The Perks of Being a Regular: Your Guide to Waypoints Wanderer Benefits
Your first charter is just the beginning. The moment you complete your first sailing vacation with Waypoints Yacht Charters, you’re automatically enrolled in the Waypoints Wanderer program.
No forms to fill out, no membership fees, no complicated point systems to track.
The Wanderer program recognizes something we’ve learned over years of hosting charter guests: the best sailors are the ones who come back.
They’re the ones who develop favorite anchorages, who greet beach bar owners by name, who know exactly which route to sail based on the wind forecast. They’re the ones who’ve transformed from visitors into insiders.
Your Wanderer benefits remain active for 36 months from your last charter, giving you plenty of flexibility to plan your next adventure. And those benefits travel with you across all Waypoints bases in the USVI, BVI, and Annapolis. As you consider planning your first (or next) yacht charter with us, let’s break down all the benefits you’ll enjoy when you continue to travel with Waypoints.
What It Means to Be a Wanderer
There’s a distinct difference between chartering once and becoming a Wanderer.
First-time charterers are still figuring out the basics: how to pick up a mooring ball, which beaches have the best snorkeling, and whether to provision before or after boat checkout. They’re learning.
Wanderers know their favorite anchorages. They’ve sailed enough to recognize which routes work best in different wind conditions. They walk into island bars and restaurants with the confidence of someone who belongs there.
That’s what the Wanderer program celebrates. You’ve crossed the line from curious visitor to genuine sailor, and we want to welcome you back like the regular you’ve become.
Your Wanderer Benefits
10% Off All Future Charters
The most straightforward benefit: every charter you book as a Wanderer saves you 10%.
On an eight-day charter costing $6,000, that’s $600 back in your pocket. Over three charters, you’re saving nearly $2,000.
This discount can not be combined with other promotional offers and is valid for direct bookings only, but it’s active for any charter you book within 36 months of your last trip. And it works at any Waypoints base, so if you sailed the USVI last year, your discount applies when you try BVI or Annapolis this year.
Exclusive Welcome Gift Package
We greet returning Wanderers with a welcome package that acknowledges you’re not a first-timer anymore. It’s waiting for you when you arrive for your next charter.
First Access to Special Events
Wanderers get priority booking for our annual Waypoints Rendezvous, where charter guests from across our fleet gather for a weekend of sailing, socializing, and celebrating the community we’ve built.
You’ll also receive invitations to our member-only happy hour at the Annapolis Boat Show and be the first to know about new yachts joining our fleet and special offerings before they’re announced publicly.
Sailing Education Discount
Save $200 off any private ASA sailing instruction course. It’s perfect for Wanderers who want to level up their skills between charters or work toward their captain’s certification.
Sail Like a Local: Your Island Insider Access
This is where being a Wanderer really shines. Walk into your favorite beach bars and restaurants across the Caribbean and Chesapeake Bay, and you’re treated like the regular you’ve become.
We’ve built partnerships with the venues where our charter guests naturally spend time, the places you’ll dinghy to after anchoring, the restaurants you’ll visit while provisioning, and the bars where you’ll watch the sunset.
In the USVI
- The Beach Bar (St. John) – Free Painkiller or Rum Punch. These signature Caribbean cocktails define island sailing, and Beach Bar serves them perfectly.
- Pizza Pi (St. Thomas) – Free frozen cocktail with pizza purchase, limit two per charter. The floating pizza boat at Christmas Cove is already a charter highlight. Now your drinks are on us.
- Shupe’s on the Boardwalk (St. Croix) – One free draft beer. Perfect for celebrating that forty-mile blue water crossing you just completed.
- Lovango Resort & Beach Club (St. John) – 10% discount on daytime beach club offerings. Access to the pool, restaurant, and beach amenities with your Wanderer discount makes this upscale stop even more appealing.
- Island Love Coffee (St. Thomas) – Buy two drinks, get a free twelve-ounce bottle of cold brew. Fuel for those early morning departures when you want to reach the next anchorage before the afternoon winds pick up.
- Lime Out (St. Thomas) – Free cocktail with taco purchase. The floating taco bar in Coral Bay represents everything great about Virgin Islands cruising. Now your first drink is included.
In the BVI
- B-Line Bar (Little Jost Van Dyke) – 10% discount on drinks and merchandise, plus the captain eats free with five or more guests. Little Jost Van Dyke is already quieter than its famous neighbor. These perks make it even better.
- Tommy Gaunt Kitesurfing (Anegada) – 10% off kite lessons, snorkel trips, and EcoMangrove SUP/Kayak tours. Explore Anegada’s shallow waters and mangrove channels with expert local guides.
- Quito’s Gazebo & Luxury Inn (Cane Garden Bay, Tortola) – 5% discount on hotel rooms booked before, during, or after your charter. Perfect for Wanderers who want to extend their trip with a night or two on land.
- Omar’s Cafe (Nanny Cay & West End, Tortola) – Breakfast brings free cups of regular coffee (drip coffee, not espresso). At lunch, enjoy complimentary Omar’s Mule or Omar’s Special Rum Punch. Start and end your sailing day the right way.
- Potters by the Sea (Anegada) – 10% discount on dinner plus complimentary Potter’s Rum Punch following your meal. Anegada’s restaurant scene rewards Wanderers who make the sail to this remote island.
In Annapolis
- Bread and Butter Kitchen – 15% off a meal or catering, excludes retail. Provision like a local before heading out into the Chesapeake Bay.
- Chart House – Free appetizer or dessert with meal purchase. Waterfront dining in downtown Annapolis with your Wanderer discount.
- O’Leary’s Seafood – Free dessert for the table, up to six people. Celebrate your Chesapeake Bay sailing with Maryland’s famous seafood.
- 727 Sailbags – 30% off any 727 product. Take home bags, accessories, and gear made from reclaimed sails, a perfect reminder of your charter.
Why These Partnerships Matter
We didn’t randomly select these venues. Every bar, restaurant, and shop on this list represents a place our charter guests naturally visit during their trips.
Beach bars you’ll dinghy to after anchoring. Restaurants near our marinas where you’ll grab dinner on your first or last night. Coffee shops you’ll pass while provisioning. Gear shops selling exactly what sailors need.
The owners know Waypoints. They know sailors. They take care of our Wanderers because they’ve built relationships with our guests over the years.
It’s the difference between being a customer and being recognized, between asking for directions and already knowing where you’re going.
Making the Most of Your 36 Months
The three-year window gives you flexibility, not pressure. Many Wanderers book their next charter before leaving, already planning which routes they want to explore next. Others take time to experience different seasons or try new destinations. Some sail annually, others every other year.
The key is sailing at least once every three years to keep your status active. Each charter resets your 36-month clock, so Wanderers who return regularly never lose their benefits.
Share your Wanderer status on social media with #WaypointsWanderer. We love seeing where our community sails and which anchorages become your favorites.
Ready to Become a Wanderer?
Your first charter automatically enrolls you. No applications, no membership fees, no complicated programs to navigate. Just sail with us once, and you’re part of the community. And we will send you your Waypoints Wanderers membership card.
Contact our Waypoints Yacht Charter Consultants to book your first charter or plan your return as a Wanderer. The benefits are waiting (and so are the free cocktails!).