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How to Spend a Romantic Weekend Getaway in Annapolis

18 September 2017 · 3 min read
Romantic Weekend in Annapolis

As the capital city of Maryland, Annapolis has plenty to see and do. Situated on the Chesapeake Bay, close to both Baltimore and Washington DC, it’s ripe with historical significance, is the home of the fabled Naval Academy, overflowing with monuments, has a thriving cultural and theatre scene and boasts hot, warm summers and cool winters. What more could you ask for when looking for your next couples weekend destination?

If you’re planning on getting out of town with your partner and are looking for an ideal location for a romantic weekend getaway, look no further than Annapolis. Here are our top picks for making the most of your weekend, meaning all you have to do is bring the romance!

Choose your hotel with care

Your getaway starts with your hotel, so be sure to choose the best possible venue. At the Annapolis Hotel Maryland, we’re on hand to help you have a truly memorable stay, with spacious rooms, great local attractions and fine dining options available. In addition, our centralized location provides the ideal vantage point for heading off to explore during your visit.

Explore the city’s romantic charm


Annapolis has plenty of history to enjoy with your special someone – over 350 years of it, in fact. Alongside unique shops selling all kinds of different wares, pubs, restaurants and heritage inns, the architecture of the city is stunning, and there are more 18th century buildings in Annapolis than in any other city in the country. 19 Maryland Avenue features ‘the most beautiful doorway in America’, placed there in 1774 as the entranceway to Anglo-Palladian mansion Hammond Harwood House. The house itself is a beautiful museum of 18th century art and architecture, and after you’ve finished perusing its civil war heritage and decorative arts from all around the world, you could even pick something up in the gift shop.

Visit a historic garden

Windsor Great Park

There’s nothing quite as romantic as flowers, so why not try a day trip a little south-west of Annapolis by visiting the Historic London Town and Gardens in Edgewater? Based on the UK’s Windsor Great Park, the gardens have free parking and Wi-Fi – ideal for capturing the trip and sharing it. There’s a guided tour every weekend at 1.30pm, and the garden is a beautiful getaway come rain or shine, with eight acres of woodland, a mile-long path and a beautiful winter walk.

Have dinner on the Annapolis dock

If you’re looking for a unique slice of the city and the ideal romantic dining spot, the O’Callaghan Hotel Group suggest you look no further than Annapolis dock. Walkable from anywhere in the city, the City Dock has lots of delightful eateries and is located within Annapolis’s historic heart. Boats regularly parade the basin, and tour boats offer you a chance to see Annapolis from the water. There’s always something happening at City Dock, so you can be sure to end your romantic break in style.