A sister splurgecation at its finest. Here’s how to experience New Hampshire during the holidays for the ultimate splurgecation experience. 

From picturesque views to quaint corner coffee shops and evenings spent at Jimmy’s Jazz & Blues Club, New Hampshire is a dream destination for those looking for a splurge-worthy escape- and might I add, one that is exceptionally beautiful during the holiday season.

HOLR recently jet set off to New Hampshire for a short and sweet sister getaway that will leave us with memories to last a lifetime. Here’s our HOLR-approved itinerary and what we learned when it comes to planning the ultimate sister splurgecation retreat in New Hampshire during the holidays:

Where To Stay

First things first, getting around. For this particular trip, we flew from Toronto Pearson International Airport to Boston Logan International Airport. This allowed us to seamlessly book and have a rental car ready upon arrival so we could embark on our roughly hour-and-a-half journey to New Hampshire. We found this to be the quickest and easiest way to get around, and the rental came in handy when going to and from the excursions that we had planned.

When it comes to booking accommodations, we fell in love with the Sheraton Portsmouth Harborside Hotel, which is located in the heart of downtown Portsmouth, New Hampshire. Marriott properties are known for offering comfortable, memorable stays, and the brand prides itself on offering excellent service which made this property a go-to for us. The Sheraton Portsmouth Harborside Hotel in particular allowed us to immerse ourselves in New Hampshire’s Seacoast region- as you can see by our stunning suite views.

The suite we stayed in featured a cozy king bed and a separate sitting room, with picturesque views of Portsmouth and the water. Amenities also included complimentary Wi-Fi and a mini-refrigerator. We were even greeted with the cutest setup complete with Sauvignon Blanc, cheese, and crackers, as a warm welcome upon arrival.

One of our favorite things about this property was its proximity to popular destinations which allowed us to conveniently walk to nearby shops and restaurants in downtown Portsmouth. It’s worth noting that you are also close to other hot spots such as Jenness State Beach, the University of New Hampshire, the Portsmouth Naval Shipyard, and Prescott Park, as outlined on the brand’s website. As we traveled during American Thanksgiving weekend, this property truly felt like our home away from home. In fact, we got to experience a traditional Thanksgiving Dinner buffet in the hotel’s Grand Ballroom. From turkey to stuffing to salad to dessert, this was everything we could’ve dreamed of and more to kick off the holidays in New Hampshire!

The staff was also incredibly accommodating and the space was delightfully decorated for the holidays, making it a welcoming, cozy, and extremely comfortable stay from check-in to check-out. If you’re planning on visiting the property, it also has full room service options and an on-site restaurant called the Two-Fifty Market which takes inspiration from local cuisine to offer guests an unforgettable Portsmouth dining experience.

What To Do

Our favorite thing to do was explore Portsmouth and take part in local outings and activities during our long weekend stay. Since we were traveling during the holiday season, we arrived in late fall, in which the foliage made for a stunning backdrop amidst the quaint downtown city streets.


For a splurge-worthy activity, it’s a must to experience Black Friday in New Hampshire by shopping in the downtown core or venturing out to the Merrimack Premium Outlets. Black Friday marks the beginning of the holiday season so this is a fun way to experience the holidays while treating yourself-or loved ones- to something special! The Merrimack Premium Outlets is an outdoor shopping center with over 100 stores that offer tax-free shopping. Some shops to pop into include Bloomingdale’s Outlet Store, Marc Jacobs, Saks Fifth Avenue Off 5th, and more. Plus, you can score some discount pricing while you shop! On another note, downtown Portsmouth offers a quieter shopping experience in which it features local shops and boutiques that offer unique pieces you can purchase and bring home with you.

We thoroughly enjoyed getting to experience Black Friday shopping first-hand during the crisp autumn season- this was a great way to spoil each other for the holidays and spend some sister bonding time out and about.

Wine Tasting

Flag Hill Distillery & Winery is a must-stop if you’re looking to experience world-class wine and spirits. As the largest vineyard in the state, Flag Hill is the first legal distillery in New Hampshire after Prohibition in the 1920s. This is the perfect spot to stop in for a 5-sample tasting for only $10 USD because you can pick and choose from a selection of delicious wines and spirits to indulge in.

We loved incorporating this activity into our day because it allowed us to experience the property’s high-quality, locally sourced ingredients.

Dinner & Jazz Show

As one of the highlights of our New Hampshire getaway, we had the opportunity to experience dinner and a Jazz Show at Jimmy’s Jazz & Blues Club. Since this was our first Jazz show (ever!), we didn’t know what to expect. However, during the performance, we were absolutely blown away by how the club is designed and built with superior acoustics and sound equipment to showcase some of the music world’s most talented jazz and blues artists. We were transported to a different world as we immersed ourselves in the dynamic swing and blue notes that filled the room. It’s no wonder that this space has been engineered to be one of the top “listening rooms” in the country.

The accompanying dinner was also delicious, in which Executive Chef Nathan Varney thoughtfully merges southern-influenced styles, with locally sourced ingredients to present his take on a traditional yet modern New Hampshire-inspired cuisine. We opted to try the Tuna Crudo and Maine Lobster Dip during our night on the town. Both were divine!

Odiorne Point State Park

For a change of scenery, it’s worthwhile to visit Odiorne Point State Park, which offers a stunning natural setting along New Hampshire’s 18-mile coastline. This breathtaking stop features expansive views- including the Gulf of Maine- and you can experience natural habitats, historic fortifications, walking trails, playgrounds, and more if you’re a true nature lover and want to escape the hustle and bustle of the city streets.

Candle Making

This is the ultimate sister activity that features a fun takeaway you can truly cherish. Sea Love Candle Bar and Boutique is located in downtown Portsmouth and offers a candle-making experience you don’t want to miss out on. This was such a special excursion because we had the opportunity to make our own candles from scratch- from scent picking to pouring to designing, this step-by-step process is the perfect activity to do with your sister, your mom, or your friends!

We loved being able to choose our favorite scents to mix (spoiler alert- I chose Chai, Vanilla Bean, and Spiced Honey!) and create our own unique candles for the holidays. Since the weather was crisp, I opted for a warm and spicy scent I could cozy up next to. Once I had picked out my trio of scents, I was taught how to properly mix them, pour, and center the wick into my vessel of choice.

From there I got to design my own label. This activity comes highly recommended by us as it’s the ideal way to bond and get a fun moment out of it!

Museum of New Art

If you’re walking along downtown Portsmouth, we would suggest popping into the Museum of New Art to experience an array of exhibitions and educational programs created to inspire. This is a great way to break up your day and take in the latest trends in contemporary art.

Fun Fact: MONA’s building was redesigned by architect Andrew Sidford.

Where To Eat

From fan favorites to seasonal bites, these are some of our favorite spots to eat and drink in Portsmouth, New Hampshire during the holidays.

The Friendly Toast

This was a delicious restaurant we stumbled upon while walking around downtown Portsmouth and let me tell you- it was a treat! I love brunch and the fact that this was an all-day brunch and bar definitely caught my attention. Since its beginnings in Portsmouth, you can now find The Friendly Toast in other locations such as Massachusetts, Vermont, and Maine.

With a slogan of “Brunch On The Bright Side” it’s no wonder the interior is something to take note of as well. Reminiscent of a vintage diner, the walls are filled with retro photos that give the entire space a homey, welcoming feel. We opted for ice coffees, the Hash Quiche (two crispy fried hash brown bowls stuffed with scrambled eggs, bacon, roasted red peppers, caramelized red onions & jalapeno-jack cheese), and pancakes. Delish!

The Press Room

Known as Portsmouth’s night out for over 45 years, The Press Room is a must-add to your list of restaurant recos for the area. As a local hot spot for enjoying an afternoon pint and a bite to eat, this space is perfect for lunch, a snack, or a night out with friends. This is because it is an intimate venue that highlights live music entertainment, as well! The overall ambiance makes this an especially cozy pick for the holidays.

As the longest-running bar, restaurant, and live entertainment venue in downtown Portsmouth, New Hampshire, The Press Room features details such as exposed brick that really give the space character. These are our top picks from The Press Room: Pretzel Bites (hot and delicious! Definitely add queso for dipping), and Autumn’s Bounty Salad (a fresh salad featuring Tuscan Kale, squash, dried cranberries, and goat cheese topped with a Maple Sage vinaigrette). We also opted for some seasonal bites such as the Chicken and Dumplings and Mini Sheppard’s Pie.

Popovers on the Square

A favorite of ours from the trip, Popovers on the Square is a delicious breakfast spot located right in the heart of downtown Portsmouth. What is a popover, you might ask? Only the best thing you could try, EVER. As outlined on the brand’s website, popovers are a classic New England pastry-crispy on the outside, eggy and hollow on the inside. The establishment serves them with their famous maple butter.

We of course had to try the original popovers as is, but we also opted to try the scrambled egg and veggie versions of this beloved treat. We can confirm popovers- any style- are the way to go!

The Wilder

Another downtown must-try, The Wilder is a modern New England gastropub. Located on the legendary 174 Fleet Street space, the menu consists of classic New England faves and highlights fresh, local ingredients with an innovative, ever-evolving craft cocktail program.

We opted to try some staff-recommended picks during our lunch stop so we went with the following picks: Kale Salad (featuring fried potatoes, roasted acorn squash, pomegranate seeds, feta, black garlic dressing), and Kirby Pickles (spicy brine, fresh dill, fleur de sel). There are also some fun specials to take advantage of during the week such as Taco Tuesdays.

Fezziwig’s Food and Fountain

This is the perfect spot to enjoy afternoon tea- which is just what we did! Known as a whimsical brasserie experience, Fezziwig’s Food & Fountain offers a full-service espresso bar, teas (from around the world!) a classic soda fountain, and delicious pastries. The interior features shabby-chic decor that is very Bridgerton-inspired making this the perfect stop during a downtown shopping trip.

During our afternoon tea outing, we opted to pair a classic scone with one of their worldly teas. This was a delectable treat!

The Library Restaurant  

We dubbed this the crème de la crème when it comes to steakhouses in Portsmouth because an evening at The Library Restaurant is unlike any other. Housed in a historic building where 7 presidents have dined since 1887, The Library Restaurant is an upscale dining spot that boasts three crackling fireplaces, a martini lounge, and a stunning private dining space. Be prepared for an evening of steaks, spirits, spritzes, and sizzle as you indulge in the delectably curated menu available at this top-rated New Hampshire gem.

We of course had to try Oysters, the classic New England Clam Chowder, the Prime Sirloin, the Lobster Mac and Cheese, and Roasted Brussels Sprouts glazed with Ginger Soy Sauce. All of these items were exceptional and made our final night in New Hampshire one to remember. For dessert, the chocolate and peanut butter pie was perfection.

This is an absolute must-add to your list of restaurants next time you’re in Portsmouth.

There you have it! Our top recommendations for visiting New Hampshire during the holidays for the ultimate splurgecation experience. New Hampshire is a must-visit travel destination for anyone and everyone because it truly caters to all- whether you love to shop, try new food, or adventure out into nature, this cozy US state has everything you need for the perfect getaway, any time of year.

Published by HOLR Magazine.