Sailing Cruises Tours & Trip Packages
Design custom trip
TrendingMachu PicchuAngkor WatDanube RiverMt. KilimanjaroRivers & SeasGalapagosMediterranean SeaCiudad Perdida (The Lost City)Mideast & N. AfricaMekong River
EuropeFranceItalyCroatiaIrelandGreeceSwitzerlandSpainPortugalScandinaviaSee all >
South AmericaPeruEcuadorBrazilArgentinaChileColombiaPatagoniaAmazon RainforestBoliviaSee all >
AsiaChinaIndiaCambodiaTurkeyThailandJapanIndonesiaNepalJordanSee all >
AfricaTanzaniaSouth AfricaKenyaMoroccoEgyptBotswanaRwandaMadagascarEthiopiaSee all >
North AmericaUnited StatesCanadaMexicoSee all >
Australia & PacificAustraliaNew ZealandPacific IslandSee all >
Antarctica & ArcticAntarcticaArcticNorwaySee all >
Caribbean & C. AmericaCosta RicaBelizeBahamasSee all >
See all destinations >
Top TripsTop 10 ListsEditor PicksMost Popular TripsAward WinnersCollectionsTop TrendingSee all activities, themes, and interests >
ActivitiesCycling & BikingSmall Ship CruisesSafariRiver CruisesClimbing and MountaineeringTrekking & CampingHiking & WalkingTrain & RailRiver RaftingYoga, Meditation & Wellness
Styles50+Family Friendly18-30LuxuryBudgetAdventure TravelSolo and Single TripsGroup Guided ToursCustom Tour PackagesIndependent Vacation PackagesPrivate Guided
InterestsCulturalWildlifeHistoryNatureBirding toursFestivals and Special EventsEco/Sustainable TravelVolunteeringLearning & EducationalRuins & ArchaeologyCulinary & Wine Tasting
See all activities, themes, and interests >
Member Savings ProgramTour operatorsRover TripFinder AIAffiliate PartnersTravel Trivia GameAbout UsTravel ArticlesContact Us
Gift Cards
ToursSailing Cruises

Sailing Cruises Tours & Trips

254 Sailing Cruises trips. Tours from 133 tour companies. 344 reviews. 4.8/5 avg rating.

Filter by trip style:

Design custom trip
254 trips exactly matchall of the the filters you selected.
My selections:
Sailing Croatia - Split to Dubrovnik
Save this trip to your favorites or other list

Sailing Croatia - Split to Dubrovnik

By G Adventures
preferred
4.8/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Croatia, Diocletian's Palace, Dubrovnik, Split

Highlights

  • Connect with history at diocletian's palace in split
  • Discover secluded islands and deserted beaches
  • Explore korčula — the birthplace of marco polo
  • Wander the forested paradise of mljet national park
  • Sail into the ancient port of dubrovnik — "the pearl of the adriatic"

Themes

Cultural, National Parks, Nature & Wildlife, Small Ship Cruise, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details
Save this trip to your favorites or other list
-26%$1,281
8 days From$950
More
Montenegro Sailing - Dubrovnik to Dubrovnik
Save this trip to your favorites or other list

Montenegro Sailing - Dubrovnik to Dubrovnik

By G Adventures
preferred
4.8/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Budva, Dubrovnik, Kotor, Montenegro

Highlights

  • Spend time exploring some of the area's nicest beaches
  • Enjoy the seaside nightlife in budva
  • Swim and snorkel in the crystal-clear waters of bigovo
  • Witness the impressive balkan landscapes

Themes

Cultural, National Parks, Nature & Wildlife, Small Ship Cruise, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details
Save this trip to your favorites or other list
-26%$1,922
8 days From$1,424
More
Dalmatian Coast & Montenegro Sailing
Save this trip to your favorites or other list

Dalmatian Coast & Montenegro Sailing

By G Adventures
preferred
4.8/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Budva, Croatia, Dalmatian Coast, Dubrovnik, Kotor, Montenegro, Split

Highlights

  • Relax as you sail the picturesque dalmatian coast
  • Explore the region through beaches and charming coastal villages
  • Enjoy the nightlife of hvar and budva after a long day of lounging
  • Get endless photo opportunities throughout the region's mountainous and green landscapes
  • Snorkel in crystal-clear waters

Themes

Cultural, Small Ship Cruise, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details
Save this trip to your favorites or other list
-26%$4,049
15 days From$2,999
More
Plan Your Sailing Cruises Trip
Top Tours
All Sailing Cruises Trips
Attractions & Things to Do
Suggested Itineraries
Iconic Sailing Cruises Landmarks
Tour Companies for Sailing Cruises
Sailing Cruises Reviews

All Sailing Cruises, expedition cruises, self guided adventures and vacation packages. Find the best guided and expert planned vacation and holiday packages. Read more about Sailing Cruises

Montenegro & Croatia Sailing
Save this trip to your favorites or other list

Montenegro & Croatia Sailing

By G Adventures
preferred
4.8/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Budva, Croatia, Dubrovnik, Kotor, Montenegro, Split

Highlights

  • See a different way of living in charming coastal fishing towns
  • Work on your tan as you relax on secluded beaches
  • Enjoy the colourful nightlife of hvar and budva
  • Sample locally-made wine and delicious homegrown flavours

Themes

Cultural, Small Ship Cruise, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details
Save this trip to your favorites or other list
-26%$4,049
15 days From$2,999
More
Sailing Thailand - Phuket to Phuket
Save this trip to your favorites or other list

Sailing Thailand - Phuket to Phuket

By G Adventures
preferred
4.8/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Andaman Islands, Ko Phi Phi, Phang Nga Bay, Phuket

Highlights

  • Relax on the deck of the catamaran in the stunning southern thai islands
  • Eat delicious thai cuisine
  • Lounge on beautiful beaches
  • Swim and snorkel in quiet bays

Themes

National Parks, Nature & Wildlife, Small Ship Cruise, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details
Save this trip to your favorites or other list
-33%$2,496
7 days From$1,664
More
Maldives Dhoni Cruise
Save this trip to your favorites or other list

Maldives Dhoni Cruise

By G Adventures
preferred
4.8/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Highlights

  • Cruise through some of the world's most beautiful islands
  • Uncover isolated beaches
  • Explore small fishing villages
  • Swim and snorkel the vibrant coral reefs of the indian ocean
  • Savour local cuisine

Themes

National Parks, Nature & Wildlife, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details
Save this trip to your favorites or other list
-26%$1,997
7 days From$1,479
More

Unlock Community Benefits

Travel better together

  • Save favorite trips and itineraries
  • Get insider insights
  • Receive personalized recommendations
  • ... and much more
Join community
Sailing Thailand - Phuket to Ko Phi Phi
Save this trip to your favorites or other list

Sailing Thailand - Phuket to Ko Phi Phi

By G Adventures
preferred
4.8/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Andaman Islands, Ko Phi Phi, Phuket

Highlights

  • Snorkel in crystal-clear water
  • Sail through stunning southern thai islands
  • Feast on tantalizing thai cuisine
  • Relax on secluded beaches

Themes

National Parks, Nature & Wildlife, Small Ship Cruise, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details
Save this trip to your favorites or other list
-33%$1,281
4 days From$854
More
Sailing Greece - Mykonos to Santorini
Save this trip to your favorites or other list

Sailing Greece - Mykonos to Santorini

By G Adventures
preferred
2/5 Disappointing
100+ reviews
Small Ship Cruise
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Mykonos, Paro, Santorini

Highlights

  • Explore the beautiful southern cyclades by sailboat
  • Stop at small off-the-beaten-path islands along the way
  • Relax on white-sand beaches
  • Try your hand at sailing (or just relax on the deck)
  • Stroll through local villages and sample traditional greek food and wine

Themes

Cultural, Small Ship Cruise, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details
Save this trip to your favorites or other list
-46%$1,881
8 days From$1,007
More
Travelstride Gift Card
One card, thousands of extraordinary trips
Explore
Gifts Card

Want a tailor-made trip instead?

Your trip, your way, planned by an expert:

  • You choose budget, destinations, activities, transport & lodging type
  • Expert designs the itinerary for you, and once approved, takes care of logistics
Design custom trip
254 trips exactly matchall of the the filters you selected.
My selections:

First

...

1

2

3

4

5

...

Last

Best Sailing Cruises Tours by Duration

1 Week
Sailing Cruises One Week Top Itineraries 

Tours, Cruises & Private Trips

10 Days
Sailing Cruises 10 Day Top Itineraries 

Tours, Cruises & Private Trips

2 Week
Sailing Cruises 2 Week Top Itineraries 

Tours, Cruises & Private Trips

Best Sailing Cruises Tours by Price

Best Sailing Cruises Luxury Tours 
Best Sailing Cruises Standard Tours 
Best Sailing Cruises Budget Tours 

Related Tours

Aegean Sea
Australia & the Pacific
Caribbean Sea
Croatia
Galapagos Islands
Greece
Mediterranean Sea
Pacific Islands
Small Ship & Expedition Cruises

Sailing Cruises Reviews & Ratings

4.8/5  Excellent
344  Reviews
Write a review
See all Sailing Cruises tour reviews
Excellent
33
Great
2
Average
0
Disappointing
0
Terrible
1
L

Linda D

Apr 2024

Written on

AMAZING from start to finish!

It was such a pleasure to work with Annie from start to finish. Annie worked patiently with my very particular husband for a good month to plan a 19 day trip. (I thi...

Tour:  Indochina Essence

h

hfarbs

Mar 2023

Written on

Fantastic Service and Trip from Exotic Voyages

"Exotic Voyages was terrific. We were originally on a group trip, and the group cancelled a couple of months before we were scheduled to leave. We found Exotic Voyag...

Tour:  Indochina Essence

C

Craig G

Feb 2023

Written on

Exotic Voyages did a great job on our Vietnam, Cambodia, and Laos trip

Great experience with Exotic Voyages on my recent trip to Vietnam, Cambodia, and Laos! I'm from Califonia and was taking a birthday trip with my mom. I started with ...

Tour:  Indochina Essence

B

Bobbydot01

Dec 2022

Written on

I will use Exotic Voyages again.

"We used Exotic Voyages for our 3 week trip. Annie made it organized and easy from the very beginning. She worked with me to develop and tweak many itineraries. All ...

Tour:  Indochina Essence

s

suspv

Jul 2022

Written on

Fantastic Indochina tour

"Fantastic Indochina tour. Diep was extremely patient working with me while we ran through several different itineraries. Very helpful and responsive in answering em...

Tour:  Indochina Essence

See all Sailing Cruises reviews

Write a Review

Additional details

Top Sailing Cruises Travel Companies
Intrepid Travel Reviews
G Adventures Reviews
Say Hueque Reviews
Real New Zealand Tours Reviews
Greece Insiders Reviews
Eskapas Reviews
Topdeck Reviews
Eros and Psyche Travel Reviews
Responsible Travel Reviews
Eastern European Experience Reviews
Asia Authentic Travel Reviews
Contiki Reviews

Always Find the Best

On Travelstride you can find 254 trips to Sailing Cruises 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!