Ultimate Break company logo

Browse our trips

November
2023
December
2023
January
2024
February
2024
March
2024
April
2024
May
2024
June
2024
July
2024
August
2024
September
2024
October
2024
November
2024
December
2024
January
2025
February
2025
March
2025
April
2025
May
2025
June
2025
July
2025
August
2025
September
2025
October
2025
November
2025
December
2025
January
2026
February
2026
March
2026
April
2026
May
2026
June
2026
July
2026
August
2026
September
2026
October
2026
November
2026
December
2026
January
2027
February
2027
March
2027
April
2027
May
2027
June
2027
July
2027
August
2027
September
2027
October
2027
November
2027
December
2027
January
2028
February
2028
March
2028
April
2028
May
2028
June
2028
July
2028
August
2028
September
2028
October
2028
November
2028
December
2028
December 2023
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31

15 trips available
An aerial view of a cove with many boats inside and bright blue water
Yellow houses side by side with bright blue doors and red detail
A person snorkeling underwater with rocks and coral below them

Cruise Greece: Hydra & the Saronic Islands

12 days, 8 cities

Save up to $400

Italy & Greece Getaway

15 days, 7 cities
5/5

Save up to $400

❗️SALE EXTENDED❗️
Ultimate Black Friday
Book and save during our best sale ever, now ending Dec. 14.
Shop the sale
A view of many brightly colored buildings with many windows packed together on a hillside in front of a calm sea with several docked boats
Aerial view of colorful coastal city with a volcano in the distance
Stone ruins of a temple with tall columns
A rocky path lined by water leading towards a white village on a hill

Rome, the Amalfi Coast & Greece

11 days, 5 cities
4.8/5

Save up to $700

White buildings with a bright blue dome on top situated at the edge of a hill overlooking the calm ocean with other islands in the background
White and blue Greek house with blue accents and pink flowers on a sunny day
The Parthenon, an ancient ruin, outdoors on a sunny day in Greece
Pink and purple sunset over buildings in Oia, Greece

The Greek Islands

11 days, 4 cities
5/5

Save up to $900

A calm harbor with clear blue water and a stone wall with many densely packed white homes in the background on a clear blue day
A view of the city of Florence with large red-domed buildings and a mountain range in the background
Many colorful houses grouped very close together built high on a cliff overlooking a rocky shore and blue water
White buildings with blue domes in Santorini next to colorful homes overlooking a cliff during a sunset

Italy & the Greek Islands

15 days, 5 cities
5/5

Save up to $700

The sun setting on colorful seaside buildings with tables and chairs in the foreground.
Chairs and umbrellas on a sandy beach.
Two donkeys standing in a field standing next to a stone wall.

Mykonos: Island Escape

7 days, 1 city

Save up to $200

An aerial view of white buildings with blue domes overlooking a cliff that leads to the sea during sunset
Tables and chairs situated at the corner of a balcony overlooking a city next to the water
A rocky shore next to clear blue water with mountains in the background

Greek Island Getaway: Crete & Santorini

11 days, 4 cities
5/5

Save up to $400

Ruins of an ancient temple on a hill dusted with snow on a sunny day
Aerial view of a city at sunset with ancient ruins on a hill in the center
Statue of a woman wearing a helmet and holding a spear and shield atop a stone column

Athens: City Experience

7 days, 1 city
5/5

Save up to $150

A gorgeous view of a city on a hillside made up of all white houses and buildings during a pink and orange sunset
A young woman looking towards a cliffside village with white buildings topped by blue domes
Mountainous coastline with a port and a white church
Stuffed grapes leaves and a spinach-filled pastry plated on a table

Greek Island Getaway: Ios & Santorini

9 days, 3 cities
4.9/5

Save up to $600

A view of several boats docked in calm blue water with many white buildings densely packed together in the background
White buildings with blue domes in Santorini next to colorful homes overlooking a cliff during a sunset
Crystal clear ocean meeting the shoreline of an empty beach in Greece
A view from the sidewalk of a colorful beachside town in Greece with plants lining the street

Ultimate Greek Islands

17 days, 7 cities
4.9/5

Save up to $800

Ruins of a large ancient temple lit up at night
A street with a Greek flag hanging from a balcony
Aerial view of a city with a mountain in the distance

Athens: Summer Escape

7 days, 1 city

Save up to $150

A view from the top of ancient ruins which seems to be a stadium in a semi-circle with many rows of seating looking over the view of a dense city in the background
Ancient Greek ruins with many columns and a broken roof during a cloudy day
Ancient ruins of rows of stairs built in a semi circle located high in the mountains
A large building structure located on its own in the middle of the ocean with a dock in the foreground and several boats attached to the dock

Greek Odyssey

9 days, 4 cities
5/5

Save up to $600

An aerial view of a large city with a stadium located in the center lit up at night
A shot of many people's legs running in sneakers and athletic gear
A statue of a bust of a man with many stairs in the background

Run Athens

7 days, 1 city
5/5
A view of a brightly colored and closely packed town located right next to the sea with a pier filled with docked boats and a rocky sea wall along the shoreline
A view of a city located alongside the shore of a deep blue ocean with boats scattered in the bay and bright pink flowers in the foreground
A bright yellow trolley traveling on its tracks through a colorful city street
A view of the city of Florence with large red-domed buildings and a mountain range in the background

European Summer

35 days, 14 cities
4.7/5

Save up to $1200

A view of a large city with many unique and brightly colored buildings with ancient ruins sitting on a hill in the background
The Eiffel Tower lit up at night with several pink airplane contrails crisscrossing in the sky
A woman smiling while standing inside a red telephone booth in London
A view overlooking Park Guell which is a vibrant outdoor collection of gardens and architecture located in Barcelona. A red brick building with a white cross and white trim details is in the foreground with several trees. The city of Barcelona can be seen in the background with clouds scattering a blue sky.

Ultimate Europe

35 days, 14 cities
4.9/5

Save up to $1300

Back to top