The winter months aren’t my favorite months, because I don’t love cold weather and gray skies. One way to make the cold temperatures of the winter more tolerable is to plan a fantastic winter vacation. Planning a vacation in the winter can be a great way to have something to look forward to in the colder months.
When you choose a winter vacation destination, you have several options. You can choose to vacation in a place with the full winter experience – a perfect option if you love winter sports like skiing and snowboarding.
Or, you can choose to escape the winter with a tropical vacation. Another option is to sightsee in a place that isn’t particularly warm or cold – but where the weather doesn’t really matter.
Disclosure: This post contains affiliate links. A purchase and/or click through one of these links may result in a commission paid to us at no additional cost to you. We have received complimentary and discounted stays at some of these locations but all opinions are my own.
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The Best Places to Visit in Winter (From the USA)
Vermont
Vermont, located in New England, is home to some of the best East Coast ski areas. It’s a beautiful state, offering great restaurants and charming inns. If you are looking to get away for vacation and want to do some skiing, you’ll have some great options.
Ski areas in Vermont include the following:
- Okemo Mountain, in Ludlow, Vermont
- Mad River Glen, in Fayston, Vermont
- Jay Peak Resort in Jay, Vermont (also offers a luxurious resort with the Pump House indoor water park)
- Killington Resort in Rutland County, Vermont
- Smuggler’s Notch in Cambridge, Vermont (one of the most family-friendly resorts in the country).
Our picks for a general family vacation are either Jay Peak or Smuggler’s Notch, where there are more things to do than just ski and snowboard.
San Diego, California
San Diego is blessed with consistent weather year-round, making it one of the most popular destinations any time of year. We’ve visited this Southern California destination during our February vacation in past years, and have always found it to be a fantastic place to visit in the winter season.
San Diego offers so much for families, including beaches, SeaWorld, the San Diego Zoo, boat rides, sports, restaurants, and much more. It’s also a short drive away from Carlsbad, home of LEGOLAND California.
We generally recommend staying right in San Diego and then driving to Carlsbad for a day trip. But, if you have LEGO-loving kids, you may want to stay right at the LEGOLAND California Hotel or the LEGOLAND Castle Hotel.
Hotel Recommendations:
We also recommend getting a San Diego CityPASS, which includes admission to either (or both) LEGOLAND California or SeaWorld San Diego and your choice of three of the following:
- San Diego Zoo® or Safari Park (You can only choose one of these two)
- The USS Midway Museum
- City Cruises
- Old Town Trolley Tours
- Birch Aquarium at Scripps
- Maritime Museum of San Diego
Florida
Florida offers the best winter vacations, especially for those in the Northeast. While sometimes the weather in Florida can be a little chilly in the winter months, it’s usually much better than the weather in the north.
If you are thinking of vacationing in Florida in the winter, you’ll have many options. The most popular of course, is Orlando, in Central Florida.
Orlando, home of theme parks like Walt Disney World, Universal Orlando, and SeaWorld, offers many activities for families. The winter months can be the best time to visit, especially if you don’t want to deal with the hot weather and crowds of the summer months.
There are many hotel options, from chain hotels to luxurious resorts. Many guests visiting the Walt Disney World theme parks also have the option of staying on property, at one of the Disney hotels. That’s an especially good option if you spend all of your Florida vacation at Walt Disney World.
Another one of my favorite Florida destinations is on the Gulf Coast. Clearwater Beach is one of the most beautiful places with a beach regularly rated as one of the best in the country. While the winter months may be a little cool for beach days (but can still be very warm), there are many other fun things to do in the area, including the Clearwater Marine Aquarium and Busch Gardens in Tampa.
The town of Sarasota is also on the Gulf of Mexico. It offers water sports, sandy beaches, and the Ringling, a museum complex with a gorgeous home and circus museum.
Our favorite hotel picks are:
- The Gaylord Palms Resort and Convention Center
- Disney’s Beach Club Resort
- Hilton Clearwater Beach Resort
Texas
Like Florida, Texas can sometimes be chilly in the winter months but is usually never freezing cold. There are sometimes unusual weather occurrences, but the temperatures are typically warmer than those in the Northeast. Average highs are usually in the 70s.
We love San Antonio, famous for the River Walk and the Alamo. In the winter, high temperatures are usually in the 60s, which is very pleasant for walking outside. Other best things to do include fun attractions and areas like the trendy Pearl District (a former brewery), the Tower of the Americas, and the Witte Museum.
Our hotel pick is the historic Omni La Mansión del Rio Hotel, which is located right along the River Walk. It’s within walking distance of many restaurants, shops, and attractions.
Puerto Rico
This gorgeous island is part of the United States, so you won’t have to worry about bringing along a passport or going through customs. It’s an easy vacation, with many things to do.
Popular activities in Puerto Rico include Old San Juan, water activities, the El Yunque National Forest, and the Bioluminescent Bay. The area has some fantastic family resorts, including many with pools and beach access. Puerto Rico is a fantastic Caribbean island destination and is so convenient to visit.
We enjoyed a stay at El Conquistador, a beautiful resort offering an outdoor water park and private island beach. It’s not located right in San Juan, but you can rent a car for the day and visit.
Colorado
Colorado is one of the best places to visit in the winter if you love to ski. There are many world-famous ski resorts in the state, including the following:
- Breckenridge Ski Resort in Breckenridge, CO
- Keystone Ski Resort in Keystone, CO
- Vail Ski Resort in Vail, CO
- Aspen Snowmass Resort in Aspen, CO
- Steamboat Ski Resort in Steamboat Springs, CO
New Hampshire
Like Vermont, New Hampshire is a New England ski destination. While its ski conditions may not be the same as those in the western part of the United States, it is still a great option for families in the Northeast.
There are several ski mountains and regions in New Hampshire within the White Mountains. These include:
- Loon Mountain Resort in North Conway, NH
- Attitash Mountain Resort in Bartlett, NH
- Waterville Valley Ski Resort in Waterville Valley, NH
- Bretton Woods Mountain Resort in Bretton Woods, NH
- Mount Sunapee Resort in Mount Sunapee State Park in Newbury, NH
One of our favorite hotels in New Hampshire is the Mountain Club on Loon, in Lincoln, NH. It’s located adjacent to Loon Mountain and is a great family resort.
Quebec City, Quebec, Canada
Quebec City in Canada is one of my favorite North American destinations in the summer, but it’s also one of the best winter destinations. This quaint city feels like it’s in Europe, but can be a doable road trip or a quick flight from the Northeast of the United States.
If you love winter, Quebec City is the perfect place to visit. The most popular time to visit Quebec City in the winter is during the beloved Quebec Winter Carnival, the world’s largest and oldest winter carnival. In 2025, this annual event takes place between February 7th to February 16, 2025 – the perfect time for a winter getaway.
The Quebec Winter Carnival activities include parades, live music concerts, shows, ice sculptures, and more. There’s a full calendar of events online, but be sure to dress warm because you’ll be walking a lot around the city.
However, if you don’t visit during the carnival time, it’s still a great place to go in the winter. There’s an ice hotel (book well in advance for this unique experience), an ice skating rink, cross-country skiing, a winter toboggan, and other winter activities over the entire season.
My hotel pick is the stunning and historic Chateau Frontenac, located in the center of the walled Old City. It’s expensive, but it is a bucket list hotel with great views, restaurants, and rooms.
Family Cruise
I love cruising, and it can be a perfect winter escape for a family vacation. There are many different cruise ports in the United States, including Miami, Florida, Port Canaveral, Fort Lauderdale, Florida, Tampa, Florida, Galveston, Texas, New Orleans, Louisiana, and San Diego, California. Mexico (especially Cozumel), the Bahamas, Key West, Florida, and the Caribbean are popular destinations in the winter months.
Cruising in January, February, and early March can also be cost-effective. These are times when you can often find some great deals. Just be sure to fly a day or more before your cruise just in case there are any flight delays or luggage issues with your flight. On our most recent cruise in December, our luggage was delayed and we received it just before we had to leave for the cruise port.
Our recommendation for family cruise lines is either Disney Cruise Line or Royal Caribbean.
Turks and Caicos
One of my favorite vacation destinations is Turks and Caicos, located in the Caribbean. This beautiful archipelago offers luxurious resorts, delicious fresh food, and gorgeous turquoise waters.
If you visit via air (and not cruise ship), you’ll probably end up in Providenciales. While there are many resorts in Provo (as it’s locally known), our favorite for families is Beaches Turks and Caicos.
This luxurious, all-inclusive resort offers water sports, pools, entertainment, a water park, beach access, and so much more. It’s one of my all-time favorite vacation spots.
Regardless of where you’ll stay, you must plan some fun at the beach. Grace Bay Beach, located in Provo, is one of the most beautiful beaches in the world.
Arizona
I’ve always enjoyed visiting the desert, and Arizona has some great places for a family vacation. You’ll want to stay in the Phoenix or Tucson areas for the warmest weather. While they are known for extremely hot weather, it’s much milder and more manageable in the winter.
Phoenix has many popular suburbs, including Tempe, Chandler, and Scottsdale. In that area and Tucson, you’ll find beautiful outdoor attractions, including botanical gardens, hiking trails, and zoos. Bring your sunscreen because the sun can be very hot, even in the winter.
Despite the name, baseball spring training does start in late February. In the greater Phoenix area, you can see the Cactus League play from the end of February through most of March. Be prepared for some very warm weather as you get closer to late March. It is a great time to visit and is one of the best ways to watch a professional baseball game.
Our hotel recommendations include:
- The Westin La Paloma Resort & Spa in Tucson
- Hilton Phoenix Resort at the Peak
- Hilton Phoenix Tapatio Cliffs Resort
Los Angeles
Los Angeles, north of San Diego, does have more temperature variability in the winter months. However, if you want to visit theme parks, it can be the perfect weather to run around the parks without getting too hot. Average temperatures in the winter are in the low 70s, and there are fewer crowds at the theme parks than in the summer, making it a great time to visit.
Theme parks in the LA area include Disneyland Resort (including Disney’s California Adventure and Disneyland Park), Universal Hollywood, and Knott’s Berry Farm. If you don’t mind driving, you can combine a trip to Los Angeles with some time in San Diego. Other nearby areas include Palm Springs, Beverly Hills, and Santa Monica.
Our two favorite hotels outside of Disneyland are the Westin Anaheim and the Howard Johnson by Wyndham Anaheim Hotel and Water Playground.
US Virgin Islands
Like Puerto Rico, the US Virgin Islands are located within the US, so there’s no need for a passport and you won’t have to spend time going through customs. There are three islands: St. Croix, St. Thomas, and St. John. US Virgin Islands are accessible via plane and/or cruise ship to St. Croix and St. Thomas, while you’ll have to catch a separate ferry to get to St. John.
The average high temperature in the US Virgin Islands is in the 80s, which is perfect for outdoor activities, including water sports. The archipelago also has several golf courses.
