Waypoints Yacht Charters

06/23/2024

Discover the thrill of sailing with our ASA Sailing courses at Waypoints in St. Petersburg! Whether you're a beginner or looking to advance your skills, our certified instructors provide hands-on training in a stunning waterfront setting. Join us and set sail with confidence, mastering the art of sailing, connecting with fellow enthusiasts, and exploring the beautiful waters of St. Petersburg. Ready to embark on your next adventure?

06/21/2024

At Waypoints, we're passionate about the stories that names tell, especially when it comes to boats. Naming a boat is a deeply personal and often meaningful process, reflecting a blend of inspiration, tradition, and sentiment. Whether it's a tribute to a loved one, a nod to a favorite literary work, or a whimsical expression of a dream or adventure, each name carries its own unique tale.

One of our favorites is ""La Dolce Vita,"" a boat that perfectly captures the essence of the sweet life on the water. We love hearing these stories, as they connect us to the heart and soul of the boating community.

So, how did you name your boat? We'd love to hear the story behind your boat name!

06/21/2024

Thank you for choosing Waypoints BVI and for sharing your wonderful experience. We're thrilled to hear that our team and ""Pau Hanna II"" made your trip unforgettable. We can't wait to welcome you back in 2025!
Ready for your own unforgettable adventure? Book with Waypoints in the BVI to get a 5-Star Experience!

06/18/2024

Thank you so much for your kind words and for choosing Waypoints for your sailing adventure. We are delighted to hear that you had such a fantastic experience and that our team made your trip memorable.

We look forward to welcoming you back aboard Knot Online for more incredible voyages!

06/17/2024

Explore the world of sailing with ASA Classes in Annapolis, available now through September! Whether you're a beginner or an experienced sailor, there's something for everyone on the Chesapeake Bay.

Set sail on the Opportune Moment (2021 Dufour 430 - 3 cab), 39 North (2018 Sun Odyssey 389), or Second Wind (2022 Fountaine Pajot Isla 40). Join us at Waypoints Annapolis for ASA-certified courses all summer long. Learn the ropes, from Basic Seamanship to Advanced Ocean Cruising, and unlock new horizons in sailing.

Our ASA-certified instructors are dedicated to helping you become more competent and confident on the water. Plus, enjoy the luxury of learning aboard sailboats and catamarans equipped with all the amenities you need for a comfortable voyage.

Don't miss out on the opportunity to sail the Chesapeake Bay this summer. Reserve your spot today and embark on a journey of adventure and discovery!

06/15/2024

Ready for a new adventure in the BVI? We've got an itinerary filled with white sand beaches, turquoise waters and endless fun!
Day 1 Start your adventure by sailing to Norman Island. Hook a mooring ball, lower the dinghy, and explore the hidden treasures of the island. Snorkel at the Caves and enjoy a late lunch at Pirates Bight. Afterward, head back to your charter boat for some fun with the onboard water toys and enjoy an evening of dancing and drinks at W***y T.
Day 2 Begin with an early morning hike for stunning vistas, followed by a leisurely breakfast. Snorkel at The Indians and dive off the wreck of the Rhone. Sail up the Sir Francis Drake Channel to Cooper Island, where you can snorkel at Cistern Point or relax at the Cooper Island Beach Club. Don’t forget to reserve your overnight mooring with BoatyBall.
Day 3 Explore The Baths with its tunnels, caves, and clear water pools. Enjoy lunch with 360° views of the BVI, then sail to Leverick Bay for the night. This marina offers everything from fresh water to shopping and spa services.
Days 4 & 5 Sail to Anegada, looking out for dolphins and whales. Enjoy a lobster dinner and visit secluded beaches like Loblolly Bay or Cow Wreck Beach. Spend an extra day exploring the island, snorkeling, or trying bonefishing.
Day 6 Sail towards Jost Van D**e, stopping at The Dogs or Monkey Point for snorkeling. Enjoy Great Harbor’s unique beach bars and the only floating spa in the BVI. Secure an overnight mooring with BoatyBall.
Day 7 Have breakfast aboard your boat, then visit the famous Soggy Dollar beach bar in White Bay. Spend the day at the beach and head to Peter Island for a quiet and picturesque last night.
Day 8 Enjoy one last snorkel adventure or stroll on the beach before setting sail back to Nanny Cay.
Book your luxury yacht charter and experience the best sailing destination in the Caribbean!

06/13/2024

Waypoints Annapolis is thrilled to welcome Chelsea to our Corporate office in Eastport! Chelsea is leading the sales and customer service team at each Waypoints base. With our expanding fleet, she is excited to meet our guests and owners at ""the Hut"" and continue to build on projects like our ASA Program and the Waypoints Wanderers Program.

Chelsea has been a part of the Waypoints Yacht Charters family since July 2021 and brings over 8 years of experience. She lives in Annapolis with her husband, Chris, and their golden retriever, Coral. Chelsea loves sailing, biking, reading, and spending time with friends.

06/12/2024

Save big on your next yacht charter! Now through August 31, 2024, enjoy up to 30% off all charters at all Waypoints Yacht Charter Bases.

Book your luxury vacation today - there’s still time to book a last-minute boutique charter in June and July in the USVI and BVI.

Sail the turquoise waters of the Caribbean - the islands are easy to get to, have ideal weather, and offer endless adventures. Cruise in the most beautiful waters of the world!

This offer is valid for new and direct bareboat bookings only and cannot be combined with any other offer. Book now and set sail in style!

06/10/2024

Celebrate Pride in Annapolis with Waypoints Yacht Charters!

We had an absolute blast at the Annapolis Pride Parade on June 1st, and we're keeping the celebration afloat all month long. Whether you're cruising the Chesapeake Bay or soaking in the sights of historic Annapolis, Waypoints Yacht Charters offers a luxurious and unforgettable experience.

Join us in honoring love, diversity, and inclusion by celebrating Pride Month in style on one of our premium yachts. Enjoy the ultimate blend of adventure and comfort as you explore the beautiful waters and scenic coastlines.

Make this Pride Month one to remember with Waypoints Yacht Charters.

 

06/05/2024

Save big on your next yacht charter! Now through August 31, 2024, enjoy up to 30% off all charters at all Waypoints Yacht Charter Bases.

Book your luxury vacation today - there’s still time to book a last-minute boutique charter in June and July in the USVI and BVI.

Sail the turquoise waters of the Caribbean - the islands are easy to get to, have ideal weather, and offer endless adventures. Cruise in the most beautiful waters of the world!

This offer is valid for new and direct bareboat bookings only and cannot be combined with any other offer. Book now and set sail in style!

Have a question or comment about Waypoints? Fill out the form below and a Charter Specialist will be in touch! 443.225.4355312 Third Street, Suite 101Annapolis, MD 21403 [email protected] Severn Avenue, Suite 36, Bldg 15Annapolis, MD 21403 443.225.4355 ext. [email protected]...

06/05/2024

Look who just pulled in this morning to Waypoints Annapolis.

Second Wind - a 2022 Fountaine Pajot Isla 40

With all the comforts of home and room to comfortably sleep up to 6 guests, this luxurious Isla 40 is perfect for family cruising. She boasts a spacious owner’s cabin with a large, comfortable bathroom as well as two more cabins with a shared head.

As a proud successor of the Lucia 40, Second Wind benefits from dynamic inverted bows and offers great performance at sea. Her L-shaped galley is complete with a 3-burner stove, oven, double sink, and drawer-type refrigerators. The interior is designed to optimize space for her guests and provide an abundance of natural light. Safe movement around the deck is ensured by wide side-decks, flush hatches, and handrails on the coachroof. Like all of our luxury yachts, this Isla 40 features numerous amenities, including a water maker, air conditioning, and a generator for your utmost convenience.

Still weeks available for charter on the Chesapeake Bay this summer.

Visit our website to book online or call Chelsea at 443.225.4355

06/01/2024

Our ASA 101/103 courses, along with ASA 104 – Bareboat Cruising, are available at our Waypoints Florida location!

ASA 101 provides the foundation with keelboat basics, while ASA 103 enhances coastal cruising skills. ASA 104 takes you further, with a multi-day cruise in moderate coastal conditions. Learn advanced sailing skills, seamanship, and the responsibilities of being a skipper. With hands-on experience in operating engines, troubleshooting, and navigation, you'll gain the confidence for liveaboard life and provisioning. Reserve your spot today through the link in our bio and set sail on an unforgettable journey!

05/30/2024

Thank you so much for chartering with us in the BVI! We’re so glad you enjoyed your trip. Our team is always dedicated to providing the best experience at all out bases. Thank you for choosing Waypoints and recognizing our exceptional service. If you don't use Waypoints, you're missing out!

05/30/2024

No passport, no problem! Dive into the turquoise waters of the US Virgin Islands with Waypoints, where every charter is an adventure in paradise! From the sheltered oasis of Christmas Cove on Great St. James Island to the vibrant coral reefs of St. John, your journey awaits. Explore the untouched beauty of Lamesure Bay, the crystal-clear waters of Caneel Bay, and the pristine beaches of Hawksnest and Cinnamon Bay. Book your charter with us to make memories in this tropical haven!

05/27/2024

From all of us at Waypoints Yacht Charters, we wish you a safe and memorable Memorial Day! Let's honor the past, celebrate the present, and look forward to a future filled with hope and possibility.

05/25/2024

Ladies, are you ready for the ultimate girls' getaway? Look no further than Waypoints Yacht Charters for a luxurious escape like no other! Whether you're craving relaxation on pristine beaches or seeking adventure on the open seas, we've got you covered!

Picture yourself soaking up the sun aboard a stunning yacht, sipping cocktails with your besties as you sail through turquoise waters and discover hidden gems in exotic destinations! With Waypoints, every moment is filled with luxury, laughter, and unforgettable memories!

Indulge in world-class service, gourmet dining experiences, and unparalleled comfort as you explore breathtaking destinations with your squad! From the Caribbean to Annapolis, the possibilities are endless!
So round up your girls, pack your bags, and let's set sail on the adventure of a lifetime! Your girls' trip awaits with Waypoints Yacht Charters! Book now and let the countdown to paradise begin!

05/22/2024

Look who we spotted watching the Blue Angels practice yesterday!

DARK STAR! 2019 Fountaine Pajot Saona 47 Maestro - 3 + 1 cab. Catamaran

She’s available for charter out of our Annapolis base this summer. Dates still available.

Dark Star’s timeless elegance and lovely entertaining areas are perfect for your Maryland vacation charter. The outdoor cockpit was designed with dining and relaxing in mind. Open the large sliding glass doors and open up to the spacious indoor salon and galley with 360-degree water views. Making meals is always a treat with the well-equipped galley with stove, oven, microwave, refrigerators, freezer, coffee maker, plenty of counter space, Bluetooth speakers, TV, and the necessary kitchen equipment.
6 people can sleep comfortably in 3 cabins. You will find an expansive owner’s version suite on the port side with all the comforts of home. The starboard hull has 2 full cabins and 2 private heads. A v-berth cabin is accessible from the inside for the little one or teen who wants to sleep alone.
She is equipped with air conditioning, a dinghy with outboard, generator, and appropriate navigational equipment and safety equipment. Your captain will love sailing at the helm, steps above the cockpit, and has a large lounging area for other guests on top deck.

Contact Chelsea for details 443.225.4355 or book online at www.waypoints.com

05/22/2024

Thank you for choosing Waypoints USVI for your bareboat charter adventure, and we're delighted to hear that your experience was nothing short of fantastic!

A huge shoutout to Chelsea, Jaime, Nancy, Andrew, Larry, and especially Dan for going above and beyond to ensure your vacation was smooth sailing from start to finish! Your kind words mean the world to us, and we're so grateful for the opportunity to be a part of your first-time sailing adventure in the Virgin Islands!

We're thrilled to hear that despite a last-minute boat switch, our team was able to handle it professionally, allowing you to enjoy a wonderful vacation filled with unforgettable memories! Thank you for your trust and recommendation, it truly means everything to us! Here's to many more amazing sailing adventures ahead!

05/20/2024

Make your next celebration unforgettable with Waypoints St. Pete! Whether it's Memorial Day, the 4th of July, or any special event, our elevated charter experiences in St. Petersburg, FL are the perfect way to celebrate in style. From our expert charter specialists to our knowledgeable captains, we'll help you navigate the best marinas, local hotspots, and more, ensuring a cruise on the Tampa Bay like no other.

Experience the wildlife and nightlife of Florida's Gulf Coast as you sail through beautiful seaside towns, anchor in secluded spots, and soak up the sun on white sandy beaches. Keep your camera ready to capture breathtaking views of the Skyway Bridge and encounters with dolphins, ospreys, herons, and more.

Waypoints in St. Pete offers sunset cruises and corporate team-building events and bachelorette parties, making every occasion an unforgettable adventure. 🥂 Book your charter today and let the festivities begin!

05/19/2024

News from the BVI-No More Off-Season

American Airlines will operate multiple daily flights from Miami to the BVI throughout 2024, ramping up frequency during peak winter travel periods.

The airline’s schedule includes:
– July: 3 flights daily
– August: 2 flights daily
– September: 1 flight daily
– October: 2 flights daily
– November: 2 flights daily, 3 on Saturdays
– December: 4 flights daily, 5 on Saturdays

https://www.284media.com/travel-and-tourism/2024/05/18/no-more-off-season-american-airlines-maintains-bvi-service-all-year/

American Airlines will offer uninterrupted flight service to the British Virgin Islands throughout 2024, even during the historically slower travel months of July to October. This marks the first time a major carrier has maintained continuous operations to the territory year-round. The BVI Airports....

05/18/2024

LAST CALL!!

We have an exclusive opportunity to watch the Blue Angels from the luxurious 39North. This Sun Odyssey 389 offers comfort, space, and exceptional quality, ensuring a luxurious and enjoyable sailing and viewing experience. With a distinctive design, bright and airy interior, and ample accommodations for up to 8 people, this is a chance you won't want to miss.

Expertly captained and featuring a wide swim platform, tech woodwork, and plush upholstery, the 39North is perfect for a thrilling day on the water. Imagine the breathtaking views as the Blue Angels soar above the Chesapeake Bay, offering a unique and memorable experience.

Call Chelsea at 443.225.4355 to book now!

A uniquely elevated charter experience. New model yachts in premier destinations.

05/16/2024

Dive into summer with an unforgettable family vacation! Whether you're craving the coastal charm of Annapolis, the tropical paradise of the BVI, USVI, Bahamas, or the sunny shores of St. Pete, Florida, Waypoints has you covered! From sailing adventures to beachfront bliss, there's something for everyone to enjoy. Book now and make this summer one to remember with Waypoints!

05/14/2024

Discover the charm of Annapolis and the beauty of the Chesapeake Bay with our sample long weekend itinerary!

Day 1: Set sail from Annapolis Harbor to Herrington Harbor South for a resort-style retreat with dining, shopping, and relaxation options galore.

Day 2: Cruise to Solomon’s Island, a picturesque fishing village offering history, seafood, and waterfront delights. Don't miss the Calvert Marine Museum and a refreshing Mai-Tai at The Tiki Bar!

Day 3: Explore the historic town of Cambridge, steeped in colonial heritage and rich with tales of the Underground Railroad. Visit museums and stroll past elegant 19th-century homes.

Day 4: Sail back to Annapolis, with a stop for a swim and snacks in Whitehall Bay or Mill Creek before returning to our docks. Book your Annapolis adventure today and create memories to last a lifetime!

05/11/2024

Come by and see us at today and tomorrow.

Book a charter with us during the VIBE Boat Show and save %15.
Available at any of our bases.

New and direct bookings only!

05/10/2024

Thank you so much for your kind words and for choosing Waypoints once again for your unforgettable BVI adventure! We're thrilled to hear that Anthony and our team made your charter experience exceed expectations. Rest assured, we'll keep striving to provide top-notch service and make every detail perfect for your next trip with us! Can't wait to welcome you back onboard for another incredible journey next year! # 5Star Experience

05/02/2024

Congrats CovingtonAlsina
Happy May Day!

CovingtonAlsina, LLC is a registered investment adviser. This platform is solely for informational purposes and is not offering advisory services or sales of securities.

05/01/2024

USVI is number one! 🏆🏝️ Trunk Bay Beach on St. John was just ranked first among The World's 50 Best Beaches on the annual list curated by travel experts, influencers and enthusiasts.

With pristine white sand and crystal-clear turquoise waters showcasing its vibrant coral reefs, Trunk Bay offers a gorgeous display both above and below the water. 🪸

Learn more about this stunning beach situated in the Virgin Islands National Park: https://worlds50beaches.com/trunk-bay/

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