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Why You’ll Love This Romantic Weekend Getaway at Saint Michaels, Maryland

Merry Lerner and her husband in Saint Michaels Maryland

Time for Some Romance…

This past weekend, my husband and I went on a romantic weekend getaway. Even though we’ve been traveling a lot for work and family obligations, this was the first time we got to spend time away together – just the two of us – in almost a year. We were only gone for 2 days but came back feeling refreshed, relaxed and much more in tune with each other. It’s amazing what 48 hours away from responsibilities and distractions can do for your relationship and wellbeing.

My husband and I wanted to go somewhere we’ve never been, within driving distance from NYC. (Fun fact: when you experience something new, it raises your dopamine levels, similar to when you’re falling in love. So if you want to add a spark back to your love life, plan a trip or activity that’s new.) We chose Saint Michaels, Maryland, a historic harbor town on the Chesapeake Bay.

Our time away was picture perfect. Here are the details of our romantic weekend away!

The Inn at Perry Cabin in Saint Michaels Maryland

Where We Stayed + Other Accommodations:

We wanted to feel pampered and taken care of for the weekend, so we used Mr. and Mrs. Smith, a travel club that’s free to join and specializes in luxury and boutique hotels to find a place to stay. Membership is free, and with the club’s discerning taste, we knew we’d be in good hands.

We chose the Inn at Perry Cabin situated right on the water and a short walk from town. While I highly recommend this hotel for a romantic weekend, it is definitely a big splurge. Rates in the spring (We visited in April), are around $350 per night plus tax and could be as much as double that in the summertime.

Pro Tip: Now, as we recover from COVID-19, rates could be drastically different. Hotels will likely slash pricing to get customers back to their properties, so it is worth asking if the Inn will be offering discounts.

While the Inn at Perry Cabin is a bigger resort with 70-plus rooms, it has the feel of a cozy B&B. The nautical décor is inviting.

As soon as we arrived, I was tempted to curl up in one of the first plush armchairs I saw. Our bedroom was no less welcoming. With a king-size bed, a claw foot tub, and a balcony with views of the water, we were in heaven. It was a great start to our romantic weekend getaway.

The Deluxe room at the Inn at Perry Cabin is perfect for a romantic weekend getaway

A clawfoot tub at the Inn at Perry Cabin in Saint Michaels Maryland

A view from our balcony at the inn at perry cabin

Other Accommodations

If you’re still interested in visiting Saint Michaels, Maryland but looking for a more affordable option, both the Saint Michaels Harbour Inn, Marina & Spa, and the Tidewater Inn, have room rates around $150 per night.

And for a quintessential bed and breakfast experience, try the Parsonage Inn, with rates starting just under $200 per night.

What We Did:

The hotel we were staying at offered sailing excursions so we jumped at the chance. Our captain took us out on a two-hour ride. First, we motored around Saint Michaels harbor and then we unfurled the sail and headed up the Miles River. The experience was magical. The sun beat down on us and the wind whipped my hair as our boat skimmed along the waves. It was the perfect afternoon.

There are also sailboat charters available at the main harbor. Sail Selina II offers various options, including a 2-hour day sail on the Chesapeake Bay for $65 per person, and a sunset champagne cruise for $85 pp.

If you have a group and want to splurge, check out St. Michaels Sailing Charters, which offers a 3 hour private charter on their catamaran. Of course, luxury doesn’t come cheap! A 3-hour outing will cost you $1000.

merry Lerner on a sailboat during a romantic weekend getaway

sailing on the Miles River in Chesapeake Bay

Merry Lerner and her husband enjoying an afternoon sail

Later in the day, we grabbed a couple of complimentary bikes to take a spin through town. After a pit-stop at the local ice cream shop, Justine’s, (which was so adorable!) we strolled down the red brick sidewalks, checking out the boutique shops and Victorian homes. There’s also a winery, brewery, the Chesapeake Bay Maritime Museum, and restaurants serving fresh seafood on the harbor front.

On Sunday morning I indulged in a free yoga class, offered right at the hotel, followed by a soak in our clawfoot tub. It was just what I needed after all of the food we indulged in the day before.

Merry Lerner enjoying a bike ride in Saint Michaels Maryland

Justine's Ice Cream Shop in Saint Michaels Maryland

What We Ate:

Normally when we travel somewhere new, I research every restaurant option in the area. If we had ventured out, I would have tried 208 Talbot.

But this trip, rather than run around, we opted for a more leisurely experience and ate every meal at the hotel’s restaurant, Stars.

In the morning, we sat in a sun-dappled room, eating our breakfast with a water view. Dinner was al fresco on the patio, watching the sailboats in the distance bobbing on the water. We feasted on oysters plucked locally and fresh seafood. But the best part was having a nightcap by the fire pit outside.

Stars Restaurant breakfast menu

oysters and sancerre al fresco at stars restaurant at the Inn at Perry Cabin

How We Relaxed:

It might seem like we did a lot, but more than anything, we relaxed and enjoyed our downtime. The resort is perfect for this, with white Adirondack chairs right at the water’s edge, beckoning you to sit down.

So that’s what we did. We shut off our phones (except when I took this picture!), tilted our heads back toward the sun, and just enjoyed sitting in the fresh air, listening to the waves.

Taking in the view at The Inn at Perry Cabin in Saint Michaels Maryland

Are You Ready for a Romantic Weekend Getaway?

Now that you know more about St. Michaels, Maryland, are you ready to plan your romantic getaway weekend?

I hope you found this post helpful for planning your trip!

I admit, a big draw for us was the Inn at Perry Cabin, where we stayed. It was a splurge and we wanted to get our money’s worth, which we did!

That said, the town is charming and we love the laid back feel. We can’t wait to come again, staying at another unique hotel the next time we visit.

Now I’d love to hear from you.

If you have recommendations for other destinations for romantic weekend getaways, send them my way, because, in my book, you can never have too many of those!

Happy travels!

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