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21 Days of Festive Fun and Winter Adventures

21 Days of Festive Fun and Winter Adventures Itinerary

Last updated: 2024 Jun 14

Iconic NYC Landmarks and Festive Delights

Morning

Start your day with a visit to Central Park. This iconic park is especially beautiful in winter, with its snow-covered landscapes and ice-skating rinks. Enjoy a leisurely walk or a horse-drawn carriage ride through the park.

Afternoon

Head over to Times Square for the afternoon. The bustling energy of Times Square is amplified during the holiday season with festive decorations and street performers. Don't forget to grab a slice at Joe's Pizza for an authentic New York experience.

Evening

Conclude your day with a visit to Broadway. Catching a Broadway show is a quintessential New York experience, especially during the holiday season when special performances are often available. For dinner, dine at the renowned Le Bernardin for an exquisite culinary experience.

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Central Park
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Times Square
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Brooklyn's Best and Holiday Cheer

Morning

Begin your day at Brooklyn Bridge Park. The park offers stunning views of Manhattan and is perfect for a morning stroll. Warm up with some hot chocolate from nearby vendors.

Afternoon

Explore Dumbo in the afternoon. This trendy neighborhood is known for its cobblestone streets, art galleries, and unique shops. Stop by Grimaldi's Pizzeria for lunch, famous for its coal-fired brick-oven pizzas.

Evening

End your day with a visit to Dyker Heights. This Brooklyn neighborhood is famous for its extravagant Christmas light displays. For dinner, head back to Manhattan and enjoy a meal at Eleven Madison Park, one of NYC's top-rated restaurants.

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Brooklyn Bridge Park
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Dumbo
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Cultural Gems and Festive Lights

Morning

Start your morning at the renowned Metropolitan Museum of Art (The Met). The museum's vast collection spans thousands of years and includes special holiday exhibits during this time of year.

Afternoon

In the afternoon, take a walk through Greenwich Village. This historic neighborhood is charming during the holidays with decorated streets and cozy cafes. Have lunch at Katz's Delicatessen, known for its legendary pastrami sandwiches.

Evening

Spend your evening exploring the festive lights at Rockefeller Center Christmas Tree Lighting Ceremony. The iconic tree lighting ceremony is a must-see during the holiday season in NYC. For dinner, dine at Per Se, offering breathtaking views of Central Park.

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Metropolitan Museum of Art (The Met)
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Greenwich Village
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Historic Sites and Winter Wonderland

Morning

Visit the historic site of One World Trade Center in the morning. The observatory offers panoramic views of New York City that are especially stunning in winter.

Afternoon

Head over to explore more history at the nearby National September 11 Memorial & Museum. It's an important site that provides deep insights into recent history. For lunch, stop by nearby restaurant options or grab something quick from food trucks around.

Evening

Conclude your day by visiting one of New York City's most beloved winter attractions: ice skating at Rockefeller Center or Bryant Park Winter Village. Enjoy dinner afterward at Gramercy Tavern, known for its warm ambiance and delicious seasonal dishes.

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One World Trade Center
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4.42
National September 11 Memorial & Museum
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Brooklyn's Hidden Gems and Festive Fun

Morning

Brooklyn Museum is a great way to start your day. The museum's diverse collection includes art from various cultures and time periods, and it often features special holiday exhibits during this season.

Afternoon

Spend your afternoon at Prospect Park. This expansive park offers winter activities such as ice skating and sledding. For lunch, try Momofuku Noodle Bar for some delicious ramen to warm you up.

Evening

Dyker Heights is a must-see in the evening. This neighborhood is famous for its extravagant Christmas light displays that attract visitors from all over. For dinner, head to Peter Luger Steak House, known for its legendary steaks.

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Brooklyn Museum
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Prospect Park
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Architectural Marvels and Winter Fun

Morning

Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). The Skydeck offers breathtaking views of the city, and during winter, you can see the snow-covered skyline. Enjoy a coffee at the Skydeck café.

Afternoon

Spend your afternoon exploring Millennium Park. The park is home to the famous Cloud Gate sculpture (The Bean) and offers ice skating in the winter. For lunch, head to Girl & The Goat, known for its innovative dishes.

Evening

End your day with a visit to Chicago Riverwalk. The Riverwalk is beautifully lit up during the holiday season. Enjoy dinner at Alinea, one of Chicago's most acclaimed restaurants.

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Skydeck Chicago at Willis Tower (Sears Tower)
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Millennium Park
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Cultural Highlights and Festive Lights

Morning

Art Institute of Chicago is a must-visit in the morning. The museum's extensive collection includes special holiday exhibits. Have breakfast at the museum's café.

Afternoon

Navy Pier is perfect for an afternoon visit. During winter, Navy Pier hosts various festive events and has an indoor ice skating rink. For lunch, try Lou Malnati's Pizzeria for some classic Chicago deep-dish pizza.

Evening

Chicago Theatre offers evening performances that are especially festive during the holiday season. Afterward, dine at The Purple Pig, known for its Mediterranean-inspired small plates.

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Historic Sites and Holiday Markets

Morning

Field Museum is ideal for a morning visit. This natural history museum has fascinating exhibits that captivate visitors of all ages. Grab breakfast at one of the museum’s cafes.

Afternoon

Christkindlmarket in Daley Plaza is a must-see in the afternoon. This traditional German Christmas market offers unique gifts, festive foods, and warm drinks like mulled wine. For lunch, enjoy some bratwurst or pretzels from market vendors.

Evening

360 Chicago Observation Deck (Formerly John Hancock Observatory) provides stunning views of Chicago’s skyline in the evening. Dine at RPM Italian afterward for a delightful Italian meal.

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Field Museum
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4.17
360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Sports Enthusiasts' Day Out

Morning

Start your day with a tour of Wrigley Field, one of baseball’s most iconic stadiums. Even if it’s off-season, guided tours offer fascinating insights into its history.

Afternoon

Head over to Soldier Field in the afternoon for another sports-related activity. Soldier Field often hosts events even during winter months or you can take a guided tour if available.

Evening

Conclude your day by visiting United Center, home to both NBA’s Bulls and NHL’s Blackhawks; catch an evening game if there’s one scheduled! For dinner nearby, try out some delicious seafood at Joe's Seafood Prime Steak & Stone Crab.

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Wrigley Field
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Soldier Field
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Chicago's Architectural Wonders and Winter Magic

Morning

Chicago River offers stunning views of the city's architecture. Take an architectural boat tour to learn about Chicago's iconic buildings while enjoying the winter scenery.

Afternoon

Adler Planetarium is perfect for an afternoon visit. The planetarium offers fascinating exhibits about space and astronomy, along with special holiday-themed shows. For lunch, try Portillo's Hot Dogs for a taste of Chicago's famous hot dogs.

Evening

Grant Park is beautifully lit up during the holiday season. Enjoy a leisurely walk through the park before heading to Gibsons Bar & Steakhouse for a delicious dinner.

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Chicago River
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Adler Planetarium
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Hollywood Glamour and Beach Vibes

Morning

Start your day with a visit to Hollywood Walk of Fame. This iconic sidewalk celebrates the stars of the entertainment industry. Grab a coffee at a nearby café to kickstart your morning.

Afternoon

Universal Studios Hollywood is perfect for an afternoon visit. The theme park offers thrilling rides and attractions, including special holiday-themed events. For lunch, enjoy a meal at one of the park's many dining options.

Evening

End your day with a stroll along Sunset Strip. The Strip is known for its vibrant nightlife and historic music venues. Dine at Spago Beverly Hills, renowned for its elegant ambiance and delicious cuisine.

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Hollywood Walk of Fame
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Universal Studios Hollywood
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Cultural Treasures and Coastal Beauty

Morning

J. Paul Getty Museum (The Getty) is a must-visit in the morning. The museum's impressive art collection and stunning architecture make it a cultural gem. Enjoy breakfast at the museum's café.

Afternoon

Santa Monica Beach and Pier is ideal for an afternoon visit. The pier offers various attractions, including an amusement park and aquarium. For lunch, try The Ivy, known for its charming setting and delicious dishes.

Evening

Griffith Observatory provides breathtaking views of Los Angeles in the evening. The observatory also offers fascinating exhibits about space and astronomy. Dine at Bestia, famous for its innovative Italian cuisine.

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J. Paul Getty Museum (The Getty)
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Santa Monica Beach and Pier
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Historic Sites and Artistic Flair

Morning

La Brea Tar Pits is perfect for a morning visit. This unique site features tar pits that have preserved prehistoric fossils. Have breakfast at a nearby café.

Afternoon

Los Angeles Original Farmers Market is great for an afternoon stroll. The market offers various food stalls, shops, and seasonal events during the holidays. For lunch, try some local delicacies from different vendors.

Evening

Walt Disney® Concert Hall hosts evening performances that are especially festive during the holiday season. Afterward, dine at Republique, known for its beautiful setting and exquisite French-inspired cuisine.

Bedtime

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La Brea Tar Pits
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Los Angeles Original Farmers Market
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Beachside Relaxation and Iconic Landmarks

Morning

Begin your day with a bike ride along Marvin Braude Bike Trail. This scenic trail runs along the coast, offering beautiful ocean views.

Afternoon

Spend your afternoon exploring Venice Canals (Venice Canal Historic District). These picturesque canals are perfect for a leisurely walk or gondola ride. For lunch, head to Guelaguetza to enjoy authentic Oaxacan cuisine.

Evening

Conclude your day with a visit to Hollywood Bowl, one of LA’s most famous music venues; check if there’s any special holiday concert happening! Dine afterward at Providence, celebrated for its seafood dishes.

Bedtime

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Venice Canals (Venice Canal Historic District)
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LA's Coastal Charms and Festive Lights

Morning

Santa Monica Place is perfect for starting your day with some shopping and breakfast at one of the many cafes.

Afternoon

Aquarium of the Pacific offers an engaging afternoon experience with its diverse marine life exhibits. For lunch, head to Grand Central Market, which has a variety of food stalls offering different cuisines.

Evening

Hollywood Sign provides an iconic backdrop for your evening. Take a hike up to get closer views or enjoy it from afar before dining at The Bazaar by José Andrés, known for its innovative dishes.

Bedtime

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Alaskan Wilderness and Scenic Beauty

Morning

Start your Alaskan adventure with a visit to Mendenhall Glacier. This stunning glacier is accessible year-round and offers breathtaking views. Enjoy a guided tour to learn about the glacier's history and geology.

Afternoon

In the afternoon, head to Alaska Wildlife Conservation Center. This sanctuary is home to various native Alaskan wildlife, including bears, moose, and bison. It's a great opportunity to see these animals up close in their natural habitat.

Evening

Conclude your day with a visit to Aurora Borealis Viewing. Alaska is one of the best places in the world to witness the Northern Lights. For dinner, enjoy a hearty meal at a local lodge or restaurant offering traditional Alaskan cuisine.

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Mendenhall Glacier
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Historic Trails and Glacial Wonders

Morning

Iditarod National Historic Trail is perfect for a morning hike or dog sledding experience. This historic trail offers beautiful winter landscapes and an insight into Alaska's rich history.

Afternoon

Portage Glacier is ideal for an afternoon visit. Take a boat tour across Portage Lake to get up close to this magnificent glacier. For lunch, pack a picnic or grab something from nearby eateries.

Evening

Chugach State Park offers stunning views of the Alaskan wilderness in the evening. Enjoy hiking or simply take in the serene beauty of the park. Dine at a nearby restaurant known for its fresh seafood and local dishes.

Bedtime

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Iditarod National Historic Trail
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Portage Glacier
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Cultural Insights and Natural Wonders

Morning

University of Alaska Museum of the North is perfect for starting your day. The museum offers fascinating exhibits on Alaskan culture, history, and wildlife. Have breakfast at the museum café.

Afternoon

Fox Island provides an excellent afternoon excursion. Take a boat tour to this remote island known for its scenic beauty and abundant wildlife. Enjoy lunch on board or at one of the island’s lodges.

Evening

Mt. Roberts Tramway offers spectacular views of Juneau in the evening. The tramway takes you up Mount Roberts where you can enjoy panoramic vistas and dine at the mountaintop restaurant.

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University of Alaska Museum of the North
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Fox Island
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Glacial Adventures and Coastal Views

Morning

Begin your day with an excursion to Kenai Fjords National Park. The park features stunning fjords, glaciers, and abundant marine wildlife such as whales, sea lions, and puffins.

Afternoon

Spend your afternoon exploring Exit Glacier. This accessible glacier allows visitors to hike right up close for an unforgettable experience amidst ice formations.

Evening

Conclude your day by visiting Prince William Sound, renowned for its breathtaking coastal scenery filled with glaciers cascading into crystal-clear waters; consider taking an evening cruise if available! Dine afterward at one of Anchorage’s top-rated restaurants specializing in fresh seafood.

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Exit Glacier
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Alaskan Wilderness Adventures

Morning

Start your day with a visit to Turnagain Arm. This scenic drive offers breathtaking views of mountains and water, especially beautiful in winter when everything is covered in snow.

Afternoon

Spend your afternoon exploring Alaska SeaLife Center. The center provides insights into Alaska’s marine life with interactive exhibits that are fun for all ages. Have lunch at one of Seward’s cozy cafes nearby.

Evening

Conclude your day by visiting Northern Lights Viewing Tour. Alaska’s dark winter skies provide perfect conditions for witnessing this natural phenomenon; consider booking a guided tour! Dine afterward at a local restaurant offering hearty Alaskan fare.

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Farewell to Festive Adventures

Morning

Begin your final day with a visit to Sheldon Jackson Museum. This museum offers a fascinating collection of Native Alaskan artifacts and provides deep insights into the region's cultural heritage.

Afternoon

Spend your afternoon exploring Tongass National Forest. This vast forest is a winter wonderland during this time of year, offering opportunities for snowshoeing, hiking, and wildlife spotting. Pack a picnic lunch or grab something from nearby eateries.

Evening

Conclude your trip with a relaxing evening at Chena Hot Springs Resort. The natural hot springs are especially soothing in the cold winter months. Enjoy dinner at the resort's restaurant, which offers delicious meals made from locally sourced ingredients.

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