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Windstar Cruises · Small-ship cruises

Windstar Cruises, sailing yachts and small ships

At Traveland, we plan Windstar voyages from start to finish. Windstar sails three classic sailing yachts and three all-suite yachts, carrying 148 to 342 guests, to Tahiti, the Mediterranean and Northern Europe. We arrange the flights and hotels around your voyage, so your time goes into enjoying it. 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

Why Windstar

Why sail with Windstar Cruises?

Small ships, attentive crew and food rooted in each destination.

Small ships

148 to 342 guests, with about one crew member for every 1.5 guests.

James Beard Foundation

Windstar is the Official Cruise Line of the James Beard Foundation.

Watersports Platform

Swim, kayak and paddleboard straight from the yacht on select days.

Open Bridge

Visit the bridge and learn chart reading from the captain.

Experiences

What would you like to experience?

Windstar sails to Tahiti year round, the Mediterranean with a new port almost every day, and Northern Europe and Iceland. These are a few of the experiences travelers ask us about most.

A Windstar sailing yacht at anchor with its watersports platform open

Sailing yachts

Classic sailing yachts with a watersports platform at the stern.

Guests serving themselves at a beach barbecue

Local cuisine

Dishes inspired by each destination, with a vegan menu across the fleet.

A couple walking arm in arm through a whitewashed old town

Time ashore

Ports such as Dubrovnik’s Old Town, Portofino and Seville.

Working with us

How do we plan your cruise?

01

A conversation

Tell us how you like to travel, who is coming, and what you hope to feel. There is no charge to begin.

02

An itinerary made for you

We design the route, hotels, transfers and experiences, then refine them with you, so you skip the hours of research and comparison.

03

Every detail handled

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

Add Your Heading Text Here

Windstar operates three classic sailing yachts and three all-suite yachts, carrying 148 to 342 guests.

Windstar sails to Tahiti year round, the Mediterranean, Northern Europe and Iceland.

Tahiti voyages run 7 to 18 nights, with departures almost every week, and include a Destination Discovery Event in Bora Bora.

Windstar is the Official Cruise Line of the James Beard Foundation, and its chefs use fresh, locally sourced ingredients.

Yes. A vegan menu is available across the fleet, developed with the National Health Association.

Planning a trip like this can take many hours of research, comparison and booking. We do that work for you, draw on decades of experience to get the details right, and keep every confirmation in one place, so you can spend that time looking forward to the journey.

We are a family-owned travel agency in Connecticut, with offices at 564 Racebrook Road in Orange (203-929-6000) and 4270 Main Street in Bridgeport (203-371-1114).

Inquire

Begin the conversation

Tell us a little about the cruise you have in mind. One of our advisors will reply personally.

    Prefer to talk?

    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

    Begin the Conversation