Sailing Cruises Tours & Trip Packages
Powered by
TrendingMachu PicchuAngkor WatDanube RiverMt. KilimanjaroRivers & SeasGalapagosMediterranean SeaCiudad Perdida (The Lost City)Mideast & N. AfricaMekong River
EuropeFranceItalyCroatiaIrelandGreeceSwitzerlandSpainPortugalScandinavia
South AmericaPeruEcuadorBrazilArgentinaChileColombiaPatagoniaAmazon RainforestBolivia
AsiaChinaIndiaCambodiaTurkeyThailandJapanIndonesiaNepalJordan
AfricaTanzaniaSouth AfricaKenyaMoroccoEgyptBotswanaRwandaMadagascarEthiopia
North AmericaUnited StatesCanadaMexico
Australia & PacificAustraliaNew ZealandPacific Island
Antarctica & ArcticAntarcticaArcticNorway
Caribbean & C. AmericaCosta RicaBelizeBahamas
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 >
ToursSailing Cruises

Sailing Cruises Tours & Trips

54 Sailing Cruises trips. Tours from 11 tour companies. 344 reviews. 4.8/5 avg rating.

Filter by trip style:

Design custom trip

54 Trips match your criteria (1 - 20 shown)

Greece: Sparta, Monemvasia & the Peloponnesian Peninsula

Greece: Sparta, Monemvasia & the Peloponnesian Peninsula

By VBT Bicycling Vacations
premier
4.9/5 Excellent
100+ reviews
Group Tour
Why we love them
Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.
Lodging level
Premium - 4 star
Physical level
Extreme
Trip pace
Full schedule

Visits

Athens, Crete, Santorini

Highlights

  • Uncover the treasures of the hillside medieval gem of Mystras, the Byzantine Empire’s cultural capital for nearly a millennium, with an expert archaeologist-guide.
  • Savor the recipes and the flavors of ancient Byzantine cuisine during a special dinner.
  • Walk through the maze of alleyways in the medieval castle town of Monemvasia, a crossroads of civilizations with Byzantine, Frankish, Venetian, and Ottoman influences.
  • Cruise around the monolithic Rock of Monemvasia.
  • Join a taverna owner on a shrimp-harvesting excursion, then join him for a cooking lesson and prepare garidopetoules—a savory shrimp pancake.

Themes

Cultural, Cycling & Biking, Nature & Wildlife, Sailing, Photography

What travelers are saying

"This trip is unbelievably fantastic. Two of the best rides of my life, were on this tour. The guides were very good and this was just the start, when we met them, at the hotel in Cortina. Cortina was the site of the 1956 Olympics, and is a small pretty village. Nothing was open the two nights we were there, so probably bad timing. Hotel was a typical ski village hotel, good Italian/German food, and very comfortable. Second day of biking was up an old railroad spur that is now a ski trail about 15-20 K up to a mountain pass called Cimabanche Pass, which is beautiful. We rode up in a snow storm, then rain, then finally clear skies. This was the number two best ride of my life. Starting out from the hotel in Cortina, up the old spur, through single track bike trails, past babbling brooks, up to this fabulous mountain pass. This is now where the fun starts. Mostly downhill on paved roads very little traffic, at good speeds, through the most spectacular valleys you would ever see on a bike ride. Breathtaking. It had to end back at the hotel for a big dinner. The best ride of my life was the last biking day out of Merano. We were bused up 1500 K, about 85-90 miles to Lake Resia, high up in the Dolomites, then rode around the lake, down, back to Merano. High mountain peaks, many valleys,small towns, many grape growing farms, scenery, the best, and cool brisk weather. This was truly a great bike tour, one I will never forget. The trip is rated easy, but maybe easy/moderate is closer. The Hotel in Merano is excellent, middle of old town, modern, has a thermal bath, rooms were very good. The town of Merano is a must see if in the area, small, beneath the high mountains of the Dolomites, good restaurants, lots of tourists."

Trip dates & details
Save this trip to your favorites or other list
7 days From$3,845
More
Vietnam: Hanoi, Hue, Hoi An & Saigon

Vietnam: Hanoi, Hue, Hoi An & Saigon

By VBT Bicycling Vacations
premier
4.9/5 Excellent
100+ reviews
Group Tour
Why we love them
Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Visits

Hanoi, Ho Chi Minh, Hoi An , Hue, Mekong Delta, Saigon

Highlights

  • Explore Hanoi on two guided tours and a cyclo (rickshaw) ride.
  • Attend a performance that’s unique to Vietnamese culture: a water puppet show.
  • Delve into Vietnam’s ancient history on a guided tour of the Imperial City and the Forbidden Purple City of Hue.
  • Admire shifting landscapes of fish and duck farms, rice paddies, palm forests, mountains, and coastline on scenic cycling routes.
  • Savor the local cuisine—including a hands-on class at a cooking school.

Themes

Cultural, Cycling & Biking, Nature & Wildlife, Sailing

What travelers are saying

"This trip is unbelievably fantastic. Two of the best rides of my life, were on this tour. The guides were very good and this was just the start, when we met them, at the hotel in Cortina. Cortina was the site of the 1956 Olympics, and is a small pretty village. Nothing was open the two nights we were there, so probably bad timing. Hotel was a typical ski village hotel, good Italian/German food, and very comfortable. Second day of biking was up an old railroad spur that is now a ski trail about 15-20 K up to a mountain pass called Cimabanche Pass, which is beautiful. We rode up in a snow storm, then rain, then finally clear skies. This was the number two best ride of my life. Starting out from the hotel in Cortina, up the old spur, through single track bike trails, past babbling brooks, up to this fabulous mountain pass. This is now where the fun starts. Mostly downhill on paved roads very little traffic, at good speeds, through the most spectacular valleys you would ever see on a bike ride. Breathtaking. It had to end back at the hotel for a big dinner. The best ride of my life was the last biking day out of Merano. We were bused up 1500 K, about 85-90 miles to Lake Resia, high up in the Dolomites, then rode around the lake, down, back to Merano. High mountain peaks, many valleys,small towns, many grape growing farms, scenery, the best, and cool brisk weather. This was truly a great bike tour, one I will never forget. The trip is rated easy, but maybe easy/moderate is closer. The Hotel in Merano is excellent, middle of old town, modern, has a thermal bath, rooms were very good. The town of Merano is a must see if in the area, small, beneath the high mountains of the Dolomites, good restaurants, lots of tourists."

Trip dates & details
Save this trip to your favorites or other list
11 days From$4,345
More
Croatia Bike & Boat: Split & the Dalmatian Islands, Aboard the Jadranska Kraljica

Croatia Bike & Boat: Split & the Dalmatian Islands, Aboard the Jadranska Kraljica

By VBT Bicycling Vacations
premier
4.9/5 Excellent
100+ reviews
Group Tour
Why we love them
Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.
Lodging level
Premium - 4 star
Physical level
Extreme
Trip pace
Full schedule

Visits

Dubrovnik, Hvar Island, Korcula Island, Split

Highlights

  • Explore the medieval fortress and fascinating fishing museum in the tiny village of Komiža on the island of Vis.
  • Cycle into historic cities central to the past and culture of the Dalmatian Islands: Korčula, Hvar, Jelsa, Stari Grad, Postira, Pučišća.
  • Learn some Croatian cooking tips during a demonstration with your onboard chef—and savor the results for dinner.
  • Visit one of the last remaining stonecutters’ schools, on the island of Brač.
  • Taste unique Dalmatian wines in one of the well-known local wineries.

Themes

Culinary & Wine, Cultural, Cycling & Biking, Nature & Wildlife, Sailing

What travelers are saying

"This trip is unbelievably fantastic. Two of the best rides of my life, were on this tour. The guides were very good and this was just the start, when we met them, at the hotel in Cortina. Cortina was the site of the 1956 Olympics, and is a small pretty village. Nothing was open the two nights we were there, so probably bad timing. Hotel was a typical ski village hotel, good Italian/German food, and very comfortable. Second day of biking was up an old railroad spur that is now a ski trail about 15-20 K up to a mountain pass called Cimabanche Pass, which is beautiful. We rode up in a snow storm, then rain, then finally clear skies. This was the number two best ride of my life. Starting out from the hotel in Cortina, up the old spur, through single track bike trails, past babbling brooks, up to this fabulous mountain pass. This is now where the fun starts. Mostly downhill on paved roads very little traffic, at good speeds, through the most spectacular valleys you would ever see on a bike ride. Breathtaking. It had to end back at the hotel for a big dinner. The best ride of my life was the last biking day out of Merano. We were bused up 1500 K, about 85-90 miles to Lake Resia, high up in the Dolomites, then rode around the lake, down, back to Merano. High mountain peaks, many valleys,small towns, many grape growing farms, scenery, the best, and cool brisk weather. This was truly a great bike tour, one I will never forget. The trip is rated easy, but maybe easy/moderate is closer. The Hotel in Merano is excellent, middle of old town, modern, has a thermal bath, rooms were very good. The town of Merano is a must see if in the area, small, beneath the high mountains of the Dolomites, good restaurants, lots of tourists."

Trip dates & details
Save this trip to your favorites or other list
8 days From$3,945
More
Plan Your Sailing Cruises Trip
Top Tours
All Sailing Cruises Trips
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

Sail Italy: Procida to Amalfi

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
-26%$1,715
4 days From$1,270
More
Croatia Sailing Adventure: Split to Dubrovnik

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
-26%$2,593
8 days From$1,921
More
Sail Greece: Santorini to Mykonos

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
-26%$1,983
8 days From$1,469
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

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
-26%$2,773
10 days From$2,054
More
Croatia Sailing Adventure: Dubrovnik to Split

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
-26%$2,475
8 days From$1,833
More

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
...

1

2

3

...

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
Contiki Reviews
Peregrine Adventures Reviews
Quark Expeditions Reviews
Great Value Vacations Reviews
Audley Travel Reviews
Lindblad Expeditions Reviews
National Geographic Expeditions Reviews
Perillo Tours Reviews
Classic Journeys Reviews
Travcoa Reviews
Culture Trip Reviews

Always Find the Best

On Travelstride you can find 54 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 >