Sometimes you just need a luxurious weekend Getaway like this.
Pampered with great food, cocktails with friendly top of the line, and award winning spots.
That’s why we chose Baltimore.
As you will see. Baltimore has Gatsby glam, Bond swagger, and cocktails that deserve their own passport stamp.
Here’s your Jetsetter-approved guide to a weekend escape that’s both indulgent and iconic.
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Stay: Sagamore Pendry Baltimore
It screams Gatsby and James Bond.
Located in historic Fells Point, the Sagamore Pendry Baltimore blends 1914 architecture with modern luxury and harbor views that practically flirt with you.
The staff is incredibly inviting and helpful.
You can lounge in your room, in the beautifully furnished lobby/sitting room, or head outside to the pool that has a view of the water.
Again, you can just stay here for everything.
That’s because of the Rec Pier Chophouse. This is where your taste buds go to graduate school.
Again, the professional staff makes you feel like you’re Gatsby or Bond.
We recommend these cocktails that we sipped and enjoyed:
- The biscotti old-fashioned that can be before dinner or dessert.
- The Strega drop martini: a spell of Italian tradition in a stemmed glass.
- The gin Brusco (where spirits meet wine in a rebellious Jetsetter style cocktail)
The food highlights are many that go perfectly with these cocktails.
Here’s what we massaged our palates with.
- Maryland blue crab cake is obviously local. And it is luscious and filling.
- Wagyu steak tartare that whispers luxury. You will eat this slowly.
- AC’s sheep’s milk ricotta dish is fan club worthy. You could have it as an appetizer or a meal.
There are so many good wines here.
We decided to pair it all with the Gothic Nevermore Pinot Noir 2022 from Willamette Valley, Oregon.
Dine: Charleston Restaurant
If your wanderlust grabs you, then take a short hike in Fell’s Point to the Charleston Restaurant. As we’ve said before, we’re not talking about the 1920’s dance that Gatsby was surrounded by.
Nope. We’re taking you to not just any restaurant – but a James Beard Award-winning fine dining experience. It is helmed by Chef Cindy Wolf, who may have time to say hello at your table, as she did with us.
The second you walk in, you feel like your net wealth increased by millions.
That’s because Charleston Restaurant has high-end, attentive service bringing you delicacies you would think only royalty could have.
First, we popped the Blanc de Blanc Eric Rodez champagne – that was a “sit back and just let your palate please you” moment.
When you see our video, watch the cheer on the faces of our Jetsetter friends joining us.
Next, we ordered some of the many great award-winning dishes. Among the highlights.
- Caviar appetizer: deliciously salty and buttery. We had to try it. It’s a James Beard winner!
- Lobster Soup: It’s rich with a butter poached lobster macerating in the heavenly broth.
- Magret of Duck Breast with Foie Gras: the perfect dish to explore new things for your palate. It had Bing cherry, blackberry, and fig compote. Mild yet complicated that made you sit and just enjoy.
- A cheese plate that’s dairy heaven: we had this after the meal along with some after dinner drinks.
The Charleston Restaurant is where you dress up, toast big, and savor slowly.
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Southpaw Bar Feels Like Award Winning Cheers.
Another short stroll from Sagamore Pendry Baltimore is another award-winner: The Southpaw. It’s a cocktail haven with neighborhood charm and its own award-winning bartender owner.
Owner Doug Atwell—twice crowned Baltimore’s best bartender—served us the “Old Sport”:
Rye whiskey, pineapple, coconut water, and sherry.
It’s a Jetsetter-style cocktail where spirits and wine play nice.
Fitzgerald would’ve toasted it with you.
Legacy Stop: F Scott and Zelda Fitzgerald Burial Site and St Mary’s Church – Clio
Spiritually, we think he did. Because F. Scott’s resting ground is not far away. It’s a literary pilgrimage worth taking – only a short drive away. Scott and his wife Zelda are buried at St. Mary’s Catholic Church Cemetery in Rockville, MD.
As we mention in our video of Baltimore, we tell you to:
- Bring a copy of The Great Gatsby
- Leave a bottle of champagne
- Whisper, “Here’s to you, Old sport,” and tip your hat.
Looking for a longer stay?
Baltimore has a lot more to do.
Baltimore’s sports scene is electric.
Whether it’s baseball at Camden Yards or football at M&T Bank Stadium, you’re in for a show.
Get tickets for Baltimore Orioles or Ravens games at Stubhub or Ticketmaster.
And if you just want to hang around the Sagamore Pendry Baltimore and relax, you can watch the Ravens and the Orioles on local TV.
Tips for First-Time Baltimore Visitors
Now, what if this is your first time in Baltimore? Well, it won’t be your last. Here are some things to do.
- Walk Fells Point: Cobblestone streets, waterfront views, and historic charm.
- Use the Charm City Circulator: Free bus service that hits major neighborhoods.
- Try the Baltimore Water Taxi: A scenic way to hop between Inner Harbor, Canton, and Fells Point.
- Safety Tip: Stick to well-lit, populated areas at night—especially if exploring solo.
- Local Flavor: Ask bartenders and servers for their favorite hidden gems. Baltimore loves to share.
Trip Planning Resources
- Visit Baltimore | Official Travel Website for Baltimore Maryland
- Charm City Circulator
- Baltimore Water Taxi
Whether you’re sipping a biscotti old-fashioned, dining at a James Beard winning restaurant, or standing at Fitzgerald’s grave, Baltimore invites you to live boldly.
It’s a city where elegance meets edge—and where every cocktail, every bite, and every story is waiting to be told.
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John Daly and Susan Anzalone are the Co-Creators and Co-Hosts of Undercover Jetsetter, a show on travel, food, and booze. They show you how to jet set the world and at home. They also co-authored the book, The TV Studio In Your Hand: How to Shoot, Edit & Deliver the Easy Way on Your iPhone. Join them for tips and hacks on the road, at home, or in the kitchen, and all over the world. And yes, as you will see, all on the iPhone. Susan is an expert in food and wine since her childhood days in Australia and then the United States, being the daughter of two lifelong employees of Pan Am Airlines. John is also a world traveler starting when he studied in Italy through his alma mater Providence College. John is also a Nevada Hall of Fame Broadcaster during his years as a Las Vegas news anchor at KTNV. He gained international fame as the host of the first all-video news magazine show, Real TV while also securing his bartending and mixology credentials from the Harvard Bartending School. You can follow them here on the free Wingding app on the Food and Travel Channels, on YouTube, Facebook, X, and Instagram.