Best Historic Stays: Fenway Hotel in Dunedin
Known as “The Grand Lady of Dunedin,” the Fenway Hotel draws the eyes of those who pass by on Edgewater Drive. This picturesque hotel, built in 1924, is an icon of the jazz age. It has seen numerous transformations over the years, but now, as a member of the Autograph Collection, I think it’s hitting all the right notes!
Back to the Beginning
Fenway’s journey began in the roaring 1920s. While its name may evoke thoughts of Boston’s Fenway Park, General Manager Adam Duffey explains the name actually derives from the hotel’s surroundings at the time.
“‘Fen’ is another name for marshland, and when this hotel was being developed, there was a bit more marshland around, so they just took ‘Fen’ and added ‘way’ to it,” said Duffey.
In addition to serving as a destination for vacationers, Fenway Hotel served as Pinellas County’s first radio station from 1925 to 1927. The WGHB Radio Station, sharing initials with the hotel's owner, G.H. Bowles, broadcasted from the rooftop, cementing the Fenway's place in broadcasting history.
Over the decades, the hotel transitioned through various phases, including stints as a private club, a minor league baseball team headquarters, and even a university. In 2018, the property reopened as the Fenway Hotel, part of the Marriott Autograph Collection, after a meticulous renovation by Mainsail Lodging & Development.
The hotel's history is proudly displayed throughout its halls. One spot that caught my eye is the door near the lobby that leads to Fenway’s original speakeasy. According to legend, you would knock three times and be asked for the password. If you said the right password, you could stop inside and enjoy a drink.
Rumor has it, Fenway’s rum was supplied by the owner of then Hog Island (now Honeymoon Island). A plaque near the speakeasy door says he hired “rum-runners” to deliver libations from Cuba to the island. From there, he would distribute the alcohol to several hotels in the area.
Today, you can’t go through the original speakeasy door, but there is another spot to have that sort of experience, if you plan accordingly. More on that soon!
Modern Elegance Meets Historical Charm
Today, Fenway Hotel has 83 guest rooms and suites. Our Classic Queen, with two queen beds, had views that overlooked the magnificent entrance of the hotel and a partial view of St. Joseph Sound.
In addition to custom Fenway robes, you’ll find a well-stocked mini bar, mini-fridge, coffee maker, and modern bathroom with fantastic lighting, beautiful tiling, and a large shower. The nods to Fenway’s history continue with the gold record mounted on the wall and the pillow embroidered with “…and I thought to myself, what a wonderful world”, a nod to famous jazz singer Louis Armstrong.
Outside of your room, you’ll find a range of amenities, including a resort-style pool, fitness center, and expansive lawn. Be sure to walk across the street to get close-up views of the beauty of St. Joseph Sound. You may just see a wading bird looking for a snack or a dolphin passing by.
Fenway is Becoming a Foodie Destination
Dining at Fenway was an absolute treat. We had dinner and breakfast at HEW Parlor & Chophouse. The team members hit it out of the park on both occasions.
For dinner, we had:
Peaches and Creme: Fresh Solena Burrata, Jamon Serrano Ham, Marinated Summer Peach, JP Chenet Rose Simple, Shallot, Red Bell Pepper, Chives, Focaccia Toast
Wild Mushroom Conserva Tartine: SPMC Wild Mushrooms, Watermelon Radish, Pain Perdu, Everything Creme De Brie, Purslane
Charred Avocado Salad: Baby Lollo Rosso, Castelfranco Chicory, Spiced Cancha, Baby Heirloom Tomato, Heirloom Carrots, Fresh Florida Lemon Tahini Dressing
8 oz Filet: Make sure to order a side of Brussel Sprouts with Lemon Citrus & Crispy Baked Russets with Persillade
I’m getting hungry just thinking about it! Word is spreading about HEW. Duffey mentioned they’re serving more and more locals, in addition to hotel guests.
Brunch was also a feast for the taste buds. I nearly ate the entire French Toast L'Orange, which was stuffed with sweet whipped cream cheese. The Beignets Paired With Cafe Au Lait and Berry Jam were a sweet and light treat.
Dinner is served Wednesday and Thursday from 5 pm to 9:30 pm, Friday and Saturday from 5 pm to 10:30 pm, and Sunday from 5 pm to 9:30 pm. Brunch is available Monday through Friday from 7 am to 2 pm and Saturday and Sunday from 7 am to 1 pm. Complimentary valet parking is available for those dining.
Sunset Celebrations Every Night
Hi-Fi Rooftop Bar at Fenway Hotel is, in my opinion, the best place in Dunedin to catch a sunset over St. Joseph Sound. You’ll find breathtaking views of over local barrier islands, along with a curated selection of cocktails, local craft beers, and wines.
The bar is named in honor of the hotel's history with WGHB. According to Fenway’s website, Hi-Fi speaks to both high-fidelity sound reproduction, especially as it relates to radio, and the quality of the experience at the bar.
Thankfully, we were able to see a beautiful sunset after the rain cleared out during our July visit. Just as the sun went down, we heard the crashing of symbols, which is a Fenway sunset tradition.
Shh… Here’s How to Have a Speakeasy Experience
One of the most unique offerings at Fenway Hotel is the Room 27 Speakeasy Experience. For just $10, guests can reserve a spot in this hidden gem. The experience includes a vintage-inspired cocktail menu. Guests must follow speakeasy traditions to gain access, complete with a secret knock and password.
Keep an eye on this webpage to reserve the experience in advance as it’s only available a few times a month.
(Pictured above is the door to the original speakeasy at the hotel. The Room 27 Speakeasy Experience is in a different location)
Exploring Downtown Dunedin
Fenway Hotel is steps away from charming downtown Dunedin. You can rent bikes from Fenway to explore the charming neighborhoods and bustling downtown.
According to the city, website, Dunedin gets its unique name from two Scottish merchants, who in 1885, came to the area and opened a general mercantile business. They petitioned the government to open a post office with the name Dunedin, which comes from the Gaelic name Dùn Èideann after their hometown of Edinburgh, meaning "castle on the rock."
Visitors today will find nods to its Scottish heritage in the naming of roads, neighborhoods, and other touches downtown. In fact, residents celebrate the heritage annually with a number of events, including the Dunedin Highland Games & Festival in the spring and the Dunedin Celtic Festival in the fall.
There’s so much to see when visiting, but here are some of my favorites to add to your list:
Dunedin History Museum: Enjoy learning more about the fascinating history behind this charming coastal town. Plus, the gift shop is wonderful!
Pinellas Trail: The Pinellas Trail stretches 45 miles and perhaps one of the most popular stretches is through Dunedin. Enjoy riding your bike or carefully walking (be on the lookout for fast riders!).
Lane’s Lemonade: Lane’s Lemonade is a staple in Dunedin. It’s nestled in an authentically converted train car and its sweet lemonade stand is a nod to the past.
The Wild Iris Cafe: This local haunt will leave you satisfied. You can’t go wrong with an Eggs Benedict.
Walk along the water: Walk to the end of the pier, around the marina, and through Edgewater Park to enjoy more views of St. Joseph Sound.
Last but certainly not least, enjoy the sprawling beaches at Honeymoon Island State Park. If you’re feeling adventurous, and have some time, take the ferry from Honeymoon Island to Caladesi Island State Park for the day. Caladesi has won awards over the years for having some of the most beautiful beaches in the world. Don’t forget to walk the trails too! There, you’ll learn more about some of the people who once called Caladesi Island home.
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Thanks to our Partners
I have to say a huge thanks to my partners in this series: Valhalla Resale & Emerson and Friends!
Valhalla Resale has locations in Tampa and St. Pete. Both locations offer a clothing membership. It’s a fantastic way to keep your wardrobe fresh while also being good to the planet! you can borrow three clothing items at a time and keep them as long as you like for just $49 a month, Or, borrow a total of five items a month for an additional 10 dollars per month (That’s the plan I’m on)! When you’re ready for a change, simply return the items and choose three new ones. I am loving taking advantage of this sustainable service!
And, thank you to Emerson & Friends! This family-run business from Clearwater, Florida, specializes in incredibly soft bamboo family matching pajamas. Each unique design is handcrafted by their in-house artist and founder, Nicole Northway, ensuring every piece is made with love and care. Click here to check out the shirt and shorts I sported in this series.
