We are open May 6th - October 8th 2022. Please book directly with us via our website! We look forward to welcoming you at our beautiful place on Cape Cod.
Pleasant Bay on Cape Cod is a serene escape offering stunning views, outdoor adventures, and luxurious experiences far from the crowds. Here's a quick look at the 7 must-visit spots:
Best Times to Visit:
Whether you're into kayaking, fine dining, or peaceful nature retreats, Pleasant Bay offers something for everyone.
Tucked away on the border of Chatham and Harwich, Jackknife Cove is a peaceful retreat along Pleasant Bay. This charming spot is open to the public for free, offering a slice of Cape Cod's calm and beauty in a naturally sheltered nook.
The warm waters here are perfect for a safe and refreshing family swim, while the unpolished sands and quiet surroundings create an authentic coastal escape.
If you're an early riser, the hours before 9:00 AM are ideal for enjoying the serene atmosphere. In the evenings, after 6:00 PM, the cove transforms into a stunning vantage point for sunsets over Pleasant Bay. Locals especially treasure these times for leisurely walks along the shore, setting the tone for relaxed evenings by the coast.
Jackknife Cove is also a fantastic starting point for kayaking. Here are three popular routes to explore:
For those seeking privacy, some high-end properties in the area provide exclusive beach access. For example, a luxury home in North Chatham offers breathtaking saltwater views of Pleasant Bay along with access to 330 feet of private beachfront [3].
Located at Cape Cod’s "elbow" [2], Jackknife Cove benefits from a naturally sheltered environment that has made it a favorite among locals. Its unique blend of accessibility and solitude makes it a true hidden treasure along Pleasant Bay.
Just 930 feet off Eastward Point in Chatham, Strong Island spans 75 acres of pure Cape Cod wilderness. This tucked-away haven is a mix of thick pine and oak forests, scenic trails, and prime spots for spotting wildlife.
Strong Island boasts a 1.7-mile trail system that winds through woodlands of pine and oak. The trails vary from packed soil to soft beach sand, with gentle hills rising up to 60 feet [8]. Along the way, you’ll encounter:
The island's isolation makes it a prime spot for observing wildlife. Birdwatchers will love May, when migratory birds return to the area [4]. On the eastern edge, visitors can often spot Cape Cod’s famous gray and harbor seals - an estimated 50,000 of them inhabit these waters [6]. Plan your visit carefully to make the most of these sights.
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To help protect Strong Island’s environment, visitors are asked to follow these simple rules:
Strong Island offers a rare chance to experience Cape Cod as it once was - untouched and wild. Whether you’re hiking, birdwatching, or just soaking in the views, this nature reserve is a must-visit for anyone craving an authentic coastal adventure.
Tucked inside an 18th-century sea captain's home, Twenty-Eight Atlantic is Cape Cod's only Forbes Five-Star restaurant [9]. With floor-to-ceiling windows offering breathtaking views of Pleasant Bay and the Atlantic Ocean, this spot blends coastal charm with an unforgettable dining experience.
Executive Chef James Hackney curates seasonal menus that highlight the best of local seafood and produce, all presented with artistic finesse. The dining options cater to a variety of tastes:
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This carefully crafted menu reflects the rich culinary traditions of Cape Cod while adding a refined, modern twist.
The dining room is a seamless mix of historic charm and modern elegance. Nautical accents and timeless details create a warm, inviting atmosphere that shifts with the time of day:
"Housed in an 18th-century sea captain's home overlooking Pleasant Bay and the Atlantic beyond, this is one of the most stunning settings in New England." – Wequassett.com [9]
The menu celebrates the flavors of the sea, with a focus on fresh, locally sourced ingredients. A standout dish? The butter-braised lobster - a true indulgence for those seeking a taste of coastal luxury.
For a more intimate experience, the restaurant offers a private dining room with sweeping water views and access to two outdoor verandahs. Guests can enjoy personalized service and tailored menus, making it a perfect choice for special occasions.
At Twenty-Eight Atlantic, dining is elevated into an art form, blending coastal elegance with Cape Cod’s rich heritage for a truly memorable experience.
Step aboard Blue Claw Boat Tours and uncover the hidden gems of Pleasant Bay through their personalized excursions. These tours offer a fresh perspective on Cape Cod's stunning waters, blending exclusivity and adventure. With an impressive 4.9/5 rating from 236 reviews [10], they’re a standout choice for exploring the area’s natural beauty and marine life.
Blue Claw’s fleet is designed with both safety and comfort in mind, meeting US Coast Guard standards. Their latest vessel, the Duffy 35, can host up to 17 passengers [11], making it perfect for family outings or small group adventures. The boat’s spacious deck allows for unobstructed views while maintaining an intimate ambiance.
Here’s a glimpse at the variety of tours available:
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Captain Rob leads guests to some of Pleasant Bay’s most picturesque spots. Along the way, you’ll likely encounter:
This combination of breathtaking scenery and expert narration creates a memorable maritime experience.
To make the most of your tour, consider these seasonal tips:
Before setting sail, keep these practical tips in mind:
"Had an amazing time. It was perfect for our family of 9, including 3 little ones. We got super close to the seals and saw a lot of beautiful homes. Captain Rob was very knowledgeable and friendly. Worth the money for a private tour, we'd do it again in a heartbeat!" - Jack D [11]
Blue Claw Boat Tours offers more than just a ride - it’s an intimate journey through Pleasant Bay’s natural wonders and Cape Cod’s maritime charm. With personalized service and local expertise, every tour promises a unique and unforgettable experience.
This isn’t your typical boat ride. The Floating Classroom offers a hands-on marine education experience aboard The Friend, a 37-foot solar-powered pontoon boat. Designed with both comfort and learning in mind, the vessel creates an intimate setting for up to 29 passengers to explore the rich coastal heritage of Pleasant Bay [13].
This eco-conscious vessel is packed with features that enhance the experience:
Guided by PBCB Science Advisor Sarah Griscom, these tours dive into Pleasant Bay’s natural and maritime history. Here’s a glimpse of what you’ll explore:
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Thanks to its quiet electric motors, The Friend offers an exceptional opportunity to observe seals, seabirds, and other marine life without disturbing their natural behavior.
Prepare for your adventure with these simple suggestions:
Looking for a more personalized outing? Private tours are available and can be tailored to your interests. These exclusive adventures include:
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Each spring, the Floating Classroom serves around 700 local students, making it a cornerstone of Pleasant Bay’s marine education efforts. Whether you join a public program or book a private excursion, this experience is a fantastic way to connect with the bay’s natural beauty and rich history.
Tucked away in a beautifully restored 1798 building between Chatham and Orleans, A Little Inn on Pleasant Bay offers a cozy waterfront escape that captures the essence of Cape Cod. This women-owned gem, with interiors designed by Matthew Yee, seamlessly blends historic charm with modern comforts [19].
The inn's location is nothing short of spectacular, with sweeping views of Pleasant Bay. Surrounded by elegant English gardens, the property feels like a serene retreat. A private dock extends right to the water, making it easy to soak in the beauty of the bay [16]. It's the perfect backdrop for an unforgettable getaway.
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Each room at the inn is individually designed with meticulous attention to detail, offering either garden or bay views. Guests can expect:
The inn's dedication to providing an outstanding experience is reflected in its flawless 5.0 rating on Tripadvisor, based on 633 glowing reviews [16].
"There's magic on the Cape and it's found at A Little Inn on Pleasant Bay... Leaving the Inn was like leaving family and friends after a wonderful visit. It is simply a magical place that reflects the heart and soul of the Cape."
What truly sets this inn apart is its warm and attentive service. The multilingual staff, fluent in English, Spanish, and French, goes above and beyond with concierge services and tailored dining recommendations. As one guest, Suzanna F., put it:
"A Little Inn on Pleasant Bay is an absolute must if you plan to go to the Cape, as they call it. The owners welcome you in a way unlike any other place I have been" [17].
From the thoughtful details to the heartfelt hospitality, every moment at A Little Inn on Pleasant Bay feels like a celebration of Cape Cod's timeless charm.
Set sail along Cape Cod's breathtaking coastline with exclusive private charters. Operating out of the Wequassett Resort & Golf Club, Down Cape Charters & Boat Rentals offers unforgettable sailing experiences aboard their elegant fleet [21]. Below, you'll find details about the charter options, highlights, and extras that make these trips truly special.
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For a more tailored experience, Sweet Yacht Charter offers full-day excursions aboard a 36-foot Hinckley yacht. These trips include activities like whale watching, exploring secluded beaches, and cruising along Chatham's scenic coastline [20]. Each charter includes an experienced captain, fuel, and refreshments to ensure a smooth and enjoyable journey.
Pleasant Bay's tranquil waters provide the perfect backdrop for exploring Cape Cod's natural beauty. Popular highlights include:
Enhance your sailing experience with these thoughtful extras:
For the calmest waters, consider a morning charter. If you're seeking a bit more excitement, opt for an afternoon sail.
What to Bring:
Whether you're planning a romantic sunset cruise or a full-day adventure to Nantucket, these charters cater to a variety of occasions. Advanced bookings are highly recommended, especially during the peak summer months from June through September.
Pleasant Bay remains one of Cape Cod's standout destinations, offering travelers a mix of natural beauty, upscale amenities, and thoughtfully designed experiences. It's the perfect retreat for those looking to escape the usual tourist spots and indulge in something more refined.
To fully appreciate all that Pleasant Bay has to offer, timing your trip is key. The shoulder seasons - April to June and September to October - offer mild weather and fewer crowds, making them ideal for a relaxed visit. If you're planning a summer getaway, be sure to book well in advance to secure top-tier accommodations and activities during the busy months.
Pleasant Bay's charm lies in its ability to create unforgettable memories through its unique blend of luxury and tranquility. As one resort eloquently puts it:
"Some places are more than a destination. They become a part of you." [1]
Here's a quick guide to help you decide the best time to visit:
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To make the most of your time at Pleasant Bay, consider these insider tips:
With its serene landscapes and carefully curated experiences, Pleasant Bay offers a true taste of Cape Cod's elegance. As one guest described it:
"There's magic on the Cape and it's found at A Little Inn on Pleasant Bay... It is simply a magical place that reflects the heart and soul of the Cape." [17]
The ideal time to visit Pleasant Bay for a calm and rejuvenating getaway is during May, June, September, and October. These months, often referred to as the shoulder season, bring pleasant weather, fewer tourists, and a peaceful ambiance. It's the perfect window to soak in the area's natural charm and upscale offerings without the busy summer crowds.
During these periods, you’ll enjoy mild temperatures, sunny skies, and quiet beaches. Whether you're wandering through hidden coves, indulging in exquisite dining, or relaxing at a cozy boutique inn, these months provide a serene and more intimate experience.
When gearing up for a kayaking adventure at Jackknife Cove, timing and preparation make all the difference. Plan your outing around the tides to steer clear of strong currents - calmer waters are usually found a few hours before or after high tide. And don’t forget to check the weather forecast to ensure conditions are safe for your trip.
Pack the essentials for safety: life jackets, a whistle, and a small first aid kit should always be on hand. If you’re heading toward Muddy Creek, keep in mind that the round trip is about 2.4 miles, making it a great choice for beginners or families looking for a manageable route. While exploring, remember to keep a respectful distance from wildlife to help protect the area’s natural charm.
To arrange a private dining experience at Twenty-Eight Atlantic, reach out to their catering team by calling 508-430-3025 or emailing Amy Farrell at afarrell@wequassett.com. Since this experience is highly sought after, securing your reservation well in advance is a smart move.
Your visit will feature an elegant atmosphere paired with breathtaking waterfront views, ideal for hosting up to 50 guests. The menu, crafted by Executive Chef James Hackney, showcases the finest local seafood and organic ingredients, promising a refined and memorable dining experience.
If you're looking for a peaceful and personal Cape Cod experience this spring, now's the time to book your stay at A Little Inn on Pleasant Bay. With its quiet setting, friendly hosts, and small seasonal touches that make a big difference, it’s a great place to relax and enjoy the best bed and breakfast in Cape Cod. Whether you’re planning a weekend getaway or a longer break, don’t wait too long—spring is one of the best times to visit, and rooms can fill up fast.
