Planning a BVI Anniversary Charter: A Couple’s Guide
We get a specific kind of booking request a few times a season: a couple who got married on a boat, or near one, coming back years later to mark the anniversary the same way. It’s a different ask than a honeymoon or a proposal charter — there’s no ring to hide, no new-marriage jitters, just two people who want a few hours back on the water together, away from the group chat planning everyone’s dinner reservations. If that’s you, here’s how we’d actually plan it.
Picking the Right Charter Length
The charter you choose shapes the whole feel of the day, so it’s worth matching it to what you actually want out of the anniversary rather than defaulting to the longest option.
Our Sunset & Dinner Charter starts at $900 and runs 3–4 hours — a cruise out to a dinner destination timed around golden hour, which is generally our top recommendation for anniversaries. It’s long enough to feel like an occasion without eating your whole day, and the timing does a lot of the romantic heavy lifting on its own.
If you’d rather spend the afternoon in the water before dinner, our Half Day Charter starts at $1,450 for 4–5 hours and two stops of your choosing — enough time to snorkel a favorite spot and still make it back for a quiet evening. And if you want the whole day, our Full Day Charter starts at $1,950 for up to 8 hours and four stops, which suits couples who want to revisit several places that mattered to them rather than picking just one.
Choosing a Setting That Feels Like Yours
Some couples want to return to the exact spot where they got engaged or married. Others just want somewhere quiet that isn’t packed with day-trippers. A few options worth considering:
- White Bay, Jost Van Dyke — for couples who want the swim-ashore, beach-bar energy of the island where a lot of BVI proposals and honeymoons happen; see our Jost Van Dyke day trip guide for the full picture of the island.
- The Baths, Virgin Gorda — dramatic granite boulders and swim-through grottos, good for a couple who wants scenery that photographs like nowhere else; our Baths guide covers logistics and timing.
- Spring Bay and Devil’s Bay, Virgin Gorda — quieter than the Baths proper, and often less crowded for a calmer version of the same coastline, covered in our Spring Bay guide.
When you book, tell us the occasion and any spot that means something to you — our crew plans routes around specific requests like this regularly, and we’re happy to build the day around a particular anchorage rather than a standard itinerary.
Marking a Milestone, Not Just a Date
There’s a difference between “we’ve been married a year” and “we’ve been married twenty-five years,” and it’s worth being honest with yourselves about which kind of anniversary you’re planning for. A first or fifth anniversary often works well as a spontaneous half-day add-on to a broader BVI trip — you’re already here, the water’s right there, why not spend an afternoon on it together. A milestone anniversary — tenth, twenty-fifth, fiftieth — tends to deserve more intention: the full day charter so you’re not clock-watching, a specific island you’ve talked about for years, maybe even timing the trip to land on the actual date rather than whatever day happens to be open.
We’ve had couples charter a boat specifically to revisit the anchorage where they got married on a sailing yacht decades earlier, and we’ve had couples who just wanted four hours away from a family reunion happening on land. Both are valid reasons to book, and both deserve a charter built around what actually matters to you rather than a generic “romantic day on the water” template.
The Small Touches Are on You (and That’s Fine)
We don’t sell a fixed “anniversary package,” so anything beyond the charter itself — champagne, flowers, a speaker for a favorite playlist — is worth bringing along yourselves. Most couples pack a bottle to open at the right moment, and our crew is glad to help time it around a sunset or a quiet anchorage once you’re aboard. If photos matter to you, say so when you book; our crew can take a few shots of the two of you at a scenic stop, though for a fully dedicated shoot you’d want to arrange your own photographer separately and coordinate the meeting point with us in advance.
Toasting the Occasion
If you want a drink that actually belongs to this part of the world rather than a bottle you packed from home, the Painkiller has real BVI roots — it was born at the Soggy Dollar Bar on Jost Van Dyke’s White Bay, and we cover the actual history (not the tourist-brochure version) in our Painkiller cocktail guide. It’s a fitting toast if your anniversary route includes a stop at White Bay itself.
What to Actually Say When You Call
A little context up front makes the whole booking process smoother and gets you a much better-planned day out on the water. When you reach out to our crew, it genuinely helps to mention:
- That it’s an anniversary, and which one, so we understand the weight of the occasion.
- Whether you have a specific anchorage, beach, or memory you want to revisit.
- Roughly what time of day you want to be on the water, especially if sunset timing matters to you.
- Whether it’s just the two of you or you’re bringing family along to share part of the day.
- Any dietary notes or drink preferences worth knowing about ahead of time.
None of this is complicated, but it’s the difference between a charter that technically happens on the right day and one that actually feels like it was built for you.
A Few Planning Notes
Anniversaries tend to land on fixed calendar dates, which means less flexibility than a trip planned purely around good weather. A couple of things help:
- Book as early as you reasonably can — our guide on how far in advance to book a BVI charter lays out why popular dates and boats fill first.
- Have a backup plan for weather, since a private charter can shift timing within the day more easily than a fixed-schedule tour.
- Budget for the crew at the end of the day — our tipping guide covers what’s typical.
Frequently Asked Questions
Can we request a specific beach or cove for our anniversary?
Yes — tell us when you book, and we’ll build the route around it where conditions and timing allow.
Is champagne included in the charter price?
Our packages include beverages, but for a specific bottle you want to open for the occasion, we’d recommend bringing your own so you get exactly what you’re after.
What’s the best charter length for a half-day anniversary celebration?
The Sunset & Dinner Charter (3–4 hours) is our most popular pick for anniversaries specifically, since the timing around golden hour does most of the atmosphere-setting for you.
Can the crew help take photos of us?
Yes, casually and happily. For a dedicated photo shoot, we’d suggest arranging your own photographer and coordinating a meeting point with us ahead of time.
Is a private charter better than a resort dinner for an anniversary?
It depends what you’re after. A resort dinner is easier to plan and doesn’t depend on weather; a private charter gets you somewhere a table on land never could — a quiet anchorage, a swim before the sun goes down, and no one else’s evening happening at the next table.
Do you offer anything different for a milestone anniversary versus a first or second?
There’s no separate package, but we do treat the planning conversation differently. For a milestone year, we’ll spend more time talking through timing, route, and any specific place you want to revisit, since there’s usually more history behind the request. Mention the milestone when you book and we’ll factor that into how we plan the day.
What happens if the weather doesn’t cooperate on the day we booked?
We keep an eye on conditions in the days leading up to your charter and will talk through options with you if the forecast looks rough — that might mean adjusting the route, shifting timing within the day, or in more serious cases rescheduling. It’s one more reason to book with some flexibility built into your travel dates if the exact anniversary date isn’t fixed in stone for you.
If an anniversary is what you’re planning, get in touch through our contact page and tell us the date, the group size, and anywhere specific you’d like to revisit — we’ll help you build the right day around it. However you choose to spend it, the goal is the same one we’ve heard from every couple who’s booked one of these with us: fewer logistics, more water, and a few hours that feel like they belong to just the two of you.
