DWY | Your 2025 Guide to the Annapolis Boat Shows

Each October, Annapolis transforms into the hub of the boating world. For two consecutive weekends, the historic harbor fills with hundreds of boats, miles of floating docks, and thousands of sailors, powerboaters, and industry leaders from across the globe. The Annapolis Powerboat Show and the Annapolis Sailboat Show are among the largest in-water shows of their kind in North America, and together they represent the ultimate opportunity to explore, compare, and learn.

As someone who has attended these shows year after year, I can confidently say they’re more than just exhibitions—they’re immersive experiences. You can step aboard everything from compact day boats to bluewater-capable yachts, meet directly with builders and brokers, and experience firsthand the innovations shaping the boating world. And, of course, you get to do all of this in one of the most charming maritime towns in America.

Two Back-to-Back Shows: One Great Location!

In this Guide:

• Powerboat Show Overview
  
  • What not to miss
  • Advice for visiting the powerboat show
    
    
• Sailboat Show Overview
  
  • What not to miss
  • Advice for visiting the sailboat show
    
    
• Why attend with David Walters Yachts
• Practical Tips
• Beyond the Docks
• Dining Recommendations
• Schedule Your Showings & DWY Consultation
  
  

Annapolis Powerboat Show

• Dates: Thursday, October 2 – Sunday, October 5, 2025
• Hours: 10 AM–6 PM (Thurs–Sat), 10 AM–5 PM (Sun)
• Location: Annapolis City Dock & Harbor
• Admission: Purchase Tickets Here

The Annapolis season begins with the Annapolis Powerboat Show, which takes over the downtown harbor and surrounding docks. What makes this show unique is its format—it’s entirely in-water, allowing you to step directly aboard a wide variety of powerboats in their natural element. From sleek center consoles built for speed to expedition-ready motor yachts designed for long-range cruising, this show is a comprehensive look at the latest innovations in powerboating.

Whether you’re looking for your first boat, exploring an upgrade, or want to experience the latest in design and technology, the Powerboat Show has something for every type of boater.

What Not to Miss

• Debuts & Premieres:  Annapolis has become a popular venue for U.S. and international debuts, with many builders timing their launches around the show. You’ll often see brand-new designs before they appear anywhere else in North America, offering an exciting chance to be among the first to see and experience them.
  
  
• Center Consoles & Sportfishers:  A key focus of the show is on versatile center consoles and high-performance sportfishing boats. These vessels are perfect for life on the Chesapeake Bay as well as offshore waters, and the show provides one of the best opportunities to compare different builders side by side. You’ll also find a wide variety of models equipped with the latest outboard technology, advanced electronics, and fishing gear.
  
  
• Luxury Motor Yachts & Trawlers:  For those interested in long-range cruising or liveaboards, Annapolis features an impressive selection of trawlers, flybridge yachts, and luxury motor yachts. These boats emphasize comfort, seaworthiness, and efficiency, offering a great chance to step aboard and compare layouts, finishes, and build quality firsthand.
  
  
• Seminars & Demos:  In addition to the boats, the Powerboat Show includes an educational component that benefits both new and experienced owners. Hands-on demonstrations cover everything from electronics and navigation to maintenance and boat handling. These sessions are an excellent way to expand your knowledge and gain practical skills while at the show.
  
  

DWY Advice for Visiting the Annapolis Powerboat Show

The Powerboat Show might be the quieter of the two weekends, but that’s precisely what makes it such a great opportunity. Crowds are lighter, and you’ll find it easier to spend quality time aboard the boats and engage in meaningful conversations with builders and brokers. If you’re seriously considering a purchase, this is the show where you’ll have more space and less pressure.

If you’re focused on center consoles or sportfishing boats, come prepared to compare. Annapolis offers one of the largest lineups of fishing and performance models side-by-side anywhere on the East Coast, making it the perfect chance to evaluate layouts, performance packages, and outfitting options.

For those looking at cruising yachts and trawlers, the show is equally valuable. Step aboard a wide range of motor yachts designed for extended cruising, and let us help you understand the differences in design philosophy, construction quality, and onboard systems.

Don’t overlook the seminars and hands-on demos. These are a great way to gain practical insights into electronics, navigation, and boat handling—whether you’re new to powerboating or refining your skills.

The Annapolis Powerboat Show is more than just a display of boats—it’s a focused, efficient way to see the market up close. With fewer crowds and a wide selection of boats in every category, it’s an ideal time to evaluate your options with the guidance of a DWY broker.

Annapolis Sailboat Show

• Dates: Thursday, October 9 – Sunday, October 12, 2025
• Hours: 10 AM–6 PM (Thurs–Sat), 10 AM–5 PM (Sun)
• Location: Annapolis City Dock & Harbor
• Admission: Purchase Tickets Here

The following weekend, Annapolis transforms again—this time into the sailing capital of the world—when the Annapolis Sailboat Show takes over the harbor. For sailors, this is the highlight of the year. It’s not only the largest in-water sailboat show in the world, but also one of the most complete, attracting exhibitors and visitors from every corner of the globe.

Whether you’re a lifelong sailor, planning to start cruising, or simply curious about the lifestyle, this show offers an unmatched opportunity to step aboard boats of every style and size, compare them side by side, and meet directly with builders, designers, and experienced sailors.

What Not to Miss

• Hundreds of Sailboats:  The Annapolis Sailboat Show fills every dock with boats ranging from small daysailers to high-performance racing yachts, luxury performance cruisers, and serious bluewater passagemakers. It’s one of the few places in the world where you can board so many sailboats, back to back, in a single weekend.
  
  
• Catamaran Dock:  Annapolis is the premier spot to evaluate catamarans. Nowhere else in North America offers such a wide selection of multihulls all together, with major builders like Lagoon, Leopard, Fountaine Pajot, Bali, and others, all in one place. If you’re considering a catamaran, this is the best chance to compare layouts, quality, and features side by side.
  
  
• Gear & Accessory Tents:  Beyond the boats themselves, the show features large tents filled with everything a sailor could need—sails, rigging, deck hardware, navigation and communication systems, clothing, safety gear, and lifestyle equipment. It’s a sailor’s marketplace, and a great opportunity to see the latest innovations.
  
  
• Cruisers University:  Held in the days before and during the show, Cruisers University is one of the most comprehensive educational programs available to sailors preparing for long-term cruising. Courses cover passagemaking, boat systems, weather routing, offshore safety, and more. For anyone serious about extended voyaging, this program is invaluable.
  
  
• Seminars & Workshops: Daily sessions hosted by industry experts cover everything from outfitting your boat for offshore cruising to practical maintenance to exploring new cruising destinations. Even if you’re not in the market for a boat, these seminars provide great insights and inspiration.
  
  

DWY Advice for Visiting the Annapolis Sailboat Show

The Sailboat Show is typically the busier of the two weekends, with large crowds—especially on Saturday and Sunday. To make the most of your time, I always recommend attending on Thursday (VIP day) or Friday if your schedule allows. You’ll have easier access to the boats and more time for one-on-one conversations.

If catamarans are on your radar, plan ahead. The most popular models often require advanced appointments to board. Having a DWY broker schedule these showings ensures you won’t miss the boats you came to see.

Finally, don’t overlook the gear tents. Even if you’re not buying a boat this year, it’s worth spending time exploring the latest products and services—many companies also offer special show pricing.

The Annapolis Sailboat Show is more than just a display of yachts—it’s a gathering of the global sailing community. Walking the docks, you’ll hear accents from around the world, meet sailors with incredible stories, and experience the excitement of an event that truly captures the spirit of sailing.

Why Attend with David Walters Yachts

The Annapolis shows are some of the busiest and most energetic in the world. With hundreds of boats on display and thousands of visitors filling the harbor, it’s easy to get caught up in the excitement and overlook the yachts that matter most to you. Having one of our brokers with you transforms the entire experience.

We don’t just wander the docks; we create a plan based on your goals. If you’re interested in a new performance cruiser, we’ll take you directly to the models that match your sailing plans. If power is your focus, we’ll guide you through the trawlers, express cruisers, and motor yachts that suit your lifestyle. And if catamarans are on your radar, we’ll ensure you have access to the most popular models, where appointments are essential.

We also manage the details that make a difference. That means securing private showings, arranging sea trials, and making sure your time is used wisely—avoiding long lines and crowded docks. With our industry connections, we can guarantee you quality time aboard the yachts that deserve your attention.

Most importantly, we act as your advocate. We’ll give you honest, unbiased comparisons—new builds versus brokerage, ownership costs, and how different builders compare in terms of design, construction, and long-term value.

And when the day winds down, we’ll share local tips to make your visit smooth: where to grab a quick lunch between appointments, the best waterfront spots for a sunset, and how to navigate Annapolis like a local. With our team by your side, the shows aren’t overwhelming—they’re efficient, enjoyable, and tailored to you.

PRE-REGISTER SHOWINGS & CONSULTATIONS WITH DWY

Practical Tips

With hundreds of boats on display, miles of docks to cover, and thousands of visitors filling the harbor, the Annapolis Boat Shows can feel overwhelming without a plan. The key is preparation. By thinking ahead—whether it’s where you’ll park, how you’ll structure your day, or which yachts you want to prioritize—you’ll transform the experience from a casual walk through the crowds into a productive, enjoyable event.

This is where our team at David Walters Yachts comes in. We help clients focus on what matters most, schedule private showings, and ensure your time on the docks is efficient and tailored to your goals. Combined with a few practical strategies, you’ll get more out of the shows, avoid the common frustrations, and truly enjoy your time in Annapolis.

• Parking & Transportation – Downtown Annapolis is closed to public parking during the shows, and parking spaces in the historic district are very limited. The best option is to park at the Navy–Marine Corps Memorial Stadium (550 Taylor Ave, Annapolis, MD 21401), where parking costs $20 per vehicle per day. Shuttle buses run continuously between the stadium and the show gates, making this the most convenient and low-stress choice. If you’re staying nearby, consider walking, biking, or using a water taxi to avoid traffic around the harbor.
  
  
• Footwear – Expect a lot of walking and frequent boarding of boats. Wear comfortable, boat-friendly shoes with non-marking soles that slip on and off easily. Most exhibitors require shoes to be removed or covered before boarding.
  
  
• Timing Your Visit – Saturdays and Sundays are the busiest. If you want meaningful conversations with builders and brokers, arrive early in the morning or consider visiting on Thursday (VIP Day) or Friday, when crowds are lighter. Late afternoons are often quieter, making it a good time for second visits to yachts of interest.
  
  
• Appointments & Sea Trials – Popular models—especially new debuts and high-demand catamarans—require advance appointments to board. Work with a David Walters Yachts broker to schedule private showings. Sea trials are often available but must be arranged beforehand and are typically reserved for qualified buyers.
  
  
• Weather Preparation – October in Annapolis is generally mild, with daytime highs in the 60s–70s and cooler evenings. Conditions can change quickly, so dress in layers, bring a light jacket, and don’t forget sunscreen, sunglasses, and a hat for bright days on the docks.
  
  Current Weather Conditions in Annapolis:
  
  ANNAPOLIS WEATHER
  
  
• Stay Hydrated & Take Breaks – The shows cover a lot of ground, and it’s easy to lose track of time. Carry a water bottle, pace yourself, and take advantage of shaded areas or seating whenever possible. A short break makes a big difference during a full day.
  
  
• Food & Refreshments – There are food vendors inside the show gates, but Annapolis offers many excellent dining options just a few steps away. Restaurants along Main Street, Dock Street, and around City Dock make it easy to grab a quick bite without losing much time. For a sit-down meal, consider Carrol’s Creek, Boatyard Bar & Grill, or one of the waterfront establishments overlooking Ego Alley.
  
  
• Two Shows, Two Weekends – Remember that Annapolis hosts two separate events: the Powerboat Show (October 2–5) and the Sailboat Show (October 9–13). If your interests cover both, consider attending each weekend—or let us help you prioritize the show that best matches your goals.
  
  
• Evening Strategy – Annapolis fills up quickly during show weekends, and reservations at popular restaurants are essential. Book early if you have specific spots in mind, or plan for an earlier dinner to avoid the rush. Alternatively, enjoy cocktails and casual food around City Dock and take in the atmosphere as boats move through Ego Alley.
  
  
• Travel Light – A small bag or backpack is ideal for carrying a notebook, show guide, water, and a jacket. Keep it light—you’ll be climbing on and off boats all day, and bulky bags can quickly become a hassle.
  
  
• Capture Notes & Photos – After seeing several boats, details can start to blur together. Jot down quick notes, take photos of layouts and features, and keep a record of your impressions. This will make comparing options later much easier and more productive.
  
  

Beyond the Docks

Part of what makes the Annapolis shows so special is the city itself. Steeped in history and brimming with nautical charm, Annapolis offers far more than just the boats on display. Even if your primary focus is the shows, it’s worth taking a little extra time to enjoy what makes Annapolis one of the most unique boating destinations in the world.

• Historic Downtown – Stroll the cobblestone streets lined with colonial-era buildings, boutique shops, and galleries. Main Street leads straight to the harbor and is the heart of the action during the shows.
  
  
• U.S. Naval Academy – Just a short walk from City Dock, the Naval Academy is one of the most storied campuses in the country. Guided tours include Bancroft Hall, the Naval Academy Chapel, and the crypt of John Paul Jones, offering a glimpse into the history and traditions of the U.S. Navy.
  
  
• Ego Alley & City Dock – This is where all the action happens on the water. Boats parade up and down the narrow channel known as Ego Alley, while visitors enjoy people-watching, waterfront cafés, and live music.
  
  
• Sailing on the Chesapeake – Annapolis is often called “America’s Sailing Capital” for good reason. Several companies offer day sails and sunset cruises on the Chesapeake Bay aboard historic schooners, modern yachts, and even former America’s Cup contenders. It’s a must-do for anyone wanting to experience the city from the water.

If you have more time, there are other highlights worth exploring:

• Maryland State House – The oldest state capitol still in continuous use, where both the Continental Congress and the Maryland legislature once met.
  
  
• Annapolis Maritime Museum – A small but engaging museum that celebrates the city’s working waterfront heritage.
  
  
• Scenic Trails & Parks – Quiet Water Park and Sandy Point State Park offer a peaceful break from the bustle, with beautiful views of the Bay.
  
  
• Chesapeake Bay Cuisine – Beyond the show, take time to enjoy the area’s culinary specialties, from Maryland crab cakes to oysters fresh from the Bay.

Annapolis is more than just a backdrop for the shows—it’s a destination in its own right. With its mix of maritime heritage, colonial history, and lively waterfront culture, the city offers plenty to explore, whether you’re here for a day or planning an extended stay.

Dining Recommendations in Annapolis

After a long day walking the docks, one of the great pleasures of being in Annapolis is deciding where to eat. The city’s dining scene blends Chesapeake Bay heritage with Maryland’s famous seafood traditions and a touch of cosmopolitan flair. Whether you’re looking for a fine dining experience overlooking the harbor, a lively raw bar with friends, or a casual spot to recharge, Annapolis has something for every appetite. Here are some of my top recommendations:

After a long day walking the docks, one of the great pleasures of being in Annapolis is deciding where to eat. The city’s dining scene blends Chesapeake Bay heritage with Maryland’s famous seafood traditions and a touch of cosmopolitan flair. Whether you’re looking for a fine dining experience overlooking the harbor, a lively raw bar with friends, or a casual spot to recharge, Annapolis has something for every appetite. Here are some of my top recommendations:

• O’Learys Seafood – A local favorite for upscale seafood in an intimate setting. Known for its fresh, inventive dishes and attentive service, it’s a great choice for a refined dinner after the show.
  
  
• Carrol’s Creek Café – Located on Spa Creek, this restaurant combines panoramic waterfront views with a creative menu featuring local seafood, steaks, and Maryland crab cakes. A perfect spot for a client dinner or a quiet evening out.
  
  
• Boatyard Bar & Grill – A true sailor’s hangout, buzzing with energy and decorated with nautical memorabilia. Known for its raw bar, crab cakes, and casual atmosphere, it’s a must-visit for anyone in town for the boat shows.
  
  
• Chart House – An Annapolis institution on the waterfront, offering upscale dining with sweeping harbor views. The menu features fresh seafood, steaks, and a well-curated wine list, making it ideal for a more formal night out.
  
  
• Chick & Ruth’s Delly – A quirky Annapolis classic on Main Street, famous for hearty breakfasts, oversized sandwiches, and Maryland crab cakes. A fun, casual option for lunch or a quick bite.
  
  
• Vin 909 Winecafé – Tucked away in Eastport, this cozy neighborhood spot is known for its farm-to-table cuisine, wood-fired pizzas, and excellent wine list. A hidden gem worth the short walk from City Dock.
  
  
• Davis’ Pub – A laid-back Eastport favorite beloved by locals. Known for its crab pretzels, pub fare, and friendly atmosphere, it’s perfect for a relaxed evening with friends.
  
  
• McGarvey’s Saloon & Oyster Bar – Located right on the harbor, McGarvey’s is a lively spot for oysters, seafood, and a cold drink. A staple for both locals and visitors, especially during show week.

Annapolis is very much a food town, and during boat show weekends, restaurants fill quickly. Reservations are highly recommended if you have your eye on a particular spot. No matter your choice, dining in Annapolis is part of the experience—casual yet sophisticated, deeply tied to the Bay, and always welcoming.

Schedule Your Meeting with DWY

The Annapolis Boat Shows are among the busiest in the country, and the most desirable yachts—especially new model debuts and popular catamarans—often require appointments well in advance. To maximize your time, we recommend registering with us before the show. By doing so, you’ll receive guidance and support that go far beyond simply walking the docks.

When you register, our team will:

• Consult with you beforehand to understand your goals, preferences, and the yachts most relevant to your plans.
  
  
• Schedule private showings aboard yachts of interest, ensuring you have uninterrupted time to explore layouts, systems, and finishes. 
  
  
• Arrange sea trials where available so that you can experience performance on the water.
  
  
• Provide concierge-level service in Annapolis, from mapping out your show itinerary to sharing insider dining, accommodations, and local recommendations.
  
  
• Be your advocate on the docks, offering candid, unbiased advice as you evaluate both new builds and brokerage opportunities. 

This preparation ensures your visit is smooth, enjoyable, and productive. Instead of spending your time navigating logistics or waiting in lines, you’ll focus on what matters most—finding the yacht that best fits your lifestyle and cruising ambitions.

We encourage you to contact us early or register below so we can tailor the Annapolis Boat Show experience to your needs.