Sailing Cruises Small Ship Cruise 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 Small Ship Cruise Tours & Trips

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

Filter by trip style:

Design custom trip
98 trips exactly matchall of the the filters you selected.
My selections:
Small Ship Cruise
Antarctica Expedition & Wild Patagonia
Save this trip to your favorites or other list

Antarctica Expedition & Wild Patagonia

By Across South America
Local Expert
Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.
5/5 Excellent
65 reviews
Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

El Calafate, Patagonia, Tierra del Fuego National Park, Ushuaia

Highlights

  • Torres del Paine Luxury Camp
  • Walk on the Perito Moreno Glacier
  • Explore the "End of the world"
  • Nature at its best at the Small Luxurious Expedition Cruise to Antarctica.
  • Adventure in Antarctica: Ice-Camp and Kayak

Themes

Birding, Cultural, High Adventure, Hiking & Walking, Nature & Wildlife, Rafting, Kayaking, Canoeing, Small Ship Cruise, Trekking & Expeditions, Sailing, Photography

What travelers are saying

"I highly recommend Across South America for a memorable experience that is personalized for YOU."

Trip dates & details
Save this trip to your favorites or other list
-19%$19,926
21 days From$16,200

Generous cancellation

More
Galápagos — South & East Islands aboard the Yolita
Save this trip to your favorites or other list

Galápagos — South & East Islands aboard the Yolita

By G Adventures
preferred
5/5 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
Premium - 4 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Darwin, Guayaquil, Isla Santa Fe, Quito, Sucre

Highlights

  • Four nights cruising in the galápagos islands aboard the yolita
  • Explore the beautiful southern and eastern islands to see iguanas and sea lions
  • Relax on the white sandy beaches
  • Cruise by the dramatic kicker rock
  • Visit some of the best snorkelling spots in the galápagos

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
-31%$4,870
7 days From$3,374
More
Sail Italy: Procida to Amalfi
Save this trip to your favorites or other list

Sail Italy: Procida to Amalfi

By Intrepid Travel
premier
4.7/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Amalfi Coast, Naples, Pompeii, Sorrento

Highlights

  • Among the pastel-hued houses of tranquil Procida, you’ll really feel like you’ve wandered off the beaten track
  • Visit the ancient Roman town of Pompeii, which emerged from the ashes after thousands of years, and take a peak inside the steaming crater of the volcano that destroyed it
  • Stroll through the flourishing countryside of the Amalfi Coast and pick olives straight from the tree
  • This region is a haven for seafood, views and relaxation. With the free time that's afforded on this trip, you're able to explore the coast's famous cuisine, find the ideal picture-postcard views and float along at your own leisure
  • The stunning landscape of the Sorrentine Peninsula is a picturesque blend of coastlines, volcanoes and distinctive islands

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
Save this trip to your favorites or other list
-50%$1,550
4 days From$782

Health Safety +

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

Yolo Yachting - Mykonos to Santorini
Save this trip to your favorites or other list

Yolo Yachting - Mykonos to Santorini

By Sail in Greece
preferred
3.9/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • Drive to fascinating Mykonos Island
  • Explore Paros which is famous for its water sports with wind surfing
  • Enjoy the Aegean archipelago of Paros
  • Explore Santorini

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-36%$529
8 days From$339
Price updated 1 year+ ago

Health Safety

More
Croatia Sailing Adventure: Split to Dubrovnik
Save this trip to your favorites or other list

Croatia Sailing Adventure: Split to Dubrovnik

By Intrepid Travel
premier
5/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Croatia, Diocletian's Palace, Dubrovnik, Split

Highlights

  • What better way to see the historic towns, protected forests and stunning islands of Croatia’s Dalmatian Coast than aboard a private yacht? All aboard for a week in paradise.
  • Explore beautiful Split, where tradition, modernity and a variety of European influences come together. A visit to the Diocletian’s Palace reveals some of the Adriatic Coast’s most important surviving Roman buildings.
  • Bliss out on Brac’s world famous Zlatni Rat beach, a spit of white sand jutting out into turquoise waters.
  • Opened to the public only in 1989, the island of Vis boasts coastal scenery and a military history just waiting to be discovered. Also, the local vugava wine is rather nice.
  • Stari Grad, Hvar’s Old Town, is quite literally one of the oldest towns in Europe, and a charming one at that. It provides a great base from which to explore the island.

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
Save this trip to your favorites or other list
-37%$2,817
8 days From$1,788

Health Safety +

More
Sail Greece: Santorini to Mykonos
Save this trip to your favorites or other list

Sail Greece: Santorini to Mykonos

By Intrepid Travel
premier
4.8/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Akrotiri, Mykonos, Santorini

Highlights

  • Spend your days island-hopping in the Cyclades, swimming in the clear waters of the Aegean and sleeping aboard a yacht
  • The blue and white villages of Santorini may cling to the rim of an ancient volcano, but the only fire you’ll see is in the island’s magnificent sunsets
  • In the sleepy fishing villages of the Small Cyclades islands, you’re more likely to break bread with a local than a tourist
  • A taste of rural life on the large island of Navos is a mix of historic neighbourhoods and Kitron liqueur
  • Stylish Mykonos is a place where Europe’s chic and beautiful come to play – offering an exclusive, boutique feel to the island

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
Save this trip to your favorites or other list
-41%$2,210
8 days From$1,301

Health Safety +

More

Unlock Community Benefits

Travel better together

  • Save favorite trips and itineraries
  • Get insider insights
  • Receive personalized recommendations
  • ... and much more
Join community
Greece Sailing Adventure: Cyclades Islands
Save this trip to your favorites or other list

Greece Sailing Adventure: Cyclades Islands

By Intrepid Travel
premier
5/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • A Santorini sunset around the caldera is a sight to behold. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs and watch as day turns to night in the most stunning of ways.
  • Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.
  • Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life. This is island living, Greek style.
  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village – a couple of the many experiences to be had around the Cyclades.
  • No Greek island adventure is complete without a stop in Mykonos. Embrace your hedonistic side with its boutique culture and nightlife or relax on one of the many beaches dotted along the coast.

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
Save this trip to your favorites or other list
-41%$3,096
10 days From$1,814

Health Safety +

More
Croatia Sailing Adventure: Dubrovnik to Split
Save this trip to your favorites or other list

Croatia Sailing Adventure: Dubrovnik to Split

By Intrepid Travel
premier
5/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Croatia, Diocletian's Palace, Dubrovnik, Split

Highlights

  • What better way to see the historic towns, protected forests and stunning islands of Croatia’s Dalmatian Coast than aboard a private yacht? All aboard for a week in paradise.
  • Set sail out of beautiful Dubrovnik. The World Heritage-listed walled city plays host to film crews every year.
  • Wander the length of car-free Lopud in the idyllic Elafiti Islands.
  • Discover the lush forests of Mljet, which are yet to be spoilt by mainstream tourism.
  • Visit Odysseus Cave where, according to legend, the king of Ithaca once found refuge after surviving a shipwreck.
Show more

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
Save this trip to your favorites or other list
-41%$2,763
8 days From$1,620

Health Safety +

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
98 trips exactly matchall of the the filters you selected.
My selections:
Small Ship Cruise
...

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 252 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!