bay.

Dunedin is called the “gateway to Honeymoon Island.” Honeymoon Island State Park and Caladesi State Park are two completely unspoiled barrier islands just off the coast of Dunedin. They’re considered two of Florida’s finest state parks and everyone that comes to visit them comes through Dunedin. Honeymoon Island State Park is reached via the Dunedin Causeway and Caladesi Island State Park can be reached via ferry from Honeymoon Island or by private boat.

The pronunciation of Dunedin (duh-KNEE-din) clues you into the town’s Scottish heritage.The town was founded by two Scotsmen in the 19th century and it’s name comes from “Dun-Eideann”…Gaelic for Edinburgh. The town hosts the annual Highland Games and Festival every April, and I must say I actually heard bagpipes at least once walking through town.

Breweries! I’m not sure what the deal is, but Dunedin is not a terribly large city and there are EIGHT breweries in the historic downtown area!

Dunedin’s historic downtown is a HUGE draw. Besides overnight visitors, Dunedin draws local visitors from around the Tampa Bay area for it’s blossoming food scene which is centered downtown. It’s pretty picturesque and there’s shops and restaurants absolutely everywhere. If there’s any kind of festival or event going on in town, it’s easy to spend the day strolling around the quaint streets and munching here and there.

It’s incredibly dog friendly. Most restaurant patios welcome dogs (and bring them a dish of water  when they bring yours), there are dog water bowls scattered throughout town, and there’s even a new doggie ice cream shop.

There are over 800 oranges painted around the city of Dunedin. What’s that? Yep, oranges! Dunedin has a deep history in the citrus business…orange groves and packing. Several years ago, a local resident and artist decided to start painting oranges inspired by vintage fruit crate labels around town and it’s really blown up! It’s fun walking around downtown and seeing how many you can spot.

***Want to save major $$$ on your next trip? I get asked ALL the time how I’m able to travel so often and stay at really nice resorts. Well, my favorite travel hack is cashing in points to score free airfare and free nights at high end resorts and hotels (including the Fenway!). Read my full guide on the exact system I use to max out credit card rewards here. Seriously, it’s going to save you soooo much money.

Where to Stay in Dunedin

If you’re looking for a historic boutique hotel in a charming small town in Florida, I’ve got a place for you. This historic 1920s “jazz age” hotel is the perfect place for a quick weekend getaway.

Located right on the bay just a couple of blocks from historic downtown Dunedin, the Fenway is historic and chic but still modern and comfortable.

Here’s a quick rundown of what I liked about staying at the Fenway Hotel:

It’s just about a 3-4 block walk to the main part of downtown Dunedin. You can walk along the water or through the neighborhood. If the weather is decent, it’s very walkable. If it’s hot, it feels FAR but they have bikes you can take.

It’s right on the bay. There’s no beach in Dunedin, but the property sits right on the water. There’s a great view from the rooftop bar, but they also have chairs set up out front that you can sit out during the evening.

It’s about four miles south of the Dunedin Causeway which is the entrance to Honeymoon Island State Park. Honeymoon Island and Caladsi is the big draw to Dunedin and honestly there aren’t a ton of places to stay. There’s a Holiday Inn about a mile or so north of the Fenway and then there’s a Hampton Inn right at the causeway. Either place you’re going to have to pack everything up in your car and drive to Honeymoon Island, so you might as well stay at the cool historic hotel closer to downtown.

The brand is pretty strong. It’s a historic 1920s hotel built in the middle of the jazz age and prohibition and they really play that up. Everything from your room key to the bedside table lamps tie back to the music theme. They’ve even left the door to the original speakeasy intact in the lobby!

While the hotel feels very historic and original, it still has all the modern comforts and conveniences you’d want.

The TV situation is excellent. This feels so oddly specific, and I hardly ever even turn on the TV when I’m in a hotel (I always have an ipad or laptop with me), but it was on the welcome screen when we arrived and I noticed it had a setup where you could login to your Netflix, Hulu, etc. But I was most impressed with all of the CHANNELS. I stayed here during the Olympics and they had pretty much every channel that they were showing the Olympics on plus a ton of specific sports channels (I have never stayed anywhere with the Tennis Channel in my life and I was in HEAVEN). They had a ton of non sports stuff too, and overall the TV situation made a huge impression on me ; )

For me, probably the best part of the Fenway Hotel is that it’s part of Marriott Bonvoy. It’s in their “Autograph Collection.” I’m pretty loyal to Marriott and I’m always trying to track and maximize points so I was THRILLED that this historic hotel in this area that there aren’t too many options happened to be part of Marriott.

Pricing starts at $169. Book directly with Marriott here.

Things to Do in Dunedin

Honeymoon Island & Caladesi Island State Parks: This is why I came to Dunedin. Dunedin is considered the “gateway to Honeymoon Island” and it’s what attracts most people to the area. These islands are two of Florida’s finest state parks. The barrier islands have great beach facilities and I was particularly impressed with the shelling. You can drive to Honeymoon Island State Park across the Dunedin Causeway. It’s $8/car to enter. Once you’re on the island, you can take a ferry over to Caladesi Island State Park ($16/adult). Both islands have good concessions with a little cafe and beach chair/umbrella and kayak rentals. I’ve put together a full post about Honeymoon Island and Caladesi Island here.

Pinellas Trail: The Pinellas Trail is a popular and well maintained “urban pathway” that runs 45 miles from Tarpon Springs (north) to St Petersburg (south). It runs right through historic downtown Dunedin and I think it’s one of the reasons Dunedin has thrived so much. If you’re a biker (or you like a good early morning walk), be sure to pack your gear!

Dunedin History Museum: Housed in an old railroad depot in downtown Dunedin, this is a great way to get an idea for the local history. It’s $5/adult (kids 12 and under are free).

Take the Ferry to Clearwater Beach: Clearwater Beach is pretty close to Dunedin, but parking can be tricky to find. Take the ferry from Dunedin and you just might see some dolphins on the way! Book your tickets in advance here.

Dunedin Downtown Market: Most Saturdays in Dunedin, there’s a great little farmers market. While fresh produce is the heart of any farmer’s market, the one in Dunedin has a pretty wide range of vendors (a lot of pet stuff!) so it’s still interesting even if you’re visiting from out of town. More info here.

Where to Shop

Back in the Day Bookstore: Indie bookstores are harder to find than they used to be, but this is a great one! It’s pretty good size and has a good variety so you’ll likely find what you’re looking for. As you would expect, the Florida non-fiction section was pretty well stocked.

The Ivory Palm: I’ll be honest…most of the shops in Dunedin are a little grandma-ish (surprising since the food scene is so “up and coming”), but I LOVED this one.

Salty Paws: A doggie ice cream shop and bakery!! I’d heard that Dunedin was super dog friendly but I didn’t really understand the extent of it until I saw this place. It’s an actual ice cream shop. For dogs. Don’t have your dog with you? That’s ok! They have a mix that you can take home to whip up.

Where to Eat in Dunedin

Lucky Lobster: Just go here every night. That’s it, that’s the whole blog post l ; ) I am a huge lobster fan and I’ve had it at plenty of fancy restaurants, but this is hands down the best I’ve ever had. Their special is a lobster roll (which I’m not usually the biggest fan of), but they have a New England style one (the traditional mayo based mix) AND a Connecticut style one (just lobster and butter). GET THE CONNECTICUT ONE. It’s basically hot, buttery lobster (at least a whole tail) served on a toasted roll. It was seriously incredible. The lobster and bacon sliders were also to die for. Overall, the menu was pretty inventive but just solid good food. I also really liked the Strawberry Sparkler drink.

Strachan’s: I pretty much rate my vacations based on the accessibility of a really good ice cream shop (you think I’m kidding), and Dunedin is not messing around when it comes to dessert. Right on the corner of Main Street, Strachan’s is ridiculously good. They have make-your-own ice cream sandwiches (pick the cookie, pick the ice cream, and pick a topping to have the edges rolled in) and I thought that was pretty ideal, until I discovered the carrot cake sundae. Yep, you read that right. Strachan’s has an award winning carrot cake (they have a big variety of homemade cakes and pies in their case to go) and they’ve turned it into a sundae. It’s a must try.

Lane’s Lemonade: This cute little lemonade stand housed in a shipping container will hit the spot when you’re strolling through town on a 90 degree day. Besides lemonade, they also have iced tea and fruity soft serves.

Sandpiper Coffee: We stopped here for breakfast on our last day and I had an egg, bacon, and cheese croissant that was amazing. I’ll be honest, it didn’t look too impressive (I didn’t even take a picture), but it was GOOD. Plenty of indoor and outdoor seating. Also, don’t be misled by the “coffee” in the name…this is more than a coffee shop. They serve a full breakfast.

On Another Note: If you’re looking for a condo or vacation rental for your trip, I always book with Vrbo. They’ve got the largest selection of rentals you’ll find anywhere and you can easily filter to find exactly what you’re looking for. Need a specific number of bedrooms and bathrooms? Narrowed it down to a certain location? Want flexible cancellation terms? Need to stay under a fixed budget? Click here to search for Florida vacation rentals for your trip.

Places to Try Next Time

The Living Room: This place was strongly recommended, but I’m sorry I failed as a travel blogger and ended up going back to Lucky Lobster twice so I didn’t have time ; ) Spanish tapas style.

HiFi: This is the rooftop bar/lounge at the Fenway Hotel and it’s a POPULAR spot around sundown. To my knowledge, it’s the only rooftop lounge in the area and it has views of the bay so it’s easy to see why. You don’t have to be staying at the Fenway to check it out.

Crown and Bull: Famous for the eggs benedict menu at brunch, which they serve everyday.

The Honu Restaurant & Tiki Bar: This “Hawaiian themed lei’d back cafe” was high on my list of places to check out but surprisingly I never made it!

The Nest: If you like a good Instagram vibe, you’re definitely going to want to check this place out.

Want to Read More Posts about Florida? I’ve got plenty!

Check out these destinations: Miami (Things to Do Besides Party & Where to Stay) // Key Biscayne // Sanibel & Captiva // Longboat Key & Anna Maria Island // Marco Island // 30a // St Augustine // Amelia Island // St Pete Beach // St Petersburg // Fort Myers // Dunedin // Crystal River & Weeki Wachee Springs // Honeymoon Island & Caladesi Island State Parks // Tarpon Springs // Matlacha & Pine Island // Apalachicola

Trying to narrow it down? Siesta Key vs Anna Maria Island // St Pete Beach vs Clearwater Beach // Sanibel vs Marco Island // Destin vs Panama City Beach // Destin vs 30a // Key Biscayne vs South Beach // Seaside vs Rosemary Beach

Best Beaches in Florida with Seashells

Best Florida Tennis Resorts

P.S. If you want to follow along on my travel adventures in real time, you can follow me on Instagram (@caitylincoln). My post captions are full of travel tips and I have a ton of story highlights and videos with great info. And share my account with your travel loving friends! Your support really helps me keep this blog running!