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Caribbean

The Caribbean islands are often lumped together because of their shared traits—dependable gorgeous weather, pristine beaches, a laid-back vibe—but they’re very distinct from one another. With the help of Indagare’s insider knowledge, a beach vacation here can include exploration of culture, history and ecology, as well as time enjoying the resort that’s right for you.

Ready to go and in need of expert trip planning? Contact us today.

Itineraries We Love

We believe that itineraries need to be personalized, and can work for anyone from honeymooners and adventurers to families and multi-gen groups as long as they are tailored to your interests. Here are some of our favorites; many more can be created by our expert team.

  • Flop and Drop

    Flop and Drop

    Sometimes, all you want to do on vacation is get settled in a beach chair with a good book and an even better view, with an excellent poolside menu and exquisite service at your fingertips.

    Sometimes, all you want to do on vacation is get settled in a beach chair with a good book and an even better view, with an excellent poolside menu and exquisite service at your fingertips.

    • When to Go

      November – May. The summer is hot, but less crowded.

    • Ideal Length of Stay

      3-5 Nights

    • Itinerary Highlights

      Ultimate relaxation, tropical fun and five-star service at one of the region’s premier resorts.

    • Day 1-5

      With the help of your Indagare travel specialist, choose the experiences that are right for you. You can plan your time around spa and wellness activities, extensive beach amenities, fabulous poolside service, relaxed hideaways, gourmet dining and so much more.

  • Top Boat Charter

    Top Boat Charter

    There’s no better way to see the Caribbean than from the water. Sample the vibes in the British Virgin Islands, Nevis and St. Barth’s by boat with your very own customized itinerary. Indagare works with a variety of boats, ranging from smaller Fun Yaks to skippered Riva Operas, majestic sailing vessels and luxury yachts for day use, as well as longer charters.

    There’s no better way to see the Caribbean than from the water. Sample the vibes in the British Virgin Islands, Nevis and St. Barth’s by boat with your very own customized itinerary. Indagare works with a variety of boats, ranging from smaller Fun Yaks to skippered Riva Operas, majestic sailing vessels and luxury yachts for day use, as well as longer charters.

    • When to Go

      November – May. The summer is hot, but less crowded.

    • Ideal Length of Stay

      1 Week

    • Itinerary Highlights

      Enjoy relaxation and adventure on the water and the best of the Caribbean at your fingertips, by boat. With your customized Indagare itinerary, you can venture to Virgin Gorda, Nevis Peak and the hotspots of St. Barth’s with the wind at your back.

    • Day 1-3

      The British Virgin Islands have some of the world’s best snorkeling, whale watching and dive sites, and balmy, tropical weather and soft trade winds make for pleasant sailing. Here, you can visit the enchanting baths at Virgin Gorda, have a candlelit dinner on the water in Tortola and explore secluded isles like Necker Island and Peter Island.

    • Day 4-5

      Set sail for a stop in Nevis, a more relaxed locale and a favorite for families. Blessed with lazy golden beaches and the jaw-dropping Nevis Peak, travelers come to the small island to experience its natural, lush and dramatic beauty. Spend a night at the superbly located Four Seasons, go on long walks to soak in the sun and scenery and hit the Golden Rock Inn for house rum punch before a dining on the water or at an Indagare-recommended restaurant.

    • Day 6-7

      End your trip in style with a visit to the glamorous St. Barth’s, where l’art de vivre meets laid-back tropical ease. See and be seen at the social and shopping hub of Eden Rock, enjoy lunch at the strikingly designed hotel Le Sereno and sip homemade cocktails on the waves before dinner at Jean-Georges Vongerichten’s masterpiece On the Rocks, which is perched on a cliff above the sea.

  • Family-Friendly Caribbean

    Family-Friendly Caribbean

    With a long list of outdoor activities, high-end resorts that suit your every need and top spots for lounging and shopping, the Caribbean is an ideal destination for families and their different interests. Antigua and Nevis are two of our favorite picks, especially for children.

    With a long list of outdoor activities, high-end resorts that suit your every need and top spots for lounging and shopping, the Caribbean is an ideal destination for families and their different interests. Antigua and Nevis are two of our favorite picks, especially for children.

    • When to Go

      November – May. The summer is hot, but less crowded.

    • Ideal Length of Stay

      3-5 Nights

    • Itinerary Highlights

      Delicious food, fun activities and stunning views at the Mill Reef Club, Hermitage Bay, Jumby Bay, Curtain Bluff, Carlisle Bay and the Golden Rock Inn.

    • Day 1-3: Antigua

      Home to the beloved Mill Reef Club, Antigua is a classic destination for family time and fun. Antigua’s pristine beaches, five-star resorts and easy access – direct flights from both the US and Europe – have made it one of the Caribbean’s most desirable getaways for multi-gen groups. Resorts such as Carlisle Bay offer excellent kids’ clubs, or the whole family can enjoy experiences such as looking for endangered hawksbill turtles in Jumby Bay and visiting the local farm that supplies the gourmet organic restaurant, Hermitage Bay.

    • Day 4-5: Nevis

      What Nevis lacks in size, it makes up for in character and charm. There are several family-friendly hotels to choose from that offer activities that can occupy the kids, while you enjoy a custom cocktail as the sun sets over the water or go snorkeling. There are many appealing off-site options as well: for example, the island boasts one of the largest orchid collections in the Caribbean.

Plan With Us

Here are the top three reasons why you should plan your next trip with us.

1

Matchmaking

You dream out loud. We listen to your travel preferences and needs. And together, we craft the perfect trip.

2

Trusted Network

For more than twenty years, we have built relationships with a network of premier partners and guides, assuring that you will travel as part of the Indagare family.

3

Peace of Mind

From planning to execution, we have you covered every step of the way. We offer support on the ground and in our office, so you have a partner at all times.

Ready to go and in need of expert trip planning? Contact us today.

Travel Guides & Articles

Everything we recommend is sourced first-hand by our well-traveled team and incredible network of insiders and resources around the world. Here are some the Destination Guides and latest articles not to be missed.

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