A seven-day St. Maarten and Anguilla itinerary offers one of the most exciting island-hopping experiences in the Caribbean, combining two beautiful destinations with distinctive cultures, spectacular beaches and unforgettable coastal adventures.

St. Maarten is famous for its unique French and Dutch heritage, lively waterfront towns, luxury resorts, excellent restaurants and beautiful tropical scenery.

Anguilla, located a short distance north of St. Martin, offers a different atmosphere, characterized by peaceful beaches, crystal-clear turquoise waters, luxury beachfront accommodation and a relaxed island lifestyle.

Together, these destinations create an excellent combination for travelers seeking both adventure and relaxation.

During the first part of your vacation, you can explore the Dutch side of St. Maarten, discover the French-Caribbean charm of Saint-Martin, visit famous beaches and enjoy the island’s vibrant culinary scene.

You can then travel to Anguilla, where some of the Caribbean’s most beautiful beaches provide an ideal setting for swimming, snorkeling, romantic dining and peaceful coastal experiences.

One of the greatest advantages of combining St. Maarten and Anguilla is their geographical proximity.

Unlike Caribbean island-hopping itineraries that require domestic flights, these destinations can be connected by ferry or authorized boat transfer, making a multi-island vacation relatively convenient.

However, St. Maarten and Anguilla are separate immigration jurisdictions, so travelers must check passport, visa and entry requirements for both destinations before departure.

For first-time visitors, a seven-day vacation provides enough time to discover the highlights of St. Maarten and spend several nights enjoying Anguilla’s quieter island atmosphere.

This comprehensive itinerary covers the best attractions, beaches, cultural experiences, accommodation areas, transportation options, travel requirements and practical planning tips for an unforgettable Caribbean island-hopping adventure.

Whether you are planning a romantic getaway, honeymoon, family holiday or luxury Caribbean vacation, this seven-day St. Maarten and Anguilla itinerary will help you make the most of both destinations.

Why Combine St. Maarten and Anguilla in One Vacation?

St. Maarten and Anguilla complement one another exceptionally well.

Although they are located close together, each destination offers a different vacation experience.

Experience Three Distinct Cultural Influences

St. Maarten is divided between Dutch Sint Maarten and French Saint-Martin.

Anguilla is a British Overseas Territory with its own Caribbean cultural traditions.

A combined vacation allows visitors to experience Dutch-Caribbean, French-Caribbean and Anguillian influences.

Discover Spectacular Caribbean Beaches

Both destinations offer beautiful beaches, but their atmospheres differ.

St. Maarten features lively resort beaches, coastal restaurants and recreational activities.

Anguilla is particularly famous for peaceful white-sand beaches and clear turquoise waters.

Enjoy Island-Hopping Adventures

Travelers can explore multiple islands without requiring a complicated series of flights.

A ferry or authorized boat transfer connects St. Martin with Anguilla.

Experience Excellent Caribbean Cuisine

St. Maarten is known for French-Caribbean dining, local barbecue restaurants and international cuisine.

Anguilla offers beachfront restaurants, fresh seafood and traditional Caribbean dishes.

Combine Adventure with Relaxation

St. Maarten provides lively towns, shopping, historical attractions and marine excursions.

Anguilla offers a slower pace, beautiful beaches and opportunities for peaceful coastal relaxation.

Suitable for Different Travelers

This itinerary is ideal for couples, honeymooners, families, groups and travelers seeking a memorable multi-island Caribbean vacation.

7-Day St. Maarten and Anguilla Itinerary at a Glance

The following itinerary includes four nights in St. Maarten and two nights in Anguilla, followed by a return to St. Maarten for departure.

This itinerary offers a practical combination of cultural exploration, beaches, marine adventures and relaxation.

For travelers with early international flights, returning to St. Maarten on Day 6 and spending the final night near the airport may be more reliable.

Day 1: Arrive in St. Maarten and Explore Philipsburg

Your Caribbean island-hopping adventure begins in St. Maarten.

Most international visitors arrive at Princess Juliana International Airport, located on the Dutch side of the island near Simpson Bay.

Morning or Afternoon: Arrival at Princess Juliana International Airport

After arriving, complete immigration and customs procedures.

Collect your luggage and meet your arranged airport transportation.

Transfer to your accommodation and check in.

Travel time depends on your hotel location and traffic conditions.

Although St. Maarten is relatively compact, traffic congestion can occur around Simpson Bay, Cole Bay and other busy areas.

Afternoon: Explore Philipsburg

Philipsburg is the capital of Dutch Sint Maarten.

The town is famous for its colorful architecture, waterfront setting, shopping and restaurants.

Front Street

Front Street is one of Philipsburg’s main shopping areas.

Visitors can explore boutiques, souvenir shops and other retail establishments.

Great Bay Beach

Great Bay Beach stretches along the waterfront near Philipsburg.

It offers beautiful coastal scenery and convenient access to restaurants and shops.

Visitors can enjoy beach relaxation and swimming when conditions are suitable.

Philipsburg Boardwalk

The boardwalk is a popular location for walking, enjoying waterfront views and discovering restaurants.

Evening: Caribbean Welcome Dinner

Enjoy dinner at a local restaurant.

Popular dishes may include grilled seafood, Caribbean-style chicken, rice dishes and locally inspired specialties.

Overnight Accommodation

Simpson Bay, Philipsburg, Maho or another suitable location on St. Maarten.

Day 2: Maho Beach, Mullet Bay and Simpson Bay Adventures

Day 2 focuses on some of the Dutch side’s most famous coastal attractions.

Morning: Visit Maho Beach

Maho Beach is internationally famous because of its location beside Princess Juliana International Airport.

Visitors gather at the beach to watch aircraft approaching the runway.

The low-flying aircraft create one of the Caribbean’s most recognizable sightseeing experiences.

Important Safety Advice

Aircraft operations can create serious hazards.

Jet blast from departing aircraft can cause injuries and send sand, stones and other objects flying.

Never stand behind aircraft during takeoff or hold onto airport perimeter fencing.

Follow posted warnings and remain in safe public viewing areas.

Flight schedules vary, so check current arrival information if plane spotting is a priority.

Late Morning: Relax at Mullet Bay Beach

Mullet Bay Beach is one of St. Maarten’s most beautiful beaches.

It is known for its white sand, turquoise water and attractive coastal scenery.

Visitors can enjoy swimming when conditions permit, beach walks and relaxation.

Some beach facilities and food vendors may be available.

Afternoon: Explore Simpson Bay

Simpson Bay is a lively tourism area known for its marinas, restaurants and entertainment.

Spend the afternoon exploring the waterfront or enjoying a suitable marine activity.

Optional Activities

Depending on availability, consider snorkeling, kayaking, a guided coastal excursion or a sunset cruise.

Evening: Waterfront Dining

Enjoy dinner overlooking the marina or return to your accommodation.

Overnight Accommodation

St. Maarten.

Day 3: Discover French Saint-Martin – Marigot and Grand Case

Day 3 introduces you to the French side of the island.

French Saint-Martin is known for its charming coastal communities, French-Caribbean cuisine, local markets and beautiful beaches.

Morning: Explore Marigot

Marigot is the principal town and administrative center of French Saint-Martin.

The town offers colorful buildings, waterfront views, shops and restaurants.

Marigot Market

The market provides opportunities to discover local crafts, clothing, souvenirs and other products.

Market activity varies by day.

Fort Louis

Fort Louis is a historic fort overlooking Marigot.

The site offers panoramic views of the surrounding coastline.

Visitors can reach the fort by climbing steps from the town.

Wear comfortable shoes and carry drinking water.

Marigot Waterfront

Spend time exploring the harbor area and enjoying the town’s French-Caribbean atmosphere.

Afternoon: Visit Grand Case

Grand Case is one of the French side’s most charming coastal villages.

It is particularly famous for its restaurants and beautiful waterfront setting.

Grand Case Beach

Grand Case Beach offers opportunities for relaxation and coastal sightseeing.

Swimming conditions vary depending on weather and sea conditions.

Experience French-Caribbean Cuisine

Grand Case is known for French-inspired restaurants, seafood and traditional local barbecue establishments called lolos.

These casual restaurants provide opportunities to experience local flavors.

Evening: Dinner in Grand Case

Enjoy a memorable dinner in Grand Case before returning to your accommodation.

Overnight Accommodation

St. Maarten or Saint-Martin.

Day 4: Orient Bay, Pinel Island and Marine Adventures

Day 4 focuses on the beaches and offshore attractions of French Saint-Martin.

Morning: Relax at Orient Bay Beach

Orient Bay is one of the island’s best-known beaches.

It offers a long sandy shoreline, turquoise water and beachfront restaurants.

Visitors can enjoy beach relaxation, swimming when conditions permit and selected water activities.

Some sections of the Orient Bay area are associated with clothing-optional recreation, so choose facilities according to your preferences.

Late Morning: Explore Orient Bay

Enjoy a beachside meal or visit nearby shops.

Depending on weather conditions, recreational activities may be available.

Afternoon: Visit Pinel Island

Pinel Island, also known as Îlet Pinel, is located off the northeastern coast of French Saint-Martin.

It is a popular destination for beach relaxation and snorkeling.

Visitors generally reach the island by a short boat transfer from the Cul-de-Sac area.

Confirm current ferry schedules and weather conditions before departure.

Enjoy the Beach

Pinel Island offers beautiful coastal scenery and shallow-water beach areas.

Snorkeling Opportunities

Selected areas provide opportunities to observe tropical fish and marine habitats.

Follow local guidance and avoid disturbing coral or wildlife.

Island Dining

Beach restaurants may operate depending on the day and season.

Alternative Activity: Guided Boat Excursion

Travelers seeking a more adventurous experience may choose a full-day guided marine excursion instead.

Evening: Prepare for Anguilla

Return to your accommodation and prepare for the next day’s island transfer.

Confirm your ferry reservation, travel documents and transportation arrangements.

Overnight Accommodation

St. Maarten.

Day 5: Travel to Anguilla and Discover Its Beautiful Beaches

Day 5 marks the beginning of the Anguilla portion of your Caribbean vacation.

Anguilla is a British Overseas Territory known for its spectacular white-sand beaches, clear turquoise waters and peaceful island atmosphere.

Compared with St. Maarten, Anguilla generally offers a quieter and more relaxed tourism experience.

Morning: Travel from St. Martin to Anguilla

One common route is the public ferry from Marigot on French Saint-Martin to Blowing Point on Anguilla.

The crossing itself generally takes approximately 20–30 minutes, depending on conditions.

Travelers must complete the applicable immigration procedures.

Ferry schedules, fares and operating arrangements can change, so confirm current information before traveling.

Private or scheduled boat services may also operate from other departure points, including routes associated with the Dutch side.

Arrival at Blowing Point

After arriving in Anguilla, complete immigration and customs procedures.

Meet your arranged transportation and travel to your accommodation.

Afternoon: Visit Rendezvous Bay

Rendezvous Bay is one of Anguilla’s most beautiful beaches.

It is known for its long sandy shoreline, clear water and spectacular views toward St. Martin.

Visitors can enjoy beach walks, relaxation and swimming when conditions are suitable.

Late Afternoon: Explore Meads Bay

Meads Bay is another famous Anguilla beach.

It features beautiful white sand, turquoise water and beachfront accommodation.

The area is particularly attractive for couples and luxury travelers.

Evening: Beachfront Dining

Enjoy dinner at a beachfront restaurant.

Anguilla is known for its seafood, Caribbean cuisine and relaxed dining atmosphere.

Overnight Accommodation

Anguilla.

Day 6: Shoal Bay East, Snorkeling and Anguilla Island Exploration

Day 6 provides an opportunity to experience Anguilla’s beautiful beaches and peaceful coastal environment.

Morning: Visit Shoal Bay East

Shoal Bay East is one of Anguilla’s most recognizable beaches.

It is famous for its white sand, clear turquoise water and beautiful coastal scenery.

Visitors can enjoy swimming when conditions permit, beach relaxation and coastal walks.

Snorkeling Opportunities

Selected areas around Shoal Bay East may offer snorkeling opportunities.

Conditions vary, and visitors should avoid entering the water during rough seas.

Afternoon: Explore Anguilla

Depending on your interests, consider visiting additional beaches or local communities.

Sandy Ground

Sandy Ground is a coastal community known for its beach, restaurants and boating activity.

The Valley

The Valley is Anguilla’s capital and administrative center.

Visitors can explore selected local shops and cultural attractions.

Crocus Bay

Crocus Bay offers beautiful coastal scenery and opportunities for relaxation.

Optional Marine Excursion

Depending on weather conditions and availability, travelers may arrange a guided boat excursion to a nearby cay.

Possible destinations include Sandy Island or Prickly Pear Cays.

These excursions may offer snorkeling, beach relaxation and marine sightseeing.

Evening: Sunset and Farewell Dinner

Enjoy your final evening in Anguilla.

Choose a beachfront restaurant or another suitable dining location.

Overnight Accommodation

Anguilla.

Day 7: Return to St. Maarten and International Departure

Your final day begins with breakfast and preparations for departure.

Morning: Transfer to Blowing Point

Check out of your accommodation and travel to the ferry terminal.

Complete the required departure procedures.

Return Ferry to St. Martin

Take your scheduled ferry or authorized boat transfer back to St. Martin.

Allow sufficient time for immigration procedures, transportation and possible delays.

Transfer to Princess Juliana International Airport

After arriving in St. Martin, arrange transportation to Princess Juliana International Airport.

Remember that the public ferry arrives in Marigot on the French side, while Princess Juliana International Airport is on the Dutch side.

Traffic can be unpredictable, so allow generous transfer time.

Important Connection Advice

Avoid booking a tight same-day connection between Anguilla and your international flight.

Ferry services can be delayed or disrupted by weather and sea conditions.

For early international departures, returning to St. Maarten on Day 6 and spending the final night near the airport is a safer planning option.

Departure

Complete airport procedures and board your international flight.

Your seven-day St. Maarten and Anguilla island-hopping adventure concludes with memories of beautiful beaches, fascinating cultures and unforgettable Caribbean experiences.

Best Places to Stay in St. Maarten

Choosing the right accommodation location can make your vacation more convenient.

Simpson Bay: Best Overall Base

Simpson Bay is one of the most practical locations for first-time visitors.

It offers restaurants, accommodation, nightlife, beaches and access to marine excursions.

It is also relatively close to Princess Juliana International Airport.

Maho: Best for Entertainment

Maho is known for its proximity to the airport, famous beach and entertainment facilities.

Philipsburg: Best for Shopping and Sightseeing

Philipsburg provides access to shopping, historical attractions and Great Bay Beach.

Grand Case: Best for Couples and Food Lovers

Grand Case is known for its restaurants, boutique accommodation and relaxed coastal atmosphere.

Orient Bay: Best for Beach Vacations

Orient Bay offers beachfront accommodation, restaurants and access to French-side coastal attractions.

Best Places to Stay in Anguilla

Anguilla offers a range of accommodation options, including luxury resorts, boutique hotels, villas and guesthouses.

Meads Bay: Best for Luxury Travelers

Meads Bay is known for its beautiful beach and upscale accommodation.

It is particularly attractive for couples and honeymooners.

Rendezvous Bay: Best for Relaxation

Rendezvous Bay offers a peaceful coastal atmosphere and beautiful views toward St. Martin.

Shoal Bay East: Best for Beach Lovers

Shoal Bay East is ideal for travelers who want convenient access to one of Anguilla’s most famous beaches.

Sandy Ground: Best for Local Atmosphere

Sandy Ground offers restaurants, beach access and a lively waterfront setting.

St. Maarten vs Anguilla: What Is the Difference?

Although the islands are close together, their vacation experiences differ.

Which Destination Is Better?

St. Maarten is particularly attractive for travelers who enjoy cultural exploration, shopping, restaurants and entertainment.

Anguilla is ideal for visitors seeking peaceful beaches, luxury accommodation and a slower vacation pace.

Combining both destinations provides an excellent balance.

How to Travel from St. Maarten to Anguilla

Transportation between the islands is relatively convenient, but planning is essential.

Public Ferry from Marigot

The public ferry between Marigot and Blowing Point is a common transportation option.

The crossing generally takes approximately 20–30 minutes.

Schedules and fares should be confirmed before departure.

Private Boat Transfers

Private transfers may be available from selected departure points.

These can be attractive for couples, families and groups seeking additional flexibility.

Scheduled Boat Services

Some operators provide scheduled services associated with Princess Juliana International Airport or nearby marinas.

Availability varies.

Important Travel Requirements

Anguilla and St. Maarten are separate immigration jurisdictions.

Travelers may need different visas or entry permissions for each destination.

Check all requirements before booking.

Entry Requirements for St. Maarten and Anguilla

Travel requirements depend on nationality and travel circumstances.

St. Maarten Entry Requirements

Visitors arriving through Princess Juliana International Airport enter Dutch Sint Maarten.

Check passport, visa and entry requirements applicable to the Dutch side.

French Saint-Martin Entry Requirements

French Saint-Martin has separate immigration rules.

A visa for Dutch Sint Maarten does not automatically guarantee entry to French Saint-Martin.

Anguilla Entry Requirements

Anguilla is a British Overseas Territory with its own immigration requirements.

Some travelers may need a visa or other entry permission.

Passport and Travel Documents

Carry a valid passport and any required visas.

Keep accommodation and return travel confirmations accessible.

Important Planning Advice

Even though travel between the French and Dutch sides of St. Martin generally involves no routine land-border checkpoint, visitors must still comply with the immigration requirements applicable to their itinerary.

For Anguilla, formal immigration procedures apply when entering and leaving the territory.

Best Time to Visit St. Maarten and Anguilla

Both destinations enjoy warm tropical weather throughout the year.

December to April

These months generally offer relatively dry conditions and comfortable temperatures.

They are popular for beach vacations and island hopping.

May to June

Late spring and early summer can provide warm weather and opportunities for marine activities.

Rainfall and humidity may increase.

July to November

These months overlap with the Atlantic hurricane season.

Travelers should monitor weather forecasts and consider flexible booking arrangements.

Best Time for Island Hopping

December through April is attractive for many travelers, although strong winds and rough seas can still affect ferry services.

Always check marine conditions before traveling.

How Much Does a 7-Day St. Maarten and Anguilla Vacation Cost?

The cost of a seven-day vacation depends on accommodation, transportation, dining and selected activities.

Accommodation

St. Maarten offers a wide range of accommodation options.

Anguilla is known for luxury resorts, although smaller hotels and guesthouses are also available.

Flights

International airfare varies according to departure location, airline and travel season.

Ferry Transfers

Budget for ferry tickets, applicable departure charges and transportation to and from terminals.

Local Transportation

Taxis, rental vehicles and arranged transfers can add to vacation expenses.

Food and Dining

Both destinations offer casual restaurants and upscale dining.

Anguilla’s luxury dining options can increase overall costs.

Excursions

Snorkeling tours, sunset cruises and private boat charters may involve additional fees.

Travel Insurance

Consider insurance covering medical emergencies, cancellations and relevant travel disruptions.

Money-Saving Tips

Book accommodation in advance.

Compare transportation options.

Choose accommodation close to your preferred attractions.

Combine free beach activities with paid excursions.

Avoid unnecessary hotel changes.

Best St. Maarten and Anguilla Vacation Packages for Different Travelers

A seven-day itinerary can be adapted for different vacation styles.

Romantic Couples Vacation

Couples may prefer boutique accommodation in Grand Case and a luxury beachfront stay in Anguilla.

Recommended experiences include sunset dining, quiet beaches and guided marine excursions.

Honeymoon Vacation

Honeymooners can combine French-Caribbean dining in St. Martin with romantic beachfront relaxation in Anguilla.

Family Vacation

Families may enjoy beaches, cultural sightseeing and age-appropriate marine activities.

Choose accommodation with suitable facilities and plan ferry transfers carefully.

Adventure Vacation

Adventure travelers may enjoy snorkeling, kayaking, hiking, boating and island exploration.

Luxury Vacation

Luxury travelers may prefer premium accommodation, private transfers and personalized excursions.

These are suggested vacation styles rather than confirmed bookable packages.

What to Pack for a St. Maarten and Anguilla Vacation

Recommended essentials include:

• Lightweight tropical clothing

• Swimwear and beachwear

• Comfortable walking shoes

• Water shoes

• Sunscreen and sunglasses

• Sun hats

• Insect repellent

• Reusable water bottle

• Lightweight rain protection

• Personal medications

• Passport and required visas

• Travel insurance information

• Waterproof phone pouch

• Suitable evening clothing

• Chargers and appropriate travel adapters

Important Travel Tips for First-Time Visitors

Confirm Ferry Schedules

Ferry schedules can change due to weather, operational requirements and seasonal demand.

Allow Time for Immigration

Travel between St. Martin and Anguilla involves formal immigration procedures.

Avoid Tight Flight Connections

Allow sufficient time when returning from Anguilla for an international departure.

Choose Suitable Beaches

Water conditions vary between beaches.

Follow local safety guidance.

Respect Marine Wildlife

Avoid touching coral reefs or disturbing marine animals.

Plan Transportation

Rental vehicles and taxis are useful for exploring both destinations.

Carry Appropriate Currency

The French side of St. Martin uses the euro.

Dutch Sint Maarten uses the Caribbean guilder.

Anguilla uses the Eastern Caribbean dollar.

US dollars are widely accepted in many tourism businesses, but exchange rates vary.

Keep Travel Documents Accessible

Carry your passport and required entry documents when traveling between jurisdictions.

Frequently Asked Questions About a 7-Day St. Maarten and Anguilla Itinerary

Is seven days enough for St. Maarten and Anguilla?

Yes. Seven days is enough to explore the highlights of St. Maarten and spend several nights enjoying Anguilla’s beaches and coastal attractions.

Can you visit Anguilla from St. Maarten?

Yes. Anguilla is accessible by ferry and authorized boat transfers from St. Martin.

How long is the ferry from St. Martin to Anguilla?

The public ferry crossing between Marigot and Blowing Point generally takes approximately 20–30 minutes, depending on conditions.

Is Anguilla worth visiting from St. Maarten?

Yes. Anguilla offers beautiful beaches, peaceful coastal scenery and a different island atmosphere.

Is St. Maarten or Anguilla better for couples?

Both are excellent. St. Maarten offers cultural exploration and dining, while Anguilla is particularly attractive for romantic beach relaxation.

Which island has better beaches?

Anguilla is especially famous for its peaceful white-sand beaches. St. Maarten offers a greater variety of lively resort beaches and coastal experiences.

Can you visit both islands without flying?

Yes. Ferry and authorized boat services connect St. Martin and Anguilla.

Do you need a passport to travel from St. Maarten to Anguilla?

Yes. Travelers should carry a valid passport and meet Anguilla’s entry requirements.

Do you need a visa for Anguilla?

Visa requirements depend on nationality and travel circumstances. Check official Anguilla immigration guidance before departure.

Where should you stay in St. Maarten?

Simpson Bay is convenient for first-time visitors, while Grand Case and Orient Bay are attractive for travelers seeking French-side experiences.

Where should you stay in Anguilla?

Meads Bay, Rendezvous Bay and Shoal Bay East are popular areas for beach vacations.

Is Anguilla expensive?

Anguilla is known for luxury accommodation and dining, but costs vary according to travel dates and accommodation choices.

What is the best time to visit St. Maarten and Anguilla?

December through April generally offers relatively dry weather and comfortable temperatures.

Can this itinerary be customized?

Yes. Travelers can adjust the number of nights, accommodation, activities and transportation according to their preferences and budget.

Plan Your St. Maarten and Anguilla Vacation with Across Caribbean Excursions

St. Maarten and Anguilla offer one of the Caribbean’s most memorable island-hopping combinations, bringing together beautiful beaches, fascinating cultural experiences, excellent cuisine and spectacular coastal scenery.

From the lively streets of Philipsburg and the French-Caribbean charm of Grand Case to the peaceful beaches of Shoal Bay East and Meads Bay, these destinations provide unforgettable experiences for every type of traveler.

A seven-day vacation allows you to discover the highlights of both islands while enjoying a balance between sightseeing, marine adventures and relaxation.

Whether you are planning a romantic escape, honeymoon, family holiday or luxury Caribbean adventure, thoughtful planning can help you create a rewarding multi-island vacation.

At Across Caribbean Excursions, we help travelers discover beautiful Caribbean destinations and explore exciting vacation experiences.

Our travel resources provide inspiration for multi-day itineraries, island-hopping adventures, family vacations, romantic getaways and marine excursions.

Visit Across Caribbean Excursions to explore Caribbean destinations and find inspiration for your next St. Maarten and Anguilla vacation.

Start planning your seven-day St. Maarten and Anguilla adventure with Across Caribbean Excursions and discover the beaches, cultures, cuisine and natural beauty that make these two islands extraordinary Caribbean vacation destinations.