8 Very “Merry” Holiday Shopping Destinations

Go to Travel Gal has partnered with CardRatings for our coverage of credit card products. Go to Travel Gal and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone and have not been reviewed, endorsed, or approved by any of these entities.

It’s November and that means the holidays are quickly swooping down upon us. But instead of being rattled and stressed about fitting in all that holiday shopping, why not make a vacation of it at some fun holiday shopping destinations?

Shopping tourism is becoming a “thing” with many people traveling specifically to shop.

Here 8 holiday shopping destinations that I think rise above the rest…


8 Holiday Shopping Destinations


Cold Weather

If you love the chill in the air with the hope of snow flurries as you wander from storefront to storefront, these shopping destinations are great choices.

1. Chicago

Christkindl Market Credit: Adam Alexander Photography, Choose Chicago
Christkindl MarketCredit: Adam Alexander Photography, Choose Chicago

You can’t go shopping in Chicago without hitting the Magnificent Mile, which is filled with stores and boutiques of every kind.

The streets are decorated to the hilt in their holiday finest and the spirit of Christmas is certainly in the air.

But beyond busy Michigan Avenue are other awesome Chicago shopping stops.

Visit The Loop area to gaze in Macy’s decorated windows, and be sure to stop by the Christkindl Market in Daley Plaza.

Head over to Millennium Park to see “The Bean” under the glow of Christmas lights and try ice skating on the “ribbon” (versus “rink”) in nearby Maggie Daley Park.

Don’t forget the American Girl shop on Michigan Avenue, which is popular with many kids.

For any online shopping you’ll be doing for kids, check out Born Cute.

The Kimpton Hotel Monaco is a convenient to many of the these spots, right on the Chicago River near Michigan Avenue and with awesome window seats.

We also love ACME Hotel Chicago (read my full review of this hotel) close to Michigan Avenue.

Here are more things to do in Chicago at Christmas and check out these things to do in Chicago in summer.


2. New York City

Holiday shopping New York City
Credit: NYC & Company Joe Buglewicz

There’s nothing quite like New York City at the holidays.

Everywhere you turn the city is decorated to the nines, and you just can’t escape the holiday spirit.

If you’re looking for luxury goods, be sure to visit Fifth Avenue, but for more unique finds, try one of several holiday markets that pop up around the city.

New York City Holiday Market
Bryant Park Holiday Market, Credit: NYC & Co, Malcolm Brown

Bryant Park in midtown has more than 100 merchants that set up shop in the park.

You’ll also find an ice skating rink and lots of warm and yummy holiday treats.

There are also holiday markets at Union Square and Columbus Circle.

We have been to both Bryant Park and Union Square and recommend both!

Bryant Park ice skating
Ice skating at Bryant Park’s Christmas market

If you’re looking for food gifts, head to a local food hall like Chelsea Market or Gansevoort Market in the Chelsea and Meatpacking districts of the city.

And if it’s a nice winter day, while you’re there, take a lovely stroll on the High Line elevated park in Chelsea.

Of course, I always love to hit Chinatown in New York City for the ultimate deal!

Macy's Thanksgiving Day Parade 2018
A very cold Macy’s Thanksgiving Day parade in 2018

We also attended the Macy’s Thanksgiving Day parade in 2018 for a once-in-a-lifetime experience.

You can actually see it from the Crowne Plaza Times Square (where we stayed using IHG points) if you’re staying on the correct side.

Macy's Thanksgiving Day Parade balloons blowing up

The night before you can also head up to Central Park West via the subway to see the balloons being inflated, which I highly recommend.

Just bring warm clothes, as you never know what the weather might be like in November in New York City.

If you’ll be staying in a vacation rental in New York City and want some help with cleaning, check out these house cleaning services for homes and apartments.

[7 Awesome Things to Do in New York City With Kids]


3. Washington, D.C.

Washington D.C. holiday market
Downtown Holiday Market, Credit: Washington.org

You may not think of D.C. as a shopping destination, but it certainly is.

One of my favorite places to shop for unusual gifts is at museum stores, and Washington, D.C., has these in abundance!

The city also offers a Holiday Market after Thanksgiving located across from the Smithsonian American Art Museum with eclectic gifts like ornaments, jewelry, accessories, pottery, handicrafts, clothing and paintings.

Washington D.C. Holiday Shopping
CityCenter, Washington, D.C., Credit: Washington.org

Stay close to both the monuments and shopping at the Marriott Marquis.

Just two blocks from the new CityCenter shopping, living and entertainment district, the hotel also has a lifesized gingerbread house in the lobby, one of the largest in the city.

Georgetown holiday shopping
Georgetown, Credit: Washington.org

Don’t miss Georgetown with its cobblestone streets for a charming Christmas feel.

Filled with local independent stores and boutiques, there are many one-of-a-kind finds you may happen upon.

The area also hosts Georgetown Glow, an outdoor exhibition of art-light installations throughout the holidays.


4. Denver

Denver Holiday Shopping
Credit: Visit Denver

If you really want a winter-y feel, visit the Mile High City of Denver.

The downtown, which is home to a stylish Hyatt Place and Hyatt House Denver/Downtown, offers a variety of shopping options.

We’ve also stayed at the Crawford Hotel inside Denver’s Union Station, which is uber cool with high ceilings and convenient to all downtown Denver.

The Denver Pavilions with 40 shops, restaurants and entertainment venues covering two city blocks is just a short distance from the Hyatt Place and Hyatt House, both GREAT redemptions for free stays with Hyatt points. 

Denver Holiday Lights
Grand Illuminations, Credit: Visit Denver

The city also has the open air 16th Street Pedestrian Mall in the heart of downtown, as well as its own Christkindl Market.

Don’t miss downtown’s Grand Illuminations with 600,000 brightly-colored floodlights lighting up Denver’s Union Station and City/County Building.


Warm Weather

Should a respite from the cold sound more like a vacation, then head to these sunny locales that offer warm weather AND fantastic shopping.

5. La Jolla

La Jolla Vacation
Credit: Visit San Diego, SanDiego.org

Nicknamed “the jewel of San Diego” for good reason, La Jolla is a seaside village north of San Diego that is not only easy on the eyes but a hot spot for shopping.

Stroll along the rocky outcroppings of the Pacific, meeting sea lions who have no fear of humans, and even kayak sea caves with Everyday California when you need a break from your “retail therapy.”

La Jolla shopping, San Diego shopping
Credit: Joanne DiBona SanDiego.org

La Jolla’s walkable streets are filled with haute couture boutiques and many of the name-brand favorites you know and love.

Keep an eye out for pampered pooches with their owners (many of them in strollers — no joke!) and make a point to stop in local favorite and San Diego icon Warwick’s Books, as well as the Cave Shop where you can literally descend down into a sea cave.

La Valencia, known as the “pink lady,” is a gorgeous hotel right in the heart of all the action that makes a wonderful place to kick up your feet and soak in the hot tub at the end of a shopping-filled day. 

La Jolla hotel, San Diego hotel
Credit: La Valencia

Also nearby is the Westfield UTC more traditional open air mall where Santa visits.

Get a Santa fast pass to get on the jolly Old Elf’s lap a little quicker. 

[35 Suntastic Things to Do in San Diego]


6. Santa Barbara

Santa Barbara holiday shopping
Credit: Mark Weber

One of my very favorite places, Santa Barbara is definitely a unique shopping destination.

Known for its “paseos,” which are Spanish-style plazas and promenades, most located along the main thoroughfare of State Street, you can find yourself endlessly winding your way through these charming mazes, which go back seemingly for blocks off the street.

Two of the main “paseos” to visit for shipping are La Arcada and Paseo Nuevo.

You’ll find charming boutiques, as well as well-known chains along State Street.

Santa Barbara shopping Paseo Nuevo
Paseo Nuevo, Credit: Jay Sinclair

The Funk Zone is also a fun area, which is located closer to the waterfront.

It has a California surfer/Bohemian feel and is the city location of many of the area’s wineries, making it a great spot to pick up a delicious California wine and gourmet cheese as a holiday gift.

Santa Barbara Inn
Simpson House Inn

A wonderful spot to stay away from the hustle and bustle of shopping, but close enough to walk to State Street, is the delightful Simpson House Inn.

You’ll feel like you’ve found your own little hidden retreat in the heart of Santa Barbara.

The Inn offers a main house and several cottages for guests, all decorated with a warm farmhouse feel and offering all the modern comforts you need to rest up after a day on your feet.

If you’re just too pooped, they’re happy to deliver breakfast right to your room!

View from Hilton Santa Barbara Beachfront Hotel
The view from the Hilton Santa Barbara Beachfront Hotel (in early summer)

For a view of the Pacific Ocean, book a stay at the Hilton Santa Barbara Beachfront Resort.

It’s one of just a handful of hotels just across the road from the beach.

Santa Barbara sunset
The most beautiful sunset I’ve ever seen — from the Santa Barbara harbor and marina

It may be a bit chilly to take a dip during the holidays, but you can’t beat the view and it’s a short walk to the marina and harbor with lots of restaurants and an incredible view of one of the world’s most beautiful sunsets.

Want more ideas of what to do in Santa Barbara? Check out my post below…

[21 Stunning Things to Do in Santa Barbara]


7. Newport Beach 

Newport Beach shopping
Credit: Visit Newport Beach

Shopping for a car? Consider a California getaway to Newport Beach in Orange County, which is home to many luxury car dealerships, including:

  • Aston Martin
  • Bentley
  • BMW
  • Ferrari
  • Jaguar
  • Maserati
  • McLaren
  • Mercedes-Benz
  • Tesla
  • Porsche

The Lexus dealership even has a $70 million facility to keep you comfy and entertained while you consider your new drive that includes a coffee bar, plasma TVs and putting green!

Newport Beach hotel & restaurant
Oak Grill, Island Hotel

The Fashion Island Hotel in Newport Beach, locally owned and across from the Fashion Island shops (thus its name), is a wonderfully stylish and relaxing place to make your shopping headquarters.

They have acoustic holiday music by the fire and dive-in holiday movies at the pool.

The Stay and Shop package includes a $50 credit at Bloomingdale’s Newport Beach, access to the Island Club lounge, two glasses of champagne at 59th & Lex restaurant, a personal shopping appointment with a style advisor and a Fashion Island tote bag.

Oh, and did we mention the amazing Oak Grill restaurant at the hotel where you can dine on delicious gourmet fare under lantern lit trees? It’s a treat all its own!

[8 Awesome Things for Couples to Do in Southern California]


8. The Palm Beaches, Florida

Worth Avenue shopping
Worth Avenue, Credit: Discover the Palm Beaches

Named the second best destination for Shopaholics by USA Today’s 10Best.com, the Palm Beaches area of Florida offers plenty of ways to get your holiday shop on no matter what you’re looking for.

How can you go wrong with Florida sunshine, palm trees and blooming plants while you’re picking out the perfect gift?

Described as the East Coast’s answer to Rodeo Drive, Worth Avenue in Palm Beach, Florida, is the high-end (note the BMW in photo above) place to shop with stores like Cartier, Chanel and Escada where you can mix and mingle with the country’s most wealthy.

CityPlace Palm Beach shopping
CityPlace, Credit: Discover the Palm Beaches

For a more down-to-earth retail experience, visit CityPlace, an Italian-inspired open air shopping mall where it “snows” nightly during the holiday season.

The gorgeous 1920’s Brazilian Court Hotel full of old world European charm is a killer place to stay during your shop-cation with an on-site art gallery, library and heated pool and hot tub.

Pets are welcome, too!

Palm Beach Hotel
Brazilian Court Hotel, Credit: Palm Beach County CVB

Are you an antique aficionado? Antique Row in West Palm Beach is considered one of the country’s premier antiquing destinations.

Stay at Eau Palm Beach Resort & Spa and take advantage of their package that sends you via vintage luxury transportation with an expert antique guide to help you score the best finds in town followed by lunch.

Have a great holiday shop-cation! May you return rested and with bags full of gifts!


Read more:


Go to Travel Gal has partnered with CardRatings for our coverage of credit card products. Go to Travel Gal and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone and have not been reviewed, endorsed, or approved by any of these entities.

Share This Post

7 secret hacks to fly my family free.
Free Download

7 Secret Hacks I Use to Fly My Family Free

Get the insider tips from years as a global travel writer that my family of four uses to fly for FREE using travel rewards.

7 secret hacks to fly my family free.
Free Download

7 Secret Hacks I Use to Fly My Family Free

Get the insider tips from years as a global travel writer that my family of four uses to fly for FREE using travel rewards.

A woman wearing a blue top and gold necklace.

Meet Lyn Mettler

I’m Lyn, a travel journalist and savvy saver. Since 2015, I’ve unlocked the secret to free flights for my family, saving over $75,000 on 40+ trips. I now share my simple strategy with families, helping them create priceless memories through travel rewards.

Free Guide

Start Flying FREE on Southwest!

Please read my privacy policy to see I take your privacy seriously.
Free Download

7 Secret Hacks I Use to Fly My Family Free

Please read my privacy policy to see I take your privacy seriously.
Free Download

Get your FREE Disney World & Disneyland Genie Plus Strategy Sheet!

Please read my privacy policy to see I take your privacy seriously.