Top St Maarten Day Trips

Anguilla Getaway Cruise

Two Islands, Twice the Fun

(705)

from $149

Maho Beach St Maarten on a no cruise ship day

5 to 6 hoursFree Cancellation

Escape to Paradise with Style and Speed! Hop aboard our 40-50 ft sleek speed boats and experience Anguilla like never before. We don’t just take you to Anguilla — we take you to the best of Anguilla: • Sandy Island – a dreamy, remote sandbar surrounded by vibrant coral reefs • Little Bay – a secluded cove perfect for swimming, snorkeling, or cliffside photos • Meads Bay – famous for its calm, clear waters and luxury beach vibes • Rendezvous Bay – a wide, peaceful stretch of beach with panoramic views of St. Martin This shared excursion feels relaxed, and effortlessly fun — the perfect mix of island exploration, swimming, social vibes, and laid-back luxury.Whether you’re chasing sun, sea, or new connections, this Anguilla escape is your Caribbean daydream come true.

(543)

from $60

Anguilla In Style

6 hoursFree Cancellation

Topper's Rhum Distillery Tour in St Maarten

(283)

from $149

1 hour 30 minutesFree Cancellation

Getting out on the water is one of the best ways to experience St. Maarten, but arranging a boat day on your own can be complicated and expensive. This fun catamaran cruise from Simpson Bay makes it simple, with a comfortable vessel and planned stops built into the day. Relax on cushioned seating as you journey along the water, then dive in when the catamaran anchors to enjoy snorkeling or stand-up paddleboarding.

(908)

from $39

The Best Catamaran Day Sail in St Maarten

Prickly Pear Catamaran Trip from St Maarten Including Lunch

(1,736)

from $145

2 big nets for you to relax on the boat.

8 hoursFree Cancellation

4.6

(405)

from $135

Just north of St. Maarten, the stunning island of Anguilla awaits—known for its powdery white-sand beaches, turquoise waters, and relaxed Caribbean charm. Embark on an unforgettable journey aboard our spacious and powerful catamaran, where you’ll experience the very best of Anguilla in comfort and style. With indoors and outdoor seating our catamaran’s stable design and smooth cruising speed of 15-20 knots promise a comfortable ride over gentle Caribbean waves. Highlights include: • World-Famous Beaches – Sink your toes into the soft sands of the many beautiful beach. • Snorkeling and Swimming – Explore Anguilla’s vibrant underwater life with snorkeling gear included. • Full Bar & BBQ Lunch – Enjoy our signature cocktails and a delicious BBQ lunch onboard. Whether you’re seeking relaxation or adventure, our Anguilla Day Charter is your ticket to paradise. Limited spots fill quickly, so book now!

Boomerang’s Best of Anguilla: Swim with Turtles Adventure

See the best of St. Maarten during this sightseeing tour from Philipsburg. Explore the Dutch and French sides as you visit key towns like Orient Bay Beach, where you can relax on the beach, the French capital of Marigot, the famous Maho Beach where you can watch planes land and take off, and much more. Enjoy complimentary beverages throughout the tour as you admire the idyllic scenery of the island.

(403)

from $169

FUN DAY St.Maarten Island Sightseeing Tour with Beach

FUN DAY St.Maarten Island Sightseeing Tour with Beach

5 to 6 hoursFree Cancellation

4.4

(239)

from $60

Mambo Sail Catamaran to Rendezvous Bay Anguilla

Board sail cat Mambo at Simpson Bay Resort Marina for a leisurely sail across the channel to Cove Bay, Anguilla and then onto Rendezvous Bay. Rendezvous Bay welcomes you with a pristine, white, sandy beach. Enjoy crystal-clear waters for swimming, cooling off, or lounging in the water with a noodle! Relax, you are here to spend the day with great views of St. Maarten across the ocean. At noon, a delicious lunch is served right on board the sailing catamaran. When your food has settled, opt to walk Rendezvous Bay...2 miles of powdery sand to stretch your legs. The call to leave comes all too soon. Board Mambo again and sail home to relaxing rhythms and the sound of the waves hugging the hulls. Your tropical experience is complete. “Tranquility wrapped in blue” is how we like to describe Anguilla!

Mambo Sail Catamaran to Rendezvous Bay Anguilla

7 hours 30 minutesFree Cancellation

4.7

(32)

from $135

Let us take you on a memorable tour of St Maarten. A must-do for any trip to the Caribbean, you can avoid the crowds by booking with us and exploring the wonders of the town at your own pace. As this is a private tour, we can cater to your needs. Swim in Mullet Bay, enjoy some duty-free shopping, feast on the local cuisine – you pick from our itinerary, and make the day one for the books.

The Best of St Maarten Private Sightseeing Tour

5 to 7 hoursFree Cancellation

From Sint Maarten, enjoy a scenic 1 hour and 15 minute boat ride to Saint Barthélemy, also known as St. Barth’s—famous for its beautiful beaches and relaxed luxury atmosphere. Your first stop is Gustavia, the island’s charming harbor town, where you’ll have free time to explore boutiques, cafés, and the waterfront. Next, we head to Colombier Beach, a quiet bay perfect for swimming, paddleboarding, or relaxing while lunch is served onboard. We then cruise to Île Fourchue, an uninhabited island known for clear water and excellent snorkeling. Enjoy marine life, floating in the calm bay, or relaxing onboard with drinks and music before returning to Sint Maarten. Included: Open bar with cocktails, liquor, beer, soft drinks, juice, and water; BBQ lunch with Jamaican curry chicken skewers, garlic shrimp skewers, Greek pasta salad, and baguette; fresh pineapple; snorkeling gear, floats, lily pad mat, noodles, flotation vests, and paddleboards; experienced captain and crew.

(558)

from $450

Per group

Special Offer

Boomerang's Best of St. Barths

Combine rides on the Flying Dutchman, the Schooner Ride and the Sentry Hill Zipline on this thrilling combination tour. First, ascend to St. Maarten's highest point on the Sky Explorer for excellent views, then zoom down the mountain on the Flying Dutchmen. Head back up the mountain and clip on to the Sentry Hill Zipline to get views over the island. Finish up with an inner tube ride down the mountain on the Schooner Ride.

Big three-Full Experience at Rainforest Adventures St Maartin

Climb aboard the catamaran "The Phoenix" for a sail around the sights of Sint Maarten. Explore the warm Caribbean Sea with ease with the supplied water gear, for a day of swimming, snorkeling, paddle boards, or relaxing. Indulge in fresh fruit, pound cake, and a freshly prepared lunch alongside refreshing cocktails, beer, and non-alcoholic beverages. Finish the day watching the planes take off as you sail past Maho Beach—a must-do when visiting the island (weather permitting).

3.9

(309)

from $159

Likely to Sell Out

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

All In One Island Tour of St. Martin | St. Maarten

(1,047)

from $139

Likely to Sell Out

4.7

(170)

from $70

With our tours we not only take you to a location but we also provide the history of the location for the customer so they can make their own memories of the tour. Our Tour guides and drivers are verse in the history of the island and are multilingual. Some tours can be groups and we also provide private tours as it is booked by the customer. Tailor made tours as per the customer requests.

Scenic view of Great Bay Beach in Philipsburg

Private Tour in St. Maarten

Private Speed Boat Charter to Anguilla

(7)

from $75

(48)

from $404

Full-Day Private Luxury Yacht Tour in Anguilla

7 hours 30 minutesFree Cancellation

St. Maarten 6 Pack Island Tour

(17)

from $1,850

Per group

Your Day of Paradise Includes: The Scenic Sprint: We start from St. Maarten at 9:00 AM sharp. Feel the salt spray and the Caribbean breeze as we cross the turquoise blue—but don't blink, because this paradise waits for no one! Island Secrets Unveiled: Hop off the boat and into our guided sightseeing tour. We’re taking you deep into the heart of Anguilla for a 2 hours bus tour of hidden gems, breathtaking vistas, and exclusive shopping stops you won't find in the brochures. Gourmet Beachside Bliss: Trade the bus for the sand. We’ve reserved a table for you on the water’s edge for a mouthwatering, authentic lunch with your toes in the sand. Snorkeling and Beach top: This is the moment you’ll be talking about all year. Dive into the crystal-clear sanctuary of Anguilla. Whether you want to glide over vibrant reefs with our complimentary snorkeling gear.

(71)

from $62

Anguilla Explorer Land and Sea Excursion

Get a taste of local culture and history with this highlights tour of St. Maarten. Ideal for first-timers to the island, enjoy an itinerary that includes monuments, museums, and beaches, as well as opportunities to shop. Learn about St. Maarten directly from your guide as you visit Cole Bay, Topper's Rhum Distillery, and Maho Beach. And don’t worry about getting sore feet when going to each destination, with transportation provided between attractions.

(26)

from $169

St. Maarten Best Island Tour

5 to 6 hoursFree Cancellation

4.5

(1,171)

from $60

Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Escape to the tranquil and world-renowned island of Anguilla while you sail aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the luxuries for a comfortable, safe, and sustainable cruising experience. This all-inclusive sailing package is a boutique experience complete with your own captain and crew catering to your every need. It's pure luxury every step of the way. From the moment you slip off your sandals and step aboard Freedom’s sprawling teak deck, you’ll be warmly welcomed with a cool scented towel and nibble a decadent handmade chocolate as you head over to one of the luxurious lounge areas to begin a leisurely morning sail. With a sparkling mimosa in hand, you set the vibe while your experienced captain and crew take care of the rest.

Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

9 hours 30 minutesFree Cancellation

(11)

from $699

Tango Caribbean Dinner Cruise

3 hoursFree Cancellation

4.7

(488)

from $85

Private Speed Boat Charter in St Maarten & Nature Reserve

3 to 7 hoursFree Cancellation

(94)

from $399

Get the mega yacht experience aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the luxuries for a comfortable, safe, and sustainable cruising experience. This all-inclusive sailing package is a boutique experience complete with your own captain and crew catering to your every need. It's pure luxury every step of the way. From the moment you slip off your sandals and step aboard Freedom’s sprawling teak deck, you’ll be warmly welcomed with a cool scented towel and nibble a decadent handmade chocolate as you head over to one of the luxurious lounge areas to begin a leisurely morning sail. With a sparkling mimosa in hand, you set the vibe while your experienced captain and crew take care of the rest.

Luxury Catamaran Private Charter in St. Maarten/St. Martin

Luxury Catamaran Private Charter in St. Maarten/St. Martin

7 hours 30 minutesFree Cancellation

(52)

from $599

St. Maarten 6 Pack Island Tour

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Top Attractions in St Maarten

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Attractions

What are people saying about St Maarten

Quwanda_F, May 2026

A great experience for first-time visitors and something worth doing again for returning guests

I really enjoyed the tour. I enjoyed all six stops, including the nude beach. The restaurants and beaches recommended by Nell during the tour were great, and the prices were reasonable. I also enjoyed learning about the history of the island. I’m looking forward to doing it again the next time I come back.

Two Islands, Twice the Fun

Diane_T, May 2026

Take this great tour!

This tour is amazing. Raj shared so much history & details about the island. During the entire time we were in the new AC van, we heard about the great history of both the Dutch & French sides of the island. He even shared details about the eco system, economy, everyday living, home prices, car prices & details of auto makers. He does all this with a grand smile! What a great tour. Thank you for making our time on the island memorable Raj.

Anguilla In Style

Erin_P, May 2026

Awesome excursion!

We had a great time. The two young men took us to four very beautiful places and served us with excellency the entire time. Lunch was good, drinks were good and the whole day was a success. Heads up- no passport stamp included. But you will need to bring it with you.

The Best of St Maarten Private Sightseeing Tour

lauclifford, Apr 2026

Hakeem is your guy!

Hakeem is a fantastic guide! From start to finish, he kept us engaged with fascinating stories and facts about Saint Martin that you won’t find in the guidebooks. He has a warm, welcoming personality that made the whole day feel relaxed and fun. If you want a guide who is both professional and a blast to hang out with, Hakeem is your guy!

St. Maarten Best Island Tour

Tina_S, Apr 2026

Best Tour in Sint Maarten with Jamal

Highly recommend for cruise ship visitors to get a good taste for all this island has to offer. Jamal was a fantastic guide - kept us on schedule and gave us the opportunity to see the best of the island, while keeping it fun and informative along the way. Only drawback and we've found this with every tour booked through Viator - they could use better instructions on meeting location. Rather just saying port location this one should instruct: walk all the way through the port, heading toward the area that says "taxi dispatch", from there head slightly left following signage to "EDC". Once at EDC, check in at the first window. Easy!!!

FUN DAY St.Maarten Island Sightseeing Tour with Beach

Jean_S, Apr 2026

Jo Junie offered a really...

Jo Junie offered a really affordable tour of both French and Dutch sides of St. Maarten. Beautiful sites, enough time to stop at several places, beaches, etc. Our guide Etienne was very knowledgeable of the areas we explored and seemed genuinely happy doing what he does. Definitely would recommend this tour to anyone visiting St. Maarten.

All In One Island Tour of St. Martin | St. Maarten

Jonathan_T, Mar 2026

We booked this tour...

We booked this tour expecting to be a group tour but turned out to be a private tour. The agency communicated well ahead of the experience and even adapted the departure time to align with the cruise ship docking times. It was a little confusing to find the meeting point at first and the map provided was essential. The tour was led by Chiky, a vibrant lady who showed us the island with enthusiasm and humour, tailoring the tour to our specific requirements, such as a short stay in Philipsburg, which was highly appreciated. The sights were nice, and we especially enjoyed the planes at Maho beach. Bring your swim wear if you want to get in the water at any of the beautiful beaches. If we had a bit more narrative about the places we visit it would have been a perfect trip.

Ultimate Prickly Pear and Anguilla Experience

Hailey_S, Feb 2026

the best excursion!!!

I had a wonderful trip in Sint Maarten but we decided to do this activity on our last day and it was EVERYTHING. I had the time of my life laying on a boat tanning, eating (really amazing bbq chicken and other things by the way), drinking, snorkeling!!! It was the best day I had by far. Shoutout to the crew Eddie, Lisandro and Samir (I can’t remember names very well but I think that’s correct lol), they made the experience that much better!

Tango Caribbean Dinner Cruise

Eric_G, Feb 2026

Amazing food and drinks. HIGHLY RECOMMEND

Highly Recommend this!!! This experience was the best service Ive ever received on a boat tour on any island. I mean it. The staff was so friendly, making drinks, bringing around food, constantly asking what we need. The food was fantastic. Chicken, beef tips, scalloped potatoes, salad, rice. The apps were great too. The night was beautiful and we met some really nice people on it. MUST BOOK WHEN HERE!!

Private Speed Boat Charter to Anguilla

Addie_D, Jul 2025

Anguilla by Boat—A Day to Remember

Sam was very responsive the day before our tour, promptly answering our questions, and he was there to meet us as soon as we arrived. There were six of us, and we specifically wanted a private experience to fully enjoy the day without the presence of other groups or children—and this tour delivered exactly that. It was an incredible experience. The boat was comfortable, and the beaches Sam took us to were absolutely stunning. He was friendly, accommodating, and had drinks readily available throughout the day. We spent nearly the entire day exploring various beaches around Anguilla, each offering its own unique charm. Everyone in our group thoroughly enjoyed each stop. Our lunch location was a highlight—gorgeous views, delicious food, and surprisingly reasonable prices. If we had one suggestion, it would be to include more commentary about the island during the trip. While we recognize we could have asked more questions, it would have been great to learn more about what we were seeing along the way.

Anguilla - Discovery Speed Boat tour

Jessica_L, Jul 2025

Loved!

We had a great time on our trip to Anguilla! Miguel and Coco were awesome!! Our safety is a priority to the crew as well as making sure we were all comfortable and having a great time! I even forgot that I couldn't swim for a second and Miguel reminded me to put on my life vest, that's why he's the captain😉😉🫡! Would highly recommend!!