The Caribbean Sailing Trips & Packages Tours & Trips

6 The Caribbean Sailing Trips & Packages trips. Tours from 3 tour companies. 0 reviews.

6 Trips match your criteria (1 - 6 shown)

Sailing the Caribbean
Save this trip to your favorites or other list
Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Sail the sparkling Caribbean Sea
  • Aboard the historic square-rigger Sea Cloud.
  • Snorkel in pristine coral reefs
  • Swim in tropical lagoons
  • Explore secluded cays and beaches.
Show more

Themes

50 Plus, Sailing, Small Ship Cruise

What travelers are saying

"We booked a National Geographic expedition Holland and Belgium by River. The promotional literature promised a 14-day deposit refund window. The “invoice” was marked “non-refundable” deposit. We completed the National Geographic Traveler Information. About 8 days later we received the “Travel Agreement” to be signed. We both approved and signed the National Geographic documents. A Cruise Line Travel agreement was enclosed but had no signature line. This document contained language which was unacceptable. We submitted the signed NatGeo documents. The following day we canceled the trip due to the unacceptable Cruise Line language. Cancellation was made 12 days after booking and no deposit was returned. We were told on the phone that the refund deadline was triggered by the 14 day window OR signatures on the Travel Agreement which ever came first. This was NEW information. To date, we have received NO refund of our $1000. We cancelled our trip within the advertised 14 day window."

Trip dates & details
Save this trip to your favorites or other list
More
Private stay at Harbour Beachfront Villa - Blue Belle
Save this trip to your favorites or other list
Private Guided
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Relax and unwind on a private island of white-powdered beaches and aqua-marine sea.
  • Take advantage of the fantastic water sports and enjoy the warm Caribbean waters.
  • Spend time with the extended family, or a group of friends in privacy.
  • Explore the crystal waters of the island on a snorkelling adventure.

Themes

Cultural, Nature & Wildlife, Sailing, Scuba Diving, Rafting, Kayaking, Canoeing

What travelers are saying

"Absolutely amazing two week trip to Mexico. Phoebe was very knowledgeable and helped us plan a fabulous itinerary. The hotels she'd recommended were perfect and in excellent locations. Our guides were helpful, friendly and spoke excellent English and when we contacted the Mexico office to squeeze in another excursion, they were responsive and immediately organised everything. All round brilliant customer service and Mexico was the most interesting and beautiful place to visit! Thank you!"

Trip dates & details
Save this trip to your favorites or other list
More
Petit St Vincent
Save this trip to your favorites or other list
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • The perfect hideaway in the seclusion of the lush forest of Petit St Vincent Island.
  • Villas are completely private, opening out onto the beach.
  • Open air beachfront restaurant serving freshly caught seafood.
  • Access to some of the best diving sites at the JM Cousteau dive facility.
  • Take a day's sailing trip out to Tobago Cays, where skipper, Jeff Stevens will take you to some of the most beautiful deserted beaches.

Themes

Nature & Wildlife, Local Immersion & Homestays, Sailing, Scuba Diving, Relaxing Retreats

What travelers are saying

"Absolutely amazing two week trip to Mexico. Phoebe was very knowledgeable and helped us plan a fabulous itinerary. The hotels she'd recommended were perfect and in excellent locations. Our guides were helpful, friendly and spoke excellent English and when we contacted the Mexico office to squeeze in another excursion, they were responsive and immediately organised everything. All round brilliant customer service and Mexico was the most interesting and beautiful place to visit! Thank you!"

Trip dates & details
Save this trip to your favorites or other list
More
Custom Designed Trip
Lodging level
lodgingLevelName
Physical level
N/A

Highlights

  • Fully customized trip based on preferences
  • Matched with a local specialist
  • From $150 per person per day
Self-Guided / Independent Tour
Blue Waters Resort break
Save this trip to your favorites or other list
Private Guided
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Play a round of golf at Antigua's only PGA rated course, Cedar Valley Golf Club, just 5 km (3 miles) away from Blue Waters Resort.
  • The Cove restaurant is situated high above the cliffs, giving a unique dining experience over the Caribbean Sea.
  • The resort is set in 17 acres of tropical gardens, which can be explored with the head gardener, John on a private tour.
  • Book a sail at sunset or lobster lunch cruise to get the most out of the tranquil ocean setting.
  • Complimentary water bottles for all guests and excellent attitude to sustainability.

Themes

Nature & Wildlife, Sailing, Yoga, Meditation & Wellness, Relaxing Retreats, Golf

What travelers are saying

"Absolutely amazing two week trip to Mexico. Phoebe was very knowledgeable and helped us plan a fabulous itinerary. The hotels she'd recommended were perfect and in excellent locations. Our guides were helpful, friendly and spoke excellent English and when we contacted the Mexico office to squeeze in another excursion, they were responsive and immediately organised everything. All round brilliant customer service and Mexico was the most interesting and beautiful place to visit! Thank you!"

Trip dates & details
Save this trip to your favorites or other list
More
Palm Island Resort & Spa break
Save this trip to your favorites or other list
Private Guided
Lodging level
Luxury - 5 star
Physical level
Very Easy
Trip pace
Flexible schedule

Highlights

  • An adult orientated castaway island with five white sand beaches and lush jungle.
  • Rooms are decorated with Caribbean charm and offer garden, beach or ocean views.
  • Two onsite restaurants serve fresh Caribbean dishes, and private dining in the pergola is a memorable experience.
  • There are a huge variety of experiences on the island, including sailing to nearby Union Island.

Themes

Nature & Wildlife, Sailing, Scuba Diving, Relaxing Retreats

What travelers are saying

"Absolutely amazing two week trip to Mexico. Phoebe was very knowledgeable and helped us plan a fabulous itinerary. The hotels she'd recommended were perfect and in excellent locations. Our guides were helpful, friendly and spoke excellent English and when we contacted the Mexico office to squeeze in another excursion, they were responsive and immediately organised everything. All round brilliant customer service and Mexico was the most interesting and beautiful place to visit! Thank you!"

Trip dates & details
Save this trip to your favorites or other list
More
Hikes and Boat Trips in Martinique
Save this trip to your favorites or other list
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Enjoy a guided hike Explore the beautiful nature on Martinique. Have fun during a boat trip and sailing day. Relax at the beach Enjoy a typical Caribbean evening.

Themes

Nature & Wildlife, Hiking & Walking, Sailing, National Parks

What travelers are saying

"We wanted a very customized culinary and art tour of Paris and France and found French Side Travel who took us under their wings and designed a most magnificent and memorable trip for us. I ended up planning a ten-day trip with Karen Hendricks in January and February 2024, and we then continued customizing it until we left Paris on September 20th. We booked the trip around my 90-year old MIL’s particular desires, tastes and fancies, and we had to make changes along the way to accommodate her changing needs. Humongous kudos to Karen for planning an impressive, impeccable truly unique, and varied trip and to Christopher Bourguignon for his extraordinary hands-on handling of our trip and ability to swerve as needed. We also especially appreciated our Paris driver Jerome, who took such excellent care of us. We spent six days in Paris and five in Provence. We stayed in unique luxury boutique hotels and villas that all gave us exceptional service. We had the most accommodating and truly amazing tour guides who all took extraordinary care of my MIL. We had an airport guide who expertly whisked us through CDG. We enjoyed a trip of a lifetime through French Side Travel."

Trip dates & details
Save this trip to your favorites or other list
More

Unlock Community Benefits

Travel better together

  • Save favorite trips and itineraries
  • Get insider insights
  • Receive personalized recommendations
  • ... and much more
Join community
Travelstride Gift Card
One card, thousands of extraordinary trips
Gifts Card

Always Find the Best

On Travelstride you can find 6 trips to The Caribbean Sailing Trips & Packages and more than 20,000 trips worldwide ranging from budget to luxury and private guided to group tours and everything in between. Only on Stride can you find and compare expert-planned trips from 1,000+ tour operators, cruise lines and local experts. Read traveler and professional reviews so you can confidently find your perfect trip.

Top Tour Companies on Travelstride:
All 1,600+ companies >
Sign in to reveal savings up to $700 per person!