15 Romantic Small Towns to Visit

You don’t have to travel far to find love in the air. It can often be found in the smaller, overlooked towns in your backyard. Here are 15 small towns we love for a quick romantic getaway.  

These towns are so beautiful that you don’t need to have an itinerary when visiting. You can plan to wander, even get lost, and take in the gorgeous scenery. We’ve included some recommendations you may enjoy while in town if you enjoy planning.

1. Carmel-by-the-Sea, California

This drive is worth taking just under two hours from San Francisco. It’s almost impossible not to fall in love with Carmel-by-the-Sea’s majestic beauty and the adjacent Big Sur coastline. Take a walk along the mile-long swath of white sand of Carmel Beach. Pause to take in view of dolphins, sea lions, and surfers alike. You can also wander around the little town to shop quirky boutiques and art galleries. Step into the many wine tasting rooms and see whimsical cottages that look like they came straight out of a fairytale.

Afterward, you can catch a show at Sunset Center, tour the Tor House, or visit the historic Carmel Mission Basilica. If you can, consider staying at the gorgeous hotel L’auberge Carmel. Indulge your weekend plans by scheduling an in-room couple’s massage to add the perfect luxurious elements to your stay. Carmel-by-the-Sea is a picture-perfect small romantic town that you will love visiting.

2. Key West, Florida

Just over three hours from Miami, this four miles long, two-mile vast stretch is loaded with quirky charm and beautiful sunsets; the continental United States’ southernmost city feels like a Caribbean getaway. At the end of the Florida Keys, the pace of life famously attracted many notable individuals through its rich history, including Ernest Hemingway and Jimmy Buffet.

First, explore the city’s best beach on a bicycle with a morning ride along Fort Zachary Taylor Historic State Park. After that, get a perfect café con Leche at Five Brothers, a Southard and Grinnell Street institution, for more than 70 years. Be sure to spend time at a spot like the Parrot Key Hotel and Villas or the historic Crowne Plaza Key West La Concha. Take it all in, relax, and enjoy the Key West vibe. 

3. Beaufort, South Carolina

Whatever you imagine southern charm to be, Beaufort has it – Antebellum architecture, moss-laden oak trees, parks, and Civil War-era homes. This small romantic destination is oozing with rich southern culture and moves at a leisurely, slower pace. Located on Port Royal Island in South Carolina’s Sea Island chain, this charming Lowcountry fishing village is a quick stop from Savannah or Charleston.

Enjoy everything from paddle boarding, kayaking, dolphin watching, and crabbing. Also, explore the nearby Hunting Island, State Park.  Enjoy discovering its maritime forest and lighthouse, the only publicly accessible lighthouse in the state. Take a moment to view the wildly gorgeous Atlantic’s white-tipped waves.  

4. Stowe, Vermont

Only three hours north of Boston, this impossibly quaint Green Mountain town is a great fit for outdoor adventures and low-key romantic getaways — right down to the general store. Get your blood pumping with a few ski runs down Mount Mansfield, one of the East Coast’s most famous (and powder-friendly) ski destinations. Also, consider taking a sleigh ride through the snowy woods.

After that, consider hiking the scenic Moss Glen Falls to reach a beautiful waterfall. Stowe is also home to the Trapp Family Lodge, an Austrian-style chalet owned by the family immortalized in The Sound of Music. Here, plan to enjoy a stellar culinary scene. Ben & Jerry’s Ice Cream Factory is also located in nearby Waterbury.  

5. Nantucket, Massachusetts

Nantucket, located 30 miles off Cape Cod, is the ultimate example of coastal New England glory. If you’re looking for the ideal small romantic town, look no further! Here you will find cobbled streets lined with clapboard cottages, gardens aglow with blooming hydrangeas, tiny seaports brimming with sailboats, and 82 miles of pristine coastline with untouched dunes.

Hailed as the “whaling capital of the world in the mid-19th century,” this 50-square-mile island is a National Historic Landmark. The whole island is fringed with picture-perfect sandy beaches. Although this island stretches roughly 17 miles from Madaket Beach to Great Point Lighthouse, Nantucket can be explored by bicycle with well-paved paths. Besides the historic lighthouses along its eastern shore, numerous small museums and landmark buildings, including the Whaling Museum and The Oldest House, were built in 1686.

Today Nantucket is also known for its thriving restaurant scene and boutique hotels. The effusively charming Main Street is lined with colorful boutiques, shops, and galleries. The White Elephant holds court with its central location on the harbor.  

6. Bar Harbor, Maine

Just over three hours from Portland, many will recognize Bar Harbor as the gateway to New England’s only national park, Acadia. However, beyond being an ideal base for exploring the area’s natural delights, Bar Harbor has plenty of charm in itself. The sleepy fishing village on Mount Desert Island is home to charming shops and restaurants with delicious seafood—especially lobster. It even has its own winery, Bar Harbor Cellars Winery.

First, take a sunrise stroll along the ½-mile-long Shore Path over the Porcupine Islands. Then, plan a visit to Bar Island at low tide, when you can walk across the sand bar for a stunning view of Bar Harbor’s bay. You can choose to wind down at the beautiful Harborside Hotel or West Street Hotel’s rooftop pool (the only one in Maine), overlooking the outer islands and Acadia. 

7. Essex, Connecticut

This tiny Connecticut town has an idyllic main street, a quaint riverfront harbor, and rows of traditional New England-style homes just under two hours from New York City. Once you get here, check into the Griswold Inn, a 1776 bolthole said to be America’s oldest continuously operating inn. Also, be sure to head down Main Street. You’ll find shops like Essex Coffee & Tea for pastries and a coffee and Weekend Kitchen for vintage houseware and cooking classes. 

8. Telluride, Colorado

According to the city’s website, “the town of Telluride is just eight blocks wide and twelve blocks long.” The size alone makes this Colorado paradise ideal for an intimate trip. Surrounded by the San Juan Mountains, the former silver-mining camp retains a historic feel through its charming Western downtown. The closest major city, Denver, is over six hours away. Still, many people feel the drive to Telluride is well worth the effort.

It might be on the smaller side, but there’s still plenty to do. Activities include skiing, snowboarding, and sledding on the gorgeous mountains. It also has a thriving arts and music scene, courtesy of a renowned film festival and jazz celebration.  Winter or summer, be sure to take a trip on the free gondola ride looking out over Telluride’s picturesque canyon. 

9. Montauk, New York

Just over two hours from New York City, you’ll find Montauk, on the far east end of Long Island. This town represents a more relaxed version of the Hamptons and is the perfect spot for long-walks-on-the-beach-type romance. You can head out to Ditch Plains to watch the surfers. Then, climb the 137 steps to the top of the Montauk Point Lighthouse to watch the sunset behind the Atlantic Ocean. Consider retreating to Gurney’s Resort or Sole East Resort to settle in for the night. 

10. Ojai, California

A little over an hour from Los Angeles, this Californian oasis has all the essentials: palm tree-dotted landscapes, Spanish Revival architecture, and a laid-back local culture. Golfers and spa lovers will want to head to Ojai Valley Inn and Spa, but there’s plenty to explore beyond the tranquil, 220-acre hotel grounds.

Near town, take a free tour and tasting of Ojai Olive Oil or take in the lush views at Meditation Mount, the town’s 32-acre public meditation center. Set aside a day to explore the wildlife and the adventure-packed Channel Islands (think dolphin-spotting via ocean kayak), accessible from the Island Packers boats operating out of nearby Ventura. 

11. Cannon Beach, Oregon

An hour and twenty minutes from Portland and named one of National Geographic’s 100 Most Beautiful Places in the World, Oregon’s Cannon Beach is a gorgeous Pacific Northwest town that boasts natural, rugged beauty and a thriving arts scene and lively cultural calendar too. Charming shingled shops line the main street, along with coffee shops and restaurants tucked in along the way.

The five-mile beach is home to Haystack Rock, a 235-foot high sea stack. Ecola State Park offers hiking trails and panoramic Pacific views just north of town. While here, stay at Stephanie Inn, a cozy maritime-inspired stay further down the shore.  

12. La Conner, Washington

Just over one hour from Seattle, visitors often come to La Conner, Washington, a small town on the waterfront. It’s also known for its delicious eateries and, for travelers, its easy access to Interstate 5 and the ferry to the San Juan Islands. Many enjoy some “retail therapy” at its galleries, needlecraft and quilt stores, gift shops, and wine bars.

Each spring, La Conner hosts its famous Daffodil Festival, where thousands of cheerful daffodils open against the backdrop of Mt. Baker. More tulips, iris, and daffodil bulbs are produced in La Conner than in any other county in the U.S.  

13. Jackson, Wyoming

Less than 60 miles from Yellowstone National Park, Jackson is the heart of Jackson Hole Valley. This is an area steeped in history and natural beauty. With welcoming arches of elk antlers, the town square is a throwback to the old west with charming storefronts. Activities like stagecoach rides and shootout shows take center stage on warm summer evenings.

This small romantic town is lined with fabulous restaurants, antique stores, and galleries. The wildlife you see all around you adds to the town’s unique feel. The Alpine House Lodge is the perfect place to spend a romantic time together after exploring the area.   

14. Bend, Oregon

Despite its rainy reputation, Bend is one of the West Coast’s best-kept secrets due to its spectacular summers and rocky terrain. Next to the Cascade Range’s eastern peaks, 175 miles southeast of Portland, Bend is known for active pursuits like hiking, rock climbing, and whitewater rafting. 

The Old Mill District, a historic area comprised of shops, restaurants, and galleries, is intersected by a calm strip of the 252-mile Deschutes River. Here, families can enjoy paddle boarding and tubing under pedestrian bridges. Summer concerts play from the riverfront Les Schwab Amphitheater. You can also hit the trails at Smith Rock State Park. 

15. Lenox, Massachusetts

Just two and a half hours from Boston and three hours from New York, Lenox, Massachusetts, is located in the heart of the Berkshires.  This area in western Massachusetts is known for its picturesque scenery, excellent hiking trails, rich history, culture, shopping, wellness (think Canyon Ranch), and incredible restaurants. The Norman Rockwell Museum is located downtown. Likewise, Tanglewood, the Boston Symphony Orchestra’s summer home, is just a few miles away.

It is a beautiful town to visit any time of the year and is always busy with its rich regional arts scene. The Mount, the Pulitzer-prize-winning novelist Edith Wharton’s home and gardens, is a must-see. The Pleasant Valley Wildlife Sanctuary, a Mass Audubon property with extensive trails through 1300 acres of wilderness, offers views, forests, wetlands, rare species, and terrain for walkers and hikers.  

There are many inspiring and beautiful small romantic towns in the U.S. We hope you feel inspired and look forward to putting a few on your bucket list.

Do you have any thoughts or recommendations on the towns we listed? Please let us know!

Are you interested in visiting a big city? Check out my favorite block in NYC here.