8 Scouted Cities That Are Perfect for a Warm-Weather Winter Getaway

If lingering chilly temperatures and unpredictable weather have you itching for a warm-weather escape, we have just the antidote: a trip to one of our vacation-ready scouted cities. Whether your getaway goals include relaxing by the water, dining al fresco, enjoying a world-class cultural experience, or doing some casual window shopping, these locations have you covered. Here, The Scout Guide editors in eight areas across the country share why their cities should be at the top of your list of ideal warm winter destinations.

PALM BEACH, FLORIDA

Flagler Mizner Fountain. Photography by Nick Mele Photography.

This palm tree-lined locale is great for a visit any time of the year, but during “season,” which falls from Thanksgiving to Easter, Palm Beach is an especially popular escape. According to Stacey Leuliette, editor of The Scout Guide Palm Beach, young families and professionals have recently moved to the area in droves to escape colder climes (and embrace the tax structure), resulting in an increasingly modern and relevant city. “There are many parts of the island that will never change—and should never change—but there is plenty of exciting development and growth going on here in South Florida,” Stacey says. “And despite all of our extraordinary iconic history and reputation for over-the-top galas and parties (which still very much take place), Palm Beach is actually a casual, carefree beach town,” she adds. With beautiful beaches, plentiful sunshine, wonderful restaurants, world-class shopping, and of course, palm trees, Palm Beach really is a little slice of paradise.  

To plan your Palm Beach winter getaway, check out the Palm Beach City Cheat Sheet, and for additional recommendations for what to do, see, and experience in Palm Beach, Florida, follow The Scout Guide Palm Beach on Instagram and visit The Scout Guide Palm Beach website, where you can browse or order the latest volume of The Scout Guide Palm Beach.

NAPLES, FLORIDA

Photography by iStock.

As its nickname, “Paradise Coast,” implies, Naples, Florida, is an ideal destination. From pristine beaches to the palm tree-lined streets of downtown, there are few places as beautiful. The Scout Guide Naples editor Jennifer Adams shares that the city also has an amazing dining scene, with everything from toes-in-the-sand options—perfect for watching the sunset—to super-fresh seafood and some of the best Italian fare you’ve ever tasted. And if you’re looking to feel right at home, you will, Adams assures, as Naples is home to some of the friendliest people you’ll meet. 

To plan your Naples winter getaway, check out the Naples Lodging Guide, the Naples Shopping Guide, and the Naples Beach Guide. And for additional recommendations for what to do, see, and experience in Naples, Florida, follow The Scout Guide Naples on Instagram and visit The Scout Guide Naples website, where you can browse or order the latest volume of The Scout Guide Naples.

ORLANDO, FLORIDA

Photography by Rooted Love Photography. 

Known as the City Beautiful, Orlando is always appealing, welcoming visitors who come for the warm climate, world-famous theme parks, shopping, golf courses, and vibrant nightlife. “Orlando is a large city with many small-town-feel communities,” Jaleh Benner, editor of The Scout Guide Orlando, says of why people flock to her area. “Each community in Orlando has its own vibe and great attractions, restaurants, and amenities.” And with 365 days of sunshine, the magic of Orlando can be enjoyed by both the young and the young at heart. 

To plan your Orlando winter getaway and for recommendations for what to do, see, and experience in Orlando, Florida, follow The Scout Guide Orlando on Instagram and visit The Scout Orlando website, where you can browse or order the latest volume of The Scout Guide Orlando.

PHOENIX & SCOTTSDALE, ARIZONA

Photography by Unsplash.

For an otherworldly escape, a trip to the awe-inspiring Sonoran Desert and the bustling desert towns of Scottsdale and Phoenix, is just the thing to chase away the winter blues. Sasha Clements, editor of The Scout Guide Phoenix & Scottsdale, notes that with iconic landscapes under picture-perfect skies, luxury resorts, stellar shopping, chef-driven restaurants, and endless exciting activities and attractions, there’s much to explore and appreciate. Adding to the area’s allure, “Creating, enjoying, and supporting the arts is a way of life here,” she says. “And with a vibe unlike anywhere else in the world, the creative spirit of the West is alive and well, and there’s room here for imagination to wander and dreams to flourish.” 

To plan your Phoenix and Scottsdale winter getaway, check out the Phoenix & Scottsdale Shopping Guide and the Phoenix & Scottsdale Dine Like a Local Guide. And for more recommendations on what to do, see, and experience in Phoenix and Scottsdale, Arizona, follow The Scout Guide Phoenix & Scottsdale on Instagram and visit The Scout Phoenix & Scottsdale website, where you can browse or order the latest volume of The Scout Guide Phoenix & Scottsdale. 

TAMPA & ST. PETERSBURG, FLORIDA

Photography by Justin Demutiis of Demutiis Photography.

Situated on Florida’s Gulf Coast, the Tampa and St. Petersburg area is known for its blue skies, expansive waterfront, and sparkling white sand beaches. “You can find access to water pretty much everywhere, including the amazing Tampa riverwalk,” explains Allison Adams, editor of The Scout Guide Tampa & St. Petersburg. And while fun in the sun is a top priority to this Gulf Coast jewel, the area’s celebration of the arts has roots that run deep, from its extensive Cuban culture to the Dali Museum and the renowned Tampa Museum of Art. Add to that a thriving environment for small businesses, and there’s much to discover and explore between sun sessions. 

To plan your Tampa and St. Petersburg winter getaway, check out the Tampa & St. Petersburg Cheat Sheet. And for more recommendations on what to do, see, and experience in Tampa and St. Petersburg, follow The Scout Guide Tampa & St. Petersburg on Instagram and visit The Scout Tampa & St. Petersburg website, where you can browse or order the latest volume of The Scout Guide Tampa & St. Petersburg.

SARASOTA, FLORIDA

Anna Maria Island. Photography by Cat Pennenga Photography.

With over 50 miles of white sand beaches and gorgeous Gulf of Mexico sunsets, the Florida west coast, home to Sarasota, Anna Maria Island, and Boca Grande, is perfect for a romantic getaway, fun family vacation, or even a relaxing solo trip. Situated on Sarasota Bay and the Gulf of Mexico, Nikki Logan Curran, editor of The Scout Guide Sarasota, Anna Maria Island to Boca Grande, notes that the area is home to some of the best fishing and boating on the west coast of Florida. Whether you opt for a private fishing charter, sunset cruise, dolphin excursion, or all three, they never disappoint. But the sun and sand aren’t the only draw: “Sarasota is known as Florida’s Cultural Coast, featuring The Sarasota Ballet, Sarasota Opera House, Asolo Repertory Theater, Orchestra, and much more,” Curran says. 

To plan your winter getaway to Sarasota, check out the Sarasota Lodging Guide, the Sarasota Dining Guide, and the Sarasota Shopping Guide. And for more recommendations on what to do, see, and experience in Sarasota, Anna Maria Island, and Boca Grande, follow The Scout Guide Sarasota, Anna Maria Island to Boca Grande on Instagram and visit The Scout Guide Sarasota, Anna Maria Island to Boca Grande website, where you can browse or order the latest volume of The Scout Guide Sarasota, Anna Maria Island to Boca Grande.

TUCSON & SOUTHERN ARIZONA

Catalina Foothills. Photography by Fletcher and Co. for TSG Tucson & Southern Arizona.

If you’re on the hunt for a true oasis and a non-traditional escape to warmer climes, Southern Arizona is the perfect place for a jaunt. There, you can experience the raw beauty of the Sonoran Desert, premier golf, exceptional museums and shopping, and unparalleled health and wellness offerings. And if you’re a foodie, MaryAnn Wittmann, editor of The Scout Guide Tucson & Southern Arizona assures that the culinary scene in the area is unparalleled. “Eating local in Tucson and the surrounding area is a culinary experience not to be missed,” she says. “As a matter of fact, Tucson is the first city to earn the City of Gastronomy from UNESCO designation.” Between outdoor adventures, a buzzing music scene, excellent dining and shopping, and exceptional wellness resorts, visitors will find many ways to enjoy this desert destination.

To plan your Tucson and Southern Arizona winter getaway, check out the Southern Arizona Dining Guide, the Southern Arizona Shopping Guide, and the Southern Arizona Lodging Guide. And for more recommendations on what to do, see, and experience in Tucson and Southern Arizona, follow The Scout Guide Tucson and Southern Arizona on Instagram and visit The Scout Guide Tucson and Southern Arizona website, where you can browse or order the latest volume (volume 2 launches in mid-March 2022) of The Scout Guide Tucson & Southern Arizona.

JUPITER & PALM BEACH GARDENS, FLORIDA

Jupiter. Photography by Eve Greendale of Palm Beach Creative Photography.

With breathtaking natural scenery and a relaxed tropical feel, it’s no wonder Jupiter and Palm Beach Gardens is a fantastic winter getaway in South Florida. Stacey Leuliette, editor of The Scout Guide Jupiter & Palm Beach Gardens, explains that the area is rich in beauty and history, and offers many amenities usually found in big cities while maintaining a small town feel. Plus, thanks to an assortment of parks and beaches, endless waterways for watersports, boating, and fishing, and golfing, this is an ideal place for those who truly love outdoor living. 

To plan your Jupiter and Palm Beach Gardens winter getaway, check out the Jupiter and Palm Beach Gardens Cheat Sheet. And for more recommendations on what to do, see, and experience in Jupiter and Palm Beach Gardens, follow The Scout Guide Jupiter and Palm Beach Gardens on Instagram and visit The Scout Guide Jupiter & Palm Beach Gardens website, where you can browse or order the latest volume of The Scout Guide Jupiter & Palm Beach Gardens.