# Raymond Bowen of EXPLR.SX on How To Plan a Private Boat Charter for a Guys Trip to St Maarten *By James Hills — Updated September 2026* I've been to St Maarten a couple of times on cruises, and it's a beautiful island with two very different cultures packed into a small space, split between the French side and the Dutch side. For a group of guys who love sun and water, it brings a bit more sophistication and European style than the Bahamas or [the US Virgin Islands](https://www.mantripping.com/united-states/us-virgin-islands.html). It also sits within reach of Anguilla and St Barts, and a private boat day is one of the easiest ways to see all of it. When Raymond Bowen, co-founder of the St Maarten charter company EXPLR.SX, reached out to ManTripping, I asked him how a local captain would plan that day for a group of buddies. His own stag do was a day on a boat around the island. We sat down with Raymond to talk about where he would take a group of first-timers, what surprises people about Anguilla, and why a seven-hour charter goes by faster than anyone expects. **Questions****Passports And Customs For A Boat Day To Anguilla Or St Barts****Article Index** ** No answer selected. Please try again. Please select either existing option or enter your own, however not both. Please select minimum {0} answer(s). Please select maximum {0} answer(s). /polls/travel-and-trip-ideas/what-do-you-prefer-to-call-your-guys-trips.html?task=poll.vote&format=json 1 Guys Trips (562 votes / 44.08%) 44.08% votes Guys Getaways (129 votes / 10.12%) 10.12% votes Mancations (118 votes / 9.25%) 9.25% votes Brocations (166 votes / 13.02%) 13.02% votes [{"id":5,"title":"Guys Weekends","votes":300,"type":"x","order":1,"pct":23.530000000000001136868377216160297393798828125,"resources":[]},{"id":6,"title":"Guys Trips","votes":562,"type":"x","order":2,"pct":44.0799999999999982946974341757595539093017578125,"resources":[]},{"id":7,"title":"Guys Getaways","votes":129,"type":"x","order":3,"pct":10.1199999999999992184029906638897955417633056640625,"resources":[]},{"id":8,"title":"Mancations","votes":118,"type":"x","order":4,"pct":9.25,"resources":[]},{"id":9,"title":"Brocations","votes":166,"type":"x","order":5,"pct":13.019999999999999573674358543939888477325439453125,"resources":[]}] ["#ff5b00","#4ac0f2","#b80028","#eef66c","#60bb22","#b96a9a","#62c2cc"] ["rgba(255,91,0,0.7)","rgba(74,192,242,0.7)","rgba(184,0,40,0.7)","rgba(238,246,108,0.7)","rgba(96,187,34,0.7)","rgba(185,106,154,0.7)","rgba(98,194,204,0.7)"] 350 ** Vote Now** Vote Form** ResultVotes A boat day off St Maarten can take you under three different flags before dinner, and the paperwork is the part groups most often forget until the night before. - **Pack a passport book -** Anguilla is a British Overseas Territory and St Barts is French, so crossing to either one means clearing immigration, even on a day trip. Charter operators ask for a valid passport, and several say passport cards will not do. - **Send passport details ahead -** Many St Maarten charter companies ask for passport copies at least 24 hours before an Anguilla trip so the captain can prepare the clearance paperwork. - **Budget for customs fees -** EXPLR.SX's own Anguilla price guide puts customs fees at roughly $30 to $35 per person, charged on top of the charter itself. - **St Barts is the longer run -** Gustavia sits about 13 to 14 nautical miles from the Philipsburg side, and a private boat usually makes the crossing in 40 minutes to an hour and a half depending on the boat and the sea. - **Tintamarre is a protected reserve -** The island is part of the Réserve Naturelle de Saint-Martin, with 17 yellow moorings for boats up to 50 feet, and boats under 33 feet may anchor only on a sandy bottom. Creole Rock and Pinel are protected sites in the same reserve. 1. [How EXPLR.SX Matches A Charter To A Group Of Friends](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html#how-explr.sx-matches-a-charter-to-a-group-of-friends) 2. [Raymond's Stag Do Boat Day Around St Maarten](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html#raymond's-stag-do-boat-day-around-st-maarten) 3. [Cliff Jumping And Snorkeling At Little Bay In Anguilla](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html#cliff-jumping-and-snorkeling-at-little-bay-in-anguilla) 4. [Tintamarre, Happy Bay And Other Boat-Only Stops](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html#tintamarre,-happy-bay-and-other-boat-only-stops) 5. [What Gets Planned Before You Leave The Dock](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html#what-gets-planned-before-you-leave-the-dock) 6. [Beach Lunches, Lolos And Drinks On The Water](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html#beach-lunches,-lolos-and-drinks-on-the-water) 7. [Pacing A Seven-Hour Charter Day](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html#pacing-a-seven-hour-charter-day) 8. [What A Private Boat Charter Costs Out Of St Maarten](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html#what-a-private-boat-charter-costs-out-of-st-maarten) 9. [How To Book A Boat Charter For Your Group Of Guys In St Maarten](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html#how-to-book-a-boat-day-for-your-group-in-st-maarten) Raymond Bowen is Co-Founder and President of [EXPLR.SX](https://explr.sx), a private boat charter specialist based in St Martin / Sint Maarten. He is a long-term resident of the island and a captain himself, and he has spent years boating and sailing in the Caribbean and in Europe. EXPLR.SX draws on a network of boats and captains around the island, with departures from spots like Simpson Bay, Philipsburg, Marigot and Grand Case. It plans private days on the water around St Maarten, Anguilla and St Barts, with half-day, full-day and sunset charters. ## How EXPLR.SX Matches A Charter To A Group Of Friends Every EXPLR.SX booking starts with questions about the group on board. **What is the one thing about EXPLR.SX you wish more people understood?** That we genuinely try to fit the right charter for our guests, rather than just sell them a boat!! We have access to a wide range of boats and captains around St Martin, so when someone contacts us, I want to know who is traveling, where they're staying, what they want to do, and what matters to them. Sometimes that means finding a boat departing close to where they're staying, while for a group of friends it might be about having enough space to hang out, or have lots of sea toys, or choosing a boat that can comfortably get them across to Anguilla or St Barts, or finding the right setup for the kind of day they have in mind. The biggest or most expensive boat isn't automatically the best one, and once we've found the right fit, we stay involved to make sure everything from where to go and when to be there to what to bring and expect is clear, so the guest can simply enjoy their day. So I suppose the simplest way of putting it is: we start with the people and the day they want to have, and then find the boat that fits. **When a group is trying to figure out what kind of boat fits their day, what is the single most useful question you ask them?** Tell me a little about your group and what you'd like the day to be like! I actually prefer that to asking what kind of boat they want, because most people shouldn't need to know that. If they tell me there are six friends staying in Simpson Bay who want to snorkel, have a few drinks, find a great beach and stop somewhere good for lunch, I can already start thinking about what will work for them. Group size obviously matters, and budget matters too, but what people want from the day often tells me much more than asking them to choose between a powerboat, catamaran or a particular size of boat. That's our job to figure out, not theirs. ### Caribbean Sip&Cook Cooking Class in Sint Maarten You will participate a fun and educational hands-on cooking class from passionate professional. You will learn mouthwatering dishes what are full of flavor and easy to re-create at home, as we will use equipment what you can find in every average household kitchen. Recipes what flavorful, decorative and will impress your guests when you make them for your next dinner party. You will learn how to make delicious Rum Punch and you can drink it during the whole class... Coffee, Tea, Water are included as well. Let us know in advance if you have any dietary restrictions, allergies. Available as shared experience or for private groups. Perfect indoor activity for rainy days or whenever you want to hide from the Sun. For last minute requests, get in touch via phone/whatsapp Viator (affiliate) $139.00[See Current Price](https://ads.flowmediamarketing.com/go/vwNK7Fu-mfYz83NHAsEazA.2413) ### Topper's Rhum Culinary and Tasting Tour Rum Food and Fun A Flavorful Hour of Rum and Island Cuisine Indulge in an intimate 60-minute experience designed for small groups, where curated tastings meet the vibrant flavors of the island. Set against the breathtaking backdrop of the Caribbean’s largest lagoon, guests enjoy a guided rum tasting with exclusive access to Topper’s rare small-batch selections that are perfectly paired with a chef-crafted sampling of rum-infused culinary delights. Highlights: • Duration: 1 hour • Personal tour guide • Leisure lagoon-view dining atmosphere • Welcome Rum Punch • Chef’s “Cooking with Rum” Sampler Platter (Bonfire Shrimp, Drunken Chicken, and Mocha Mama Ribs) • St. Maarten’s National Drink - Guavaberry Colada sampler • Signature & Specialty (exclusive, not sold elsewhere) Rum sampling • Rhum cake • Homemade Rhum-infused Gelato • Shop for exclusive small-batch rhums and island gifts Perfect for: Couples, small groups, foodies, and rum lovers seeking a more exclusive, culinary-driven experience. Viator (affiliate) $75.00[See Current Price](https://ads.flowmediamarketing.com/go/vwNK7Fu-mfYz83NHAsEazA.2411) ### Topper's Rhum Distillery Tour in St Maarten You will be greeted with a refreshing rhum punch upon arrival at this gorgeous landmark building located directly on the Caribbean’s largest Lagoon, which stunningly accommodates Topper’s Rhum distillery and its restaurant, bar, gelateria, and gift shop. A knowledgeable and entertaining guide will give you a hands-on tour where you will learn a little history of rum and get a behind-the-scenes look at how they ferment, distill, blend, age, and expertly bottle their handcrafted rums and ensure their products meet the highest quality standards. You will learn how to nose and taste rhum. You will be treated to over 20 samples of their 124 different flavored rhums, rum cake, and rum-infused Italian gelato, and cook and taste food prepared with Topper’s Rhum. As St. Maarten’s official rum, Topper’s has been named USA Today’s Best Caribbean Rum Distillery for four years and has won over thirty prestigious tasting medals. Come and have fun enjoying this world-class rhum. Viator (affiliate) $39.00[See Current Price](https://ads.flowmediamarketing.com/go/vwNK7Fu-mfYz83NHAsEazA.2408) Promoted by FlowAds ## Raymond's Stag Do Boat Day Around St Maarten A boat charter is a fantastic idea for a St Maarten stag do and that's exactly what Raaymond did for his [bachelor party](https://www.mantripping.com/bachelor-party-ideas.html)! **If you were putting together a day on the water for a group of guys visiting St Maarten for the first time, where would you take them and what would you have them do?** I've actually done this myself! Years ago, for my own stag do, I spent a day out on a boat around St Maarten with a group of friends, and I'd still recommend a very similar kind of day now. We snorkeled at Creole Rock, stopped at Pinel for drinks, swam at Tintamarre and spent time chilling at Baie Longue. We didn't actually stop for lunch that day, although these days I'd probably build a good lunch stop into it as well, definitely Grand Case or a restaurant on Pinel. What made it such a good day was that there wasn't really a schedule to tick off. We snorkeled, swam, stopped for drinks and just enjoyed being out on the water together. If we were having a good time somewhere, we stayed; when we felt like moving on, we moved on. That's what I'd want for a group of friends visiting St Maarten for the first time, a few great stops, but enough freedom that the day takes on a life of its own. ## Cliff Jumping And Snorkeling At Little Bay In Anguilla For a first boat day with the guys, Raymond points straight across the channel to Anguilla. **If you had to pick one destination for first-timers who have never been out on the water around St Maarten, where would you point them, and what tends to catch them off guard there?** Anguilla! One of my favourite stops is Little Bay, a tiny cove you can only really reach from the water (over land can be dangerous), it has incredibly clear water, great snorkeling and a rock you can cliff-jump from if you're feeling brave! The contrast of Anguilla is what catches most people off guard. We have Anguilla in our heads as perfect white sand beaches and resorts and then you arrive in Little Bay by boat and you're swimming beneath the cliffs and daring your friends to make the jump. It's only around 15 to 35 feet depending on where you jump from, but it looks considerably higher when you're standing at the top! Then back on the boat and twenty minutes later you're having lunch and a rum punch on one of those beaches Anguilla is famous for. That contrast is one of the reasons I love taking people there for the first time. ## Tintamarre, Happy Bay And Other Boat-Only Stops St Maarten has its own boat-only stops, and a few that Raymond keeps quiet on purpose. **Are there places around St Maarten itself that you simply cannot get to any other way than by boat?** Tintamarre is probably the obvious one. It's an uninhabited island just off St Martin, and if you're lucky you can end up swimming with turtles there. Happy Bay is another favourite, you can reach it on foot, but it's a bit of a walk and there are no facilities, whereas arriving from the water is completely different. There are also a few tiny beaches and coves that I deliberately don't tell guests too much about beforehand. We prefer to let the captain surprise them with those, that's part of the fun of having someone local take you out. ## What Gets Planned Before You Leave The Dock Customs paperwork for Anguilla or St Barts is handled before departure, and much of the route is left to the captain. **How much of the itinerary do you typically lock in before a group leaves the dock, and how much do you deliberately leave open?** We plan the things that need planning. If you're going to Anguilla or St Barts, for example, we'll make sure the customs side is prepared in advance, the guests have all the information they need and everyone knows exactly where and when they're getting on the boat. If a guest has told us there's something they absolutely want to do, we'll make sure the captain knows that too. But once you're on the water, I like the captain to be the captain. They have the final say on the route, weather and safety, and they know where the best places are on any given day. So unless there's a particular must-do, we deliberately leave plenty of the day open. Some of the best charter days are the ones you don't try to plan down to the last stop. - [Viator (affiliate) Sint Maarten Wine Tasting Brewery Shopping and Jet-Blast Tour $130.00](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2415) [See Current Price](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2415) - [Viator (affiliate) Caribbean Sip&Cook Cooking Class in Sint Maarten $139.00](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2413) [See Current Price](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2413) - [Viator (affiliate) Topper's Rhum Culinary and Tasting Tour Rum Food and Fun $75.00](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2411) [See Current Price](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2411) - [Viator (affiliate) Boomerang’s Best of Anguilla: Swim with Turtles Adventure $169.00](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2409) [See Current Price](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2409) - [Viator (affiliate) SeaTrek Tour St. Maarten $109.65](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2407) [See Current Price](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2407) - [Viator (affiliate) Topper's Rhum Distillery Tour in St Maarten $39.00](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2408) [See Current Price](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2408) - [Viator (affiliate) Zipline Experience: Sentry hill Zip & Flying Dutchman St Maartin $129.00](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2412) [See Current Price](https://ads.flowmediamarketing.com/go/-asggglTof5U2SbMQIUV9w.2412) Promoted by FlowAds ## Beach Lunches, Lolos And Drinks On The Water On a full-day charter, lunch is a stop in its own right. **How should a group handle food and drink on a charter day?** Enjoy themselves! I always advise not to overthink it! You're on vacation! The captain and crew will look after you, and we'll make sure you know beforehand what's included on the boat and what, if anything, you might want to bring. For a full day, I'd definitely plan to stop somewhere for lunch rather than pack a meal and eat on board. Stopping at a beach restaurant or lolo's (local food shacks) is part of the day, get off the boat, have a proper lunch and a couple of drinks, then get back on the water. Beyond that, bring water, sunscreen and anything particular you know you'll want, and let the day unfold. A good captain knows how to pace the day so you're not spending your charter worrying about logistics. ## Pacing A Seven-Hour Charter Day The most common planning mistake Raymond sees is a list that is too long for the day. **What do groups almost always underestimate about a day on the water around St Maarten?** Probably how quickly the day goes! Seven hours sounds like a long time when you're planning it, and it's very easy to arrive with a list of six or seven places you want to see. But then you find a great snorkeling spot and stay a little longer, somebody wants another swim, or lunch by the beach turns into a couple of hours because everyone's having a good time. Suddenly it's late afternoon. I'd much rather have three or four really good stops and enjoy them than spend the whole day racing around trying to tick places off a list. You're very well looked after on a private charter, so my advice is to tell us the things you really don't want to miss and then give the captain some freedom with the rest. **How many spots can a group realistically visit and enjoy in a seven-hour day, and what does a well-paced itinerary look like?** For a seven-hour charter I'd normally think in terms of two or three main stops, plus lunch, rather than trying to plan six different destinations. For example, you might snorkel at Creole Rock in the morning, spend some time swimming at Tintamarre, then head to Pinel for a relaxed lunch. If there's time afterwards, the captain can always add another swim or beach stop on the way back. That's a much better day than constantly checking the time because you're trying to get to the next place. ## What A Private Boat Charter Costs Out Of St Maarten EXPLR.SX publishes starting prices by boat size, which makes it easy to split the math across a group before anyone commits. - **Compact speedboats -** 25 to 29 feet for up to eight guests, from $750 for a half day and $1,250 for a full day. - **Mid-size boats -** 30 to 35 feet for up to 10 or 12 guests, from $1,050 for a half day and $1,450 for a full day. - **Larger boats -** 38 feet and up, from $1,750 for a half day and $2,100 and up for a full day. An Anguilla day on a standard boat generally lands between $1,400 and $2,200 by the company's own price guide, with customs fees and any fuel surcharge added depending on the destination. Split six ways on a mid-size boat, a full day around St Maarten works out to roughly $240 a head before lunch and tip. ## How To Book A Boat Charter For Your Group Of Guys In St Maarten When you contact a charter company, lead with three things. Tell them how many of you there are, where you are staying and the one stop nobody wants to miss, whether that is the Little Bay cliff jump or a long lunch on Pinel, and let the captain handle the rest. If Anguilla or St Barts is on the list, collect everyone's passport details when you collect their share of the deposit. That one step keeps the customs side off the morning of the trip. You can start that conversation with Raymond and his team at [EXPLR.SX](https://explr.sx). Details Written by: James Hills Last Updated: 23 September 2026 ### 🚢Ready To Book A Vacation? Let us help you plan a cruise, all-inclusive resort, or tour for your next guys trip, family vacation, or romantic getaway. Click here to [**Book Your Next Vacation**](https://www.mantripping.com/vacation-planning.html). #### Which Style Of Amazon Cruise Should You Pick To Explore World's Largest River? Aug 17, 2026 [Which Style Of Amazon Cruise Should You Pick To Explore World's Largest River?](https://www.mantripping.com/travel/amazon-river-cruise-planning-ship-options.html) [Plan Your Next Vacation Today!](https://www.mantripping.com/vacation-planning.html) ### Products & Gift Ideas #### LiberNovo Maxis Chair Review - Finally A Seat That Lets Big Dudes Feel Comfortable At The Desk Sep 10, 2026 [LiberNovo Maxis Chair Review - Finally A Seat That Lets Big Dudes Feel Comfortable At The Desk](https://www.mantripping.com/stuff/libernovo-maxis-big-and-tall-office-chair-review.html) #### FRESKO 4-in-1 Immersion Hand Blender Review Sep 09, 2026 [FRESKO 4-in-1 Immersion Hand Blender Review](https://www.mantripping.com/stuff/fresko-4-in-1-immersion-hand-blender-review.html) #### UGREEN Air Review: Four Slim Chargers And Power Banks I Traveled With This Summer Aug 25, 2026 [UGREEN Air Review: Four Slim Chargers And Power Banks I Traveled With This Summer](https://www.mantripping.com/stuff/ugreen-air-chargers-power-banks-review.html) ### Top Guys Trip Ideas: #### Beyond Daytona: Six Race Weekends That Make Better Guys Trips in 2026 Feb 24, 2026 [Beyond Daytona: Six Race Weekends That Make Better Guys Trips in 2026](https://www.mantripping.com/travel/nascar-race-weekend-guys-trip-ideas.html) #### I Had a Ball During My Stay at Disney's All-Star Sports Resort Nov 08, 2015 [I Had a Ball During My Stay at Disney's All-Star Sports Resort](https://www.mantripping.com/travel/i-had-a-ball-during-my-stay-at-disney-s-all-star-sports-resort.html) #### Best Massachusetts Mancation Ideas Jul 26, 2016 [Best Massachusetts Mancation Ideas](https://www.mantripping.com/travel/best-massachusetts-mancation-ideas.html) ### Related Articles #### How to Plan a Caribbean Golf Trip That Will Make The Guys That Didn't Join You Jealous [How to Plan a Caribbean Golf Trip That Will Make The Guys That Didn't Join You Jealous](https://www.mantripping.com/travel/caribbean-guys-golf-trip-planning-guide.html) #### 4Patriots CEO Allen Baler on Why Family Preparedness Doesn't Make You a Prepper [4Patriots CEO Allen Baler on Why Family Preparedness Doesn't Make You a Prepper](https://www.mantripping.com/stuff/4patriots-ceo-allen-baler-family-preparedness-interview.html) #### The UnWipe Founder Jim Kaslik on Why Flushable Wipes Are the Travel Problem Nobody Talks About [The UnWipe Founder Jim Kaslik on Why Flushable Wipes Are the Travel Problem Nobody Talks About](https://www.mantripping.com/stuff/the-unwipe-founder-jim-kaslik-interview.html) #### South America Bachelor Party Ideas: From Cartagena Villas To Patagonia Treks [South America Bachelor Party Ideas: From Cartagena Villas To Patagonia Treks](https://www.mantripping.com/travel/bachelor-party-ideas-south-america.html) #### A. Erazo From Las Verandas Shares Why Men Love Roatán for a Caribbean Guys Trip [A. Erazo From Las Verandas Shares Why Men Love Roatán for a Caribbean Guys Trip](https://www.mantripping.com/travel/las-verandas-roatan-guys-trip-interview.html) - [**](https://www.mantripping.com/search.html) - [**](https://www.mantripping.com/sitemap.html) - [** Polls](https://www.mantripping.com/polls.html) - [Community Login](https://www.mantripping.com/registration/login.html) - [Brand Engagement Newsletter](https://www.mantripping.com/pr-ops-newsletter.html) - [Links](https://www.mantripping.com/links.html) - [Pitch Portal](https://www.mantripping.com/pitch.html) - [Men's Travel Survey](https://www.mantripping.com/the-mantripping-guys-trip-report-spring-2026.html) --- *Source: [Raymond Bowen of EXPLR.SX on How To Plan a Private Boat Charter for a Guys Trip to St Maarten](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html)* **Tags:** Caribbean Guys Trip Ideas, Interview, Your Guide to Boats, Ownership, and Getting Started So You Can Have Fun On The Water, International Bachelor Party and Stag Do Ideas