Valentine’s Day Getaways: Romantic Historic Towns in Florida
When I think of a Valentine’s Day getaway, I think of romantic historic towns. You know the ones – quaint B&Bs where you enjoy morning coffee on a cute balcony surrounded by soft light; cobblestone streets lined with small shops, the scent of freshly baked bread wafting down the street; stunning architecture that evokes daydreams of simpler times.
If this is your idea of the perfect Valentine’s Day getaway, too, I’ve got the ideal romantic historic towns in Florida for you to consider. These small towns are steeped in history and natural beauty and give you the experience of being somewhere uniquely and authentically Florida. They are among the best small town weekend getaways Florida offers.
In this guide, I’ll share my favorite options for a romantic getaway, why I chose these towns, attractions in each, and where to stay. And stick around to the end where I share practical tips for a romantic weekend getaway.
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Apalachicola
Apalachicola sits close to Florida’s Big Bend region, a part of Florida often referred to as the Forgotten Coast. The geography of the state here leans towards salt marshes, small towns, and large forests. Apalachicola is an historic fishing village with immense Old Florida charm and fewer crowds than some of the other small towns on this list.
The town was named for the Apalachicola River. It’s probably best known for oyster production, though the town has a long history which has been instrumental in shaping lives in Florida and across the South. For instance, John Gorrie developed the refrigeration techniques which led to the invention of air-conditioning. In the 19th century, Apalachicola was also the third busiest port in the Gulf of Mexico and the busiest on Florida’s Gulf Coast.
Romantic Highlights
This entire area holds a ton of great activities for anyone who loves history or nature. Spend a romantic getaway here strolling the waterfront or learning more about history at one of the state parks. Two state parks, a maritime museum, and several historic buildings offer great ways to learn about the history of the area.
For nature lovers, take a kayak tour along the river, visit one of the many parks, or take a fishing charter. With loads of nature and history, there are no shortages of opportunities for romantic encounters in Apalachicola.
Where to Eat
Most restaurants in Apalachicola lean towards seafood and raw bars, not surprising considering the area and that Apalachicola is known for oysters. Try these local favorites:
- The Owl Cafe – Historic eatery dating back to 1900 offering fresh local seafood and other favorites.
- Hole-in-the-Wall Seafood – Super casual raw bar offering oysters, shrimp baskets, crab claws, and gumbo.
- Up the Creek Raw Bar – A local’s favorite off the beaten path with waterfront views and fresh, farmed oysters.
Where to Stay
Lodging options in Apalachicola range from historic inns to franchise options. Of course, there are vacation rentals, too, and often present one of the best options. Here are a few favorites:
- Gibson Inn – Historic inn with spacious rooms and a great location in the historic district.
- Water Street Hotel & Marina – An Ascend Hotel Collection property offering a riverfront location.
- Vacation Rentals – Most highly rated option with waterfront and historic district locations.
Cedar Key
Cedar Key, Florida, is a small island town in the Gulf of Mexico, known for its laid-back charm and historic ties to Florida’s seafood industry. Surrounded by unspoiled mangroves and salt marshes, it offers kayaking, birdwatching, and breathtaking sunsets. The town’s main street features eclectic shops, art galleries, and seafood restaurants serving fresh clams and fish.
A true hidden gem, accessible only by boat or one road, Cedar Key is known for its historic buildings and artistic community as much as for its nature and seafood. A romantic getaway to Cedar Key appeals to a wide range of interests, and its location and island vibe encourage slowing down and enjoying each other.
Romantic Highlights
Let’s start with one of the best sunsets in Florida. The wide-open Gulf, shops and restaurants on stilts, and offshore keys offer so many amazing photo ops or just visual showpieces to enjoy on an evening walk. And speaking of location, there are no true hotels on the island so the best place to stay is at a vacation rental, many of which are the most adorable waterfront cottages you’ve ever seen.
History lovers will be enchanted by Atsena Otie, the island which was the original city center, as well as the town’s history, on display at Cedar Key Museum State Park. And nature lovers have so many activities to choose from – go kayaking, hiking, fishing, scalloping. Or just stroll around town enjoying the boutiques and art galleries.
Where to Eat
There are no fancy romantic restaurants in this island town, but there are amazing seafood restaurants. If you love fresh fish and shrimp, you’ll be in heaven at one of these:
- Steamers Clam Bar & Grill – Waterfront dining, fresh shrimp, amazing water and sunset views.
- 83 West – Waterfront dining with a pet-friendly patio. Try the fresh grouper and key lime pie.
- 1842 Daily Grind & Mercantile – THE place for breakfast and lunch.
Where to Stay
There is one B&B (hotel?) and lots of vacation rentals. If you’re looking for an historic stay, choose the B&B.
- Island Hotel – The original general store on the island, built in 1859, it’s one of the oldest hotels and restaurants in Florida.
- Vacation rentals – From studio condo-hotels to 3 bedroom waterfront homes, if it’s a vacation rental you seek, it’s a vacation rental you’ll find in Cedar Key.
Fernandina Beach
Like St. Augustine, Fernandina Beach is one of the oldest towns in Florida, and that means a lot of historic places to spend a romantic weekend. Fernandina Beach’s historic downtown district holds a beautiful waterfront location on the Amelia River, the streets lined with stunning brick buildings and Victorian-era architecture. Amelia Island, the island where Fernandina Beach is located, is also known as a very romantic place, too, and has flown eight flags so has a ton of history to add to its romantic appeal.
Romantic Highlights
The 50-block historic district is lined with quaint shops, antique stores, and art galleries. After a day of strolling around downtown, enjoy a drink at the Palace Saloon, Florida’s oldest bar. If taking in Florida’s oldest is on your bucket list, stay at the Florida House Inn, Florida’s oldest hotel.
If nature is more your speed, you might opt for an oceanfront walk along several miles of beach. Restaurants and bars periodically pop up where there’s public beach access so you can walk, eat, walk, drink, and make a day of it. Alternatively, you might enjoy a horseback ride on the beach at Amelia Island State Park or a kayak tour through the mangroves and marshes of the Amelia River.
Where to Eat
Fine dining establishments on Fernandina Beach run the gamut from historic fare to seafood and everything in between. No matter what you enjoy, though, there’s a restaurant to cater to your tastes and provide an intimate and romantic meal.
- David’s Restaurant & Lounge – Located in the heart of the historic district, David’s offers a sophisticated dining experience.
- Burlingame Restaurant – Small seasonal menu which is always changing, offering a unique experience each time you eat here.
- España Restaurant & Tapas – Spanish and Portuguese family recipes in an intimate main dining room or garden or casual patio seating.
Where to Stay
As one would expect from a romantic historic town, Fernandina Beach offers a variety of bed and breakfasts, luxury hotels, and boutique hotels to choose from.
- Amelia Schoolhouse Inn – Original Amelia Island schoolhouse built in 1886 turned into an adults-only boutique hotel in the heart of the historic district.
- The Addison on Amelia Island – Eco certified B&B in the historic district.
- Hoyt House Amelia Island – Adults-only B&B centrally located in the historic district.
Mount Dora
Mount Dora sits about an hour and a half north of Orlando and holds a reputation as an artsy and antiquey town. Located at the eastern side of the Harris Chain of Lakes, the town draws visitors from all over the world for its southern charm and beautiful streets.
Founded in 1880, the historic downtown overlooks Lake Dora and is full of antique shops, boutiques, cafes, and art galleries. One of Florida’s three freshwater lighthouses stands at Grantham Point, a beacon for boaters as well as the seaplanes which use the adjacent seaplane basin. The town also hosts many festivals leading to its nickname “Festival City”.
Romantic Highlights
The highlight of visiting Mount Dora is exploring the historic downtown district. Quaint boutiques, cafes, and art galleries create a romantic atmosphere as you walk the quiet streets, window shopping or popping into the stores that interest you. It’s not the only thing to do on Mount Dora though.
Other romantic activities in this small Florida town include touring the Sydonie Mansion or Donnelly House. If your tastes run more adventurous, you might enjoy a flightseeing tour on a Jones Air seaplane. Or take a railroad tour with the Orange Blossom Cannonball.
Where to Eat
Some small towns in Florida don’t offer many romantic fine dining options, and Mount Dora definitely falls into that category. There are more casual options, though, which are just as delicious and fit the Mount Dora vibe perfectly.
- 1921 Mount Dora – Located in an historic home and featuring historically Florida ingredients such as rabbit, oysters, and duck.
- The Goblin Market – Located in the historic district, three book-lined dining rooms welcome diners to try seafood, poultry, and other favorites.
- Magical Meat Boutique – Authentic British gastro-pub offering all the best British dishes like bangers and mash and a full English breakfast.
Where to Stay
Mount Dora is known as much for its amazing B&Bs as for its art scene. When in this town, you’ll want to enjoy one of these beautiful places.
- Adora Inn – An adults-only B&B within walking distance of the historic district.
- Heron Cay Lakeview Bed & Breakfast Inn – Pet-friendly B&B with views of Lake Dora.
- Hampton Inn Mount Dora – Located a short drive from downtown Mount Dora, Hampton Inn offers the comfort of familiarity.
St. Augustine
St. Augustine is America’s oldest, continuously occupied city and is filled with centuries-old architecture, Spanish colonial charm, and romantic activities like horse-drawn carriage rides. The perfect Valentine’s Day getaway in St. Augustine includes three days of intimate dining, unique activities, and scenic walks.
Romantic Highlights in St. Augustine
History lovers should visit the historic sites such as Castillo San Marcos, Lightner Museum, Flagler College, and the St. Augustine Lighthouse. Each of these has its own romantic story, such as Henry Flagler’s love for his wife, showcased in the Lightner Museum which was formerly a luxury hotel built by Flagler.
While in St. Augustine, take advantage of the mild weather to take scenic walks hand-in-hand with your significant other. The cobblestone streets and historic buildings in St. Augustine’s historic district are a perfect backdrop for romance. Or head to the Matanzas River to take a sunrise walk with waterfront views.
Carve out a little time for a horse-drawn carriage ride or hop aboard a luxurious sailboat for a sunset cruise. If you’re into the supernatural, you might also enjoy one of the many ghost tours.
Where to Eat
There are some really great restaurants in St. Augustine including one of the most romantic restaurants in Florida. Try one of these local favorites for an amazing, intimate experience, but be sure to make reservations well in advance.
- Collage Restaurant – A nationally recognized, award-winning restaurant in St. Augustine’s historic district
- Casa Benedetto’s Ristorante – Authentic homestyle Sicilian cooking in an intimate setting
- Old City House Inn and Restaurant – An historic restaurant and B&B situated among Flagler’s three hotels built in the 1800s.
Where to Stay
You’ll be spoilt for choice of romantic places to stay in St. Augustine. The historic district is full of great choices, from franchise hotels to quaint bed & breakfasts. Try one of these favorites for a truly romantic stay.
- Bayfront Westcott House St Augustine B&B – Waterfront, adults-only B&B located in an historic Victorian building.
- Carriage Way Inn – Adults-only B&B with a spa located in St. Augustine’s historic district.
- The Kenwood Inn – Pet and family friendly B&B located in St. Augustine’s historic district.
Practical Tips for a Romantic Historic Getaway
If you haven’t booked a romantic getaway in an historic location before, I have a few tips you might find helpful.
Plan Ahead
This goes without saying for most getaways. And still, I’m always surprised by the amount of people who just show up in Florida and expect to find vacancies at quality hotels or romantic restaurants. We might be laid back around here, but that doesn’t mean you can be 100% spontaneous, especially during business times of the year.
Many people head to Florida in February when it’s colder in other parts of the country and world. It’s not surprising, then, that hotels, campgrounds, and vacation rentals fill up fast at this time of year. If you’re planning a romantic getaway to an historic Florida town, be sure to book your accommodations and restaurants well in advance.
Packing Essentials
I’m not a big packer which is why you won’t find many packing lists on this site. February in Florida, however, might be hot or cold or both in the same day. Pack accordingly though you can probably leave your heavy winter clothes back home.
Likewise, if you’re planning a romantic dinner at a high-end restaurant, wear something appropriate. Beach wear will be turned away from many places in the evening, especially those which require reservations.
Respect the Local Heritage
Respect historic places by staying on designated paths and not taking photos or flash photos where they are restricted. Take a moment to learn about Florida’s unique history wherever you are. And support local businesses. You might find many of the local businesses have been around for decades.
Wrapping Up Valentine’s Day Getaways
Florida’s historic towns offer tons of romantic opportunities, perfect for a Valentine’s Day getaway or another romantic milestone such as an anniversary. These historic towns provide great restaurants, beautiful B&Bs, and romantic activities like carriage rides. They’re hard to beat when you’re looking for a unique experience.
I invite you to check back as I add other historic Florida towns to this list. And, please, let me know in the comments which historic Florida town is your go-to when planning a romantic getaway.
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I really loved this great list of towns with practical information for a Valentine’s Getaway. I have made some notes, and save your post to pinterest to come back to. I agree that planning ahead is key – I appreciate your expert advice!
Considering many of these are small towns, which give it that romantic charm, I haven’t actually heard of most of them! Thanks for sharing.
Great post! I love the idea of taking a getaway for Valentine’s Day! Escaping somewhere warmer than Kansas, like Florida, is ideal. Thank you for the great ideas
We often plan our winter travel and don’t think about planning around Valentine’s Day. But these spots in Florida look like good options for a special few days. Sunsets and seafood are always big hits for romantic outings for us! A small adults only spot to stay sounds perfect.
These are great tips! I love St. Augustine – it’s exactly what I’d think of when thinking of romantic places in Florida, such a cute town!