The Caribbean · Planned start to finish
Traveland plans personal trips to the Caribbean, from the beaches of Aruba and Turks and Caicos to the Pitons of St. Lucia and the reefs of the Bahamas, and handles every detail from the first conversation to your flight home. We are a family-owned travel agency in Connecticut, planning trips since 1978 as a member of the Signature Travel Network.
Since 1978Family-owned and operated
Signature Travel NetworkMember agency
Orange & BridgeportTwo Connecticut offices
Every detail handledSo you can simply enjoy the trip
How we plan the Caribbean
Some islands are made for doing very little, others for diving, hiking or long dinners in town. We match the island and the resort to how you like to travel, then arrange the flights, transfers and reservations, so your time goes to the water instead of the research.
Destinations
Each island has its own pace. Choose one to see how we plan it, or ask us to help you compare.
Calm beaches, Oranjestad and Arikok National Park.
Nassau, the Exumas and Harbour Island.
Calm west coast beaches and historic Bridgetown.
Pink sand beaches, pastel harbors and historic St. George, two hours from New York.
Punta Cana, La Romana and Santo Domingo.
Montego Bay, Negril and Ocho Rios.
Cancún beaches, Tulum’s clifftop ruins, Cozumel reefs and jungle cenotes.
Old San Juan, El Yunque rainforest, Culebra, Vieques and the surf towns of the west coast.
The Pitons, the rainforest and sheltered Caribbean bays.
Grace Bay, coral reefs and quiet cays.
Working with us
01
Tell us how you like to travel, who is coming, and what you hope to feel. There is no charge to begin.
02
We design the route, hotels, transfers and experiences, then refine them with you, so you skip the hours of research and comparison.
03
We book the flights, stays, cruises and tours and keep track of every confirmation, so all you have to do is enjoy the journey.
Questions
It depends on what you want from the trip. Aruba and Turks and Caicos are known for calm beaches and easy travel, St. Lucia for its mountains and rainforest, and Jamaica and the Dominican Republic for a wide choice of resorts. We will ask a few questions and suggest the island that fits.
December through April is the driest and most popular season. Hurricane season runs from June through November, and some islands, such as Aruba, sit south of the main storm belt. We will help you weigh weather, crowds and availability for your dates.
U.S. citizens need a valid passport for most Caribbean islands. Puerto Rico is a U.S. territory, so a passport is not required when flying in from the mainland. We will confirm the entry requirements for your destination before you travel.
Yes. We can combine islands linked by short flights, or plan a Caribbean cruise with hotel stays before or after the sailing.
It can be, especially for families and for travelers who would rather not plan every meal. On islands with strong restaurant scenes, such as Barbados and St. Lucia, a hotel with breakfast can be the better fit. We will explain the trade-offs for the island you choose.
Send us a note through the form below or call our office. We will talk through your dates, budget and interests, then come back with a plan for you to review.
Keep exploring
Each region has its own page with the destinations we plan most often.
Italy, France, Greece, Spain, Portugal, Croatia, Ireland, Switzerland and the Nordics, from Paris and the Amalfi Coast to Alpine villages.
Japan, South Korea, Thailand, the Philippines, the Maldives, Australia, New Zealand, Fiji, Tahiti and the Hawaiian Islands.
The United States and Canada, Alaska and the Yukon, Costa Rica, Peru, Chile, Colombia and Buenos Aires.
Dubai, Abu Dhabi, Qatar, Saudi Arabia, Jordan, Israel, Egypt, Morocco and South Africa.
Inquire
Tell us a little about the journey you have in mind. One of our advisors will reply personally.
Choose a time for a call with one of our advisors.
Orange
564 Racebrook Road, Orange, CT 06477
203-929-6000
Bridgeport
4270 Main Street, Bridgeport, CT 06606
203-371-1114
Monday to Friday, 9am to 6pm
info@traveland.net