Waypoints Yacht Charters

09/04/2026

Wishing you a happy Labor Day weekend! 🇺🇸☀️

Take some time to relax, enjoy the sunshine, and make the most of the long weekend.

09/03/2026

Mark your calendars! 🗓️

Waypoints Yacht Charters is hitting the docks at two of the biggest sailing events of the fall.

⛵ Newport International Boat Show
September 17–20 | Newport, RI

⛵ Annapolis Boat Shows' Fall Sailboat Show
October 15–18 | Annapolis, MD

Stop by, talk to the team, and start planning your next adventure with Waypoints.

More details coming soon!

09/01/2026

🍂 Fall Special — Save 15% on Caribbean charters booked October 1 through December 15!

And this year, Waypoints is excited to welcome to our 2026 fleet a stunning lineup of Fountaine Pajot catamarans now sailing the BVI and USVI.

New boats, fewer crowds, trade winds — the BVI and USVI don't have an off season — just better deals.

📅 Valid for Caribbean charters October 1 – December 15, 2026
💰 Save 15% when you book today
⛵ New fleet additions now available
👉 Book now at waypoints.com or call 443.225.4355

*New and direct bookings only. Blackout dates may apply. May not be combined with any other promotion.

08/28/2026

🍂 Fall is one of the best times to sail into Downtown Annapolis.

Dock just steps from charming shops, waterfront restaurants, and years of history. With crisp air, colorful foliage, and endless places to explore, there's no better way to experience America's Sailing Capital. ⛵

08/27/2026

A Caribbean charter has its own rhythm, and it rarely begins the week you step aboard.

We help travelers plan charters across our Caribbean bases in the British Virgin Islands, the US Virgin Islands, the Bahamas, and Belize, and the questions we hear this time of year tend to circle the same handful of things:

✔️ When to go
✔️ What’s worth timing a trip around
✔️ How far ahead any of it needs to be locked in

Here’s what’s worth knowing before you build your 2027 itinerary.

A Caribbean charter has its own rhythm, and it rarely begins the week you step aboard.  It begins months earlier, with a calendar open on the kitchen

08/24/2026

☀️ A Great Day on the Bay with Visit Annapolis & Anne Arundel County! ⛵️

There’s no better place to connect than out on the Chesapeake Bay! We had a fantastic day welcoming members of Visit Annapolis & Anne Arundel County aboard Waypoints Yacht Charters for an afternoon of sailing, networking, and incredible views. With a catered lunch, mimosa bar, and a cruise past the iconic Thomas Point Lighthouse, it was networking — Chesapeake style. 🥂⛵️

Looking for a fresh idea for your next company gathering? Our Annapolis fleet is available now for Day Charters, perfect for:

⚓ Corporate retreats
⚓ Team-building outings
⚓ Client appreciation events
⚓ Networking gatherings
⚓ Celebrations & group charters

Trade the boardroom for the Bay and let Waypoints customize a charter experience for your group — from catering and cocktails to an itinerary designed just for you.

Your team. Your charter. Your day on the Bay.

https://waypoints.com/destinations/annapolis-md/

BWI Airport Marriott
Maritime Conference Center
Annapolis Waterfront Hotel, Autograph Collection
Visit Annapolis & Anne Arundel County
Hampton by Hilton Arundel Mills

08/22/2026

Three charters. Countless memories. ✨

We’re grateful to have guests who continue to choose Waypoints for their time on the water. From first-time sailors to seasoned charterers, like this review reflects, our team is dedicated to making every experience seamless — from check-in to cast-off and beyond.

Thank you for continuing to trust Waypoints with your Annapolis adventures. We can’t wait to welcome you back for your next journey! ⚓

08/20/2026

⚓ Captained by day. Bareboat by night. 🐷

Turquoise water? Check.
Zero itinerary stress? Double check.
A confident pig who's 100% convinced he's crew? Absolutely non-negotiable.

This winter, trade your skis and mittens for the warmth of sun. Cruise the Bahamas your way — full crew when you want it, total freedom when you don't (and yes, the pig comes with strong opinions about anchor spots).

☀️ Winter in the Bahamas is calling
🌊 Create your own itinerary
🐖 Crew morale: surprisingly high

Book your Bahama winter getaway with Waypoints Yacht Charters today: https://waypoints.com/destinations/bahamas/

08/18/2026

🎉 Celebrate Life's Biggest Moments on the Water 🎉

🎂 Birthdays
💍 Engagements
⌛ Anniversaries
🎓 Graduations
✨ Milestones

Some moments deserve more than a dinner reservation. Enjoy your next big occasion with open water, new adventures, and memories made aboard a Waypoints charter.

View all of our charter locations and find your perfect celebration destination at Waypoints.com.

08/14/2026

🌴 Leave the planning behind and enjoy a truly effortless getaway.

With a Waypoints All-Inclusive Crewed Charter, every detail is taken care of:

• Professional captain
• Private chef
• Customized itineraries
• Gourmet meals & open bar
• Access to water toys
• and more!

Our crewed charters let you relax, reconnect, and make the most of every moment.

Book yours at Waypoints.com