Five Day Caribbean Business Retreat Itinerary in Philipsburg, St. Maarten (10-15 pax)
If you are organizing an executive summit in the Caribbean, consider St. Maarten / St. Martin. Due to its excellent connections with major airports in North- America and Europe, its proximity and airlift to Miami and New York, its cosmopolitan culture, safety record and reputation for high end cuisine as well as praised variety of things to do on a compact surface makes this dual nation beach paradise an ideal setting for care-free meetings, incentives, conferences and exhibitions in the Caribbean. Last but not least, its wholly revamped airport (2024) being considered the most advanced in the Kingdom of the Netherlands guarantees ease of travel from all major hub connections it serves.
Out of a suggested series of business trip itineraries, todays focus is on capital Philipsburg. As one of the very few beachside capitals in the world, it allows for a business retreat, team building event or strategic planning brainstorm right in between the bustling city feel and pristine Great Bay Beach.
To assist with your corporate getaway, see below a possible 4 night day-by-day plan for a high-end executive retreat in Philipsburg.
Planning
A monday to friday stay is highly recommended as this avoids the busier weekends at St. Maarten airport popular for arrival and departure with leisure travelers. In addition, it will return your team home right before the weekend. If your team is equipped with a private jet, consider to have experts like Execujet cater to your logistics needs. DMCs like Rising Sun Tours are experts on group logistics in general.
With a 10 to 15 person group, consider Holland House Beach Hotel as your base of operations. This high end boutique hotel is popular amongst diplomats and government representatives for its service level, Caribbean feel and beachfront location allowing to mix work with a swim in the Caribbean.
Should your group be somewhat larger, the Divi Little Bay Convention room can cater to your needs up to 40 people in theatre setting. Divi Little Bay Resort is a 5 minute drive from the city center. This itinerary will focus on a downtown Philipsburg setting and activity plan; for a corporate retreat at Divi see our dedicated Little Bay Beach Business Retreat recommendations. Whether your group is small or large, ensure they fill in their Embarkation / Disembarkation card in advance.
In all cases, itineraries ensure a short visit to both the southern “Dutch” side and northern “French” side of the island and some of the best island excursions and restaurants.
Should your group want to book a local expert trainer, consider HR expert consultants of PPC or HR Strategic Elements for a partial or full day of training.
Day 1: Arrival (Sunday afternoon or Monday)
Welcome to St. Maarten / St. Martin! From the airport, it is only 20 to 30 minutes to Philipsburg’s city center.
At your first evening, try Holland House Beach Hotel’s renowned Ocean Lounge restaurant for its European fusion cuisine. The restaurant was selected by USA Today as top 20 Caribbean restaurants. Its lobster was used for American newspaper campaigns.
Day 2: Meeting Day 1 (Tuesday)
Today, your Caribbean leadership getaway commences after a sumptuous beachfront breakfast. Start at 8.30am. The Holland House Beach Hotel meeting and training room offers all your technology needs for corporate presentations. As the room is right outside Ocean Lounge, coffee and refreshments are at constant availability both inside and outside your brainstorm location.
At 10.30am, take a cultural break by exploring some of the dozens of artistic murals that have seen the day of light in the capital over the past years. Guided tours can be arranged too for this purpose. This short creative excursion will be a great addition for innovation workshops.
At 1pm, consider a 5 minute strawl to local favorite Aziana Restaurant for lunch today. Make sure to book in advance for this popular Asian Fusion restaurant with views over Bobby’s marina and decorated with beautiful pictures of St. Maarten history.
At 2pm, head back for your private team retreat room for the final part of the day. Take a 3.30pm “virgin cocktail” or “mocktail” break for a true taste of the Caribbean – unless you assess a shot of rum to widen the scope of the brainstorm session or creativity in your workshop at that point.
At 5pm, it is time to explore the Caribbean sea. Nearby Eagle Tours in Bobby’s Marina organizes sunset sailing tours. Given your exclusive business retreat setting, also consider a private boat charter either from the same company or Private Yacht Charters located in the same marina. See the sun set over the Caribbean and enjoy snacks and drinks on board or as part of a package of aforementioned companies.
Day 3: Team Building Effort Continues
On the third day of your 5 day corporate retreat, continue your strategic brainstorm, workshop or course at 8.30 in your Holland House co-working space.
For a 10.30 break, take a strawl to the Museum only some blocks down the boardwalk.
For a lunch suggestion at noon, move to Seaview hotel and rent a seaside Cabana for some hours. These well equipped open-air rooms provide for a “lunchroom with a view” over the Caribbean. The screens and sofa even allow to continue your strategy sessions whilst enjoying lunch.
Dinner at stylish Mix Rooftop Bar is only a 5 minute cab ride away from Philipsburg. See the sun set over the Caribbean while enjoying its vast array of professionally crafted cocktails and upscale bites – all of this from roughly ten floors up from the beach.
Day 4: Caribbean “Bleisure” Day
After two days of Philipsburg, it is time to break out. An ATV tour will provide a great outdoor activity exploring the island in the process. Let it take you to historic Emilio’s restaurant, where the secluded wine cellar can serve as a final wrap-up moment of discussions of the previous days. This group room allows for privacy during lunch in a historic, high end setting.
To end your active team building day, take the Soualiga Sky Explorer chairlift at 2pm at Rainforest Adventure Park. Take the thrilling Flying Dutchman zipline down to base station, where your quads are parked.
For dinner, move to Grand Case this evening. Its many upscale restaurants like Ocean82 and Auberge Gourmande provide for a great culinary hotspot to end your final productive retreat day.
Day 5: Souvenir Shopping
Holland House Beach Hotel is not just well situated for an exclusive corporate retreat, it is also a perfect base of operations for a souvenir shopping spree because of its position in the middle of main street Front Street. See our dedicated Philipsburg shopping itinerary what bargains can be hunted on this famed square mile of shopper’s paradise before you leave.
Whether you came from European airports, American or Canadian gateways or via Panama, you will be able to relax during the larger part of the weekend – either by being home timely or by a private extension of your stay!
Above itinerary is only a suggested one – have your executive assistant use the activity guide to choose your elements befitting an unforgettable company outing, or be inspired by fun island facts and other day-by-day plans.
