Annapolis Valentine’s Day Activities in 2020

Love is in the air! When you’re coming to Annapolis for Annapolis Valentine’s Day Activities, you’re coming to the right city. Let us share with you some of our favorite romantic activities to do here on the most romantic holiday of the year.

Take a Stroll at the Dock

This is a little activity that you can do which costs nothing and allows you to spend quality time together. Walk hand in hand along the Annapolis City Dock and drink in the views of the water, along with the interesting and beautiful boats moored here, and those passing by. It’s a quaint area, and worth a visit if you’re nearby.

Visit a Winery Together

Walk around the vineyard at Great Frogs and enjoy the romantic solitude that you only find in places such as these, where human mastery meets the wonders of mother nature. You can order wine from the walk-up window for quick service (glasses of wine can range from $8 to $10, whereas bottles range from $30 to $50). There’s even an outdoor patio here where guests can enjoy a bottle of wine without prior reservation. If you’d like to get the most out of your visit to Great Frogs, make a reservation ahead of time for a tasting experience. Let the masters walk you through the wonders of wine! What’s more romantic than a classy wine date?

Plan a Date at Sandy Point State Park

This state park is 786 acres of pure earthly beauty. Find it on the Northwestern shore of the Chesapeake Bay, and plan to stay for at least a few hours. A romantic way to experience the joys of Sandy Point might be to pack along a picnic and surprise your loved one! Or, you can simply eat when you get there. There are places to buy food in the area; picnics are certainly, romantic, though. You’ll find a marina store here, along with boat rentals, so you can really wow your date by taking them out onto the water for some fun activities, like fishing, or the simple joy of sailing. The sight of the sun sparkling on the surface of the water will make this Valentine’s Day one that you’ll never forget.

Spend Annapolis Valentine’s Day 2020 with At Home Annapolis

Give your valentine the best gift of all; a luxurious vacation rental home where you can stay together during the lovely month of February. Get in touch with us today at (888) 508-9661 or (435) 571-0024 to get started.

How to Enjoy Your First Annapolis Vacation in 2020

As the decade turns and we head from 2019 into 2020, you’ll want to refresh yourself for the new decade. Take some time off, relax a little, and do something fun to reset your inner Zen. Annapolis is the perfect place to head for your first vacation of 2020! Here are some handy ideas for how to spend your Annapolis Vacation in 2020:

See Gilbert Gottfried Onstage

What better way to kick off 2020 than with comedy legend Gilbert Gottfried? Comedy shows are the best way to release all the steam of the previous year. Kick back and let your worries slip away at Rams Head On Stage in Annapolis on January 16th, 2020. This event is 21+ and tickets are on sale now for $39.50.

Explore Chesapeake Bay

For anyone coming to Annapolis, Chesapeake Bay is undoubtedly one of the biggest draws. Take a boat tour out onto the water and get up close and personal with the waves! You’ll get an unparalleled view of the city, and you’ll also get to experience sea life from the best possible vantage point. You simply haven’t seen the Chesapeake until you’ve boarded a boat and left the shore behind for a few solid hours of ocean adventure.

Celebrate Chinese New Year / Spring Festival 2020

The world will be celebrating Spring Festival the last week of January, so you should too! Explore traditional Chinese customs, cuisine, and arts at this cultural celebration held at Wellsview Cottage: Center for Holistic and Integrative Health. Put it on your calendar for Saturday, January 25th, 2020, 6:30 – 9:30pm. Tickets are on sale now for $25.

Visit the Annapolis Historic District

The architecture of Annapolis is unique, preserving older buildings that you simply don’t see in many other cities in the United States. As one of the oldest cities in the country, it’s simply brimming with historic buildings, colonial architecture, and colorful houses that will fill the start of your year with an aesthetic breath of fresh air, good vibes, and fun times. Seeing all the sights in the Annapolis Historic District is a great way to fill a winter afternoon and evening before you head back to your rental home for the night.

Start Your Year with a Annapolis Vacation in 2020

The first month of the year can really define your mood for the entire year going forward. That’s why you should choose a top rental home to maximize your comfort and surround yourself with a good atmosphere. Head over to our catalog right now to get started!

Plan a 2019 Annapolis Thanksgiving Getaway

Thanksgiving is the time of year when you’re ready for a break from day to day life. Fall is in full swing, winter is on the horizon, and you want to get cozy with the ones you love! There’s no better place to enjoy this holiday together than in Annapolis, Maryland.

Wednesday

Explore the heart of Annapolis on your first day in town with Annapolis Urban Adventures. Take this 1.5-hour tour with the whole family by climbing aboard the electric vehicle to make your way around town. See all the historic landmarks, get acquainted with the city you’ll be spending your Thanksgiving in, and hear some fun stories and facts from your tour guide as well! It’s a small group tour, which makes it perfect for a family holiday vacation.

Thursday – Thanksgiving Day!

On Thanksgiving Day you’ll want the focus to be on the family. Choose some quiet activities where you can enjoy each other’s company. Head to Sandy Point State Park for a quiet day of fun by the water and have your Annapolis Thanksgiving dinner at your comfortable rental home, utilizing the available amenities to cook up a delicious meal with the ones you love.

Friday

After your relaxing Thanksgiving Day, you’ll want to get up and get active with some outdoor activities! Take the Chesapeake Wine Tour hosted by Vino 302 Wine Concierge Tours and you’ll get to explore two different wineries, Crow Farm and Vineyard and Mark Cascia Vineyards. This tour is five hours long, and on the way, you’ll get to bask in the beauty of the region and its waterways and beaches. If you don’t have kids with you, or if you have older family members to leave the kids with, this is a great way to get some alone time!

Saturday & Sunday

Do a family activity! How about a game that’s a cross between a scavenger hunt, self-guided tour, and thrilling race? Check out Puzzling Adventures and complete their adventure at your own pace, all while learning fun things about your surroundings. The point is to get you outdoors and having fun together. Spend some time in the gardens at Quiet Waters Park, have a bite to eat at Carrol’s Creek Cafe by the waterside, and grab some souvenirs at Annapolis Harbor Center.

Spend Thanksgiving 2019 With At Home Annapolis

Wherever you are and whatever you do, family is always the most important part of Thanksgiving. So give your family the best home-away-from-home that there is to be found in Annapolis! Just get in touch with us today at (888) 508-9661 or (435) 571-0024 and we’ll help you get started.

Our Favorite Annapolis Activities in the Fall

Annapolis in the fall is cozy, stunning, and wildly fun all at once. With the leaves changing color around you, the weather brisk and pleasant, and a plethora of fall activities to participate in, you’re going to have one unforgettable vacation. Make some time while you’re here to check out our favorite Annapolis activities in the Fall:

Greenstreet Gardens Fall Festival

This festival runs from September all the way through October in Greenstreet Gardens, so there are six whole weekends of festivities and themed events to enjoy. Get lost with your friends in the corn maze, go bowling with pumpkins, take a haunted hayride, and take a ride on an underground slide. That’s not all, but you’ll have to come and check out this fun fall festival if you want to know more!

U.S. Sailboat Show

This October come and see this one-of-a-kind gathering, where sailors from around the world come together. You’ll never have seen so many interesting boats all in one place before. If you love the sea and sailing, you’ll adore this show, and if you don’t know much about it this is a great chance to learn.

Visit the Renaissance Fair

The Maryland Renaissance Fair runs between August 24th and October 20th, so you have ample time this fall season to come down and catch the fair while you’re here. The Renaissance Fair is always a world of fun, and Maryland truly goes all out. The Renaissance Fair is definitely one of our favorite things to do in Annapolis in the Fall!

Winterbrook Farms

We adore this pumpkin patch for many reasons, including but not limited to the moonlight maze, the private campfires, and the mountain slides. This is a great day activity for any family and evening activity for anyone who wants to do a corn maze in the dark.

Walking Ghost Story Tour

This activity is exactly as exciting and off-the-wall as it sounds. Experience Annapolis in an entirely unique way by taking this 90-minute nighttime walking tour through the city to some of the most ‘haunted’ places in Annapolis. Between haunted taverns, Joe Morgue, and “The Headless Man,” this is a great way to wake you up when the sun goes down!

Book a Stay To Experience The Best Annapolis Activities in the Fall

Planning an autumn trip to Annapolis this year? Plan your trip right by picking an awesome rental home to stay in through At Home Annapolis. Just call us today at (888) 508-9661 or (435) 571-0024 and we’ll help you get started!

Your Annapolis Labor Day Weekend Vacation

Annapolis is a hotspot of beautiful sights to see and wildly fun activities. There is so much to do here, and September is a great time of year to visit. The long weekend that Labor Day provides gives you the perfect amount of time to see the best Annapolis has to offer. Here are some ideas for what to do each day to get the most out of your Annapolis Labor Day Weekend visit:

Saturday

Do something crazy on the first day that will get the entire family excited about the three-day weekend in Annapolis, like a family-friendly pirate cruise with Pirate Adventures on the Chesapeake! Afterward, you can check out some of the amazing museums in town, like the Annapolis Maritime Museum. Keeping with the sailing theme, you can grab some dinner at the Boatyard Bar & Grill, a proudly nautical-themed seafood joint with an amazing vibe and even more amazing food.

Sunday

Sunday is a great day to plan some peak relaxation and sight-seeing. Head to the aptly named Quiet Waters Park, where you can explore hiking trails on foot or on a bike, and even rent a kayak if you want to head out onto the water. If you pack a picnic, you can grab a shady spot under a tree and have your lunch there while you soak in the lovely weather and the scenery. Later on, head to Sandy Point State Park for one of the most gorgeous views you’ll ever lay eyes on. You can see the bridge from there, and the ocean in all its glory. Lay out some towels and chill out with some music on.

Monday

Since you’ve thoroughly enjoyed the waters, on Monday, you’ll want to enjoy the city itself! Check out local favorites like the Maryland Federation of Art for some culture, the Historic Annapolis Museum for some history, and the Old Fox Books & Coffeehouse for some afternoon coffee and a nice quiet look around a good old-fashioned bookstore. Pick up some fancy teas and spices from The Spice & Tea Exchange to take home with and maybe give out to friends as souvenirs! Top off your trip with an ice-cold craft beer from The Brass Tap on your last night in town.

Where Do I Start?

The first thing you’ll want to do is find an awesome place to stay, so you can make the most of your weekend getaway! Here at At Home Annapolis, that’s the most important thing to us. Just give us a call today at (443) 837-6870, and we’ll help you get started.

Best Dessert in Annapolis to Beat the Summer Heat

Summer is a gorgeous and lively time of year to visit Annapolis. There are a million things to do here, and you’ll find yourself on the go from the time you arrive, just trying to see it all! When you’re out and about this summer soaking in the sights and sounds of Annapolis, and you start to feel the sun beating down on you, remember these three pro-tips for defeating the summer sunshine:

Cool Off in Style with Annapolis Ice Cream

Conveniently located right on Main Street, this place is a one-stop shop for the creamiest gourmet ice cream you’ll ever taste. This company only uses the finest ingredients available; you won’t find another shop quite like in all of New England! You can even order a custom ice cream cake if you’re having an event, or even if you just want to surprise the family or your group of friends after a long warm day of summer fun in the sun with an ice cold treat to cool off with back at your rental home. This ice cream is definitely the most popular dessert in Annapolis among tourists!

Enjoy a Cold Drink by the River at Boatyard Bar & Grill

This nautical themed restaurant will start cooling you off through aesthetic alone before you even take your first sip of a refreshing ice-cold drink! Dine on crab cakes, clams, and sailor-style mussels while you take your pick from the rick drink menu. Consider trying one of the specialty drinks here, perfect for summertime, like the Fresh Fruit Crushes (made with fresh juices, triple sec, lemon soda, and your choice of lemon, grapefruit, or orange vodka), or the Boatyard’s Bloody (Tito’s Vodka, a delicious house-made Bloody Mary mix, spicy pickled green beans, pepperoncini, olive, and fresh lime).

Hit the Water for the Ultimate Cool-Down

Without a doubt, the best way to beat the sun in Annapolis will always be to head out and enjoy the pride and joy and heart of the city, the gorgeous waters of Chesapeake Bay. Take your pick between sailing, paddleboarding, or even windsurfing! Sporty activities can be hard to enjoy in the heat of the summer sun, but you don’t have to worry about that with water sports on the bay. The waves are nice, the water is refreshing, and that ocean breeze will keep you smiling in the sunshine all day long.

Book Your Annapolis Summer Vacation

The best place to start when you’re coming to Annapolis will always be with Annapolis Vacation Rentals. Get in touch with us today at (443) 837-6870 and we’ll help you get started in finding the perfect rental home to spend your summer evenings in Annapolis.

Plan an Unforgettable Luxury Annapolis Getaway

Annapolis is a hot spot of culture, activity, history, and sightseeing. There are endless ways to fill the day—so many that it can be hard to pick and choose. Make this Annapolis getaway the most fun and comfortable you’ve ever taken by using this handy guide:

What to Do During Your Annapolis Getaway

Charter a fishing boat while you’re in town to enjoy the beautiful waters of the bay. You’ll want to see some of the famous museums while you’re here too, like the Annapolis Maritime Museum & Park, the U.S. Naval Academy, and the Maryland Federation of Art. For a breath of fresh air and nature, head down to Sandy Point State Park and the lovely Helen Avalynne Tawes Garden. If you really want to splurge, consider finishing out your trip with a helicopter tour on the very last day to see all the sights one last time. These are the top 5 tourist attractions in Annapolis!

Where to Eat

Treat yourself to some of the best fine dining experiences you’ll ever have for your Annapolis getaway. Have the best steak you’ll ever eat at Lewnes’ Steakhouse. Take a deep dive into French cuisine at Les Folies Brasserie where you can try dishes like ahi tuna, beignets, or venison in lingonberry sauce. Check out Osteria 177 for some high-end Italian. Try the Caprese, the Cioppino, or the Sacchetti di pasta ai Porcini! You really can’t go wrong at this restaurant, which is a big favorite among locals.

Where to Stay

For historic style, make your home-away-from-home at Submariner’s Gate. This property has a beautiful private courtyard, and a basement game room complete with a shuffleboard table, darts, and even a bar. For something even more spacious, consider the Magical Memories, which overlooks the breathtaking Chesapeake Bay. The yard is lush, the home is beautiful, and it’s only five miles from Historic Downtown Annapolis. If you’re coming with a really big group, you’re going to want to stay at the Ogleton Porticos. This luxury home is 6000 square feet, provides enough sleeping room for 17 people, and sits directly on the waterfront. With a built-in bar, a fireplace on every level, multiple porches and balconies, and a private pier on Lake Ogleton, this will without a doubt be the nicest home you’ve ever vacationed in. Check out our pet-friendly vacation rentals today!

How to Get Started

The most important step in planning any vacation is choosing your perfect place to stay, so when you’re planning a vacation of utmost luxury, you’ll want a rental property of utmost luxury to match! That’s where At Home Annapolis can help you. Get in touch with us today at 443-837-6870 to get started on planning the most unforgettable Annapolis getaway you’ve ever had!