A Month In The Caribbean
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The Caribbean boasts some of the world's most beautiful beaches, crystal clear blue waters, and rich cultural heritage. From Anguilla to St. Vincent and everything in between, hike along stunning ridges, explore historic landmarks, and indulge in internationally renowned cuisine.
You'll discover that every island is unique from the next, each providing a stunning backdrop to your island-hopping holiday.
December 27th - January 2nd: Anguilla
- 7 nights | Four Seasons Anguilla
January 3rd - January 8th: St. Martin
- 5 nights | La Samanna by Belmond
January 8th - January 13th: St. Barth's
- 5 nights | Rosewood Le Guanahani
January 13th - January 18th: St. Kitts
- 5 nights | Park Hyatt St. Kitts
January 18th - January 24th: Canouan
- 6 nights | Mandarin Oriental Canouan
January 24th - January 27th: Barbados
- 3 nights | Sandy Lane
January is a fabulous time of year in the Caribbean as we see the least amount of rain all year long. While climates will vary from island to island, expect temperatures to range from the upper 80s during the day to mid-60s at night.
US Passport holders do not need a visa to visit any of the islands on the itinerary.
There are currently no COVID-related requirements to enter any of the countries in the itinerary. We will regularly check for updates and ensure you are provided with the most current information prior to departure.
These guidelines are for reference only. Scenset holds no responsibility for travel restrictions. Travelers are responsible for ensuring the right documentation to travel.
We have designed some great playlists for you to enjoy during your trip through the Caribbean full of local talent to discover!
- Summer Chill is the perfect soundtrack for basking in the sun and enjoying the laid-back island life.
- Lazy Beach Days is designed for you to unwind on the beach and relax.
Today, depart from Miami and head to the islands for a month of sun and sand.
- Flight details below
Booked Independently
Your driver will meet you after customs and transport you via private car to the hotel.
Booked by Scenset
Check into your hotel and get ready to explore!
Melt the travel day away at the Spa at the Four Seasons with a 90 minute massage for two.
- Appointment Time: Evening
- Massage Type: Four Seasons Signature Massage, 80 minutes
Booked by a scenset
Have a casual early dinner at Sunset Lounge at the Four Seasons on your first night in the Caribbean.
- Reservation Time: Early evening
- Reservation Name: will be provided
Booked by Scenset | Paid locally
- Deluxe Ocean View One Bedroom Suite
- This room features a living area, private plunge pool and sweeping sea views.
- Breakfast included
Booked by someone
Why do we love it for you? Centrally located along the island’s northwest shore, this five-star resort has direct beach access, a world-class spa and fitness center, and 4 restaurants to choose from.
Ease into Anguilla with a long walk down one of the island's most beloved beaches. Stop for a seaside lunch, reset with a massage, and then head out for an evening by the sea.
Your next activity is walkable down the beach from the hotel.
- Suggested Departure Time: Afternoon
- Approximate Walk Time: 25 minutes on the beach
After breakfast and a leisurely morning, walk down the beach to Straw Hat for a pre-booked lunch reservation. Named by Condé Nast as one of the 50 Hot New Restaurants of the World, they're best known for serving up delicious and innovative Caribbean cuisine.
- Reservation Time: Lunchtime
- Reservation Name: will be provided
Booked by Scenset | Taxi Paid Locally
We will pre-arrange a taxi to dinner, to be paid locally to the driver.
- Departure Time: Evening
- Drive Time: A few minutes
Arranged by Scenset | Paid Locally
Cip's by Cipriani offers a casual Italian menu rich with comfort food in an open, al fresco setting. Delicious fresh produce becomes tempting antipasti salads, pastas and the famous Cipriani carpaccio.
- Reservation Time: Evening
- Reservation Name: will be provided
Booked by Scenset | Paid Locally
Four Seasons Anguilla | Deluxe Ocean View One Bedroom Suite
Booked by someone
Enjoy a day at leisure before dinner at one of the most renowned restaurants in Anguilla.
Enjoy a relaxed lunch at Bamboo Bar & Grill at the Four Seasons. The trio of ceviche is a guest favorite!
- Note: Bamboo Grill does not take reservations and is walk-in only.
Suggestion by Scenset | Paid Locally
We will pre-arrange a taxi to dinner, to be paid locally to the driver.
- Departure Time: Evening
- Drive Time: 15 minutes
Arranged by Scenset | Paid Locally
Veya is well known as one of the most exclusive restaurants on the island, delicately combining a fusion of international flavors to satisfy any palate.
- Reservation Time: Evening
- Reservation Name: will be provided
- Confirmation Number: will be provided
Booked by Scenset | Paid Locally
A phone number will be provided to call a taxi after dinner, to be paid locally to the driver. It's recommended to call about 10-15 minutes before your desired departure time.
Four Seasons Anguilla | Deluxe Ocean View One Bedroom Suite
Booked by a guest
Begin the day with a hiking tour of Anguilla's caves, followed by dinner at the Malliouhana.
This privately guided experience will take you to Katouche, an 80-acre estate on Anguilla known for its unique vegetation and two significant caves, including Cavannaugh Cave. The hiking tour, lasting about 1.5 hours, explores this rich biodiversity and the fascinating history of the caves, ending at Katouche Bay. Transportation is included.
- Pickup Time: Morning
- Duration: About 1.5 hours
Booked by Scenset
After returning to the hotel, walk down the beach to Mango's Seaside Grill, serving only the freshest caught fish and lobster.
- Note: Mango's does not take reservations and is walk-in only.
Suggestion by Scenset | Paid Locally
Take the rest of the afternoon to relax by the pool, or let us know if you'd like to hit the spa for some post-hike rejuvenation and we'd be happy to secure you a booking.
We will pre-arrange a taxi to dinner, to be paid locally to the driver.
- Departure Time: Evening
- Drive Time: 15 minutes
Arranged by Scenset | Paid Locally
Celeste Restaurant at the Malliouhana is renowned for its luxurious dining experience, offering a fusion of Mediterranean and Caribbean flavors against a backdrop of breathtaking ocean views.
- Reservation Time: Evening
- Reservation Name: will be provided
- Transportation: The hotel will arrange transportation from the lobby in the late afternoon/early evening.
Booked by Scenset | Paid Locally
A phone number will be provided to call a taxi after dinner, payable directly to the driver. It's recommended to call 10-15 minutes before your planned departure.
Four Seasons Anguilla | Deluxe Ocean View One Bedroom Suite
Booked by a guest
Wave goodbye to 2023 with a private charter boat to Prickly Pear Cay, where you'll find some of the best snorkeling in Anguilla. Later, a dinner reservation at a premiere restaurant followed by an exclusive New Years event hosted by the hotel.
Set out with your snorkels on a private charter to Prickly Pear Cay, where you'll find beautiful sea life and less of a crowd. Refreshments and snacks will be provided on board.
- Departure Time: Morning
- Duration: Approximately 4 hours
Booked by a client
After your snorkel trip, head over to Half Shell Beach Bar on the Four Seasons property for a light lunch with ocean views.
- Note: Half Shell does not take reservations and is walk-in only.
Suggestion by Scenset | Paid Locally
- Nighttime: Dinner at Salt by Four Seasons, which will be serving a specially curated New Year's Eve menu.
- Late Night: Entertainment begins at Sunset Lounge. You are free to keep your table at Salt if you are enjoying the view of the fireworks and entertainment from there, or you're welcome to stand closer to the entertainment area.
Booked by Scenset | Paid Locally
Hello 2024! Today is a day for recharging at the resort and exploring at your leisure.
After a late breakfast, head down to the lounge chairs at the adults-only pool or snag a prime spot on the beach for a day of rest and relaxation. The day is left open for you to enjoy at your own pace, with the option to book a spa treatment or go out for lunch in town.
Booked by Scenset
We will pre-arrange a taxi to dinner, to be paid locally to the driver.
- Departure Time: Evening
Arranged by Scenset | Paid Locally
Pimm's at Cap Juluca offers a menu of elevated Anguillan cuisines and international specialties, set at the water's edge of a chic Anguilla hotel.
- Reservation Time: Evening
- Reservation Name: will be provided
Booked by Scenset | Paid Locally
A phone number will be provided to call a taxi after dinner, to be paid locally. It's recommended to call about 10-15 minutes before your planned departure.
Four Seasons Anguilla | Deluxe Ocean View One Bedroom Suite
Booked by a traveler
Experience another side of the island at Shoal's Bay, a secluded beach in the Northwest. Stroll down to lunch on the beach, before heading home to reset for your final dinner in Anguilla.
We will pre-arrange a taxi to the beach, to be paid locally to the driver.
- Departure Time: midday
- Drive Time: 30 minutes
Arranged by Scenset | Paid Locally
Head over to Shoal's Bay, a treasured stretch of beach perfect for walking at leisure. You'll wind up at 20 Knots for lunch, perched in a beautiful hotel by the water and serving up Caribbean cuisine with a Latin American flair.
- Reservation Time: Around midday
- Reservation Name: will be provided
Booked by Scenset | Paid Locally
A phone number will be provided to call a taxi after lunch, to be paid locally to the driver. It's recommended to call about 10-15 minutes before your desired departure time.
Head home to reset before dinner and take in one final sunset on Anguilla.
We will pre-arrange a taxi to dinner, to be paid locally to the driver.
- Departure Time: Evening
- Drive Time: A few minutes
Arranged by Scenset | Paid Locally
Blanchard's promises a menu infused with bold flavors and a global influence. Surrounded by tropical gardens with the sea steps beyond, guests rave about the impeccable service and a laid-back atmosphere providing a perfect last evening on the island.
- Reservation Time: Evening
- Reservation Name: will be provided
Booked by Scenset | Paid Locally
A phone number will be provided to call a taxi after dinner, to be paid locally. It's recommended to call about 10-15 minutes before your planned departure.
Four Seasons Anguilla | Deluxe Ocean View One Bedroom Suite
Booked by a person
After breakfast, check out of your hotel and meet your driver, who will take you to the airport. You're headed to Barbados by private charter plane to round out your island hopping holiday.
Barbados has something for everyone: pink sand beaches, exotic wildlife, and sunsets just begging to be enjoyed with a fresh cocktail. Named by Condé Nast as one of the 10 Most Beautiful Islands of the Caribbean, its beauty is complemented by the delicious cuisine and high-end resorts that line its sandy shores.
After checkout, a private car will take you to the Canouan airport for your private charter flight to Barbados.
- Departure Time: Late morning
Booked by Scenset
Board a private jet that will transport you to Barbados.
- Departure Time: Late morning
- Duration: Approximately 20 minutes
Booked by Scenset
- Airport Arrival: You will be accompanied by resort staff from the resort all the way to boarding the plane.
- Tail Number: J8-JET
A private car will meet you at the boat terminal and transfer you to your hotel.
Booked by Scenset
Head up the hill for a relaxed lunch at Sandy Lane Country Club with views over the golf course.
- Reservation Time: Afternoon
- Reservation Name: will be provided
Booked by Scenset | Paid locally
L'Acajou on the beach of your hotel specializes in refined, modern, classical and contemporary renditions on European cuisine with an emphasis on French and Mediterranean, paired with an impressive range of Old and New World wines.
- Reservation Time: Evening
Booked by Scenset | Paid Locally
- One Bedroom Luxury Ocean Room
- This room features a king bed, sitting area private sea view terrace.
- Breakfast included
Booked by someone
Why do we love it for you? Sandy Lane's legendary style makes it one of the most prestigious resorts in the Caribbean. Boasting four restaurants, a golf course, and a spa voted #1 in the Caribbean by Travel + Leisure, this gorgeous property will be the perfect end to your Caribbean holiday.
- Free wifi
- Complimentary room upgrade on arrival to the next category (based on availability)
- Complimentary early check-in/late checkout (based on availability)
After a leisurely morning, take a tour of the Mount Gay Rum Distillery followed by a tasting of the spirit Barbados is best known for. Later, a multi-course tasting menu at a must-visit Barbados restaurant.
Have brunch by the sea and enjoy a morning to sleep in and relax.
Recommendation by Scenset
We will pre-arrange a taxi to your tour, to be paid locally to the driver.
- Departure Time: Early afternoon
- Drive Time: Approximately 20 minutes
Arranged by Scenset | Paid Locally
The Mount Gay Rum Historic Distillery Tour takes you through the fully-operational rum-making headquarters. To follow, a food and rum pairing takes place in the beautiful Great House on the distillery estate.
- Start Time: Afternoon
- Duration: Approximately 2 hours
Booked by a scenset
A phone number will be provided to call a taxi after dinner, to be paid locally. It's recommended to call about 10-15 minutes before your desired departure time.
Take some time to rest at the hotel before your dinner reservation in the evening.
We will pre-arrange a taxi to dinner, to be paid locally to the driver.
- Departure Time: Early evening
- Drive Time: A few minutes
Arranged by Scenset | Paid Locally
The Cliff promises a luxurious fine dining experience on the water’s edge, with a 3 course gourmet meal created by a Michelin Star chef.
- Reservation Time: Evening
- Reservation Name: will be provided
Booked by Scenset | Paid Locally
Enjoy your last day in the Caribbean at leisure with a morning massage. Later, reminisce over a final farewell dinner in the Caribbean.
Enjoy a 90-minute massage at the Sandy Lane Spa as you ease into your final day in the Caribbean.
- Reservation Time: Late morning
- A guest: 80-Minute Deep Tissue Massage
- A guest: 80-Minute Sandy Lane Signature (Swedish) Massage
Booked by Scenset
Take the rest of the day to relax at your own pace.
Recommendation by Scenset
The Tides Barbados delivers waterfront fine dining with a stunning interior and fresh-caught seafood specialties.
- Reservation Time: Evening
- Reservation Name: will be provided
Booked by Scenset | Paid Locally
All good things must come to an end. Check out of your hotel and take one final look at the beach, before meeting your private driver who will take you to the Barbados airport.
A private driver will take you to the Barbados airport for your flight home.
- Departure Time: Afternoon
- Drive Time: 30 minutes
Booked by Scenset
Details below.
Booked Independently
Thank you for travelling with us. We hope you had a fantastic trip and we wish you a safe flight home!
While on the trip, you can access your support team if any need arises to make your trip as smooth as possible. We are here to support you.
The Scenset Trip Planning Fee has been waived.
If you like what you read and are ready to pull the trigger on this once-in-a-lifetime adventure, please send a chat in the app or an email to let us know.
We would be thrilled to secure all the reservations and make sure everything is taken care of, including special surprises along the way.
Please refer to our Terms & Conditions prior to booking your trip.
Scenset invests in making the world a better place. Scenset will offset the fuel used during the trip. On top of that, we will offset an extra 10% to make your trip a carbon-positive experience.
Currently, we support Gold Standard Climate+ Projects from the Gold Standard Foundation.