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Using Points and Miles to Get to Seattle

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Thanks to Brynn’s club volleyball schedule, I’ve logged plenty of miles traveling with my older daughter over the years. But somehow, I’d never taken a trip with just Rory, my younger daughter. So when we both had President’s Day off, I saw the perfect opportunity to plan a quick getaway for the two of us. My goal was to find a destination that wouldn’t break the bank and offered enough teen-friendly attractions to keep things fun.

Living in Chicago, February travel plans naturally start with warmer weather. I began my search with the usual suspects like Florida, California and Arizona, but quickly hit a wall. Flights were pricey and hotels even more so, whether paying cash or redeeming points. I considered places like Atlanta, Charleston, and Nashville, but recent snowfall in all three meant no guarantee of escaping the Midwest chill.

So I flipped the strategy. Instead of chasing sunshine, I chased value, searching for cheap flights and seeing where they’d lead us.

Almost immediately, Seattle rose to the top. It might seem counterintuitive, given it’s north of Chicago, but the weather is surprisingly mild in February. The average high hovers around 49°F. That’s not exactly beach weather, but a welcome upgrade from Chicago’s deep freeze. Yes, there could be rain, but I’ll take drizzle over snow any day. Flights were affordable, hotels were reasonably priced, and just like that, our Pacific Northwest adventure was set in motion.

In This Post

Airfare

Chicago to Seattle

For the flight out to Seattle, cash prices were inexpensive as were the number of miles needed. I found economy tickets on American Airlines for only 7,000 miles per ticket. That’s about as low as any one-way redemption I’ve seen lately. I also checked in First Class and American Airlines was only asking for 18,500 miles per ticket. I wanted to make this quick trip a little more special for the two of us, so I booked the First Class seats using miles.

Two tickets in First Class cost me 37,000 American AAdvantage miles.

The cash price for the two First Class tickets was $929. Instead of paying cash, I used 37,000 miles and paid $11.20 in taxes and fees. The redemption value of those miles was 2.5 cents per mile, which is well above the average value for AAdvantage miles.

The cash price of two First Class tickets would’ve cost $929.

Seattle to Chicago

After a $100 reduction, my total cost was $377.

For the flight home, I decided to pay cash. I did that because the membership year for American Airlines AAdvantage elite status was about to end on February 28th. At the time of booking, I was very close to achieving Platinum Pro elite status for the very first time. Paying for the flight in cash is probably going to be the thing to put me over that threshold.

I was still able to reduce the total cost because I have a Hilton Honors American Express Aspire Card. It offers an airline credit perk of up to $50 in statement credits each quarter, for a total of up to $200 back each year on eligible flight purchases. To make sure I utilize this perk, I buy a $50 American Airlines gift card at the beginning of every quarter. It automatically triggers the statement credit and I can use any gift cards I’ve accumulated on upcoming flights.

At the time of booking, I had two gift cards for a total of $100. So my total cost was $376.96.

Hotel

Sheraton Grand Seattle

When it came to hotel options, I wanted to use my free night award with Marriott. As a cardholder of the Marriott Bonvoy Business™ American Express® Card, I receive a free night award certificate every year. The award, valid at hotels costing up to 35,000 points per night, is given annually on your card-opening anniversary. Even better, you can add up to 15,000 extra points from your account to redeem your free night award at hotels above the 35,000 point redemption limit.

There were a few downtown options, but the Sheraton Grand Seattle was well-reviewed and in an excellent location. I decided to use the free night award for the first night’s stay and then pay cash for the other two nights. The points rate for one night was 40,000 points, so I had to add 5,000 points to my free night certificate in order to book it. 5,000 Marriott points are worth about $35, so it was no big deal to part with those points.

The cash price for a 3-night stay was $675.

Had I paid cash for all three nights, the total would’ve come to $675. But by applying a free night award certificate, I knocked one night off the bill. That brought the out-of-pocket cost down to $452, for a solid $223 in savings. That’s a fantastic return, especially considering the Marriott Bonvoy Business Amex card only carries a $125 annual fee. Redeeming a certificate for a $200+ night easily justifies the cost of the card, and then some.

I booked 1 night using my free night certificate and 5,000 Marriott points.

All in all, I saved $223 on our 3-night stay in the heart of downtown Seattle!

My total hotel cost was $452 since one night was free!

Seattle 2025 Redemption Table

Retail CostOur CostMiles and Points UsedPoints Source
2 one-way tickets from Chicago (ORD) to Seattle (SEA)$465 per person ($929 total)$11 (taxes and fees)37,000 AA miles- Citi AAdvantage credit cards
- AAdvantage eShopping
- Simply Miles
2 one-way tickets from Seattle (SEA) to Chicago (ORD)$239 per person
($477 total)		$377$100 AA gift cards- Amex Hilton Aspire card
3 nights at Sheraton Grand Seattle$165 per night + taxes ($675 total)$4521 free night certificate and 5,000 Marriott points- Marriott Bonvoy Business American Express Card
Total$2,081$840- 37,000 AA miles
- $100 AA gift cards
- 1 free night certificate
- 5,000 Marriott points		- $1,241 in total savings
- 60% off retail cost

Bottom Line

In the end, I saved about 60% off the retail cost of this trip thanks to points and miles. I say “only” because I could’ve pushed the savings further by redeeming airline miles for the flight home or using more Marriott points to cover the remaining hotel nights. But I’m more than satisfied with how it all played out. This trip helps me lock in Platinum Pro elite status with American Airlines, and I know I’ll get even better value from my Marriott points on future stays.

More importantly, this weekend is about quality time with Rory. We’ve got plans to ride up the Space Needle, explore a few museums, and dive into a food tour at Pike Place Market. And if your teenager is anything like mine, skipping the original Starbucks simply isn’t an option.

Using Points and Miles to get to Seattle
We made it to Starbucks!

Trip Report Index

  1. Using Points and Miles to get to Seattle
  2. Flight from Chicago to Seattle
  3. Sheraton Grand Seattle

Bar Harbor Inn

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Originally a men’s social club, the elegant Bar Harbor Inn is an iconic New England vacation destination. Guests of the oceanfront hotel will enjoy modern luxury and be entranced by the grandeur of a bygone era. Its guestrooms are spread amongst three buildings on beautifully landscaped grounds. There’s the historic 1887 Main Inn, which has been remodeled with beautiful Bayview windows, and two buildings with exterior-entry rooms. One is the Oceanfront Lodge, which has rooms with private decks overlooking Frenchman Bay. The other is the two-story Newport Building, which is the only guestroom building without waterfront views.

The Bar Harbor Inn also offers amenities such as luxury spa services, an infinity pool and fitness center. There’s terrific dining options as well, including the upscale Reading Room, famous for its lobster bisque and the outdoor Terrace Grill, which has killer views of the harbor.

The iconic Bar Harbor Inn.

While the level of luxury and history certainly make the hotel special, it’s the outstanding customer service that will keep you coming back. The Inn, and the town’s shops and restaurants for that matter, rely heavily on foreign workers. The local workforce simply isn’t large enough to meet the demand during peak summer months. All the Inn’s employees, both foreign and domestic, are well trained. They’re very friendly and willing to go above and beyond for their guests. You can see how much they enjoy working in Bar Harbor.

In This Post

History

The Bar Harbor Inn traces its roots back to 1887. That’s when the Oasis Club, who’s mission was to promote “literary and social culture” completed construction of their new clubhouse, named the Mount Desert Reading Room. The club flourished for many years until economic hardships due to World War I persisted. It was sold in 1922, and for the next 25 years the building had a number of proprietors and served a variety of tenants.

In the 1950s a group of townspeople joined together to develop the Hotel Bar Harbor, which included the Mount Desert Reading Room and the addition of a 40-room wing. In 1960, a 20-room motel overlooking the Porcupine Islands was added.

In 1987, the property was purchased by David J. Witham, who changed the name to the Bar Harbor Inn. A year later, the Oceanfront Lodge building was constructed, adding 64 additional guest rooms to the property. Five years after that, the 20 room motel was torn down and replaced with the two story Newport Building, adding an additional 38 guest rooms to the property.

In the decades after, the hotel has continued to remodel the existing structures and build new ones like the Spa, the Birch Point building and an infinity edge pool.

Location

If location’s your priority, the Bar Harbor Inn is tough to beat. The Inn stands on eight beautifully landscaped acres along the coast of Frenchman Bay. Fabulous water views can be seen while walking the famous Shore Path, which follows the shoreline directly in front of the Inn. Originally created around 1880, people from all over the world have walked on this 3/4 of a mile path. Along the path, right by the Terrace Grill is a long pier which extends out from the water’s edge. During the summer and fall seasons, you can board the Margaret S. Todd schooner to enjoy a scenic cruise. 

When you’re on hotel grounds, it feels really self-contained. So it’s hard to believe you’re only a block away from the bustle of downtown Bar Harbor. The town is immensely charming and really comes alive as summer gets into full swing. It has so many wonderful locally-owned stores and restaurants, where tourists can find quality souvenirs and fresh seafood. The town of Bar Harbor is also a popular homebase and gateway to Acadia National Park, one of the nation’s most visited national parks. 

Map of the Resort

Lobby

The lobby is found inside the Main Inn. Just like many of the other buildings on the property, it was renovated within the past few years. The lobby is a great example of how they masterfully blended modern luxury while keeping the traditional New England style.

While not pictured here, the concierge desk is also located in the Main Inn. Towards the end of our stay, I wanted to talk to the concierge about an activity we could do before heading home. The concierge had left for the day, so I asked my question to the front desk. Without hesitation the front desk said there was an employee still around who could help me. Within minutes I was sitting with someone at the concierge desk going over a few options.

There are several seating areas scattered throughout the Main Inn, including one with an inviting fireplace.

The Room

We stayed in the Newport Building, which is the most cost-effective of the three guestroom buildings. Remodeled in 2022, it’s the only building without waterfront views. These rooms have patios or balconies, however, that overlook the grounds.

The guestroom decor fits into the “country chic” style found throughout the property. It’s large enough to fit a king bed, a couch, a desk and TV.

Our room had a balcony, which overlooked the grounds to our left. Unfortunately the view straight ahead and to our right was of a parking lot.

The Bathroom

The bathroom was updated and clean, but was pretty ordinary. This was the one area on the entire property that wasn’t renovated with modern luxury in mind.

Regardless, it was still very functional and the hotel did a good job utilizing the available space.

Hotel Amenities

The Pool

The infinity edge pool, along with two adjacent hot tubs, were installed in 2019 to compliment the view of Frenchman Bay. Just a year later the neighboring Birch Point building was completed. It houses the new continental breakfast area, fitness room, and the pool bar & grill.

While many guests come to Bar Harbor to hike in Acadia or otherwise be active, I’d recommend saving at least part one day to enjoy the pool area.

The infinity edge pool provides terrific views out to the bay, but the pool amenities are also pretty great. The pool bar & grill serves all the typical drinks, as well as “drinks-of-the-day” crafted by the bartender of the day. Food options include snacks, but also lunch items like salads and sandwiches. Once a week, the hotel staff sets up a large portable grill in the corner of the pool grounds and serves a special lunch menu to guests. We had lunch at the pool the day they were grilling and enjoyed all the fun of a backyard barbeque with none of the work!

The Spa

The Inn offers a full menu of spa services, from manicures and facials to massages and body treatments.

Dining

A view of the Bar Harbor Inn from the Shore Path.

The Bar Harbor Inn offers four unique dining experiences. Options include continental breakfast, snacks by the pool, outdoor dining overlooking the harbor and a fine dining experience with nightly entertainment. The Oasis Club lounge, which is connected to the fine dining restaurant, is a fabulous place for a pre-dinner cocktail.

Reading Room

The Reading Room offers Inn guests and visitors to Bar Harbor a fine dining experience overlooking Frenchman Bay. It provides daily breakfast and dinner service, complete with local Maine cuisine, attentive service and panoramic ocean views. This is the place to go to celebrate a special occasion. Reservations are recommended.

Terrace Grill

The Terrace Grille is one of Bar Harbor’s premier outdoor restaurants. It overlooks the town pier and is famous for its iconic yellow umbrellas. Open for lunch and dinner, it does not accept reservations, so seating is first-come, first-served. Luckily, hotel guests receive priority over other visitors.

The restaurant is outdoor only, so service moves into the Reading Room during inclement weather. It offers a full menu with a variety of fresh seafood options, healthy salads, and satisfying sandwiches. Do yourself a favor and order a local brew from Mount Desert Island — you won’t be disappointed.

Oasis Lounge

Just beyond the Reading Room is the casual cocktail lounge with a rich history. It dates back to 1887 when it was the home of the Oasis Club. Offering cozy tables, inside bar seating and a few seats out on their balcony, this is a great place to have a relaxed drink.

Birch Point

The Birch Point building is where the complimentary continental breakfast is served. There you can find typical breakfast fare like fresh fruit, breakfast breads, bagels, assorted muffins, pastries, cereals, yogurt, hard boiled eggs, juice, coffee, and tea. This building is also home to the pool bar & grill, which features excellent cocktails, local beers and pool bites.

The Grounds

Just look at the picture below! These are the gardens which run alongside the Main Inn guestrooms and lead to the pool. Everything was in bloom in July when we were there and it was really beautiful.

There are also a couple large open areas onsite where people can congregate and relax. One is a large sloped lawn area in between the Main Inn guestrooms and the harbor. In addition, there’s a circular lawn area between the Main Inn and the parking lot. Every night, the staff uses this circular lawn to build a bonfire. Guests can roast marshmallows and enjoy smores!

Miscellaneous

The view of the infinity pool and Spa from the Shore Path.
The magnificent Bar Harbor Inn at night.

Bottom Line

There’s something special about the Bar Harbor Inn. It’s one of the more pricy options in Bar Harbor, but it’s worth every penny. I loved it’s modern luxury while also feeling like I stepped back in time. The location is second to none, the grounds are immaculate and the hotel staff is overwhelmingly nice. If you’re going to Bar Harbor and can swing the cost, I would highly recommend the Bar Harbor Inn.

Trip Report Index

  1. Using Points and Miles to get to Portland and Bar Harbor
  2. Flight from Chicago to Portland
  3. Canopy by Hilton Portland Waterfront
  4. Bar Harbor Inn
  5. Best Things to Do and Eat between Portland and Bar Harbor, Maine

Using Points and Miles to Get to Boston October 2024

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Our daughter Brynn is a freshman volleyball player at Northeastern University in Boston. Once her team’s schedule was released over the summer, we wanted find a weekend to see her play in her home arena. We had a few dates to choose from and decided to visit the last weekend of October. That weekend was also parents weekend, so Annie, Rory and I traveled to Boston to visit her.

I began researching flights and hotels while we were still deciding which weekend to visit. In general, I found prices to be pretty high across the board. After watching airfare for several months, I noticed that as soon as the calendar flipped to August, prices went up and never came back down.

These days, most flights are full flights, so there’s no incentive for airlines to reduce prices as the departure date nears. For future air travel, I’m going to book tickets at least three months in advance. In this case, I had a stash of airline miles, travel credits and points, and used all three to book this “free” trip!

In This Post

Airfare

Brynn had games Friday and Saturday afternoon. So we chose to fly to Boston on a 7a.m. flight Friday morning. For the trip home, we knew we were going to leave on Sunday but were very flexible on the departure time. I compared costs on multiple airlines, both using miles and paying cash. After an extensive amount of research, the best options for us were a United Airlines flight out to Boston and an American Airlines flight coming home.

Chicago to Boston

Initially, we planned to visit Brynn in November and I had booked one-way tickets on United. The cash price was $475.41, but I used $400 in United TravelBank cash to bring the cost down to just $75.41. I received those TravelBank credits from my Hilton Honors American Express Aspire Card. Until late 2023, the card had a $250 annual airline reimbursement perk, meant to offset incidental airline fees. However, adding money to TravelBank was a loophole that would qualify for reimbursement. So at the start of every calendar year, I would add $250 to my TravelBank to use at some future date. Within a few days, that money would be credited back to me as statement credit.

Note: The Hilton Honors Aspire Card airline credit perk now offers up to $50 in statement credits each quarter, for a total of up to $200 back each year on eligible flight purchases.

When we changed the weekend of our visit, I cancelled the original United flight and received $475.11 as a travel credit. The new flight cost only $355.41, so I applied my travel credit, which covered the entire amount. Plus, I still have $120 in travel credits to use on my next United flight.

Boston to Chicago

Flights back to Chicago on Sunday were expensive. It didn’t matter what airline or the time of day. So I decided to use some of my American Airlines AAdvantage miles to book our tickets home. I didn’t get amazing value from this redemption, but it still reduced my cash cost to almost nothing.

The cash cost for three tickets on the 10:23am flight was $835. Instead of paying cash, I used 79,500 miles and paid $16.80 in taxes and fees.

Hotel

Hyatt Centric Faneuil Hall Boston

Northeastern University is located in Boston’s Back Bay neighborhood. It’s a nice neighborhood but doesn’t have as many restaurants or activities as downtown Boston. Since the school is only a handful of subway stops from downtown, I decided to book a hotel downtown instead.

I had free night awards available from both Marriott and IHG, so I started my search with them. The issue I ran into is that those free night awards are capped at 35,000 points (Marriott) and 40,000 points (IHG). While it’s possible to top those off with some points, I still couldn’t find any hotels in the area with point prices low enough for me to utilize my award certificates.

So I turned my search over to Hyatt. I had Hyatt points that I intended to use for a trip to Hawaii in 2020 that never happened. Those points were basically a sunk cost at this point, so I decided it was time to put them to use.

I was deciding between the Hyatt Regency Boston and the Hyatt Centric Faneuil Fall Boston. The Hyatt Regency didn’t have any two bedroom rooms available, so the choice was made for the Hyatt Centric. The Hyatt Centric brand is described as full-service lifestyle hotels located in prime destinations. That was certainly true for the Hyatt Centric in Boston. It’s located next door to the Old Statehouse, which is a stop along the Freedom Trail. Plus, as the hotel’s name suggests, it’s also very close to Faneuil Hall and Quincy Market, other vary popular tourist attractions.

Hyatt Centric Faneuil Fall Boston (Photo Courtesy of Hyatt).

Cash prices were sky high, coming in at $1,337 the day I finally booked the hotel.

Luckily they had rooms with two beds available for 29,000 points per night. I already had 43,000 points in my Hyatt account, so I transferred another 15,000 points from Chase to Hyatt. I’ve been rapidly building my Chase Ultimate Rewards points balance recently, so I didn’t mind parting with some points to top of my Hyatt balance. Chase Ultimate Rewards is my favorite transferable points program because it’s relatively easy to earn points and you can transfer those points to airlines and hotel partners.

So two nights in Boston cost me 58,000 Hyatt points, saving me $1,337.

Boston 2024 Redemption Table

Retail CostOur CostMiles and Points UsedPoints Source
3 one-way tickets from Chicago (ORD) to Boston (BOS)$118 per person ($355 total)$0$355 United TravelBank credits- Amex Hilton Aspire card
3 one-way tickets from Boston (BOS) to Chicago (ORD)$278 per person
($835 total)		$17 (taxes and fees)79,500 AA miles- Citi AAdvantage credit cards
- E-rewards surveys
- Miles for Opinions surveys
2 nights at Hyatt Centric Faneuil Hall Boston$549 per night + taxes ($1337 total)$058,000 Hyatt points- Chase Ultimate Rewards
Total$2,527$17- 79,500 UA miles
- 58,000 Hyatt points
- $355 travel credits		- $2,510 in total savings
- 99% off retail cost

Bottom Line

All in all, we saved 99% off the retail cost of this trip by using points and miles. Better yet, we spent some quality time with Brynn and got to see a Northeastern volleyball victory!

Trip Report Index

  1. Using Points and Miles to get to Boston

Canopy by Hilton Portland Waterfront

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The Canopy by Hilton Portland Waterfront is a new and modern hotel located just steps from Portland, Maine’s Old Port neighborhood. It opened in July 2021 and was the first Canopy by Hilton in all of New England. The hotel’s design incorporates the red brick aesthetic of the area with industrial metal accents that pay homage to the working waterfront across the street. The hotel also features local touches, including artwork by Portland artist Matt Chamberlain and a Winter Garden-Reception Area with an artificial skylight that changes colors throughout the day.

Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront

The 135-room hotel features a rooftop restaurant and bar with waterfront views, a ground-level restaurant and bar, meeting and event spaces, and a glass-walled library with a conference table. Other amenities include a 24-hour gym with Peloton bikes and complimentary cruiser bikes.

In This Post

Location

Located on the corner of Center and Commercial Streets, the hotel’s in a great spot to take advantage of both of Portland’s main attractions. It’s across from the waterfront and also just a few blocks from Portland’s Old Port business district.

Parking

On-site, valet parking is available for $40 per day. There is a self-park lot right next to the hotel, but the daily rate doesn’t work out to be much cheaper than valet.

Lobby

The first thing you notice about the lobby is the unique artificial skylight. It changes colors throughout the day, so the vibe in the lobby is always changing. The hotel designers smartly used greenery located throughout the lobby to provide pops of color and bring the outside in. The combination of these features gives the lobby a nice and welcoming indoor/outdoor aesthetic.

After our almost disaster of a flight out of O’Hare, we didn’t arrive to the hotel until 6 a.m. the next morning. During the flight fiasco, I had messaged the hotel from the Hilton app, so they knew we were going to be late. Check-in went very fast, which is to be expected at that time of day, but still very appreciated. We were in our room within a few minutes of arriving and were able to grab a quick nap before exploring the city.

The Room

Everything in the hotel still looks fresh and new, even three years after opening. That includes the hallways and the hotel rooms. The room has a nice entryway complete with an all-in-one unit featuring a dresser, open closet and coffee station.

The rooms are neither large nor small, but the design is all about ease and comfort. The bed was cozy and there were plenty of outlets and USB ports to charge all of your gadgets. I loved the decision to go with wood vinyl flooring instead of carpet. More newer hotels seem to be ditching the old carpet look for this more modern design. It feels much cleaner but doesn’t take away from the room’s warmth.

I also enjoyed finding locally made macarons waiting for us in the room. It was a nice touch that and got our stay off to a pleasant start.

The Bathroom

The modern design continues in the bathroom as they utilized the the same wood for the vanity that’s found on the all-in-one unit. It’s clean and well maintained, showing no signs of wear and tear.

The shower is quite large and there’s a sliding door to separate the shower and toilet from the vanity area.

Hotel Amenities

Amenities include a rooftop restaurant and bar, a ground-level restaurant and bar, a 24-hour gym and complimentary cruiser bikes.

Dining

Salt Yard

The Salt Yard Cafe + Bar offers breakfast, lunch, and dinner in a chic and welcoming space. During the day, food is ordered at a counter and guests are invited to linger as long as they’d like. They have wonderful pastries and typical breakfast and lunch fare.

In the evening Salt Yard transforms into a cocktail bar with daily happy hours from 2pm to 5pm and a small bar plates dinner menu.

Luna Rooftop Bar

The hotel is very proud of the Luna Rooftop Bar and it’s easy to see why. Located on the sixth floor, the main draw is it’s panoramic view of the working waterfront and Casco Bay.

Luna captures the artistic spirit of Portland, with communal tables, intimate lounges, and accordion glass walls welcoming the outside in. It’s a great spot for people watching and an expertly made cocktail. It also offers shareable plates and small bites, perfect for a round of drinks and appetizers before dinner.

Fitness Center

The 24-hour, complimentary fitness center has everything you could want. Equipment includes treadmills, elliptical trainers, free weights, yoga mats and even Peloton bikes.

Complimentary Bikes

The hotel also offers complimentary bikes to its guests. We love when hotels offer this because it’s a free and fun way to explore a new city. The day we arrived, we rented bikes and had a fun time getting to know the different areas of the city. We asked the staff for suggestions on where to go and they recommended a waterfront trail that goes around the peninsula that is Portland.

Bottom Line

Portland is a classic New England city with so much to offer. If you’re looking for a hotel to setup a homebase, I would highly recommend the chic Canopy by Hilton Portland Waterfront. It’s location is stellar, within an easy walk to the Old Port and a stone’s throw from diverse dining and shopping options. It’s modern and stylish rooms and top-notch cleanliness makes it feel like you’re one of the first customers, even three years after opening.

Trip Report Index

  1. Using Points and Miles to get to Portland and Bar Harbor
  2. Flight from Chicago to Portland
  3. Canopy by Hilton Portland Waterfront
  4. Bar Harbor Inn
  5. Best Things to Do and Eat between Portland and Bar Harbor, Maine

Where to Eat in Charleston

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Charleston, South Carolina is a full-fledged foodie town. The city’s restaurants expertly use the sea and surrounding areas to create quintessential Southern menus. The city sits below the original coastline of the Carolinas and is therefore often referred to as the Lowcountry. Regional favorites, such as she-crab soup, shrimp and grits and fried green tomatoes are staples of Lowcountry cuisine.

This past fall, I spent a long weekend with Annie and two of our friends, eating and drinking our way through Charleston. While there’s no shortage of fabulous dining options, below are my favorites.

In This Post

The Top 4

Poogan’s Porch

My favorite meal of the trip was lunch at Poogan’s Porch. The restaurant opened in 1976 and is located in the heart of downtown on Queen Street. Originally a spacious home built in the late 1800s, it still exhibits much of that old-world charm.

Even on a Monday in October, we had to wait around 20 minutes without a reservation. That’s usually a good sign! Luckily they have a decent-size bar, so we enjoyed cocktails while we waited. Once seated, we browsed the menu of typical Lowcountry staples. This was our last full day in Charleston and I had already checked off most of the “must-have” dishes on my list. So for this meal, I focused on regional favorites I’d yet to sample.

Where to Eat in Charleston
You have to order the Fried Green Tomatoes!

The four of us began our meal by splitting the fried green tomatoes appetizer. The tomatoes themselves are outstanding but the delectable pimento cheese and bacon jam sauce takes it to a new level. The dish combines the crispy texture of the tomatoes and hits you with a mix of sweet and savory flavors. It was a definite highlight!

Annie and I decided to split an entree, so I also ordered a cup of she-crab soup for myself. It’s a traditional Charleston soup that incorporates blue crab meat, heavy stock, sherry and crab roe. It was very similar to a lobster bisque, with a beautiful rich taste.

Leon’s Oyster Shop

My favorite dinner of the trip was the one we had at Leon’s Oyster Shop. Even though the casual and relaxed restaurant is located on “famous” King Street, it’s not actually downtown. However, it’s not far, taking only 10 minutes by car from our downtown hotel.

Leon’s opened in 2014 in an old autobody shop. They preserved much of its old life, with functioning garage doors and concrete floors. It gives off a “roadside joint” kind of vibe and is known for its oysters, Southern-style seafood & fried chicken. In 2020 they intensified that vibe by whitewashing the front facade and adding a large “filling station-style” covered patio.

The old industrial history is still alive in the huge inside dining room.

My order was the fried chicken and I didn’t even need the menu. A few months before the trip, Leon’s fried chicken was featured on an episode of Bravo’s Southern Charm. In the episode, cast members Shep Rose and Whitney Sudler-Smith ordered in Leon’s fried chicken for a boys night in. It looked so good on television, I knew I’d order if given the opportunity.

The fried chicken entree comes in either a 2-piece or half chicken size, and you get to choose a couple sides as well. It came out hot and crispy and had a great flavor.

While the food is certainly the draw, I think Leon’s is so popular because of the atmosphere. It’s a fun and lively place where people can enjoy everything from cheap beer to fine champagne.

167 Raw Oyster Bar

Our first lunch of the trip was at 167 Raw Oyster Bar, located on King Street. The restaurant’s interior has a Cape Cod feeling to it and they also have a cozy courtyard. Luckily we didn’t have to wait for a table because that doesn’t seem to be the norm.

Food-wise, we decided to split a bunch of dishes including raw oysters, ceviche, a lobster roll and an oyster po’ boy sandwich.

With “raw bar” literally in the restaurant’s name, of course we had to try the raw oysters. The oyster varieties change daily based on what the fishermen bring in. We didn’t know the differences between the various oyster varieties, but our waiter went over everything for us. The ones we chose were quite good.

The Lobster Roll is solid!

The ceviche was fine but I’d skip it next time. However, the lobster roll was terrific and so was the oyster po’ boy. They also offer shrimp po’ boys and scallop po’ boys and I’m sure they’re delicious as well.

Blind Tiger Pub

The Blind Tiger Pub was another food destinations that came to our attention from Bravo’s Southern Charm. Shep Rose mentioned it as a favorite spot of his and that was good enough for us. Located on Broad Street, the restaurant’s entrance is unassuming, giving it speakeasy vibes.

From the street, you couldn’t even tell if anybody was inside the place. However, upon entering, it was full of people enjoying weekend brunch. While the inside reminded me of your standard college bar, it’s their enormous back patio and elevated pub fare that makes it a destination.

We had to wait for a table on a Sunday at lunchtime. To pass the time we enjoyed cocktails at the bar and waited patiently for a table to open up outside. The award winning outdoor patio is really cool. There’s nice brick work all over the patio and it seems to go on forever. It also has a full bar right out on the patio.

The Shrimp and Grits are amazing!

For this meal, I zeroed in on the shrimp and grits. It was another Lowcountry staple I wasn’t going to miss! The dish had pan-seared shrimp, andouille sausage, peppers and caramelized onions, in a sherry cream sauce and served over grits. My arteries might’ve been angry with me, but the flavor was so rich and fabulous! I wanted to slurp up that sherry cream sauce with a straw!

Other Restaurants

Home Team BBQ

Barbecue was the last regional food we’d yet to try on our trip. There’s no shortage of available options in Charleston, so we searched online reviews to narrow down the choices. We settled on the downtown location of Home Team BBQ for our final dinner of the trip. The place itself is looks very cool and is decorated just how you’d imagine a barbecue joint should be. They have plenty of seating and a large bar inside. They also have a big open air patio, plus a screened-in patio that can host private events.

The food itself was good, but not remarkable. We have good barbecue in Chicago and this was on par with that. However, it didn’t compare with the outstanding barbecue we had in Austin, Texas. I don’t know whether to chalk that up to Texas barbecue being better or if we would’ve been more impressed somewhere else.

While the food was solid, the main disappointment was the service. It was a Monday evening, so the place wasn’t packed. However, it took a really long time to get the waitress to take our order. Once the food arrived, we pretty much never saw her again. I even had to flag her down to ask for the check. It could’ve been an off night, but it definitely left a bitter taste in my mouth.

Mesu

Another Southern Charm inspired meal was dinner at Mesu, located right in the heart of the action on King Street. It’s owned by Leva Bonaparte, who’s been a cast member on the show for a few years. The food is a fusion of Mexican and Sushi, which sounded really interesting.

As we’d done a few times in Charleston, we split a bunch of items so we could try more dishes than we could on our own. We started with chips and salsa, which were just as you’d expect. For our entrees, we split a variety of tacos and sushi rolls. I found the food to be quite good, but I wouldn’t really call it fusion. The menu just has both Mexican food and sushi.

The atmosphere, however, was not what I expected. Leva owns several restaurants and bars around Charleston, and the vibe that comes through on the show is very upscale. That being said, I don’t think I’ve ever seen Mesu on the show, so I shouldn’t have assumed it would be similar. As it turns out, it’s not an upscale place at all. It’s way more casual than I expected and felt more like a neighborhood sports bar than anything else. The decorations are vibrant, but the restaurant was loud and hot. Plus the seating wasn’t too comfortable which made me not want to hang out long after we were finished.

Bottom Line

Almost our entire Charleston trip was focused around food. Dining out was the entertainment and there’s no shortage of incredible establishments to choose from. Charleston’s history, dating back to the 1600s, and its proximity to the Atlantic Ocean have inspired a hyper-local food known as Lowcountry cuisine. Experiencing the different culinary specialties Charleston has to offer is a great way to experience the city and absorb the culture.

Trip Report Index

  1. Using Points and Miles to get to Charleston
  2. The Lindy Renaissance Charleston Hotel
  3. Where to Eat in Charleston