Select the month that you will be traveling from the table below to view the packing list:
What Annapolis is like to visit throughout the year:
January
When visiting the charming city of Annapolis in January, it’s important to dress in layers to combat the changing temperatures. A light jacket or sweater is essential for brisk mornings, while a heavier coat and scarf will keep you warm during cold evenings. As for footwear, comfortable walking shoes are a must for exploring the historic cobblestone streets and waterfront. And don’t forget to pack a raincoat or umbrella, as January can bring occasional showers. In terms of what to wear, I highly recommend dressing casually but neatly. Annapolis is a relaxed and laid-back city, but it’s also home to the prestigious United States Naval Academy, so it’s important to show respect by avoiding overly casual or revealing clothing. And if you plan on visiting any of the historic sites or museums, be sure to bring a hat and sunglasses to protect yourself from the bright winter sun. Lastly, don’t forget to pack a camera to capture the beautiful views and memories of your trip to Annapolis in January.
When visiting Annapolis in January, there are several must-see attractions and activities to add to your itinerary. Start your day with a stroll through the charming historic district, taking in the colonial architecture and quaint shops. Be sure to stop by the Maryland State House, the oldest state house in continuous legislative use, and learn about the state’s rich history. For a taste of local culture, head to the Annapolis Maritime Museum, where you can explore the city’s maritime heritage and even take a boat tour of the Chesapeake Bay. As the weather can be chilly in January, it’s the perfect time to warm up with a bowl of Maryland’s famous crab soup. Many local restaurants offer their own unique twist on this classic dish, so be sure to try a few and decide for yourself which one is the best. After lunch, take a tour of the United States Naval Academy, where you can learn about the history and traditions of the prestigious institution. End your day with a sunset cruise on the bay, admiring the picturesque views of the city from the water. With its charming atmosphere, rich history, and delicious cuisine, Annapolis is the perfect destination for a January getaway.
February
When visiting Annapolis in February, it’s important to dress in layers as the weather can be quite unpredictable. Start with a base layer of thermal clothing, as temperatures can drop below freezing at night. On top of that, I recommend a warm sweater and a waterproof jacket to protect against any potential rain or snow. Don’t forget to bring a sturdy pair of boots to navigate the cobblestone streets and sidewalks, as well as to keep your feet warm and dry. In terms of what to wear, I suggest opting for comfortable and practical clothing that can easily transition from day to night. Annapolis is a charming and historic city, so it’s always a good idea to bring a nice outfit for dinner or a night out on the town. Additionally, don’t forget to pack a hat, scarf, and gloves to keep yourself warm while exploring the city. And of course, no trip to Annapolis is complete without a camera to capture the beautiful sights and memories of your visit. Happy travels!
February is a wonderful time to visit Annapolis, Maryland, as the city is alive with winter festivities and a cozy charm. One must-see activity during this time is the Annapolis Winterfest, a month-long celebration of all things winter. Stroll through the streets and admire the stunning ice sculptures, watch the annual polar bear plunge, and warm up with a cup of hot cocoa from one of the many vendors. For history buffs, the city also offers a Colonial Chocolate Festival, where you can learn about the role of chocolate in colonial America and even sample some delicious treats. In addition to these fun events, February is also a great time to explore the city’s vibrant art scene. The First Sunday Arts Festival takes place on the first Sunday of every month, and in February, the artists and vendors showcase their talents in a winter wonderland theme. It’s the perfect opportunity to pick up some unique souvenirs and support local artists. And for a dose of culture, don’t miss the annual Maryland House and Garden Pilgrimage, where historic homes and gardens open their doors to the public. With so much to see and do, February in Annapolis is a truly charming and memorable experience.
March
March is a beautiful time to visit the charming city of Annapolis, and with the arrival of spring, it’s important to dress appropriately. The weather can vary, so it’s best to bring layers that can easily be added or removed. A light jacket, a scarf, and a pair of comfortable walking shoes are essential items to have in your suitcase. Annapolis can be quite windy, so a hat or a hair tie is also recommended to keep your hair in place. Don’t forget to bring a small umbrella, as the city is known for its sudden rain showers. When exploring Annapolis, it’s important to dress comfortably and casually. Jeans, a nice shirt, and comfortable shoes are perfect for a day of sightseeing. However, if you plan on visiting any of the historical sites or museums, I suggest wearing closed-toe shoes as some of the paths can be uneven. As for accessories, a crossbody bag or a small backpack is ideal for carrying your essentials while keeping your hands free. And of course, don’t forget to bring a camera to capture all the picturesque views of this charming city by the bay.
March is a fantastic time to visit Annapolis, with mild temperatures and fewer crowds than the peak summer months. While visiting this charming city on the Chesapeake Bay, be sure to take a stroll along the waterfront and admire the historic homes and sailboats bobbing in the harbor. For a taste of local culture, head to the Annapolis Maritime Museum and learn about the city’s rich maritime history. One of the highlights of visiting Annapolis in March is the annual Annapolis Oyster Roast and Sock Burning festival. This quirky event celebrates the start of spring and the sailing season by burning winter socks and feasting on delicious local oysters. It’s a must-see for any seafood lover or anyone looking for a unique cultural experience. And for a bit of adventure, take a scenic cruise on the bay and enjoy the stunning views of the city from the water. March in Annapolis truly offers something for everyone.
April
April in Annapolis is a delightful time to visit this charming colonial city. As the weather starts to warm up, it’s important to dress comfortably and appropriately for exploring the city. A light jacket or sweater is a must, as the mornings and evenings can still be a bit chilly. However, as the day progresses, the temperatures can rise, so be sure to wear layers that can easily be removed. Comfortable walking shoes are also a must, as the cobblestone streets and historic sites are best explored on foot. When packing for your trip to Annapolis in April, be sure to bring a rain jacket or umbrella as spring showers are not uncommon. A hat or sunglasses can also come in handy on sunny days. As for attire, the locals tend to dress casually but neatly. A nice pair of jeans or khakis paired with a collared shirt or blouse is perfect for a day of sightseeing. And don’t forget to bring a camera to capture the beauty of Annapolis in the springtime. With its blooming gardens, colorful sailboats on the harbor, and charming architecture, you’ll want to capture every moment of your visit.
As you wander the charming streets of Annapolis in April, you’ll notice the city coming alive with the arrival of spring. One of the best ways to soak up the seasonal atmosphere is by strolling along the waterfront, where you can watch the sailboats and enjoy the fresh sea breeze. Be sure to stop by the Annapolis City Dock, a bustling hub of activity with street performers, local vendors, and picturesque views of the harbor. For history buffs, April is the perfect time to visit the United States Naval Academy. As the weather warms up, the campus is filled with midshipmen practicing drills and preparing for graduation. Take a tour of the academy and learn about its rich history and the impressive young men and women who call it home. And don’t miss the famous Herndon Monument Climb, where plebes (freshmen) work together to climb a greased monument and replace a hat on top, symbolizing the end of their first year at the academy. It’s a unique and exciting event that only happens once a year in April.
May
As you prepare for your trip to Annapolis in May, it’s important to plan your wardrobe accordingly. The weather in this charming city can be quite unpredictable, with warm sunny days followed by cool and breezy evenings. To stay comfortable and stylish, I recommend packing layers. Start with a lightweight, breathable shirt and pants for exploring the historic downtown area during the day. Bring a light jacket or sweater for cooler evenings, and don’t forget a sturdy pair of walking shoes for all the cobblestone streets and waterfront strolls. Annapolis is a city with a rich maritime history, so don’t be afraid to embrace the nautical theme in your wardrobe. A classic striped shirt paired with khaki shorts or a navy blue dress will fit right in with the local style. For a more formal evening out, a collared shirt and dress pants will do the trick. And of course, don’t forget a hat and sunglasses to protect yourself from the sun’s rays while admiring the boats in the harbor. As for accessories, a small crossbody bag or backpack is perfect for carrying your essentials while leaving your hands free to take pictures and explore. With these tips, you’ll be dressed to impress and ready to experience all that Annapolis has to offer in May.
Welcome to Annapolis, the charming capital city of Maryland. In the month of May, this historic town is bursting with energy and activities for visitors to enjoy. Start off your day by taking a stroll along the picturesque streets, admiring the beautiful colonial architecture and quaint shops. Make sure to stop by the United States Naval Academy, where you can catch a glimpse of the future officers in training and learn about the academy’s rich history. As the weather warms up in May, head down to the City Dock and hop on a boat tour of the Chesapeake Bay. You’ll get a chance to see the stunning waterfront homes and learn about the city’s maritime heritage. For a unique experience, join in on one of the local sailing races or rent a kayak and explore the bay on your own. Don’t forget to try some delicious seafood at one of the many waterfront restaurants before ending your day with a sunset cruise. Annapolis in May is the perfect blend of history, culture, and outdoor adventure.
June
When visiting Annapolis in June, it’s important to dress for the warm and humid weather. Light, breathable fabrics like cotton and linen are ideal for staying comfortable while exploring this charming city. A light jacket or cardigan may also come in handy for cooler evenings and air-conditioned buildings. While strolling through the historic streets of Annapolis, it’s important to wear comfortable and supportive shoes. The city is known for its cobblestone streets and uneven sidewalks, so leave the high heels at home. Don’t forget to bring a sunhat, sunscreen, and sunglasses to protect yourself from the strong summer sun. And of course, a camera to capture the beautiful waterfront views and historic architecture. Lastly, don’t forget to bring a light bag or backpack to carry water, snacks, and any souvenirs you may pick up along the way. With these tips in mind, you’ll be ready to enjoy all that Annapolis has to offer in the warm and sunny month of June.
When visiting Annapolis in June, there is no shortage of activities to partake in. This charming coastal town is bustling with energy and offers a variety of experiences for travelers. One of the must-do activities is to take a stroll along the picturesque waterfront. Here, you can admire the historic buildings and boats, and even catch a glimpse of the US Naval Academy midshipmen going about their daily routine. June also happens to be the perfect time to explore Annapolis’ rich history. Take a tour of the Maryland State House, the oldest state capitol still in use, and learn about the city’s role in the American Revolution. You can also visit the William Paca House and Garden, a beautifully restored colonial mansion that offers a glimpse into life in the 18th century. And for a taste of local culture, be sure to check out the many festivals and events happening in June, such as the Annapolis Arts and Crafts Festival and the Annapolis Irish Festival. With so much to see and do, Annapolis is the perfect destination for a summer getaway.
July
When visiting Annapolis in July, it’s important to dress for both the warm weather and the casual, laid-back vibe of this historic city. Opt for lightweight, breathable fabrics such as cotton or linen to stay cool and comfortable in the summer heat. Shorts, sundresses, and sandals are all perfect choices for exploring the cobblestone streets and waterfront of Annapolis. In addition to dressing appropriately for the weather, it’s also important to bring along some essentials for your visit. A wide-brimmed hat and sunglasses will provide much-needed shade and protection from the sun. And don’t forget to bring a reusable water bottle to stay hydrated while you’re out and about. Annapolis is known for its delicious seafood, so be sure to pack a light jacket or sweater for evenings by the water. And of course, don’t forget to bring your camera to capture all the charming sights and memorable moments of your trip to Annapolis.
July is a fantastic time to visit the charming city of Annapolis. With warm, sunny weather and a variety of events and activities, there is something for everyone to enjoy. One of the must-see sights in July is the United States Naval Academy, where visitors can take a tour of the impressive campus and learn about the history and traditions of the Navy. Be sure to catch the Noon Formation, where you can witness the midshipmen marching in formation – a truly patriotic experience. For a taste of local culture, head to the Annapolis Maritime Museum, where you can learn about the city’s rich maritime heritage and even take a sail on a traditional Chesapeake Bay skipjack. July also brings the annual Annapolis Arts and Crafts Festival, where you can browse unique handcrafted items and sample delicious local food. And no visit to Annapolis is complete without a stroll along the picturesque waterfront, where you can admire the beautiful boats and soak in the laid-back atmosphere of this charming coastal town.
August
As you plan your trip to charming Annapolis this August, it’s important to consider the weather and dress accordingly. August in this historic city can be quite hot and humid, so light and breathable clothing is a must. Opt for cotton or linen fabrics to keep cool and comfortable while exploring the city’s cobblestone streets and waterfront. A light jacket or sweater may also come in handy for cooler evenings, especially if you plan on taking a sunset cruise on the Chesapeake Bay. When it comes to footwear, comfortable walking shoes are a must. Annapolis is a walkable city, and you’ll want to be able to explore all it has to offer without any discomfort. Sun protection is also essential, so be sure to pack a hat, sunglasses, and sunscreen to shield yourself from the sun’s rays. And don’t forget to bring a reusable water bottle to stay hydrated while you’re out and about. With the right clothing and gear, you’ll be able to fully immerse yourself in the beauty and history of Annapolis this August.
August is a fantastic time to visit Annapolis, the charming capital city of Maryland. As the summer heat begins to wane, there are plenty of outdoor activities to enjoy in this beautiful coastal town. Start your day with a stroll along the waterfront, taking in the stunning views of sailboats and historic buildings. Then, head to the United States Naval Academy for a tour of this prestigious institution and its impressive campus. For a taste of local culture, be sure to visit the Annapolis Maritime Museum, where you can learn about the city’s rich maritime history. As the sun sets, make your way to the City Dock area, where you’ll find a lively atmosphere and an array of delicious seafood restaurants. Enjoy a traditional Maryland crab feast or sample some local oysters while watching the boats come in. Don’t miss the opportunity to take a sunset cruise on the Chesapeake Bay, where you’ll witness the city’s picturesque skyline from a different perspective. And for a truly unique experience, visit Annapolis in late August during the U.S. Sailboat Show, where you can tour some of the world’s most magnificent yachts and even take a ride on one yourself. With its charming atmosphere and endless activities, August is the perfect time to experience all that Annapolis has to offer.
September
September is a lovely time to visit the charming city of Annapolis. The weather is mild and comfortable, making it the perfect time to explore the city on foot. When it comes to dressing for this time of year, it’s important to keep in mind the changing temperatures throughout the day. I recommend wearing layers, such as a light jacket or sweater, that can easily be added or removed as needed. Comfortable walking shoes are also a must, as the city’s cobblestone streets and sidewalks can be a bit uneven. As for what to bring, don’t forget to pack a raincoat or umbrella as showers are not uncommon during this time of year. Also, be sure to bring a hat and sunglasses to protect yourself from the sun while strolling along the waterfront. And for those planning to visit the United States Naval Academy, keep in mind that proper attire is required, including closed-toe shoes and covered shoulders. Lastly, don’t forget your camera! The historic architecture and stunning waterfront views are not to be missed and make for great photo opportunities. With the right clothing and gear, you’ll be prepared to fully enjoy all that Annapolis has to offer in September.
September is a fantastic time to visit the charming city of Annapolis, located on the picturesque Chesapeake Bay. As summer winds down and the crowds disperse, visitors can fully appreciate the laid-back and historic atmosphere of this colonial capital. One of the best ways to experience Annapolis is by taking a stroll along its scenic waterfront. Watch the sailboats glide through the harbor, stop for a delicious seafood lunch at one of the many waterfront restaurants, and take in the views of the iconic U.S. Naval Academy. September is also the perfect time to take a boat tour of the bay, where you can learn about the city’s rich maritime history and spot some local wildlife. Another must-do activity in September is to attend the Maryland Renaissance Festival, just a short drive from Annapolis. Step back in time to the 16th century and immerse yourself in the sights, sounds, and smells of this lively festival. Watch jousting tournaments, shop for handcrafted goods, and indulge in some delicious medieval fare. This family-friendly event is a favorite among locals and visitors alike, and is a unique way to experience the culture and traditions of the Chesapeake region. So grab your turkey leg and join in on the fun at the Maryland Renaissance Festival this September!
October
When visiting Annapolis in October, it’s important to dress in layers as the weather can be quite unpredictable. The mornings may start off chilly, but by midday, the sun may be shining and the temperature can rise significantly. I recommend bringing a light jacket or sweater that you can easily take off or put on. It’s also a good idea to pack a rain jacket or umbrella, as October in Annapolis can bring some showers. When it comes to footwear, comfortable walking shoes are a must. Annapolis is a city best explored on foot, with its charming cobblestone streets and historic sites. Be sure to bring a sturdy pair of shoes that you can walk in for hours without discomfort. And don’t forget to pack a hat and sunglasses to protect yourself from the sun while strolling along the waterfront. As for accessories, a small crossbody bag or backpack is ideal for carrying your essentials while keeping your hands free to take photos or try some delicious seafood. With these items packed, you’ll be ready to fully enjoy all that Annapolis has to offer in the beautiful month of October.
Annapolis, with its charming historic streets and scenic waterfront, is a perfect destination to visit in October. As the leaves begin to change and the temperatures cool down, the city takes on a cozy and inviting atmosphere. One of the best ways to experience Annapolis in October is by taking a stroll through the city’s vibrant downtown area. From quaint boutiques to delicious seafood restaurants, there is something for everyone to enjoy. And if you’re lucky, you may even catch a glimpse of the colorful sailboats gliding along the harbor. No trip to Annapolis in October would be complete without a visit to the United States Naval Academy. This prestigious institution is not only a top-ranked university, but also a beautiful and historic campus. Visitors can take a guided tour, learn about the academy’s history and traditions, and even catch a glimpse of the midshipmen in their dress uniforms. And for those interested in the maritime history of the region, the Annapolis Maritime Museum is a must-visit. With interactive exhibits and a stunning collection of boats, it’s a great way to spend a crisp autumn day. So pack your sweaters and come experience the charm of Annapolis in October.
November
As the crisp autumn air settles over the charming city of Annapolis in November, it’s important to pack accordingly for your visit. The key to dressing for this time of year is to layer, layer, layer. Start with a lightweight base layer, such as a long-sleeved shirt or sweater, and then add a medium-weight jacket or coat on top. This will allow you to adjust to the changing temperatures throughout the day. Don’t forget to bring a scarf, hat, and gloves to keep you warm while strolling through the picturesque streets. When it comes to footwear, comfortable walking shoes are a must for exploring the cobblestone streets and historic sites. A pair of waterproof boots or shoes would also come in handy in case of any rain showers. As for what to wear, opt for comfortable and casual clothing that can easily be dressed up for a nice dinner or evening out. And of course, don’t forget to bring a rain jacket or umbrella, as November in Annapolis can be quite unpredictable. With these essentials in your suitcase, you’ll be ready to fully enjoy all that this charming city has to offer during your visit.
November is the perfect time to visit Annapolis, Maryland. The crisp autumn air, colorful foliage, and charming historic streets make for a delightful trip. One must-do activity in November is to take a stroll along the city’s waterfront. As you walk along the harbor, you’ll see the beautiful sailboats and historic ships that call Annapolis home. You can also stop by the U.S. Naval Academy and take a tour of the campus, which is especially stunning in the fall. After your walk, warm up with a cup of hot cider from one of the many cozy cafes in the area. For history buffs, November is the ideal time to explore Annapolis’ rich colonial past. The city is home to numerous historic landmarks, including the Maryland State House, which is the oldest state capitol still in use. You can also visit the William Paca House, a beautifully preserved 18th-century mansion that offers a glimpse into the lives of the city’s early inhabitants. And for a taste of local culture, don’t miss the First Sunday Arts Festival, where you can browse through unique artwork, listen to live music, and sample delicious food from local vendors. No matter your interests, November in Annapolis is sure to be a memorable experience.
December
As you pack your bags for a December trip to Annapolis, it’s important to remember that the weather can vary greatly during this time of year. The key to staying comfortable and stylish is to dress in layers. Start with a base layer of thermal underwear or long-sleeved shirts to keep you warm, then add a sweater or fleece for extra insulation. A waterproof and windproof jacket is a must-have, as Annapolis can get quite windy and rainy in December. Don’t forget to pack a warm hat, gloves, and a scarf to protect your head, hands, and neck from the chilly temperatures. When it comes to footwear, bring a comfortable pair of walking shoes or boots with good traction. Annapolis is a city best explored on foot, and you’ll want to be prepared for any unexpected rain or snow. For men, a nice pair of dress shoes is also recommended for evenings out. As for clothing, opt for versatile pieces that can be dressed up or down. A pair of dark jeans paired with a button-down shirt and a blazer works well for both casual and more formal occasions. And of course, don’t forget to pack a swimsuit if you plan on taking a dip in the hotel pool or the nearby Chesapeake Bay, which surprisingly can be quite pleasant in December. With these essential items, you’ll be prepared for whatever December weather Annapolis throws your way.
Visiting Annapolis in December is an absolute delight for any traveler. This charming city is filled with history, culture, and an enchanting holiday spirit. One of the must-see attractions during this time of year is the annual lighting of the Annapolis City Dock and Ego Alley. Stroll along the waterfront and take in the twinkling lights as you enjoy the crisp winter air. For a truly unique experience, hop on a boat tour and view the dazzling lights from the water. Another highlight of the holiday season in Annapolis is the annual Midnight Madness event. This festive shopping extravaganza takes place on the first three Thursdays in December and features extended store hours, live music, and special discounts. It’s the perfect opportunity to find unique gifts for your loved ones while supporting local businesses. Aside from holiday festivities, there are plenty of other things to do in Annapolis during the month of December. Take a guided tour of the United States Naval Academy and learn about the history and traditions of this prestigious institution. For a taste of the city’s culinary scene, head to the Annapolis Market House and sample some delicious local treats. And if you’re in need of some relaxation, book a spa day at one of the city’s many luxurious spas. Whether you’re interested in history, shopping, or simply soaking up the festive atmosphere, Annapolis has something for everyone in December. So bundle up and come experience the magic of this charming city during the most wonderful time of the year.
Hey there! I’m Jason, a total travel junkie who is always on the go. I live for discovering new places, meeting cool people, and experiencing different cultures. I’m here to help you with your travels.
